US20190276386A1 - Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness - Google Patents
Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness Download PDFInfo
- Publication number
- US20190276386A1 US20190276386A1 US16/345,921 US201516345921A US2019276386A1 US 20190276386 A1 US20190276386 A1 US 20190276386A1 US 201516345921 A US201516345921 A US 201516345921A US 2019276386 A1 US2019276386 A1 US 2019276386A1
- Authority
- US
- United States
- Prior art keywords
- residue
- hydroxy
- acetate
- methoxyphenyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000002148 esters Chemical class 0.000 title claims description 23
- 235000019633 pungent taste Nutrition 0.000 title description 53
- 238000002360 preparation method Methods 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000000796 flavoring agent Substances 0.000 claims abstract description 85
- 235000019634 flavors Nutrition 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims description 94
- -1 1,1-dimethylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate Chemical compound 0.000 claims description 72
- AWPMWZHWVKXADV-UHFFFAOYSA-N ethyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(OC)=C1 AWPMWZHWVKXADV-UHFFFAOYSA-N 0.000 claims description 69
- 235000002639 sodium chloride Nutrition 0.000 claims description 63
- 239000000126 substance Substances 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 229910001868 water Inorganic materials 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 238000010792 warming Methods 0.000 claims description 37
- 230000000694 effects Effects 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- GMPZIQIDEYHGLZ-UHFFFAOYSA-N butyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCCCOC(=O)CC1=CC=C(O)C(OC)=C1 GMPZIQIDEYHGLZ-UHFFFAOYSA-N 0.000 claims description 32
- 235000019640 taste Nutrition 0.000 claims description 28
- 235000019613 sensory perceptions of taste Nutrition 0.000 claims description 26
- 230000035923 taste sensation Effects 0.000 claims description 26
- ANSYMFFOUMIZJJ-UHFFFAOYSA-N 2-phenylethyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound C1(=CC=CC=C1)CCOC(CC1=CC(=C(C=C1)O)OC)=O ANSYMFFOUMIZJJ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 16
- 210000000214 mouth Anatomy 0.000 claims description 16
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 16
- SYEBQVUZYCJAEQ-UHFFFAOYSA-N propyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCCOC(=O)CC1=CC=C(O)C(OC)=C1 SYEBQVUZYCJAEQ-UHFFFAOYSA-N 0.000 claims description 15
- CAZMLKCZUMAWOL-UHFFFAOYSA-N heptyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCCCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 CAZMLKCZUMAWOL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- XCAJPVHAKFDCQH-UHFFFAOYSA-N C1(=CC=CC=C1)CCCOC(CC1=CC(=C(C=C1)O)OC)=O Chemical compound C1(=CC=CC=C1)CCCOC(CC1=CC(=C(C=C1)O)OC)=O XCAJPVHAKFDCQH-UHFFFAOYSA-N 0.000 claims description 13
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 235000016709 nutrition Nutrition 0.000 claims description 11
- 230000035764 nutrition Effects 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000003765 sweetening agent Substances 0.000 claims description 9
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 8
- 230000001965 increasing effect Effects 0.000 claims description 8
- 208000035824 paresthesia Diseases 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 235000019204 saccharin Nutrition 0.000 claims description 8
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 8
- 229940081974 saccharin Drugs 0.000 claims description 8
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 8
- 235000019658 bitter taste Nutrition 0.000 claims description 7
- 229930003944 flavone Natural products 0.000 claims description 7
- 235000011949 flavones Nutrition 0.000 claims description 7
- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 claims description 6
- QJYNZEYHSMRWBK-NIKIMHBISA-N 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose Chemical compound OC1=C(O)C(O)=CC(C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 QJYNZEYHSMRWBK-NIKIMHBISA-N 0.000 claims description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 6
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 6
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 6
- 235000003599 food sweetener Nutrition 0.000 claims description 6
- 229930182470 glycoside Natural products 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000001103 potassium chloride Substances 0.000 claims description 6
- 235000011164 potassium chloride Nutrition 0.000 claims description 6
- 229960002816 potassium chloride Drugs 0.000 claims description 6
- 229940088594 vitamin Drugs 0.000 claims description 6
- 229930003231 vitamin Natural products 0.000 claims description 6
- 235000013343 vitamin Nutrition 0.000 claims description 6
- 239000011782 vitamin Substances 0.000 claims description 6
- 150000003751 zinc Chemical class 0.000 claims description 6
- 108010011485 Aspartame Proteins 0.000 claims description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 5
- 159000000013 aluminium salts Chemical class 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 239000000605 aspartame Substances 0.000 claims description 5
- 235000010357 aspartame Nutrition 0.000 claims description 5
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 5
- 229960003438 aspartame Drugs 0.000 claims description 5
- 235000019606 astringent taste Nutrition 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 235000009508 confectionery Nutrition 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 235000018102 proteins Nutrition 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims description 4
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 4
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 4
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 claims description 4
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- HLCFGWHYROZGBI-JJKGCWMISA-M Potassium gluconate Chemical compound [K+].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O HLCFGWHYROZGBI-JJKGCWMISA-M 0.000 claims description 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 4
- KNAHARQHSZJURB-UHFFFAOYSA-N Propylthiouracile Chemical compound CCCC1=CC(=O)NC(=S)N1 KNAHARQHSZJURB-UHFFFAOYSA-N 0.000 claims description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 4
- NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 239000004376 Sucralose Substances 0.000 claims description 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 4
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 claims description 4
- 229960001948 caffeine Drugs 0.000 claims description 4
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 235000014633 carbohydrates Nutrition 0.000 claims description 4
- 235000005513 chalcones Nutrition 0.000 claims description 4
- WDRWZVWLVBXVOI-QTNFYWBSSA-L dipotassium;(2s)-2-aminopentanedioate Chemical compound [K+].[K+].[O-]C(=O)[C@@H](N)CCC([O-])=O WDRWZVWLVBXVOI-QTNFYWBSSA-L 0.000 claims description 4
- CVOQYKPWIVSMDC-UHFFFAOYSA-L dipotassium;butanedioate Chemical compound [K+].[K+].[O-]C(=O)CCC([O-])=O CVOQYKPWIVSMDC-UHFFFAOYSA-L 0.000 claims description 4
- 229940045109 genistein Drugs 0.000 claims description 4
- 235000006539 genistein Nutrition 0.000 claims description 4
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims description 4
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims description 4
- 150000002338 glycosides Chemical class 0.000 claims description 4
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 4
- 229960000310 isoleucine Drugs 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 230000000873 masking effect Effects 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 235000013919 monopotassium glutamate Nutrition 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229960003975 potassium Drugs 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229940093956 potassium carbonate Drugs 0.000 claims description 4
- 235000011181 potassium carbonates Nutrition 0.000 claims description 4
- 239000004224 potassium gluconate Substances 0.000 claims description 4
- 235000013926 potassium gluconate Nutrition 0.000 claims description 4
- 229960003189 potassium gluconate Drugs 0.000 claims description 4
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 4
- 235000011085 potassium lactate Nutrition 0.000 claims description 4
- 239000001521 potassium lactate Substances 0.000 claims description 4
- 229960001304 potassium lactate Drugs 0.000 claims description 4
- SVICABYXKQIXBM-UHFFFAOYSA-L potassium malate Chemical compound [K+].[K+].[O-]C(=O)C(O)CC([O-])=O SVICABYXKQIXBM-UHFFFAOYSA-L 0.000 claims description 4
- 239000001415 potassium malate Substances 0.000 claims description 4
- 235000011033 potassium malate Nutrition 0.000 claims description 4
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 4
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 4
- 239000001120 potassium sulphate Substances 0.000 claims description 4
- 235000011151 potassium sulphates Nutrition 0.000 claims description 4
- 229960002662 propylthiouracil Drugs 0.000 claims description 4
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 claims description 4
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 4
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 claims description 4
- 229940120668 salicin Drugs 0.000 claims description 4
- 235000019408 sucralose Nutrition 0.000 claims description 4
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 claims description 4
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 4
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 4
- 239000004474 valine Substances 0.000 claims description 4
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 3
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 3
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VHLJDTBGULNCGF-UHFFFAOYSA-N Limonin Natural products CC1(C)OC2CC(=O)OCC23C4CCC5(C)C(CC(=O)C6OC56C4(C)C(=O)CC13)c7cocc7 VHLJDTBGULNCGF-UHFFFAOYSA-N 0.000 claims description 3
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004384 Neotame Substances 0.000 claims description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 3
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 3
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 3
- 229930003451 Vitamin B1 Natural products 0.000 claims description 3
- 229930003756 Vitamin B7 Natural products 0.000 claims description 3
- 239000000619 acesulfame-K Substances 0.000 claims description 3
- 229920002770 condensed tannin Polymers 0.000 claims description 3
- 229940109275 cyclamate Drugs 0.000 claims description 3
- KQNGHARGJDXHKF-UHFFFAOYSA-N dihydrotamarixetin Natural products C1=C(O)C(OC)=CC=C1C1C(O)C(=O)C2=C(O)C=C(O)C=C2O1 KQNGHARGJDXHKF-UHFFFAOYSA-N 0.000 claims description 3
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims description 3
- 159000000014 iron salts Chemical class 0.000 claims description 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 3
- KBDSLGBFQAGHBE-MSGMIQHVSA-N limonin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@@H]2[C@]34COC(=O)C[C@@H]3OC2(C)C)C=COC=1 KBDSLGBFQAGHBE-MSGMIQHVSA-N 0.000 claims description 3
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 claims description 3
- 235000007743 myricetin Nutrition 0.000 claims description 3
- 229940116852 myricetin Drugs 0.000 claims description 3
- 235000019412 neotame Nutrition 0.000 claims description 3
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 claims description 3
- 108010070257 neotame Proteins 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960005489 paracetamol Drugs 0.000 claims description 3
- 235000013824 polyphenols Nutrition 0.000 claims description 3
- 235000005875 quercetin Nutrition 0.000 claims description 3
- 229960001285 quercetin Drugs 0.000 claims description 3
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims description 3
- OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 claims description 3
- 229930188195 rebaudioside Natural products 0.000 claims description 3
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims description 3
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000005493 rutin Nutrition 0.000 claims description 3
- 229960004555 rutoside Drugs 0.000 claims description 3
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 3
- 229940013618 stevioside Drugs 0.000 claims description 3
- 235000019202 steviosides Nutrition 0.000 claims description 3
- 235000021092 sugar substitutes Nutrition 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000010436 thaumatin Nutrition 0.000 claims description 3
- 239000000892 thaumatin Substances 0.000 claims description 3
- 229960003495 thiamine Drugs 0.000 claims description 3
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 claims description 3
- 235000010374 vitamin B1 Nutrition 0.000 claims description 3
- 239000011691 vitamin B1 Substances 0.000 claims description 3
- 235000011912 vitamin B7 Nutrition 0.000 claims description 3
- 239000011735 vitamin B7 Substances 0.000 claims description 3
- PZHWYURJZAPXAN-ILOFNVQHSA-N (+)-absinthin Chemical compound C([C@H]1[C@H](C)C(=O)O[C@@H]11)C[C@](C)(O)[C@@H]2[C@H]3[C@@H]4[C@H]5[C@@](C)(O)CC[C@H]6[C@H](C)C(=O)O[C@@H]6C5=C(C)[C@@H]4[C@]21C(C)=C3 PZHWYURJZAPXAN-ILOFNVQHSA-N 0.000 claims description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- DBOVHQOUSDWAPQ-UHFFFAOYSA-N (4aS)-6c-[O2-(3,5,3'-trihydroxy-biphenyl-2-carbonyl)-beta-D-glucopyranosyloxy]-5t-vinyl-(4ar)-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one Natural products OC1C(O)C(CO)OC(OC2C(C3C(C(OCC3)=O)=CO2)C=C)C1OC(=O)C1=C(O)C=C(O)C=C1C1=CC=CC(O)=C1 DBOVHQOUSDWAPQ-UHFFFAOYSA-N 0.000 claims description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 2
- GHODAOZUPBDHHO-UHFFFAOYSA-N 10',11'-epiabsinthin Natural products CC1CC2C3C4C(=C(C)C3C15C6OC(=O)C(C)C6CCC(C)(O)C25)C7OC(=O)C(C)C7CCC4(C)O GHODAOZUPBDHHO-UHFFFAOYSA-N 0.000 claims description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 claims description 2
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 claims description 2
- PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 claims description 2
- PZHWYURJZAPXAN-UHFFFAOYSA-N Absynthin Natural products C12OC(=O)C(C)C2CCC(C)(O)C2C3C4C5C(C)(O)CCC6C(C)C(=O)OC6C5=C(C)C4C21C(C)=C3 PZHWYURJZAPXAN-UHFFFAOYSA-N 0.000 claims description 2
- BZXINCMCFVKGKB-UHFFFAOYSA-N Amarogentin Natural products OCC1OC(OC2OC=C3C(CCOC3=O)C2C=C)C(OC(=O)c4cc(O)cc(O)c4c5cccc(O)c5)C(O)C1O BZXINCMCFVKGKB-UHFFFAOYSA-N 0.000 claims description 2
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 claims description 2
- 235000003097 Artemisia absinthium Nutrition 0.000 claims description 2
- 240000001851 Artemisia dracunculus Species 0.000 claims description 2
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 claims description 2
- 235000003261 Artemisia vulgaris Nutrition 0.000 claims description 2
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims description 2
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 2
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 2
- GMTUGPYJRUMVTC-UHFFFAOYSA-N Daidzin Natural products OC(COc1ccc2C(=O)C(=COc2c1)c3ccc(O)cc3)C(O)C(O)C(O)C=O GMTUGPYJRUMVTC-UHFFFAOYSA-N 0.000 claims description 2
- KYQZWONCHDNPDP-UHFFFAOYSA-N Daidzoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-UHFFFAOYSA-N 0.000 claims description 2
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical class OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims description 2
- 239000001512 FEMA 4601 Substances 0.000 claims description 2
- 239000001776 FEMA 4720 Substances 0.000 claims description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 2
- 241001071795 Gentiana Species 0.000 claims description 2
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004378 Glycyrrhizin Substances 0.000 claims description 2
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims description 2
- HYQNKKAJVPMBDR-HIFRSBDPSA-N Hernandulcin Chemical compound CC(C)=CCC[C@](C)(O)[C@@H]1CCC(C)=CC1=O HYQNKKAJVPMBDR-HIFRSBDPSA-N 0.000 claims description 2
- HYQNKKAJVPMBDR-UHFFFAOYSA-N Hernandulcin Natural products CC(C)=CCCC(C)(O)C1CCC(C)=CC1=O HYQNKKAJVPMBDR-UHFFFAOYSA-N 0.000 claims description 2
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 claims description 2
- 235000008694 Humulus lupulus Nutrition 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 108050004114 Monellin Proteins 0.000 claims description 2
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 claims description 2
- ZIKZPLSIAVHITA-UHFFFAOYSA-N Nomilinic acid Natural products CC(=O)OC(CC(O)=O)C1(C)C(C(C)(C)O)CC(=O)C(C23OC2C(=O)O2)(C)C1CCC3(C)C2C=1C=COC=1 ZIKZPLSIAVHITA-UHFFFAOYSA-N 0.000 claims description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 claims description 2
- LUJAXSNNYBCFEE-UHFFFAOYSA-N Quercetin 3,7-dimethyl ether Natural products C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(O)C(O)=C1 LUJAXSNNYBCFEE-UHFFFAOYSA-N 0.000 claims description 2
- QJTYCCFDQWFJHU-UHFFFAOYSA-N Quercetin-5-O-beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC2=C1C(=O)C(O)=C(C=1C=C(O)C(O)=CC=1)O2 QJTYCCFDQWFJHU-UHFFFAOYSA-N 0.000 claims description 2
- PUTDIROJWHRSJW-UHFFFAOYSA-N Quercitrin Natural products CC1OC(Oc2cc(cc(O)c2O)C3=CC(=O)c4c(O)cc(O)cc4O3)C(O)C(O)C1O PUTDIROJWHRSJW-UHFFFAOYSA-N 0.000 claims description 2
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 claims description 2
- YWPVROCHNBYFTP-UHFFFAOYSA-N Rubusoside Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC1OC(CO)C(O)C(O)C1O YWPVROCHNBYFTP-UHFFFAOYSA-N 0.000 claims description 2
- 229930187719 Soyasaponin Natural products 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- GMKDAIKQCOMFGO-UHFFFAOYSA-N absinthin Natural products CC1C2CCC(C)(O)C34C5CC(C)(C3C=C(C)C4C2OC1=O)C6=C5C(C)(O)CCC7C(C)C(=O)OC67 GMKDAIKQCOMFGO-UHFFFAOYSA-N 0.000 claims description 2
- OXGUCUVFOIWWQJ-XIMSSLRFSA-N acanthophorin B Natural products O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-XIMSSLRFSA-N 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- DBOVHQOUSDWAPQ-WTONXPSSSA-N amarogentin Chemical compound O([C@H]1[C@H](O[C@H]2[C@@H]([C@H]3C(C(OCC3)=O)=CO2)C=C)O[C@@H]([C@H]([C@@H]1O)O)CO)C(=O)C1=C(O)C=C(O)C=C1C1=CC=CC(O)=C1 DBOVHQOUSDWAPQ-WTONXPSSSA-N 0.000 claims description 2
- 229960005174 ambroxol Drugs 0.000 claims description 2
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229960000271 arbutin Drugs 0.000 claims description 2
- 239000001138 artemisia absinthium Substances 0.000 claims description 2
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 claims description 2
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 2
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 claims description 2
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 claims description 2
- 235000004883 caffeic acid Nutrition 0.000 claims description 2
- 229940074360 caffeic acid Drugs 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000001789 chalcones Chemical class 0.000 claims description 2
- 229940074393 chlorogenic acid Drugs 0.000 claims description 2
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 claims description 2
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 claims description 2
- 235000001368 chlorogenic acid Nutrition 0.000 claims description 2
- PCHDRYNTOQFRPK-UHFFFAOYSA-L chromium(2+);pyridine-2-carboxylate Chemical compound [Cr+2].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 PCHDRYNTOQFRPK-UHFFFAOYSA-L 0.000 claims description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 2
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 claims description 2
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 2
- 235000020971 citrus fruits Nutrition 0.000 claims description 2
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 claims description 2
- 235000007240 daidzein Nutrition 0.000 claims description 2
- KYQZWONCHDNPDP-QNDFHXLGSA-N daidzein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-QNDFHXLGSA-N 0.000 claims description 2
- VWTINHYPRWEBQY-UHFFFAOYSA-N denatonium Chemical compound [O-]C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C[N+](CC)(CC)CC(=O)NC1=C(C)C=CC=C1C VWTINHYPRWEBQY-UHFFFAOYSA-N 0.000 claims description 2
- 229960001610 denatonium benzoate Drugs 0.000 claims description 2
- 229960003720 enoxolone Drugs 0.000 claims description 2
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002213 flavones Chemical class 0.000 claims description 2
- 229930182486 flavonoid glycoside Natural products 0.000 claims description 2
- 150000007955 flavonoid glycosides Chemical class 0.000 claims description 2
- 229940124307 fluoroquinolone Drugs 0.000 claims description 2
- 229940074391 gallic acid Drugs 0.000 claims description 2
- 235000004515 gallic acid Nutrition 0.000 claims description 2
- FODTZLFLDFKIQH-FSVGXZBPSA-N gamma-Oryzanol (TN) Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)O[C@@H]2C([C@@H]3CC[C@H]4[C@]5(C)CC[C@@H]([C@@]5(C)CC[C@@]54C[C@@]53CC2)[C@H](C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-FSVGXZBPSA-N 0.000 claims description 2
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 2
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 2
- 229960004949 glycyrrhizic acid Drugs 0.000 claims description 2
- 235000019410 glycyrrhizin Nutrition 0.000 claims description 2
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 2
- 229960002146 guaifenesin Drugs 0.000 claims description 2
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 claims description 2
- 229940025878 hesperidin Drugs 0.000 claims description 2
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001461 hydrolysable tannin Polymers 0.000 claims description 2
- NQYPTLKGQJDGTI-FCVRJVSHSA-N hyperoside Natural products OC[C@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3[C@H]2O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@H]1O NQYPTLKGQJDGTI-FCVRJVSHSA-N 0.000 claims description 2
- 229930013032 isoflavonoid Natural products 0.000 claims description 2
- 150000003817 isoflavonoid derivatives Chemical class 0.000 claims description 2
- 235000012891 isoflavonoids Nutrition 0.000 claims description 2
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 claims description 2
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 claims description 2
- 125000000067 limonoid group Chemical group 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 claims description 2
- 229940052490 naringin Drugs 0.000 claims description 2
- 229930019673 naringin Natural products 0.000 claims description 2
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002715 nicotine Drugs 0.000 claims description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
- KPDOJFFZKAUIOE-WNGDLQANSA-N nomilin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@H]2C(C)(C)OC(=O)C[C@@H]([C@]42C)OC(=O)C)C=COC=1 KPDOJFFZKAUIOE-WNGDLQANSA-N 0.000 claims description 2
- KPDOJFFZKAUIOE-HPFWCIFASA-N nomilin Natural products O=C(O[C@H]1[C@@]2(C)[C@@H](C(C)(C)OC(=O)C1)CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@H](c3cocc3)OC(=O)[C@@H]3O[C@@]123)C KPDOJFFZKAUIOE-HPFWCIFASA-N 0.000 claims description 2
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940055726 pantothenic acid Drugs 0.000 claims description 2
- 235000019161 pantothenic acid Nutrition 0.000 claims description 2
- 239000011713 pantothenic acid Substances 0.000 claims description 2
- 229930182487 phenolic glycoside Natural products 0.000 claims description 2
- 150000007950 phenolic glycosides Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- OVSQVDMCBVZWGM-DTGCRPNFSA-N quercetin 3-O-beta-D-galactopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-DTGCRPNFSA-N 0.000 claims description 2
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 claims description 2
- OEKUVLQNKPXSOY-UHFFFAOYSA-N quercetin 3-O-beta-D-glucopyranosyl(1->3)-alpha-L-rhamnopyranosyl(1->6)-beta-d-galactopyranoside Natural products OC1C(O)C(C(O)C)OC1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OEKUVLQNKPXSOY-UHFFFAOYSA-N 0.000 claims description 2
- SZDMSNWMQAMVTJ-UHFFFAOYSA-N quercetin-3-O-glucoside Natural products OC1OC(COC2=C(C(=O)c3cc(O)cc(O)c3O2)c4ccc(O)c(O)c4)C(O)C(O)C1O SZDMSNWMQAMVTJ-UHFFFAOYSA-N 0.000 claims description 2
- FZKBNCDAGYDHTP-UHFFFAOYSA-N quercetin-3-O-glycoside Natural products OC1C(O)C(O)C(O)OC1COC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O FZKBNCDAGYDHTP-UHFFFAOYSA-N 0.000 claims description 2
- QPHXPNUXTNHJOF-UHFFFAOYSA-N quercetin-7-O-beta-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 QPHXPNUXTNHJOF-UHFFFAOYSA-N 0.000 claims description 2
- 229960000948 quinine Drugs 0.000 claims description 2
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 2
- 235000019203 rebaudioside A Nutrition 0.000 claims description 2
- GSGVXNMGMKBGQU-PHESRWQRSA-N rebaudioside M Chemical compound C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSGVXNMGMKBGQU-PHESRWQRSA-N 0.000 claims description 2
- YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical compound O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YWPVROCHNBYFTP-OSHKXICASA-N 0.000 claims description 2
- 229930182490 saponin Natural products 0.000 claims description 2
- 150000007949 saponins Chemical class 0.000 claims description 2
- 235000017709 saponins Nutrition 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims description 2
- 229920002258 tannic acid Polymers 0.000 claims description 2
- 235000015523 tannic acid Nutrition 0.000 claims description 2
- 229960004559 theobromine Drugs 0.000 claims description 2
- 229960000278 theophylline Drugs 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 1
- DRSKVOAJKLUMCL-MMUIXFKXSA-N u2n4xkx7hp Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DRSKVOAJKLUMCL-MMUIXFKXSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 101
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 55
- QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 41
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 36
- 239000000843 powder Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 239000004615 ingredient Substances 0.000 description 23
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 22
- 235000000346 sugar Nutrition 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 20
- 239000000284 extract Substances 0.000 description 20
- 150000001408 amides Chemical class 0.000 description 19
- 229960004036 nonivamide Drugs 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 17
- 229940007061 capsicum extract Drugs 0.000 description 17
- 239000001943 capsicum frutescens fruit extract Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 15
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 14
- 239000003925 fat Substances 0.000 description 14
- 239000003607 modifier Substances 0.000 description 13
- 230000035807 sensation Effects 0.000 description 13
- 235000019615 sensations Nutrition 0.000 description 13
- 230000003111 delayed effect Effects 0.000 description 12
- 235000019197 fats Nutrition 0.000 description 12
- 239000007967 peppermint flavor Substances 0.000 description 12
- 235000010323 ascorbic acid Nutrition 0.000 description 11
- 229960005070 ascorbic acid Drugs 0.000 description 11
- 239000011668 ascorbic acid Substances 0.000 description 11
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 10
- 235000015752 Aframomum melegueta Nutrition 0.000 description 10
- 244000227206 Aframomum melegueta Species 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000001857 aframomum melegueta rosc. k. schum. Substances 0.000 description 10
- 239000000306 component Substances 0.000 description 10
- 239000002324 mouth wash Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 235000013311 vegetables Nutrition 0.000 description 10
- 0 *C([4*])C([1*])([2*])OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound *C([4*])C([1*])([2*])OC(=O)CC1=CC=C(O)C(OC)=C1 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 244000269722 Thea sinensis Species 0.000 description 9
- MAGQQZHFHJDIRE-VVKPDYKWSA-N cis-pellitorine Natural products C(C(C)C)NC(\C=C\C=CCCCCC)=O MAGQQZHFHJDIRE-VVKPDYKWSA-N 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- MAGQQZHFHJDIRE-BNFZFUHLSA-N pellitorine Chemical compound CCCCC\C=C\C=C\C(=O)NCC(C)C MAGQQZHFHJDIRE-BNFZFUHLSA-N 0.000 description 9
- 235000013599 spices Nutrition 0.000 description 9
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 235000002566 Capsicum Nutrition 0.000 description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 235000017663 capsaicin Nutrition 0.000 description 8
- 229960002504 capsaicin Drugs 0.000 description 8
- 235000015218 chewing gum Nutrition 0.000 description 8
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 8
- 235000013923 monosodium glutamate Nutrition 0.000 description 8
- 229940051866 mouthwash Drugs 0.000 description 8
- 229940073490 sodium glutamate Drugs 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- QMIWSRNEYNUYFE-WKOVGYJXSA-N N-Isobutyldeca-trans-2-trans-4-dienamide Natural products O=C(N[C@@H](CC)C)/C=C/C=C/CCCCC QMIWSRNEYNUYFE-WKOVGYJXSA-N 0.000 description 7
- 244000203593 Piper nigrum Species 0.000 description 7
- 235000008184 Piper nigrum Nutrition 0.000 description 7
- 235000013405 beer Nutrition 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- MAGQQZHFHJDIRE-UHFFFAOYSA-N pellitorine Natural products CCCCCC=CC=CC(=O)NCC(C)C MAGQQZHFHJDIRE-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 235000014347 soups Nutrition 0.000 description 7
- 239000006002 Pepper Substances 0.000 description 6
- 235000016761 Piper aduncum Nutrition 0.000 description 6
- 235000017804 Piper guineense Nutrition 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 244000299461 Theobroma cacao Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 235000019221 dark chocolate Nutrition 0.000 description 6
- 235000020094 liqueur Nutrition 0.000 description 6
- 230000005923 long-lasting effect Effects 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- VLDFMKOUUQYFGF-UHFFFAOYSA-N 4-(butoxymethyl)-2-methoxyphenol Chemical compound CCCCOCC1=CC=C(O)C(OC)=C1 VLDFMKOUUQYFGF-UHFFFAOYSA-N 0.000 description 5
- OLDLQHJTLADERG-PLNGDYQASA-N CC/C=C\CCOC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CC/C=C\CCOC(=O)CC1=CC=C(O)C(OC)=C1 OLDLQHJTLADERG-PLNGDYQASA-N 0.000 description 5
- ZDFYRQJTMMZCLH-UHFFFAOYSA-N CCC(C)COC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCC(C)COC(=O)CC1=CC=C(O)C(OC)=C1 ZDFYRQJTMMZCLH-UHFFFAOYSA-N 0.000 description 5
- JUNQWDYMKNUDEP-UHFFFAOYSA-N CCCCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCCCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 JUNQWDYMKNUDEP-UHFFFAOYSA-N 0.000 description 5
- HNXJEQOQBHFRED-UHFFFAOYSA-N CCCCCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCCCCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 HNXJEQOQBHFRED-UHFFFAOYSA-N 0.000 description 5
- CBWRGVNEUOJXPF-UHFFFAOYSA-N CCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 CBWRGVNEUOJXPF-UHFFFAOYSA-N 0.000 description 5
- UXXAIUVETJGEEL-VMPITWQZSA-N COC1=CC(CC(=O)OC/C=C/C2=CC=CC=C2)=CC=C1O Chemical compound COC1=CC(CC(=O)OC/C=C/C2=CC=CC=C2)=CC=C1O UXXAIUVETJGEEL-VMPITWQZSA-N 0.000 description 5
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000010411 cooking Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 150000002212 flavone derivatives Chemical class 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000000606 toothpaste Substances 0.000 description 5
- 229940078465 vanillyl butyl ether Drugs 0.000 description 5
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 5
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 4
- 240000006108 Allium ampeloprasum Species 0.000 description 4
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 4
- HOTXQJCNUXAOAS-UHFFFAOYSA-N CCC(C)(C)OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCC(C)(C)OC(=O)CC1=CC=C(O)C(OC)=C1 HOTXQJCNUXAOAS-UHFFFAOYSA-N 0.000 description 4
- YRZOZIGTYFDIDB-AATRIKPKSA-N CCC/C=C/COC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCC/C=C/COC(=O)CC1=CC=C(O)C(OC)=C1 YRZOZIGTYFDIDB-AATRIKPKSA-N 0.000 description 4
- ZJSIUGQLOXXLBG-UHFFFAOYSA-N CCCC(CC)OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCCC(CC)OC(=O)CC1=CC=C(O)C(OC)=C1 ZJSIUGQLOXXLBG-UHFFFAOYSA-N 0.000 description 4
- ARNLJJWVHKXYOK-UHFFFAOYSA-N COC1=CC(CC(=O)OC2CC(C)CCC2C(C)C)=CC=C1O Chemical compound COC1=CC(CC(=O)OC2CC(C)CCC2C(C)C)=CC=C1O ARNLJJWVHKXYOK-UHFFFAOYSA-N 0.000 description 4
- YTWAADUPRCSBKM-UHFFFAOYSA-N COC1=CC(CC(=O)OCC(C)C)=CC=C1O Chemical compound COC1=CC(CC(=O)OCC(C)C)=CC=C1O YTWAADUPRCSBKM-UHFFFAOYSA-N 0.000 description 4
- BSPJAOXQGMTTNW-UHFFFAOYSA-N COC1=CC(CC(=O)OCC=C(C)C)=CC=C1O Chemical compound COC1=CC(CC(=O)OCC=C(C)C)=CC=C1O BSPJAOXQGMTTNW-UHFFFAOYSA-N 0.000 description 4
- TYXDILLUJWDLRM-UHFFFAOYSA-N COC1=CC(CC(=O)OCCCCC2=CC=CC=C2)=CC=C1O Chemical compound COC1=CC(CC(=O)OCCCCC2=CC=CC=C2)=CC=C1O TYXDILLUJWDLRM-UHFFFAOYSA-N 0.000 description 4
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 239000005913 Maltodextrin Substances 0.000 description 4
- 229920002774 Maltodextrin Polymers 0.000 description 4
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229940112822 chewing gum Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 229940035034 maltodextrin Drugs 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000002773 nucleotide Substances 0.000 description 4
- 125000003729 nucleotide group Chemical group 0.000 description 4
- 239000006072 paste Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 description 4
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229960004793 sucrose Drugs 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZPSGREUUQGTKDE-ZICOIJLXSA-N (2e,4e)-1-piperidin-1-yldeca-2,4-dien-1-one Chemical compound CCCCC\C=C\C=C\C(=O)N1CCCCC1 ZPSGREUUQGTKDE-ZICOIJLXSA-N 0.000 description 3
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 3
- CBGDIJWINPWWJW-UHFFFAOYSA-N 6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid Chemical compound O=C1C(C(O)=O)=C(O)C(C)=C2C(C)C(C)OC=C21 CBGDIJWINPWWJW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010006784 Burning sensation Diseases 0.000 description 3
- QITYFLXMUSDLKH-UHFFFAOYSA-N CCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCC(C)OC(=O)CC1=CC=C(O)C(OC)=C1 QITYFLXMUSDLKH-UHFFFAOYSA-N 0.000 description 3
- WUIYBQPAJSKVOF-UHFFFAOYSA-N CCCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 WUIYBQPAJSKVOF-UHFFFAOYSA-N 0.000 description 3
- AUWPOLXJHFZONI-UHFFFAOYSA-N COC1=CC(CC(=O)OC(C)C)=CC=C1O Chemical compound COC1=CC(CC(=O)OC(C)C)=CC=C1O AUWPOLXJHFZONI-UHFFFAOYSA-N 0.000 description 3
- IEJBKAVZNKQNGT-UHFFFAOYSA-N COC1=CC(CC(=O)OCCC(C)C)=CC=C1O Chemical compound COC1=CC(CC(=O)OCCC(C)C)=CC=C1O IEJBKAVZNKQNGT-UHFFFAOYSA-N 0.000 description 3
- 241000208293 Capsicum Species 0.000 description 3
- 240000004160 Capsicum annuum Species 0.000 description 3
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- BLILOGGUTRWFNI-UHFFFAOYSA-N Monomenthyl succinate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O BLILOGGUTRWFNI-UHFFFAOYSA-N 0.000 description 3
- 229930182473 O-glycoside Natural products 0.000 description 3
- 150000008444 O-glycosides Chemical class 0.000 description 3
- KIEMFBKYNJBCSN-UHFFFAOYSA-N OC=1C(CC(C=1C1=C(C=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)CO)=O Chemical compound OC=1C(CC(C=1C1=C(C=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)CO)=O KIEMFBKYNJBCSN-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 241000218595 Picea sitchensis Species 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000004141 Sodium laurylsulphate Substances 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 235000006468 Thea sinensis Nutrition 0.000 description 3
- 235000009470 Theobroma cacao Nutrition 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UJNOLBSYLSYIBM-WISYIIOYSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2r)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@@H](C)O UJNOLBSYLSYIBM-WISYIIOYSA-N 0.000 description 3
- INAPMGSXUVUWAF-GCVPSNMTSA-N [(2r,3s,5r,6r)-2,3,4,5,6-pentahydroxycyclohexyl] dihydrogen phosphate Chemical compound OC1[C@H](O)[C@@H](O)C(OP(O)(O)=O)[C@H](O)[C@@H]1O INAPMGSXUVUWAF-GCVPSNMTSA-N 0.000 description 3
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 3
- LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000020279 black tea Nutrition 0.000 description 3
- 235000010216 calcium carbonate Nutrition 0.000 description 3
- 235000005487 catechin Nutrition 0.000 description 3
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 3
- 150000001765 catechin Chemical class 0.000 description 3
- 235000013351 cheese Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001055 chewing effect Effects 0.000 description 3
- 235000019219 chocolate Nutrition 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000009569 green tea Nutrition 0.000 description 3
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 3
- 235000013928 guanylic acid Nutrition 0.000 description 3
- 235000014109 instant soup Nutrition 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000019684 potato crisps Nutrition 0.000 description 3
- 239000013074 reference sample Substances 0.000 description 3
- 235000020374 simple syrup Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BXOCHUWSGYYSFW-HVWOQQCMSA-N spilanthol Chemical compound C\C=C\C=C/CC\C=C\C(=O)NCC(C)C BXOCHUWSGYYSFW-HVWOQQCMSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 235000013616 tea Nutrition 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- 235000019871 vegetable fat Nutrition 0.000 description 3
- KJXSIXMJHKAJOD-LSDHHAIUSA-N (+)-dihydromyricetin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC(O)=C(O)C(O)=C1 KJXSIXMJHKAJOD-LSDHHAIUSA-N 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 2
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 2
- KONGRWVLXLWGDV-BYGOPZEFSA-N (-)-cubebol Chemical compound CC(C)[C@@H]([C@H]12)CC[C@@H](C)[C@]32[C@@H]1[C@@](C)(O)CC3 KONGRWVLXLWGDV-BYGOPZEFSA-N 0.000 description 2
- LYUZYPKZQDYMEE-IZZDOVSWSA-N (9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl) (e)-2-methylbut-2-enoate Chemical compound C1=CC(=O)OC2=C3C(OC(=O)C(/C)=C/C)C(OC(C)=O)C(C)(C)OC3=CC=C21 LYUZYPKZQDYMEE-IZZDOVSWSA-N 0.000 description 2
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 description 2
- BBZPUGFXXAPEJY-ZHACJKMWSA-N (e)-n-(2-methylpropyl)dec-2-enamide Chemical compound CCCCCCC\C=C\C(=O)NCC(C)C BBZPUGFXXAPEJY-ZHACJKMWSA-N 0.000 description 2
- CRPTXKKKIGGDBX-UHFFFAOYSA-N (z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 2
- IMFQYAJJXFXVMM-UHFFFAOYSA-N 1-(isothiocyanatomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CN=C=S)C=C1 IMFQYAJJXFXVMM-UHFFFAOYSA-N 0.000 description 2
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 description 2
- BFZBGTMIBOQWBA-HRCSPUOPSA-N 1-[(2E,4E)-2,4-decadienoyl]pyrrolidine Chemical compound CCCCC\C=C\C=C\C(=O)N1CCCC1 BFZBGTMIBOQWBA-HRCSPUOPSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical compound CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 description 2
- IJKPVUGDJJFSQF-UHFFFAOYSA-N 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-methylfuran-3-one Chemical compound C1=C(O)C(OC)=CC(C=C2C(C=C(C)O2)=O)=C1 IJKPVUGDJJFSQF-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- SLXYXRCDJQKOQD-UHFFFAOYSA-N 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)cyclopent-2-en-1-one Chemical compound OC=1C(CC(C=1C1=CC(=C(C=C1)O)OC)CO)=O SLXYXRCDJQKOQD-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RCEFMOGVOYEGJN-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one Chemical compound OC1=CC=CC=C1N1C(=O)NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CC1 RCEFMOGVOYEGJN-UHFFFAOYSA-N 0.000 description 2
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 2
- ATKWJXUJUNLTFU-UHFFFAOYSA-N 4-Hydroxybenzyl isothiocyanate Chemical compound OC1=CC=C(CN=C=S)C=C1 ATKWJXUJUNLTFU-UHFFFAOYSA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- KAWOEDMUUFFXAM-UHFFFAOYSA-N CC1(C)CCCC2(C)C(C)C(C=O)=CCC21 Polymers CC1(C)CCCC2(C)C(C)C(C=O)=CCC21 KAWOEDMUUFFXAM-UHFFFAOYSA-N 0.000 description 2
- JQIWSSFSRMMUBQ-UHFFFAOYSA-N COc1cc(CC(O)(C(O)=O)C2(O)CCOC2=O)ccc1O Chemical compound COc1cc(CC(O)(C(O)=O)C2(O)CCOC2=O)ccc1O JQIWSSFSRMMUBQ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 235000002568 Capsicum frutescens Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical class N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 229920001202 Inulin Polymers 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- RWAXQWRDVUOOGG-UHFFFAOYSA-N N,2,3-Trimethyl-2-(1-methylethyl)butanamide Chemical compound CNC(=O)C(C)(C(C)C)C(C)C RWAXQWRDVUOOGG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 description 2
- BMZMBORRKVFYRO-UHFFFAOYSA-N O1C(=CC=C1)C(CC1=C(C=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)=O Chemical compound O1C(=CC=C1)C(CC1=C(C=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)=O BMZMBORRKVFYRO-UHFFFAOYSA-N 0.000 description 2
- AEGNBIGHYMDQKJ-UHFFFAOYSA-N O1C(=CC=C1)C(CC1=CC(=C(C=C1)O)OC)=O Chemical compound O1C(=CC=C1)C(CC1=CC(=C(C=C1)O)OC)=O AEGNBIGHYMDQKJ-UHFFFAOYSA-N 0.000 description 2
- CLGSYVSRYLDTOU-UHFFFAOYSA-N OC=1C(CC(C=1C1=CC(=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)CO)=O Chemical compound OC=1C(CC(C=1C1=CC(=C(C(=C1)OC)O)CC1=CC(=C(C=C1)O)OC)CO)=O CLGSYVSRYLDTOU-UHFFFAOYSA-N 0.000 description 2
- PKFZZZIIBYUHGG-UHFFFAOYSA-N OC=1C(CCOC=1CC1=CC(=C(C=C1)O)OC)=O Chemical compound OC=1C(CCOC=1CC1=CC(=C(C=C1)O)OC)=O PKFZZZIIBYUHGG-UHFFFAOYSA-N 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
- AZJUJOFIHHNCSV-KCQAQPDRSA-N Polygodial Polymers C[C@@]1([C@H](C(C=O)=CC2)C=O)[C@@H]2C(C)(C)CCC1 AZJUJOFIHHNCSV-KCQAQPDRSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 108010073771 Soybean Proteins Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QGMWDUUHVVLHNP-AEGPPILISA-N Warburganal Chemical compound C[C@@]1([C@@](C(C=O)=CC2)(O)C=O)[C@@H]2C(C)(C)CCC1 QGMWDUUHVVLHNP-AEGPPILISA-N 0.000 description 2
- 239000005862 Whey Substances 0.000 description 2
- 102000007544 Whey Proteins Human genes 0.000 description 2
- 108010046377 Whey Proteins Proteins 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229940072056 alginate Drugs 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 2
- SBXYHCVXUCYYJT-UEOYEZOQSA-N alpha-Sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C(=O)NCC(C)C SBXYHCVXUCYYJT-UEOYEZOQSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000008429 bread Nutrition 0.000 description 2
- 125000005510 but-1-en-2-yl group Chemical group 0.000 description 2
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001390 capsicum minimum Substances 0.000 description 2
- 235000013736 caramel Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- KONGRWVLXLWGDV-UHFFFAOYSA-N cubebol Natural products C12C(C(C)C)CCC(C)C32C1C(C)(O)CC3 KONGRWVLXLWGDV-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 235000012734 epicatechin Nutrition 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000989 food dye Substances 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 229940029982 garlic powder Drugs 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 2
- AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 description 2
- 229960001587 hesperetin Drugs 0.000 description 2
- 235000010209 hesperetin Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229940029339 inulin Drugs 0.000 description 2
- BUOFMLFXULBHJK-UHFFFAOYSA-N isobungeanool Natural products CCC=CCC=CCCC=CC=CC(=O)NC(O)C(C)C BUOFMLFXULBHJK-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 235000013622 meat product Nutrition 0.000 description 2
- 229930007503 menthone Natural products 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940074371 monofluorophosphate Drugs 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000012149 noodles Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 2
- 235000019100 piperine Nutrition 0.000 description 2
- 229940075559 piperine Drugs 0.000 description 2
- 239000000419 plant extract Substances 0.000 description 2
- FPGPDEPMWUWLOV-UHFFFAOYSA-N polygodial Natural products CC1(C)CCCC2(C)C(C=O)C(=CC(O)C12)C=O FPGPDEPMWUWLOV-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229920002414 procyanidin Polymers 0.000 description 2
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 2
- DSDNAKHZNJAGHN-UHFFFAOYSA-N resinferatoxin Natural products C1=C(O)C(OC)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-UHFFFAOYSA-N 0.000 description 2
- DSDNAKHZNJAGHN-MXTYGGKSSA-N resiniferatoxin Chemical compound C1=C(O)C(OC)=CC(CC(=O)OCC=2C[C@]3(O)C(=O)C(C)=C[C@H]3[C@@]34[C@H](C)C[C@@]5(O[C@@](O4)(CC=4C=CC=CC=4)O[C@@H]5[C@@H]3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-MXTYGGKSSA-N 0.000 description 2
- 229940073454 resiniferatoxin Drugs 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 235000013580 sausages Nutrition 0.000 description 2
- 230000009291 secondary effect Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000011888 snacks Nutrition 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229940001941 soy protein Drugs 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 235000015192 vegetable juice Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 1
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 1
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 1
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 1
- JDGJLPHFRJNJMN-OUAUKWLOSA-N (1s,2r,4r)-2-methoxy-4-methyl-1-propan-2-ylcyclohexane Chemical compound CO[C@@H]1C[C@H](C)CC[C@H]1C(C)C JDGJLPHFRJNJMN-OUAUKWLOSA-N 0.000 description 1
- YKHVVNDSWHSBPA-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienoic acid Chemical compound CCCCC\C=C\C=C\C(O)=O YKHVVNDSWHSBPA-BLHCBFLLSA-N 0.000 description 1
- MAGQQZHFHJDIRE-QNRZBPGKSA-N (2E,4Z)-N-Isobutyl-2,4-decadienamide Chemical compound CCCCC\C=C/C=C/C(/O)=N/CC(C)C MAGQQZHFHJDIRE-QNRZBPGKSA-N 0.000 description 1
- GJDPGFHVEKFXEZ-SQIWNDBBSA-N (2e,4e)-n-(2-hydroxy-2-methylpropyl)tetradeca-2,4-dienamide Chemical compound CCCCCCCCC\C=C\C=C\C(=O)NCC(C)(C)O GJDPGFHVEKFXEZ-SQIWNDBBSA-N 0.000 description 1
- SAJGCUXAHBJVRH-VFQQELCFSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;hydrate Chemical compound O.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SAJGCUXAHBJVRH-VFQQELCFSA-N 0.000 description 1
- MAGQQZHFHJDIRE-XESWYYRISA-N (2z,4z)-n-(2-methylpropyl)deca-2,4-dienamide Chemical compound CCCCC\C=C/C=C\C(=O)NCC(C)C MAGQQZHFHJDIRE-XESWYYRISA-N 0.000 description 1
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 1
- XEYZAKCJAFSLGZ-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) formate Chemical compound CC(C)C1CCC(C)CC1OC=O XEYZAKCJAFSLGZ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical class OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- OWEMTCOXFULTNW-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanoic acid Chemical class CC(C)C(C)(C(C)C)C(O)=O OWEMTCOXFULTNW-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GEZAUFNYMZVOFV-UHFFFAOYSA-J 2-[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphastannetan-2-yl)oxy]-1,3,2$l^{5},4$l^{2}-dioxaphosphastannetane 2-oxide Chemical compound [Sn+2].[Sn+2].[O-]P([O-])(=O)OP([O-])([O-])=O GEZAUFNYMZVOFV-UHFFFAOYSA-J 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- FLYJSXDJKBHQAU-IBSWDFHHSA-N 2-hydroxypropyl [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] carbonate Chemical compound CC(O)COC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C FLYJSXDJKBHQAU-IBSWDFHHSA-N 0.000 description 1
- UDOOPSJCRMKSGL-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one Chemical class OC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 UDOOPSJCRMKSGL-UHFFFAOYSA-N 0.000 description 1
- FQELCANCOKLAGK-UHFFFAOYSA-N 3-(5-methyl-2-propan-2-ylcyclohexyl)oxy-3-oxopropanoic acid Chemical compound CC(C)C1CCC(C)CC1OC(=O)CC(O)=O FQELCANCOKLAGK-UHFFFAOYSA-N 0.000 description 1
- SXIDVHLMAKILQP-UHFFFAOYSA-N 3-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one Chemical compound O=C1CCC(C)=C1N1CCCC1 SXIDVHLMAKILQP-UHFFFAOYSA-N 0.000 description 1
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- CTMTYSVTTGVYAW-FRRDWIJNSA-N 5-[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxy-5-oxopentanoic acid Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)CCCC(O)=O CTMTYSVTTGVYAW-FRRDWIJNSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 102100034033 Alpha-adducin Human genes 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 240000006914 Aspalathus linearis Species 0.000 description 1
- 235000012984 Aspalathus linearis Nutrition 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BLOUXCHLBIOTMR-UHFFFAOYSA-N C.COC1=CC(CC(=O)OCCCCC2=CC=CC=C2)=CC=C1O Chemical compound C.COC1=CC(CC(=O)OCCCCC2=CC=CC=C2)=CC=C1O BLOUXCHLBIOTMR-UHFFFAOYSA-N 0.000 description 1
- YLAWCJHZGCOEGV-UHFFFAOYSA-N CCOC(=O)C(O)(CC1=CC=C(O)C(OC)=C1)C1(O)CCOC1=O Chemical compound CCOC(=O)C(O)(CC1=CC=C(O)C(OC)=C1)C1(O)CCOC1=O YLAWCJHZGCOEGV-UHFFFAOYSA-N 0.000 description 1
- SLJDPPDICCJDOK-UHFFFAOYSA-N CCOC(=O)CCOCC(=O)CC1=CC=C(O)C(OC)=C1 Chemical compound CCOC(=O)CCOCC(=O)CC1=CC=C(O)C(OC)=C1 SLJDPPDICCJDOK-UHFFFAOYSA-N 0.000 description 1
- MMSRZRQFUSGMDB-UHFFFAOYSA-N COC1=C(O)C=CC(CC2(O)C(=O)OC3C(O)COC32O)=C1 Chemical compound COC1=C(O)C=CC(CC2(O)C(=O)OC3C(O)COC32O)=C1 MMSRZRQFUSGMDB-UHFFFAOYSA-N 0.000 description 1
- QAVWHMJKUXLNLR-UHFFFAOYSA-N COC1=CC(C(C(=O)C2=CC=CO2)C(C2=CC=C(O)C(OC)=C2)C2OC(C)=CC2=O)=CC=C1O Chemical compound COC1=CC(C(C(=O)C2=CC=CO2)C(C2=CC=C(O)C(OC)=C2)C2OC(C)=CC2=O)=CC=C1O QAVWHMJKUXLNLR-UHFFFAOYSA-N 0.000 description 1
- DGEMXZXSQQYAEL-UHFFFAOYSA-N COC1=CC(C=C2OC(CO)CC2=O)=CC=C1O Chemical compound COC1=CC(C=C2OC(CO)CC2=O)=CC=C1O DGEMXZXSQQYAEL-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- OMYRBCZBTQDJHF-UHFFFAOYSA-N Dihydrobungeanool Natural products CCCCCC=CCCC=CC=CC(=O)NCC(C)(C)O OMYRBCZBTQDJHF-UHFFFAOYSA-N 0.000 description 1
- AANLCWYVVNBGEE-IDIVVRGQSA-L Disodium inosinate Chemical compound [Na+].[Na+].O[C@@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 AANLCWYVVNBGEE-IDIVVRGQSA-L 0.000 description 1
- 244000080152 Drimys aromatica Species 0.000 description 1
- 235000008496 Drimys aromatica Nutrition 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
- 241000818016 Euphorbia resinifera Species 0.000 description 1
- 101150107824 FCPC gene Proteins 0.000 description 1
- 239000001936 FEMA 3992 Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004348 Glyceryl diacetate Substances 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- 244000061944 Helianthus giganteus Species 0.000 description 1
- 101000799076 Homo sapiens Alpha-adducin Proteins 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 235000017309 Hypericum perforatum Nutrition 0.000 description 1
- 244000141009 Hypericum perforatum Species 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- NOOLISFMXDJSKH-OPRDCNLKSA-N Isomenthol Chemical compound CC(C)[C@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-OPRDCNLKSA-N 0.000 description 1
- NOOLISFMXDJSKH-LPEHRKFASA-N Isomenthol Natural products CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 240000007707 Mentha arvensis Species 0.000 description 1
- 235000018978 Mentha arvensis Nutrition 0.000 description 1
- 235000016278 Mentha canadensis Nutrition 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- JFKCVAZSEWPOIX-UHFFFAOYSA-N Menthyl ethylene glycol carbonate Chemical compound CC(C)C1CCC(C)CC1OC(=O)OCCO JFKCVAZSEWPOIX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- 101710084933 Miraculin Proteins 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 101001068640 Nicotiana tabacum Basic form of pathogenesis-related protein 1 Proteins 0.000 description 1
- LRVGQYYQYQQPRL-UHFFFAOYSA-N O(O)C=1C=C(C=CC=1O)CC1(C(OC2C1(OCC2O)O)=O)O Chemical compound O(O)C=1C=C(C=CC=1O)CC1(C(OC2C1(OCC2O)O)=O)O LRVGQYYQYQQPRL-UHFFFAOYSA-N 0.000 description 1
- GLBGLPUGBZOCHX-UHFFFAOYSA-N OCC(O)C1OC(O)C2=CC=C(O)C(O)=C21 Chemical compound OCC(O)C1OC(O)C2=CC=C(O)C(O)=C21 GLBGLPUGBZOCHX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 235000010503 Plantago lanceolata Nutrition 0.000 description 1
- 244000239204 Plantago lanceolata Species 0.000 description 1
- 229920001100 Polydextrose Polymers 0.000 description 1
- 229920002535 Polyethylene Glycol 1500 Polymers 0.000 description 1
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 description 1
- 229920000124 Prodelphinidin Polymers 0.000 description 1
- 101000629598 Rattus norvegicus Sterol regulatory element-binding protein 1 Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PSKIOIDCXFHNJA-UHFFFAOYSA-N Sanshool Natural products CC=CC=CC=CCCC=CC=CC(=O)NC(C)C PSKIOIDCXFHNJA-UHFFFAOYSA-N 0.000 description 1
- 241001247145 Sebastes goodei Species 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- CGQCWMIAEPEHNQ-UHFFFAOYSA-N Vanillylmandelic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC=C1O CGQCWMIAEPEHNQ-UHFFFAOYSA-N 0.000 description 1
- QGMWDUUHVVLHNP-UHFFFAOYSA-N Warburganal Natural products C1C=C(C=O)C(C=O)(O)C2(C)C1C(C)(C)CCC2 QGMWDUUHVVLHNP-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- UJNOLBSYLSYIBM-NOOOWODRSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2s)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@H](C)O UJNOLBSYLSYIBM-NOOOWODRSA-N 0.000 description 1
- CSZKNSMAMITXAD-FRRDWIJNSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] 2-methylpropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)C CSZKNSMAMITXAD-FRRDWIJNSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 229940095602 acidifiers Drugs 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BXOCHUWSGYYSFW-UHFFFAOYSA-N all-trans spilanthol Natural products CC=CC=CCCC=CC(=O)NCC(C)C BXOCHUWSGYYSFW-UHFFFAOYSA-N 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940011037 anethole Drugs 0.000 description 1
- 235000010208 anthocyanin Nutrition 0.000 description 1
- 229930002877 anthocyanin Natural products 0.000 description 1
- 239000004410 anthocyanin Substances 0.000 description 1
- 150000004636 anthocyanins Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940111136 antiinflammatory and antirheumatic drug fenamates Drugs 0.000 description 1
- 229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 1
- 229960001671 azapropazone Drugs 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 235000004251 balanced diet Nutrition 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229960005430 benoxaprofen Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 1
- 229940036350 bisabolol Drugs 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 235000013532 brandy Nutrition 0.000 description 1
- 235000015496 breakfast cereal Nutrition 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000015155 buttermilk Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 235000012182 cereal bars Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229940073639 ceteareth-6 Drugs 0.000 description 1
- 229940093528 cetearyl ethylhexanoate Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- YILGKTWKKDLHAF-DUXFSIBLSA-M chembl2368344 Chemical compound [Na+].O([C@@H]1[C@H](CO)O[C@H]([C@H]([C@H]1O)O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C([O-])=O)[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O YILGKTWKKDLHAF-DUXFSIBLSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 229960005233 cineole Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 description 1
- 150000001885 cortisol derivatives Chemical class 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960004833 dexamethasone phosphate Drugs 0.000 description 1
- VQODGRNSFPNSQE-CXSFZGCWSA-N dexamethasone phosphate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)C[C@@H]2O VQODGRNSFPNSQE-CXSFZGCWSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- XJQPQKLURWNAAH-UHFFFAOYSA-N dihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O XJQPQKLURWNAAH-UHFFFAOYSA-N 0.000 description 1
- RBCYRZPENADQGZ-UHFFFAOYSA-N dihydrocapsaicin Natural products COC1=CC(COC(=O)CCCCCCC(C)C)=CC=C1O RBCYRZPENADQGZ-UHFFFAOYSA-N 0.000 description 1
- KQILIWXGGKGKNX-UHFFFAOYSA-N dihydromyricetin Natural products OC1C(=C(Oc2cc(O)cc(O)c12)c3cc(O)c(O)c(O)c3)O KQILIWXGGKGKNX-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 229940105576 disalcid Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- PVBRXXAAPNGWGE-LGVAUZIVSA-L disodium 5'-guanylate Chemical compound [Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O PVBRXXAAPNGWGE-LGVAUZIVSA-L 0.000 description 1
- 235000013890 disodium inosinate Nutrition 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- CVRSZZJUWRLRDE-PWNZVWSESA-N drimane Chemical compound CC1(C)CCC[C@]2(C)[C@@H](C)[C@@H](C)CC[C@H]21 CVRSZZJUWRLRDE-PWNZVWSESA-N 0.000 description 1
- 229930001542 drimane Natural products 0.000 description 1
- 150000003483 drimane derivatives Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229950006236 fenclofenac Drugs 0.000 description 1
- IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 description 1
- HAWWPSYXSLJRBO-UHFFFAOYSA-N fendosal Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3C4=CC=CC=C4CCC=32)C=2C=CC=CC=2)=C1 HAWWPSYXSLJRBO-UHFFFAOYSA-N 0.000 description 1
- 229950005416 fendosal Drugs 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 150000002216 flavonol derivatives Chemical class 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 235000020336 flavoured green tea Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229940091249 fluoride supplement Drugs 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005428 food component Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- KVUKDCFEXVWYBN-UHFFFAOYSA-N gamma-sanshooel Natural products CC=CC=CC=CCCC=CC=CC(=O)NCC(C)C KVUKDCFEXVWYBN-UHFFFAOYSA-N 0.000 description 1
- KVUKDCFEXVWYBN-JDXPBYPHSA-N gamma-sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C=C\C(=O)NCC(C)C KVUKDCFEXVWYBN-JDXPBYPHSA-N 0.000 description 1
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 231100000734 genotoxic potential Toxicity 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 235000002780 gingerol Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000019443 glyceryl diacetate Nutrition 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 235000011617 hard cheese Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000015092 herbal tea Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 235000006486 human diet Nutrition 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229960001524 hydrocortisone butyrate Drugs 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- LHFKHAVGGJJQFF-UHFFFAOYSA-N hydroxyl-alpha-sanshool Natural products CC=CC=CC=CCCC=CC(=O)NCC(C)(C)O LHFKHAVGGJJQFF-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 235000021539 instant coffee Nutrition 0.000 description 1
- 235000020344 instant tea Nutrition 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000905 isomalt Substances 0.000 description 1
- 235000010439 isomalt Nutrition 0.000 description 1
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Natural products CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 description 1
- 229940095045 isopulegol Drugs 0.000 description 1
- BFZBGTMIBOQWBA-UHFFFAOYSA-N iyeremide A Natural products CCCCCC=CC=CC(=O)N1CCCC1 BFZBGTMIBOQWBA-UHFFFAOYSA-N 0.000 description 1
- 235000015141 kefir Nutrition 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940094522 laponite Drugs 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-M naproxen(1-) Chemical compound C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-M 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 1
- 239000000879 neohesperidine DC Substances 0.000 description 1
- 229930007461 neoisomenthol Natural products 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- VHRNEYGNJFZGQI-UHFFFAOYSA-N octyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCCCCCCCOC(=O)CC1=CC=C(O)C(OC)=C1 VHRNEYGNJFZGQI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000008375 oral care agent Substances 0.000 description 1
- JLPJFSCQKHRSQR-UHFFFAOYSA-N oxolan-3-one Chemical compound O=C1CCOC1 JLPJFSCQKHRSQR-UHFFFAOYSA-N 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical compound CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 description 1
- 229930006948 p-menthane-3,8-diol Natural products 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001931 piper nigrum l. white Substances 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- UIRPOZKMSMHJBQ-KXPSTEIISA-N pubchem11605 Chemical compound OC(=O)C(F)(F)F.C([C@H]1OB(O[C@]11C)[C@@H](N)C)[C@H]2C(C)(C)[C@@H]1C2 UIRPOZKMSMHJBQ-KXPSTEIISA-N 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000020330 rooibos tea Nutrition 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229960000414 sodium fluoride Drugs 0.000 description 1
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- PESXGULMKCKJCC-UHFFFAOYSA-M sodium;4-methoxycarbonylphenolate Chemical compound [Na+].COC(=O)C1=CC=C([O-])C=C1 PESXGULMKCKJCC-UHFFFAOYSA-M 0.000 description 1
- 235000008983 soft cheese Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000013322 soy milk Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 description 1
- 229960002871 tenoxicam Drugs 0.000 description 1
- GJDPGFHVEKFXEZ-UHFFFAOYSA-N tetrahydrobungeanool Natural products CCCCCCCCCC=CC=CC(=O)NCC(C)(C)O GJDPGFHVEKFXEZ-UHFFFAOYSA-N 0.000 description 1
- VUYXVWGKCKTUMF-UHFFFAOYSA-N tetratriacontaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO VUYXVWGKCKTUMF-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- 239000008513 turmeric extract Substances 0.000 description 1
- 229940052016 turmeric extract Drugs 0.000 description 1
- 235000020240 turmeric extract Nutrition 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
- 235000019220 whole milk chocolate Nutrition 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B4/00—General methods for preserving meat, sausages, fish or fish products
- A23B4/06—Freezing; Subsequent thawing; Cooling
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/84—Flavour masking or reducing agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/15—Flavour affecting agent
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/16—Taste affecting agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention particularly relates to novel uses of compounds of formula (I) (as described herein), partly also of novel compounds of formula (I) as such, aroma compositions containing compounds of formula (I), new preparations as well as new methods using compounds of formula (I). Further aspects of the present invention arise from the patent claims and the following description including examples.
- Capsaicin [N-(4-hydroxy-3-methoxybenzyl)-8-methyl-(6E)-nonenoic acid amide] and other capsaicinoids such as nonivamide ([N-(4-hydroxy-3-methoxybenzyl)-nonanoic acid amide) have been known for a long time as pungent and spicy flavours from different Capsicum species, in particular, chili pepper.
- nonivamide [N-(4-hydroxy-3-methoxybenzyl)-nonanoic acid amide)
- chili pepper At an appropriately low dosage of capsaicinoids, a neutral pungency and a warm sensation is perceived in the mouth, wherein the threshold for pain-inducing pungency and hot sensation is exceeded very quickly.
- capsaicin in food is not allowed in the European Union (was deleted from the Community Flavouring List in 2004), since evaluation of the genotoxic potential of the compound yielded a negative result (European Food Safety Authority (EFSA), P., Italy, Opinion of the Scientific Committee on Food on Capsaicin. European Commission 2002, (SDF/CS/FLAV/FLAVOUR/8 ADD1 Final).
- EFSA European Food Safety Authority
- SDF/CS/FLAV/FLAVOUR/8 ADD1 Final European Commission 2002
- use in foods is often difficult, since capsaicin has a very low taste threshold and a high potency as a pungent substance (16,000,000 Scoville units, cf. http://en.wikipedia.org/wiki/Capsaicin; version of the record as last amended on 11 Nov. 2011, 9:02 ⁇ m).
- capsaicin is used almost exclusively in the form of Capsicum extract, which contains residues of other flavouring substances, which taste or smell like Capsicum , besides other pungent substances and is, therefore, only limitedly suitable for broad use.
- Capsicum extract which contains residues of other flavouring substances, which taste or smell like Capsicum , besides other pungent substances and is, therefore, only limitedly suitable for broad use.
- piperine (1-piperoyl piperidine) that occurs in white pepper also causes a strongly pungent sensation (Römpp Lexicon Chemistry of Natural Compounds, Thieme 1997, p. 500) it has a relative pungency of only about 1% as compared to capsaicin. Furthermore, piperine has an intense taste of its own, reminiscent of pepper, so that the use in many preparations can only occur to a limited extent.
- pungent vanilloid substances Due to the lipophilic nature of these pungent vanilloid substances, the onset of the pungent sensation often is delayed by a few seconds and also persists for a particularly long time, especially in preparations containing weakly lipophilic components (e.g. triglycerides), wherein at the same time the solubility is only insufficient.
- weakly lipophilic components e.g. triglycerides
- pungent substances such as gingerol-[6] from ginger or paradol-[6] from grains of paradise, both of which have a pungent taste, but have a strong aftertaste.
- pungent-tasting substances such as the drimane, polygodial (from Kenyan pepper, Tasmannia lanceolata ) or resiniferatoxin from Euphorbia resinifera are known (Szallasi, A.; Biro, T.; Modarres, S.; Garlaschelli, L.; Petersen, M.; Klush, A.; Vidari, G.; Jonassohn, M.; De Rosa, S.; Sterner, O.; Blumberg, P.
- the methyl ester of homovanillic acid was determined in various woods, which are used for storing wine and spirits (e.g. Fernandez de Simon, B.; Esteruelas, E.; Munoz, A. M.; Cadahia, E.; Sanz, M., J. Agric. Food Chem. 2009, 57, 3217-3227.).
- the ethyl ester of homovanillic acid was detected in wine and spirits themselves, mostly in connection with a storage in oak barrels (e. g. Cabaroglu, T.; Canbas, A.; Baumes, R.; Bayonove, C.; Lepoutre, J. P.; G ⁇ nata, Z., J. Food Sci.
- US 2009/0170942 A1 discloses specific ester derivatives of homovanillinic acid and various (medical) applications thereof.
- ethanol is a small hydrophilic molecule, which causes a fast and pleasant pungent sensation that does not last very long. Since this only works at relatively high concentrations of 0.5% or more, but the consumption of ethanol causes health disorders and may also result in addiction upon prolonged consumption, flavour formulations, which can simulate the pungency profile of ethanol, without posing the disadvantages mentioned are sought after.
- EP 1,515,943 B1 describes specific longer-chain vanillylmandelic acid alkylamides or WO 2009 065,239 describes polygodial and warburganal as pungent substances to obtain an ethanol-like pungent sensation; long-lasting pungent sensation, which is not described by the testers as sensation typical of ethanol is again observed due to the lipophilicity.
- FIG. 1 is a chromatogram graph of the compounds from the primary reaction mixture containing ethyl homovanillate by reaction of ascorbic acid with vanillyl alcohol after 6 h at 100° C. according to aspects of the invention
- FIG. 2 is a chromatogram graph of the primary reaction mixture divided into 12 fractions based on the UV trace at 210 nm using LCTaste® in accordance with aspects of the invention.
- FIG. 3 is a graph of the pungency profile of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate compared with nonivamide according to aspects of the invention.
- the compounds described herein are advantageously suitable for use (in particular, as described above) in a pharmaceutical preparation, a preparation serving nutrition, oral hygiene, or pleasure, preferably wherein the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is sufficient to
- the total amount of compound(s) of the formula (I) and/or salt(s) thereof in the preparation is not sufficient to create a warming or pungent effect on the tongue or in the oral cavity, but is sufficient to mask or reduce an unpleasant taste sensation of an unpleasant tasting substance or mixture of substances.
- Another aspect of the present invention relates to new compounds of the formula (I), salts thereof, their mixtures, namely a compound of the formula (I) or a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or a mixture comprising one or several different compounds of formula (I) and/or one or several physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or consisting of a plurality of different compounds of formula (I) and/or physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively,
- the present invention also relates, in particular, to novel flavour compositions, namely a flavour composition,
- compounds of formula (I) or their salts or mixtures thereof advantageously often do not have any significant other or undesired flavour effects, and thus can be used particularly well in many different types of flavours.
- Flavour compositions which contain combinations of compounds of the formula (I) or their salts with one or several other trigeminally (pungent, warming, stinging, biting, scratching, cooling, numbing, tingling, astringent) effective substances, are particularly advantageous, wherein their trigeminal (primary) effect can be advantageously modulated by compounds of the formula (I) or their salts. For example, a warming, pungent or cooling effect can thereby be amplified, while an astringent effect can be mitigated.
- flavour composition which additionally contains one or several substances which do not correspond to the formula (I) and have an unpleasant, in particular, bitter taste, or an astringent, bitter, dry, dusty, floury, chalky and/or metallic touch, preferably selected from the group consisting of:
- the present invention further relates to a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, comprising
- a preparation according to the invention preferably also comprises
- Preferred according to the invention also is a preparation as described above, wherein the total quantity of compound(s) of the formula (I) and/or salt (s) thereof in the preparation is sufficient to
- Preparations serving nutrition or pleasure are, e.g. bakery products (e.g. bread, dry biscuits, cakes, other pastries), sweets (e.g. chocolates, chocolate bars, other sweet bars, fruit gum, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. cocoa, coffee, green tea, black tea, extracts enriched with (green, black) tea, tea drinks, rooibos tea, other herbal tea, wine, wine cocktails, beer, beer cocktails, liqueurs, schnapps, brandy, fruit juices, isotonic drinks, refreshment drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant beverages (e.g.
- bakery products e.g. bread, dry biscuits, cakes, other pastries
- sweets e.g. chocolates, chocolate bars, other sweet bars, fruit gum, hard and soft caramels, chewing gum
- alcoholic or non-alcoholic beverages e.g. cocoa, coffee, green tea, black tea, extracts
- instant cocoa drinks, instant tea drinks, instant coffee drinks meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dry egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, cereal bars, pre-cooked readymade rice products), dairy products (e.g. full-fat or fat-reduced milk or fat-free milk drinks, rice pudding, yoghurt, kefir, fresh cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed lactoprotein-containing products), products from soy protein or other soybean fractions (e.g.
- soy milk and products made from it isolated or enzymatically treated beverages, drinks containing soy protein, drinks containing soybean flour, soya-lecithin-containing preparations, fermented products such as tofu or tempe or products made from them and mixtures with fruit preparations and optional flavours), fruit preparations (e.g. jams, fruit ice-cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, boiled vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, corn or peanut-based pastes), fat and oil-based products or emulsions thereof (e.g.
- full-fat or fat-reduced mayonnaise, remoulade, dressings mayonnaise, remoulade, dressings
- other ready-to-serve meals and soups e.g. dry soups, instant soups, pre-cooked soups
- spices e.g., pepperener preparations, tablets or sachets, other preparations for sweetening or whitening beverages or other foodstuffs.
- the preparations according to the invention can also serve as semi-finished products for the preparation of further preparations serving nutrition or pleasure.
- compositions comprise a pharmaceutical active ingredient.
- pharmaceutical active ingredients are, for example, steroidal anti-inflammatory substances of the corticosteroid type, such as for example hydrocortisone, hydrocortisone derivatives, such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone.
- non-steroidal pharmaceutical active ingredients are, for example, inflammatory inhibitors such as oxicams such as piroxicam or tenoxicam; salicylates such as Aspirin® (acetylsalicylic acid), disalcid, solprin or fendosal; acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, or clindanac; fenamates such as mefenamic, meclofenamic, flufenamic or niflumic; propionic acid derivatives such as ibuprofen, naproxen, flurbiprofen, benoxaprofen or pyrazoles, such as phenyl butazone, oxyphenyl butazone, febrazone or azapropazone.
- inflammatory inhibitors such as oxicams such as piroxicam or tenoxicam
- salicylates such as Aspirin® (acety
- Particularly preferred pharmaceutical preparations are non-prescription products and OTC (over-the-counter) preparations containing active pharmaceutical ingredients such as paracetamol, acetylsalicylic acid or ibuprofen, vitamins (for example vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, panthotenic acid, preferably in the form of (effervescent) tablets or capsules), minerals (preferably in the form of (effervescent) tablets or capsules) such as iron salts, zinc salts, selenium salts, products containing active pharmaceutical ingredients or extracts of ribwort (e.g. in cough syrup) or St. John's Wort.
- active pharmaceutical ingredients such as paracetamol, acetylsalicylic acid or ibuprofen
- vitamins for example vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, panthotenic acid, preferably in the form of (effervescent) tablets or capsule
- the preparations according to the invention which may also contain unpleasantly tasting substances or mixtures of substances (cf. hereto above), can also be in the form of capsules, tablets (uncoated as well as coated tablets, e.g. gastric juice-resistant coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations as well as as a preparation with functional ingredients, as a food supplement or as balanced diets.
- Mouth-care preparations according to the invention are, in particular, oral and/or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral care agents.
- Dental care products (as the basis for mouth-care preparations) generally comprise an abrasive system (abrasive or polishing agent), such as e.g. crystalline silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxylapatites, surfactants, e.g. sodium lauryl sulphate, sodium lauryl sarcosinate and/or cocamidopropyl betaine, humectants such as e.g. glycerin and/or sorbitol, thickeners such as e.g. carboxymethyl cellulose, polyethylene glycols, carrageenan and/or Laponite®, sweeteners such as e.g.
- an abrasive system abrasive or polishing agent
- abrasive or polishing agent such as e.g. crystalline silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxylapatites
- surfactants e.
- taste modifiers e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid
- cooling active ingredients such as e.g. menthol, menthol derivatives (e.g. L-menthol, L-menthyl lactate, L-menthylalkyl carbonate, menthone ketals, menthane carboxamides), 2,2,2-trialkyl aceteamides (e.g.
- 2,2-diisopropyl propionic acid methylamide 2,2-diisopropyl propionic acid methylamide
- methylene dioxy cinnamic acid-N, N-diphenylamide methylene dioxy cinnamic acid-N-ethyl-N-phenylamide
- methylene dioxy cinnamic acid-N-pyridyl-N-phenylamide icilin derivatives
- stabilisers and active ingredients such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulphate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetyl pyridinium chloride, aluminium lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavours and/or sodium bicarbonate or o
- Chewing gums (as a further example of mouth-care preparations) generally comprise a chewing gum base, i.e. a chewing mass that plasticises during chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols, other taste modifiers for unpleasant tastes, taste modifiers for other, generally not unpleasant tastes, taste modifiers (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxy propionic acid), the cooling active ingredients, humectants, thickeners, emulsifiers, flavours and stabilisers or odour modifiers mentioned in the previous section.
- a chewing gum base i.e. a chewing mass that plasticises during chewing
- taste modifiers
- Examples of usual base materials, auxiliaries and additives for preparations according to the invention are water, mixtures of fresh or processed, plant or animal base or raw materials (e.g. raw, fried, dried, fermented, smoked and/or cooked meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar alcohols (e.g. sorbitol), natural or hardened fats (e.g.
- plant or animal base or raw materials e.g. raw, fried, dried, fermented, smoked and/or cooked meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof
- digestible or indigestible carbohydrates e.g. sucrose, maltose,
- oils e.g. sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil
- fatty acids or salts thereof e.g. potassium stearate
- proteinogenic or non-proteinogenic amino acids and related compounds e.g. taurins
- peptides native or processed proteins (e.g. gelatin), enzymes (e.g. peptidases), nucleic acids, nucleotides, taste modifiers other than those used according to the invention for unpleasant taste sensations (e.g.
- taste modifiers for other, generally not unpleasant taste sensations
- taste modifiers e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid
- emulsifiers e.g. lecithins, diacylglycerols
- stabilisers e.g. carrageenan, alginate
- preservatives e.g.
- saccharin cyclamate, aspartame, neotame, stevioside, rebaudioside, acesulfame K, neohesperidine dihydrochalcone, thaumatin, superaspartame
- mineral salts e.g. sodium chloride, potassium chloride, magnesium chloride, sodium phosphates
- anti-enzymatic-browning agents e.g. sulphites, ascorbic acid
- essential oils e.g. carotenoids, flavonoids, anthocyanins, chlorophyll and derivatives thereof
- spices synthetic, natural or nature-identical flavours or fragrances as well as odour modifiers.
- the present invention also relates to a method for producing a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, preferably a preparation according to the invention, in particular, one as described herein as being preferred, comprising the following steps:
- preparations according to the invention are preferably prepared by incorporating an ester of homovanillic acid to be used according to the invention, as a substance, as a solution or in the form of a flavour composition into a pharmaceutical base preparation serving nutrition, oral care or pleasure.
- preparations according to the invention being present as liquids can also be converted into a solid preparation, e.g. by spray drying.
- flavour compositions according to the invention here: containing ethyl homovanillate (17) is described by way of example by reacting
- This flavour preparation (primary reaction mixture) preferably contains 1,000-200,000 ppm, preferably 10,000-100,000 ppm ethyl homovanillate (17) and can be used as such or, if appropriate, further purified in admixture with other flavourings and carriers as a flavour composition.
- flavour compositions preferably contain 100-100,000 mg/kg, preferably 250-40,000 mg/kg, particularly preferably 250-15,000 mg/kg ethyl homovanillate (17) or physiologically acceptable salts, in particular, its sodium, potassium, ammonium, calcium, magnesium or zinc salts, wherein the concentration of ethyl homovanillate (17) or mixtures of ethyl homovanillate (17) with the corresponding salts in the final food products preferably corresponds to 0.1-1,000 mg/kg, preferably 1-750 mg/kg, particularly preferably 5-500 mg/kg.
- Ascorbic acid and vanillyl alcohol are each found in nature in foodstuffs and are permitted as food additives or flavourings; therefore, the use of isolated or naturally obtained ascorbic acid, as well as of isolated or naturally obtained vanillyl alcohol, which can also be used in the form of incompletely purified extracts or fractions is particularly advantageous.
- Vanillyl alcohol is present, e.g. in beer (Flavor-Base, 9th Edition, Leffingwell & Associates, 2013) or the Sitka spruce ( Picea sitchensis , P. J. Kohlbrenner, C. Schuerch, Benzene-Alcohol-Soluble Extractives of Sitka Spruce, J. Org. Chem. 1961, 24(2), 166-172).
- flavour preparations according to the invention are characterised by the fact that they can contain, in addition to ethyl homovanillate (17), at least one further substance from the following Table 1 (The same applies accordingly to the flavour preparations according to the invention described herein):
- the primary reaction mixture can be purified by one or several of the following methods:
- compounds of formula (I) or their salts or an aroma composition according to the invention in particular, the primary reaction mixture (as described above by way of example) or the purified flavour composition (as described above by way of example) and other components of the preparation according to the invention in the form of emulsions, in liposomes, e.g. starting from phosphatidyl choline, in microspheres, in nanospheres, or also in capsules, granules or extrudates from a matrix suitable for standard and luxury food, e.g. from starch, starch derivatives, cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g.
- the compounds of formula (I) or their salts are complexed with one or several suitable complexing agents, for example with cycloglycans, e.g. cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably alpha, beta and gamma cyclodextrin, and are used in this complexed form.
- suitable complexing agents for example with cycloglycans, e.g. cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably alpha, beta and gamma cyclodextrin, and are used in this complexed form.
- Example 1 Production of a Flavour Preparation (Primary Reaction Mixture) Containing Ethyl Homovanillate (17) by Reaction of Ascorbic Acid with Vanillyl Alcohol
- FIG. 1 LC-MS/QTOF chromatogram of the primary reaction mixture after 6 h at 100° C.; upper chromatogram mass trace ESI positive, lower chromatogram UV-VIS totalled; the numbers represent the compounds according to Table 1 and EHV stands for ethyl homovanillate (17)).
- the primary reaction mixture is pre-fractionated using medium-pressure liquid chromatography (MPLC) (column material: Lewatit VP OC 1064; water/ethanol 3/1; v/v). Subsequently, further separation is carried out via preparative high-pressure liquid chromatography (pHPLC) (column: Phenomenex Luna C18 5 ⁇ 150 ⁇ 21.2 mm, flow rate 30 ml/min, detection 210 nm) in the isocratic mode (63% H 2 O, 37% MeOH).
- MPLC medium-pressure liquid chromatography
- pHPLC preparative high-pressure liquid chromatography
- ethyl homovanillate (17) is carried out via semi-preparative high-pressure liquid chromatography (sPHPLC) in the gradient mode (column: YMC Triart 018 5 ⁇ 250 ⁇ 10 mm; A: H 2 O; B: MeOH; 0 min 65% A, 35% B; 25 min 40% A, 60% B; 30 min 100% B; flow rate 3 ml/min; detection: 250 nm).
- sPHPLC semi-preparative high-pressure liquid chromatography
- the primary reaction mixture is divided into 12 fractions using LC-Taste® (according to WO 2006 111,476) in the gradient mode (Hamilton PRP-1 10 ⁇ 250 ⁇ 21.5 mm; A: H 2 O, B: EtOH; 0 min 100% A; 25 min 75% A, 25% B; 40 min 100% B; flow rate: 10 ml/min, oven temperature: 80° C.), wherein the fractions were divided based on the UV trace at 210 nm. Following the narrowing of the fractions to 0.5 ml on the B ⁇ chi Syncore at 40° C., the residue was dissolved in 10 ml water.
- Homovanillic acid (1.5-3 g) was provided with the respective alcohol (equimolar) in toluene (100 ml), conc. sulphuric acid was added to it and heated to the boiling point at the water separator for 5 h. It was washed once with saturated aqueous NaHCO 3 solution, twice with water or alternately with saturated aqueous NaCl solution and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a yield of about 70%.
- Homovanillinic acid (1.5-3 g) was stirred with the respective alcohol (100 ml) and 0.2-0.5 equivalent of sulphuric acid for 7 h at 90° C. (heating block temperature). Majority of the alcohol was removed under vacuum, saturated aqueous NaHCO 3 solution and EtOAc were added, the organic phase separated and the aqueous phase extracted once with EtOAc. The combined organic phases were washed once with saturated aqueous NaHCO 3 solution and with water or alternately with saturated aqueous NaCl solution, dried over NaSO 4 and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a 90% to quantitative yield.
- esters of homovanillic acid can also be obtained by transesterification, as shown by way of example on substance 2:
- Ethyl homovanillate (5 g) was mixed with cinnamyl alcohol (7.5 g) and 25% sodium methylate solution (0.52 g) and heated to 150-170° C., vacuum applied above approximately 130° C. and MeOH/EtOH distilled from the reaction mixture for 1-3 h. It was diluted with MTBE, the organic phase was washed once with saturated aqueous NH 4 Cl solution and once with water and the solvent was removed under vacuum. Excess cinnamyl alcohol was then removed by distillation and the product was obtained by column chromatographic purification on silica gel or fractionated distillation with a yield of 40-50%.
- the substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 25 ppm).
- sugar solution final concentration: 25 ppm
- the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the sugar solution.
- the pungency was assessed on a scale of 1 (very weak)-9 (very strong) and the profile was assessed.
- Example 6 Isointensity of Esters of Homovanillinic Acid when Compared to Nonivamide and a Capsicum Extract
- the substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 10 ppm).
- 5% sugar solution final concentration: 10 ppm.
- Capsicum extract with 1,000,000 SHU (0.3-10 ppm) and nonivamide (0.1-1 ppm) were prepared in 5% sugar solution in increasing concentration.
- the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the solution to be tasted and assessed against the reference series.
- the pungency of 10 ppm of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) is comparable to the one of 8.5 ppm Capsicum extract with 1,000,000 SHU.
- the thresholds were determined according to ASTM E 679-91 (“Standard Practice for Determination of Odor and Taste Thresholds By a Forced-Choice Ascending Concentration Series Method of Limits1”). It is the respective flavour stimulus threshold to Vittel® water.
- the threshold of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) in water is at 1.7 ppm (1700 ppb).
- the threshold of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in water is at 29.5 ppm (29460 ppb).
- the threshold of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) in water is at 3.5 ppm (3540 ppb).
- Example 9 Combination of Esters of Homovanillic Acid with Grains of Paradise Extract, Nonivamide and a Capsicum Extract
- Capsicum 2 2 2 2 2 5 5 5 5 5 5 5 2 2 extract HVE 17 — 50 100 — — — 50 100 — — — — 50 100 — — — — 50 100 — — — — 50 HVE 19 — — 10 25 — — — 10 25 — 10 — — *not according to the invention
- Esters of homovanillic acid have an intensifying effect on the used compounds.
- a faster onset of the pungency was detected for the combination of grains of paradise extract (PN 300953, Symrise) with ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, examples 2 and 3).
- ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) with nonivamide examples 7 and 8 as well as 12 and 13
- the pungency of nonivamide was intensified at both of the tested concentrations, wherein this intensification corresponded to more than just the additive effect. Furthermore, a faster onset of the pungency was detected.
- Example 10 Increase in the Alcohol Pungency of an Ethanolic Solution by ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17)
- the base solution (5% sugar solution with 20% ethanol, example 1) was described as alcoholic, burning.
- Further increase to 20 ppm and 50 ppm (examples 2-5) resulted in an additional pungency effect.
- Polymethoxylated flavone PMF 60 on its own (example 6) resulted in an increase of the alcoholic taste in the tasting solution, but not a burning sensation in the mouth compared to example 1.
- Test solutions with 4-10 ppm ester of homovanillic acid were sensorially evaluated in a 5% sugar solution and were compared to a test solution of 10 ppm vanillyl butyl ether.
- Ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) had a milder warming effect compared to vanillyl butyl ether.
- Butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) had a more marked warming effect than vanillyl butyl ether.
- Isobutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (9) showed a warming effect similar to vanillyl butyl ether, but which lasted for a longer period.
- Propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18) also showed a long-lasting warming effect, but which occurred at a comparatively later time.
- ingredients are mixed in the above-specified quantity ratios and then taken up in propylene glycol and dissolved completely by slight warming.
- the two components are dissolved in a mixture of ethanol and demineralised water and are spray-dried afterwards.
- flavour compositions were used in the below-described application examples.
- Parts A to D are mixed and kneaded intensively.
- the obtained raw mass can then be processed to ready-to-eat chewing gums, e.g. in the form of thin strips.
- Version A liqueur base 5.5% v/v+0.3% of a 10% solution of an extract of grains of paradise in ethanol
- Version B liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.2% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 20 ppm).
- Version C liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.01% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 1 ppm).
- the alcohol pungency of the reference sample is sensorially imitated better than in version A.
- Version A and the reference sample are sensorially evaluated as being very similar.
- Preparation Heat the components of phases A and B separately to about 80° C. Stir phase B intro phase A while homogenising. Cool to about 40° C. while stirring, add the phases C and D and shortly homogenise again. Cool to room temperature while stirring.
- palatinite was mixed with water. The mixture was then melted at 165° C. and subsequently cooled to 115° C. The peppermint flavour and the flavour preparation (example 1) were then added. The mixtures were poured into moulds after mixing, removed from the moulds after solidifying, and then packaged individually.
- the green tea concentrate is mixed with the 1% solution of ethyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (17) in propylene glycol in the case of drink A, and with the 1% solution 3-phenylpropyl-2-(4-hydroxy-3-methoxyphenyl) acetate (22) in propylene glycol in the case of drink B. Subsequently, it is filled with demineralised water and mixed again thoroughly. The product is filtered afterwards, packaged ready-to-use, and sterilised at 118° C.
- the taste of the drinks A and B is evaluated by a panel of educated testers as clearly preferred to the non-flavoured green tea concentrate.
- the bitterness and the astringency is reduced by the addition of the compounds according to the invention.
- the esters of homovanillic acid were pre-dissolved in 10% or 1% ethanol, respectively.
- Black tea extract was dissolved in water and stirred together with sugar, a flavour preparation (peach taste), as well as the ethanol solutions of the esters of homovanillic acid in a beaker.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Tea And Coffee (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
- Preparation Of Fruits And Vegetables (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Alcoholic Beverages (AREA)
Abstract
Compounds of formula (I) and novel uses of compounds of formula (I), such as for flavour compositions. New preparations and new methods using compounds of formula (I).
Description
- This application is a national stage application (under 35 U.S.C. § 371) of PCT/EP2015/058004, filed Apr. 14, 2015, which claims benefit of priority of European Application No. 14165020.0, filed Apr. 16, 2014, which are incorporated herein by reference in their entireties.
- The present invention particularly relates to novel uses of compounds of formula (I) (as described herein), partly also of novel compounds of formula (I) as such, aroma compositions containing compounds of formula (I), new preparations as well as new methods using compounds of formula (I). Further aspects of the present invention arise from the patent claims and the following description including examples.
- Capsaicin [N-(4-hydroxy-3-methoxybenzyl)-8-methyl-(6E)-nonenoic acid amide] and other capsaicinoids such as nonivamide ([N-(4-hydroxy-3-methoxybenzyl)-nonanoic acid amide) have been known for a long time as pungent and spicy flavours from different Capsicum species, in particular, chili pepper. At an appropriately low dosage of capsaicinoids, a neutral pungency and a warm sensation is perceived in the mouth, wherein the threshold for pain-inducing pungency and hot sensation is exceeded very quickly. However, the use of capsaicin in food is not allowed in the European Union (was deleted from the Community Flavouring List in 2004), since evaluation of the genotoxic potential of the compound yielded a negative result (European Food Safety Authority (EFSA), P., Italy, Opinion of the Scientific Committee on Food on Capsaicin. European Commission 2002, (SDF/CS/FLAV/FLAVOUR/8 ADD1 Final). Moreover, use in foods is often difficult, since capsaicin has a very low taste threshold and a high potency as a pungent substance (16,000,000 Scoville units, cf. http://en.wikipedia.org/wiki/Capsaicin; version of the record as last amended on 11 Nov. 2011, 9:02 μm). Moreover, due to the high price of the pure substance, capsaicin is used almost exclusively in the form of Capsicum extract, which contains residues of other flavouring substances, which taste or smell like Capsicum, besides other pungent substances and is, therefore, only limitedly suitable for broad use. Thus, there is a need for less problematic pungent substances despite the good sensory properties.
- Although the piperine (1-piperoyl piperidine) that occurs in white pepper also causes a strongly pungent sensation (Römpp Lexicon Chemistry of Natural Compounds, Thieme 1997, p. 500) it has a relative pungency of only about 1% as compared to capsaicin. Furthermore, piperine has an intense taste of its own, reminiscent of pepper, so that the use in many preparations can only occur to a limited extent.
- Due to the lipophilic nature of these pungent vanilloid substances, the onset of the pungent sensation often is delayed by a few seconds and also persists for a particularly long time, especially in preparations containing weakly lipophilic components (e.g. triglycerides), wherein at the same time the solubility is only insufficient. The same applies to pungent substances such as gingerol-[6] from ginger or paradol-[6] from grains of paradise, both of which have a pungent taste, but have a strong aftertaste.
- Other (e.g. Starkenmann, C.; Cayeux, I.; Birkbeck, A. A., Exploring Natural Products for New Taste Sensations. Chimia 2011, 65, (6), 407-410) pungent-tasting substances such as the drimane, polygodial (from Tasmanian pepper, Tasmannia lanceolata) or resiniferatoxin from Euphorbia resinifera are known (Szallasi, A.; Biro, T.; Modarres, S.; Garlaschelli, L.; Petersen, M.; Klush, A.; Vidari, G.; Jonassohn, M.; De Rosa, S.; Sterner, O.; Blumberg, P. M.; Krause, J. E., Dialdehyde sesquiterpenes and other terpenoids as vanilloid. Eur. J. Pharmacol. 1998, 356, 81-89), but the drimanes are limited in their use due to their dialdehyde structure, since they react with free amino groups of, e.g. proteins and thus lose their effect and resiniferatoxin is highly toxic and unsuitable for human diet. Moreover, these substances are also strongly lipophilic.
- The methyl ester of homovanillic acid was determined in various woods, which are used for storing wine and spirits (e.g. Fernandez de Simon, B.; Esteruelas, E.; Munoz, A. M.; Cadahia, E.; Sanz, M., J. Agric. Food Chem. 2009, 57, 3217-3227.). In contrast, the ethyl ester of homovanillic acid was detected in wine and spirits themselves, mostly in connection with a storage in oak barrels (e. g. Cabaroglu, T.; Canbas, A.; Baumes, R.; Bayonove, C.; Lepoutre, J. P.; Gũnata, Z., J. Food Sci. 1997, 62, 680-692. van Jaarsveld, F. P.; Hattingh, S.; Minnaar, P., S. Afr. J. Enol. Vitic. 2009, 30, 24-37). However, the low concentrations of e.g. 2 μg/L are not sufficient to cause a warm and/or pungent effect.
- US 2009/0170942 A1 discloses specific ester derivatives of homovanillinic acid and various (medical) applications thereof.
- In a study of pain sensation towards different capsaicin derivatives in rat eyes, methyl, propyl, octyl, nonyl and dodecyl esters of homovanillic acid were tested and assessed as being active (Szolcsanyi, J.; Jancso-Gabor, A., Arzneim.-Forsch. (Drug. Res.) 1975, 25, 1877-1881).
- Unlike the aforementioned pungent substances, ethanol is a small hydrophilic molecule, which causes a fast and pleasant pungent sensation that does not last very long. Since this only works at relatively high concentrations of 0.5% or more, but the consumption of ethanol causes health disorders and may also result in addiction upon prolonged consumption, flavour formulations, which can simulate the pungency profile of ethanol, without posing the disadvantages mentioned are sought after. Some pungent substances have already been described for this application, for instance, EP 1,515,943 B1 describes specific longer-chain vanillylmandelic acid alkylamides or WO 2009 065,239 describes polygodial and warburganal as pungent substances to obtain an ethanol-like pungent sensation; long-lasting pungent sensation, which is not described by the testers as sensation typical of ethanol is again observed due to the lipophilicity.
-
FIG. 1 is a chromatogram graph of the compounds from the primary reaction mixture containing ethyl homovanillate by reaction of ascorbic acid with vanillyl alcohol after 6 h at 100° C. according to aspects of the invention; -
FIG. 2 is a chromatogram graph of the primary reaction mixture divided into 12 fractions based on the UV trace at 210 nm using LCTaste® in accordance with aspects of the invention; and -
FIG. 3 is a graph of the pungency profile of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate compared with nonivamide according to aspects of the invention. - Thus, there is the need for less lipophilic, quickly sensorially onsetting and not long-lasting pungent substances that create a warming taste sensation. There is special need for substances that possess the above-mentioned properties and occur naturally or are formed in usual food processes from naturally occurring food components or flavourings.
- This need can now be met according to the invention by using a compound of formula (I)
-
- wherein
- (i) R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
- R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms (for example, selected from the group consisting of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, tert-butyl, 2-methylprop-1-yl, 1-, 2- or 3-pentyl, 2-methylbut-1-yl, 2-methylbut-2-yl, 3-methylbut-1-yl and 3-methylbut-2-yl, preferably of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, tert-butyl, 2-methylprop-1-yl and 1-pentyl), a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms (for example, selected from the group consisting of ethenyl, prop-2-en-1-yl, prop-1-en-1-yl, prop-1-en-2-yl, 1- or 2-cyclopropenyl, but-1-en-1-yl, but-1-en-2-yl, but-1-en-3-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-en-2-yl, 2-methylprop-1-en-1-yl, 2-methylprop-2-en-1-yl, 1,3-butadien-1-yl, 1,3-butadien-2-yl, and the respective possible Z and E-isomers, if applicable) or an alkenylphenyl residue or a phenylalkylene residue,
- or
- (ii) R1 and R3 along with the carbon atoms linking them form a cyclohexyl ring (the residues R2 and R4 are substitutes of the cycloalkyl ring; refer to, in this regard, e.g. formula (Ia) further below), which optionally is substituted with an additional residue R5, wherein R5 is an alkyl residue with 1-2 carbon atoms,
- R2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
- R4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms (for example, selected from the group consisting of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, tert-butyl, 2-methylprop-1-yl, 1-, 2- or 3-pentyl, 2-methylbut-1-yl, 2-methylbut-2-yl, 3-methylbut-1-yl and 3-methylbut-2-yl, preferably of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, tert-butyl, 2-methylprop-1-yl and 1-pentyl), a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms (for example, selected from the group consisting of ethenyl, prop-2-en-1-yl, prop-1-en-1-yl, prop-1-en-2-yl, 1- or 2-cyclopropenyl, but-1-en-1-yl, but-1-en-2-yl, but-1-en-3-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-en-2-yl, 2-methylprop-1-en-1-yl, 2-methylprop-2-en-1-yl, 1,3-butadien-1-yl, 1,3-butadien-2-yl, and the respective possible Z and E-isomers, if applicable) or an alkenylphenyl residue or a phenylalkylene residue,
- or of a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or of a mixture comprising one or several compounds of formula (I) and/or physiologically acceptable salts thereof (in particular, its sodium, potassium, ammonium, calcium, magnesium or zinc salts), wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or consisting of a plurality of different compounds of formula (I) and/or salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively,
as flavouring.
- In the case of a mixture of different compounds of formula (I) (as described herein), it applies within the scope of the present text that the different compounds may, for example, not only be compounds with different molecular formula, but also different stereoisomers with identical molecular formula. The compounds of formula (I) described herein are suitable, in particular,
-
- as flavouring and/or pungent substance that creates a warm and/or pungent effect, i.e. as a substance that can sensorially create a warm sensation,
- and/or
- as flavouring for reducing or masking an unpleasant taste sensation, preferably selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic (more details hereto arise from the descriptions further below),
- and/or
- as flavouring for increasing a pleasant taste sensation, preferably selected from the group consisting of warming, pungent and cooling (more details hereto arise from the descriptions further below).
- At this point, it should be noted that the advantages and effects of the compounds of formula (I) described herein usually accordingly apply to their salts (as described herein).
- Use as described above is preferred, wherein the following applies to the compound of formula (I) and/or one, several or all of the compounds of formula (I), independently of each other, in the mixture:
-
- (i) R1 and R2 represent, independently of each other, a hydrogen atom or methyl,
- R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue (e.g. as described above),
- or
- (ii) Formula (I) corresponds to the following formula (Ia)
- (i) R1 and R2 represent, independently of each other, a hydrogen atom or methyl,
-
-
- R2 represents a hydrogen atom,
- R4 represents 2-propyl.
-
- Use as described above is also preferred, wherein the following applies to the compound of formula (I) and/or one, several or all of the compounds of formula (I), independently of each other, in the mixture:
-
- R1 and R2 represent a hydrogen atom, respectively,
- R3 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue,
- R4 represents a hydrogen atom.
- Particularly preferred is the compound of formula (I) and/or one, several or all compounds of the formula (I) in the mixture selected or from the group consisting of
- 2-phenylethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (1)
- [(E)-cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2)
- 1-ethylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (3)
- 3-methylbut-2-enyl-2-(4-hydroxy-3-methoxyphenyl) acetate (4)
- [(E)-hex-2-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (5)
- [(Z)-hex-3-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (6)
- isopropyl-2-(4-hydroxy-3-methoxy-phenyl) acetate (7)
- sec-butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (8)
- isobutyl-2-(4-hydroxy-3-methoxy-phenyl) acetate (9)
- 1,1-dimethylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (10)
- isopentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (11)
- 2-methylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (12)
- 1-methylpentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (13)
- heptyl-2-(4-hydroxy-3-methoxyphenyl) acetate (14)
- 1-methylhexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (15)
- (2-isopropyl-5-methyl-cyclohexyl)-2-(4-hydroxy-3-methoxyphenyl) acetate (16)
- ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17)
- propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18)
- butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19)
- pentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (20)
- hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21)
- 3-phenylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (22)
- 4-phenylbutyl 2-(4-hydroxy-3-methoxyphenyl) acetate (23)
- The compounds described herein are advantageously suitable for use (in particular, as described above) in a pharmaceutical preparation, a preparation serving nutrition, oral hygiene, or pleasure, preferably wherein the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is sufficient to
-
- (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when used or consumed,
- and/or
- (b) reduce or mask an unpleasant taste sensation, preferably selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic (more details hereto arise from the descriptions further below),
- and/or
- (c) increase a pleasant taste sensation, preferably selected from the group consisting of warming, pungent and cooling (more details hereto arise from the descriptions further below).
- (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when used or consumed,
- It is preferred according to a particular aspect of the present invention when the total amount of compound(s) of the formula (I) and/or salt(s) thereof in the preparation is not sufficient to create a warming or pungent effect on the tongue or in the oral cavity, but is sufficient to mask or reduce an unpleasant taste sensation of an unpleasant tasting substance or mixture of substances.
- Another aspect of the present invention relates to new compounds of the formula (I), salts thereof, their mixtures, namely a compound of the formula (I) or a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or a mixture comprising one or several different compounds of formula (I) and/or one or several physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or consisting of a plurality of different compounds of formula (I) and/or physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively,
-
- wherein
- (i) R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
- R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms (e.g. as described above), a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms (e.g. as described above) or an alkenylphenyl residue or a phenylalkenyl residue,
- or
- (ii) R1 and R3 along with the carbon atoms linking them form a cyclohexyl ring, which optionally is substituted with an additional residue R5, wherein R5 is an alkyl residue with 1-2 carbon atoms,
- R2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
- R4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms (e.g. as described above), a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms (e.g. as described above) or an alkenylphenyl residue or a phenylalkenyl residue,
- provided that
- R1, R2, R3 and R4 do not all represent hydrogen atoms,
- and
- in case R1, R2 and R4 represent hydrogen, R3 neither stands for a linear alkyl residue with 1, 2, 4 or 5 carbon atoms (corresponding alkenyl residues are not excluded) nor 2-propyl or phenyl, preferably also not phenylmethyl or methylphenyl,
- and
- in case R2, R3 and R4 represent hydrogen, R1 does not represent linear alkyl residue with 1 or 2 carbon atoms,
- R3 and R4 do not represent methyl, if R1 and R2 represent hydrogen, preferably neither R3 nor R4 represent methyl, if R1 and R2 represent hydrogen,
- and
- R1 and R2 do not represent methyl, if R3 and R4 represent hydrogen, preferably neither R1 nor R2 represent methyl, if R3 and R4 represent hydrogen.
- It is particularly preferred when the compound of formula (I) and/or one, several or all compounds of the formula (I) in the mixture are selected or from the group consisting of
- [(E)-cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2)
- 1-ethylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (3)
- 3-methylbut-2-enyl-2-(4-hydroxy-3-methoxyphenyl) acetate (4)
- [(E)-hex-2-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (5)
- [(Z)-hex-3-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (6)
- 1,1-dimethylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (10)
- 2-methylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (12)
- 1-methylpentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (13)
- 1-methylhexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (15)
- (2-isopropyl-5-methyl-cyclohexyl)-2-(4-hydroxy-3-methoxyphenyl) acetate (16)
- pentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (20)
- 4-phenylbutyl 2-(4-hydroxy-3-methoxyphenyl) acetate (23)
- Apart from that, what has been stated in connection with the compounds, salts and mixtures to be used according to the invention applies accordingly to the novel compounds of formula (I) and their salts as well as mixtures thereof.
- In the context of the present invention, it has been found that compounds of the formula (I) or their salts and mixtures thereof, advantageously from concentrations of 0.1 mg/kg, particularly from 1.0 mg/kg, create quickly onsetting and little long-lasting, pleasant pungency or warming and slightly sharp sensations.
- Accordingly, the present invention also relates, in particular, to novel flavour compositions, namely a flavour composition,
-
- (A) comprising or consisting of a novel mixture according to the invention as described above,
- preferably wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the flavour composition is in the range of 100-100,000 mg/kg, preferably in the range of 250-40,000 mg/kg, particularly preferably in the range of 250 to 15,000 mg/kg, based on the total weight of the flavour composition
- or
- (B) comprising a compound of the formula (I), as defined above in connection with a use according to the invention, or a physiologically acceptable salt thereof, as defined above in connection with a use according to the invention, or comprising or consisting of a mixture as defined above in connection with a use according to the invention,
- wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the flavour composition is in the range of 100-100,000 mg/kg, preferably in the range of 250-40,000 mg/kg, particularly preferably in the range of 250 to 15,000 mg/kg, based on the total weight of the flavour composition,
preferably additionally comprising one or several further flavours, which do not correspond to the formula (I), for example selected from the group consisting of
- a) warming or pungent substances, preferably selected from the list consisting of: capsaicinoids, such as for example, capsaicin, dihydrocapsaicin or nonivamide; gingerols, such as for example, gingerol-[6], gingerol-[8], or gingerol-[10]; shogaols such as shogaol-[6], shogaol-[8], shogaol-[10]; gingerdiones, such as for example gingerdione-[6], gingerdione-[8] or gingerdione-[10]; paradols such as for example paradol-[6], paradol-[8] or paradol-[10]; dehydrogingerdiones such as for example dehydrogingerdione-[6], dehydrogingerdione-[8] or dehydrogingerdione-[10]; piperine and piperine derivatives;
- b) substances perceivable as as pungent or biting, preferably selected from the group consisting of: aromatic isothiocyanates, such as for example, phenylethyl isothiocyanate, allyl isothiocyanate, cyclopropyl isothiocyanate, butyl isothiocyanate, 3-methylthiopropyl isothiocyanate, 4-hydroxybenzyl isothiocyanate, 4-methoxybenzyl isothiocyanate;
- c) alkamides described as causing a tingling sensation, preferably selected from the group consisting of 2E,4E-decadienoic acid-N-isobutylamide (trans-pellitorine) (in particular, those as described in WO 2004/043906, which become part of this application by way of reference with respect to the corresponding compounds disclosed therein); 2E,4Z-decadienoic acid-N-isobutylamide (cis-pellitorine) (in particular, those as described in WO 2004/000787, which become part of this application by way of reference with respect to the corresponding compounds disclosed therein); 2Z,4Z-decadienoic acid-N-isobutylamide; 2Z,4E-decadienoic acid-N-isobutylamide; 2E,4E-decadienoic acid-N-([2S]-2-methylbutyl)amide; 2E,4E-decadienoic acid-N-([2S]-2-methylbutyl)amide; 2E,4E-decadienoic acid N-([2R]-2-methylbutylamide); 2E,4Z-decadienoic acid-N-(2-methylbutyl)amide; 2E,4E-decadienoic acid-N-piperide (achilleamide); 2E,4E-decadienoic acid-N-piperide (sarmentine); 2E-decenoic acid-N-isobutylamide; 3E-decenoic acid-N-isobutylamide; 3E-nonenoic acid-N-isobutylamide; 2E,6Z,8E-decatrienoic acid-N-isobutylamide (spilanthol); 2E,6Z,8E-decatrienoic acid-N-([2S]-2-methylbutyl)amide (homo-spilanthol); 2E,6Z,8E-decatrienoic acid-N-([2R]-2-methylbutyl)amide; 2E-decen-4-yne-acid-N-isobutylamide; 2Z-decen-4-yne-acid-N-isobutylamide; 2E,6Z,8E,10E-dodecatetraenoic acid-N-(2-methylpropyl)amide (alpha-sanshool); 2E,6Z,8E,10E-dodecatetraenoic acid-N-(2-hydroxy-2-methylpropyl)amide (alpha-hydroxysanshool); 2E,6E,8E,10E-dodecatetraenoic acid-N-(2-hydroxy-2-methylpropyl)amide (gamma-hydroxysanshool); 2E,4E,8Z,10E,12E-tetradecapentaenoic acid-N-(2-hydroxy-2-methylpropyl)amide (gamma-hydroxysanshool); 2E,4E,8E,10E,12E-tetradecapentaenoic acid-N-(2-hydroxy-2-methylpropyl)amide (gamma-hydroxyisosanshool); 2E,4E,8Z,10E,12E-tetradecapentaenoic acid-N-(2-methyl-2-propenyl)amide (gamma-dehydrosanshool); 2E,4E,8Z,10E,12E-tetradecapentaenoic acid-N-(2-methylpropyl)amide (gamma-sanshool); 2E,4E,8Z,11Z-tetradecatetraenoic acid-N-(2-hydroxy-2-methylpropyl)amide (bungeanool); 2E,4E,8Z,11E-tetradecatetraenoic acid-N-(2-hydroxy-2-methylpropyl)amide (isobungeanool); 2E,4E,8Z-tetradecatrienoic acid-N-(2-hydroxy-2-methylpropyl)amide (dihydrobungeanool) and 2E,4E-tetradecadienoic acid-N-(2-hydroxy-2-methylpropyl)amide (tetrahydrobungeanool);
- d) substances with physiological cooling effect, preferably selected from the following list: menthol and derivatives thereof (e.g. L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthyl ether (e.g. (L-menthoxy)-1,2-propanediol, (L-menthoxy)-2-methyl-1,2-propanediol, L-menthylmethyl ether), menthyl ester (e.g. menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy) acetate, menthyl-(2-methoxyethoxy) acetate, menthyl pyroglutamate), menthyl carbonate (e.g. menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glycerol carbonate or mixtures thereof), the half-esters of menthols with a dicarboxylic acid or derivatives thereof (e.g. mono-menthyl succinate, mono-menthyl glutarate, mono-menthyl malonate, O-menthyl succinic acid ester-N, N-(dimethyl)amide, O-menthyl succinic acid esteramide), menthane carboxamides other than those mentioned in the present invention (e.g. menthane carboxylic acid-N-ethylamide [WS3], menthane carboxylic acid-N-(p-methoxyphenyl)amide [SC1], Nα-(menthane carbonyl) glycine ethyl ester [W55], menthane carboxylic acid-N-(4-cyanophenyl)amide, menthane carboxylic acid-N-(alkoxyalkyl)amides), menthone and derivatives thereof (e.g. L-menthone glycerine ketal), 2,3-dimethyl-2-(2-propyl) butanoic acid derivatives (e.g. 2,3-dimethyl-2-(2-propyl) butanoic acid-N-methylamide [W523]), isopulegol or its esters (|-(−)-isopulegol, 1-(−)-isopulegol acetate), menthane derivates (e.g. p-menthane-3,8-diol), cubebol or synthetic or natural mixtures, containing cubebol, pyrrolidone derivatives of cycloalkyldione derivatives (e.g. 3-methyl-2(1-pyrrolidinyl)-2-cyclopenten-1-one) or tetrahydropyrimidin-2-ones (e.g. icilin or related compounds, as described in WO 2004/026840), other coolants as described in WO2011061330, in particular, derivatives of differently substituted cinnamic- and 2-phenoxy acids, particularly preferred methylene dioxy cinnamic acid-N,N-diphenylamide, methylene dioxy cinnamic acid-N-ethyl-N-phenylamide, methylene dioxy cinnamic acid-N-pyridyl-N-phenylamide;
- e) substances having astringent effect, preferably selected from the following list: catechins, e.g. epicatechins, gallocatechins, epigallocatechins and their respective gallic acid esters, e.g. epigallocatechin gallate or epicatechin gallate, their oligomers (procyanidines, proanthocyanidins, prodelphinidines, procyanirins, thearubigenins, theogallines) as well as their C- and O-glycosides; dihydroflavonoids such as dihydromyricetin, taxifolin as well as their C- and O-glycosides, flavonols such as myricetin, quercetin as well as their C- and O-glycosides, such as quercetrin, rutin, gallic acid esters of carbohydrates such as tannin, pentagalloyl glucose or their reaction products, such as elligatannine, aluminium salts, e.g. alum,
- (A) comprising or consisting of a novel mixture according to the invention as described above,
- Particularly at the concentrations described herein to be used according to the invention or preferably according to the invention, compounds of formula (I) or their salts or mixtures thereof advantageously often do not have any significant other or undesired flavour effects, and thus can be used particularly well in many different types of flavours.
- Flavour compositions which contain combinations of compounds of the formula (I) or their salts with one or several other trigeminally (pungent, warming, stinging, biting, scratching, cooling, numbing, tingling, astringent) effective substances, are particularly advantageous, wherein their trigeminal (primary) effect can be advantageously modulated by compounds of the formula (I) or their salts. For example, a warming, pungent or cooling effect can thereby be amplified, while an astringent effect can be mitigated.
- Therefore, a flavour composition is also preferred, which additionally contains one or several substances which do not correspond to the formula (I) and have an unpleasant, in particular, bitter taste, or an astringent, bitter, dry, dusty, floury, chalky and/or metallic touch, preferably selected from the group consisting of:
-
- f) xanthin alkaloids, xanthines (caffeine, theobromine, theophylline and methylxanthine), alkaloids (quinine, brucine, strychnine, nicotine), phenolic glycosides (e.g. salicin, arbutin), flavonoid glycosides (e.g. neohespereidin, hesperidin, naringin, quercitrin, rutin, hyperosid, quercetin 3-O-glucoside, myricetin-3-O-glycosides), chalcones or chalcone glycoside (e.g. phloridzine, phloridzinxyloside), hydrolyzable tannins (gallic or ellagic acid esters of carbohydrates, e.g. pentagalloyl glucose, tannic acids), non-hydrolyzable tannins (if applicable galloylated catechins, gallocatechins, epigallocatechins or epicatechins and their oligomers, e.g. proanthyocyanidins or procyanidins, thearubigenin), flavones (e.g. quercetin, taxifolin, myricetin), phenols such as e.g. salicin, polyphenols (e.g. gamma-oryzanol, caffeic acid or their esters (e.g. chlorogenic acid and isomers)), terpenoid bitter and tanning agents (e.g. limonoides such as limonin or nomilin from citrus fruits, lupolones and humulones from hops, iridoids, secoiridoids), absinthin from wormwood, amarogentin from gentian, metallic salts (especially potassium, magnesium and calcium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, sodium sulphate, magnesium sulphate, aluminium salts, zinc salts, tin salts, iron (II) salts, iron (III) salts, chromium (II) picolinate), active pharmaceutical ingredients (e.g. fluoroquinolone antibiotics, paracetamol, aspirin, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], guaifenesin), vitamins (e.g. vitamin H, vitamins from the B-series such as vitamin B1, B2, B6, B12, niacin, pantothenic acid), denatonium benzoate, sucralose octaacetate, iron salts, aluminium salts, zinc salts, urea, unsaturated fatty acids, especially unsaturated fatty acids in emulsions, amino acids with a bitter/astringent taste (e.g. leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine) and peptides or proteins with a bitter/astringent taste (especially peptides with an amino acid from the group of leucine, isoleucine, valine, tryptophan, proline or phenylalanine at the N or C-terminus), saponins, in particular, soya saponins, isoflavonoids (in particular genistein, daidzein, genistein, daidzin, their glycosides and acylated glycosides);
- g) substances with a non-unpleasant primary taste (e.g. sweet, salty, spicy, sour) and/or smell, preferably selected from the group of sweeteners or sugar substitutes, preferably potassium salts (especially potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate), aspartame, acesulfame K, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, stevioside, rebaudiosides, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside X, rubusoside, hernandulcin, thaumatin, miraculin, glycyrrhizin, glycyrrhetinic acid, balansin A or balansin B, or derivatives thereof, cyclamate or the pharmaceutically acceptable salts of the above-mentioned compounds.
- The present invention further relates to a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, comprising
-
- (A) a novel mixture according to the invention as described above,
- preferably wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the preparation,
- or
- (B) a compound of the formula (I), as defined above in connection with a use according to the invention, or a physiologically acceptable salt thereof, as defined above in connection with a use according to the invention, or a mixture as defined above in connection with a use according to the invention,
- wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the preparation,
- or
- (C) a flavour composition as described above,
- preferably wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof in the preparation is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the composition
- (A) a novel mixture according to the invention as described above,
- A preparation according to the invention preferably also comprises
-
- one or several usual base materials, auxiliaries and additives in a quantity of 5-99.9999% w/w, preferably 10 to 80% w/w, based on the total weight of the preparation,
- and/or
- water in a quantity of up to 99.9999% w/w, preferably in a quantity of 5 to 80% w/w, based on the total weight of the preparation.
- Preferred according to the invention also is a preparation as described above, wherein the total quantity of compound(s) of the formula (I) and/or salt (s) thereof in the preparation is sufficient to
-
- (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation isused or consumed,
- and/or
- (b) reduce or mask an unpleasant taste sensation, preferably of another substance contained in the preparation, in particular, a taste sensation selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic (cf. hereto above),
- and/or
- (c) increase a pleasant taste sensation, preferably of another substance contained in the preparation, in particular, a taste sensation selected from the group consisting of warming, pungent and cooling (cf. hereto above),
- (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation isused or consumed,
- Preferred is also a preparation according to the invention that at least comprises one further substance for modifying, masking or reducing the unpleasant taste sensation of an unpleasant-tasting substance or mixture of substances, besides the compounds of the formula (I) or their salts (as defined above). Accordingly, a combination of at least two taste modifiers is then present.
- Preparations serving nutrition or pleasure according to the invention are, e.g. bakery products (e.g. bread, dry biscuits, cakes, other pastries), sweets (e.g. chocolates, chocolate bars, other sweet bars, fruit gum, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. cocoa, coffee, green tea, black tea, extracts enriched with (green, black) tea, tea drinks, rooibos tea, other herbal tea, wine, wine cocktails, beer, beer cocktails, liqueurs, schnapps, brandy, fruit juices, isotonic drinks, refreshment drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant beverages (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dry egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, cereal bars, pre-cooked readymade rice products), dairy products (e.g. full-fat or fat-reduced milk or fat-free milk drinks, rice pudding, yoghurt, kefir, fresh cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed lactoprotein-containing products), products from soy protein or other soybean fractions (e.g. soy milk and products made from it, isolated or enzymatically treated beverages, drinks containing soy protein, drinks containing soybean flour, soya-lecithin-containing preparations, fermented products such as tofu or tempe or products made from them and mixtures with fruit preparations and optional flavours), fruit preparations (e.g. jams, fruit ice-cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, boiled vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, corn or peanut-based pastes), fat and oil-based products or emulsions thereof (e.g. full-fat or fat-reduced mayonnaise, remoulade, dressings), other ready-to-serve meals and soups (e.g. dry soups, instant soups, pre-cooked soups), spices, seasonings, and in particular, sprinkle seasonings, which are used, for example, in the snack sector, sweetener preparations, tablets or sachets, other preparations for sweetening or whitening beverages or other foodstuffs. The preparations according to the invention can also serve as semi-finished products for the preparation of further preparations serving nutrition or pleasure.
- Pharmaceutical preparations comprise a pharmaceutical active ingredient. Advantageous pharmaceutical active ingredients are, for example, steroidal anti-inflammatory substances of the corticosteroid type, such as for example hydrocortisone, hydrocortisone derivatives, such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone. Advantageous non-steroidal pharmaceutical active ingredients are, for example, inflammatory inhibitors such as oxicams such as piroxicam or tenoxicam; salicylates such as Aspirin® (acetylsalicylic acid), disalcid, solprin or fendosal; acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, or clindanac; fenamates such as mefenamic, meclofenamic, flufenamic or niflumic; propionic acid derivatives such as ibuprofen, naproxen, flurbiprofen, benoxaprofen or pyrazoles, such as phenyl butazone, oxyphenyl butazone, febrazone or azapropazone.
- Particularly preferred pharmaceutical preparations are non-prescription products and OTC (over-the-counter) preparations containing active pharmaceutical ingredients such as paracetamol, acetylsalicylic acid or ibuprofen, vitamins (for example vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, panthotenic acid, preferably in the form of (effervescent) tablets or capsules), minerals (preferably in the form of (effervescent) tablets or capsules) such as iron salts, zinc salts, selenium salts, products containing active pharmaceutical ingredients or extracts of ribwort (e.g. in cough syrup) or St. John's Wort.
- The preparations according to the invention, which may also contain unpleasantly tasting substances or mixtures of substances (cf. hereto above), can also be in the form of capsules, tablets (uncoated as well as coated tablets, e.g. gastric juice-resistant coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations as well as as a preparation with functional ingredients, as a food supplement or as balanced diets.
- Mouth-care preparations according to the invention are, in particular, oral and/or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral care agents.
- Dental care products (as the basis for mouth-care preparations) generally comprise an abrasive system (abrasive or polishing agent), such as e.g. crystalline silicas, calcium carbonates, calcium phosphates, aluminium oxides and/or hydroxylapatites, surfactants, e.g. sodium lauryl sulphate, sodium lauryl sarcosinate and/or cocamidopropyl betaine, humectants such as e.g. glycerin and/or sorbitol, thickeners such as e.g. carboxymethyl cellulose, polyethylene glycols, carrageenan and/or Laponite®, sweeteners such as e.g. saccharin, other taste modifiers of unpleasant taste sensations, taste modifiers of other, generally not unpleasant taste sensations, taste modifiers (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid), cooling active ingredients such as e.g. menthol, menthol derivatives (e.g. L-menthol, L-menthyl lactate, L-menthylalkyl carbonate, menthone ketals, menthane carboxamides), 2,2,2-trialkyl aceteamides (e.g. 2,2-diisopropyl propionic acid methylamide), methylene dioxy cinnamic acid-N, N-diphenylamide, methylene dioxy cinnamic acid-N-ethyl-N-phenylamide, methylene dioxy cinnamic acid-N-pyridyl-N-phenylamide, icilin derivatives, stabilisers and active ingredients, such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulphate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetyl pyridinium chloride, aluminium lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavours and/or sodium bicarbonate or odour modifiers.
- Chewing gums (as a further example of mouth-care preparations) generally comprise a chewing gum base, i.e. a chewing mass that plasticises during chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols, other taste modifiers for unpleasant tastes, taste modifiers for other, generally not unpleasant tastes, taste modifiers (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxy propionic acid), the cooling active ingredients, humectants, thickeners, emulsifiers, flavours and stabilisers or odour modifiers mentioned in the previous section.
- Examples of usual base materials, auxiliaries and additives for preparations according to the invention are water, mixtures of fresh or processed, plant or animal base or raw materials (e.g. raw, fried, dried, fermented, smoked and/or cooked meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar alcohols (e.g. sorbitol), natural or hardened fats (e.g. tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (e.g. sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or salts thereof (e.g. potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. taurins), peptides, native or processed proteins (e.g. gelatin), enzymes (e.g. peptidases), nucleic acids, nucleotides, taste modifiers other than those used according to the invention for unpleasant taste sensations (e.g. hesperetin, phloretin or other hydroxychalcone derivatives to be used according to US 2008/0227867, as well as the lactones described therein, if applicable), taste modifiers for other, generally not unpleasant taste sensations, taste modifiers (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxy propionic acid), emulsifiers (e.g. lecithins, diacylglycerols), stabilisers (e.g. carrageenan, alginate), preservatives (e.g. benzoic acid, sorbic acid), antioxidants (e.g. tocopherol, ascorbic acid), chelators (e.g. citric acid), organic or inorganic acidifiers (e.g. malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid, lactic acid), bitter additives (e.g. quinol, caffeine, limonin, aminogentin, humolones, lupolones, catechins, tannins), sweeteners (e.g. saccharin, cyclamate, aspartame, neotame, stevioside, rebaudioside, acesulfame K, neohesperidine dihydrochalcone, thaumatin, superaspartame), mineral salts (e.g. sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), anti-enzymatic-browning agents (e.g. sulphites, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or colour pigments (e.g. carotenoids, flavonoids, anthocyanins, chlorophyll and derivatives thereof), spices, synthetic, natural or nature-identical flavours or fragrances as well as odour modifiers.
- The present invention also relates to a method for producing a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, preferably a preparation according to the invention, in particular, one as described herein as being preferred, comprising the following steps:
-
- i) Providing
- (A) a mixture according to the invention as described herein,
- preferably wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof is selected such that the total quantity in the preparation to be made is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the preparation,
- or
- (B) a compound of the formula (I) as defined herein according to the invention or to be used according to the invention, or a physiologically acceptable salt thereof as defined herein or a mixture as defined herein,
- wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) thereof is selected such that the total quantity in the preparation to be made is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the preparation,
- or
- (C) a flavour composition according to the invention as described herein,
- preferably wherein
- the total quantity of compound(s) of formula (I) and/or salt(s) is selected such that the total quantity in the preparation to be made is in the range of 0.1-1,000 mg/kg, preferably in the range of 1-1,000 mg/kg, preferably in the range of 1 to 750 mg/kg, particularly preferably in the range of 5-500 mg/kg, based on the total weight of the preparation,
- (A) a mixture according to the invention as described herein,
- ii) providing one or several further components of the preparation to be made, and
- iii) contacting or mixing the further components provided in step ii) with the component(s) provided in step i), preferably in a sensorially effective quantity.
- i) Providing
- The described preparations according to the invention are preferably prepared by incorporating an ester of homovanillic acid to be used according to the invention, as a substance, as a solution or in the form of a flavour composition into a pharmaceutical base preparation serving nutrition, oral care or pleasure. Advantageously, preparations according to the invention being present as liquids can also be converted into a solid preparation, e.g. by spray drying.
- Below, the production of flavour compositions according to the invention (here: containing ethyl homovanillate (17) is described by way of example by reacting
-
- i) 1 equivalent ascorbic acid or one of its physiologically acceptable salts with
- ii) 1 equivalent vanillyl alcohol
- iii) in a (50/50; v/v) mixture of water and a representative from the group of substance of alcohols, particularly preferred are ethanol, propanol, butanol, pentanol, hexanol and isopropyl alcohol
- iv) at a temperature of 100-150° C. (under pressure, if applicable)
- v) for a time period of 4-6 h.
- This flavour preparation (primary reaction mixture) preferably contains 1,000-200,000 ppm, preferably 10,000-100,000 ppm ethyl homovanillate (17) and can be used as such or, if appropriate, further purified in admixture with other flavourings and carriers as a flavour composition. These flavour compositions preferably contain 100-100,000 mg/kg, preferably 250-40,000 mg/kg, particularly preferably 250-15,000 mg/kg ethyl homovanillate (17) or physiologically acceptable salts, in particular, its sodium, potassium, ammonium, calcium, magnesium or zinc salts, wherein the concentration of ethyl homovanillate (17) or mixtures of ethyl homovanillate (17) with the corresponding salts in the final food products preferably corresponds to 0.1-1,000 mg/kg, preferably 1-750 mg/kg, particularly preferably 5-500 mg/kg.
- Ascorbic acid and vanillyl alcohol are each found in nature in foodstuffs and are permitted as food additives or flavourings; therefore, the use of isolated or naturally obtained ascorbic acid, as well as of isolated or naturally obtained vanillyl alcohol, which can also be used in the form of incompletely purified extracts or fractions is particularly advantageous. Vanillyl alcohol is present, e.g. in beer (Flavor-Base, 9th Edition, Leffingwell & Associates, 2013) or the Sitka spruce (Picea sitchensis, P. J. Kohlbrenner, C. Schuerch, Benzene-Alcohol-Soluble Extractives of Sitka Spruce, J. Org. Chem. 1959, 24(2), 166-172).
- The above-described flavour preparations according to the invention are characterised by the fact that they can contain, in addition to ethyl homovanillate (17), at least one further substance from the following Table 1 (The same applies accordingly to the flavour preparations according to the invention described herein):
-
TABLE 1 Retention time Molar mass No. [min]* m/z (Found: ESI+) IPUAC name Structure 1* 2.88 found 227.0546 calc. 226.047189 for C10H10O6 3-(1,2-dihydroxyethyl)-1,3- dihydroiso-benzofuran-1,4,5- triol 2 3.73 found 313.0921 calc. 312.083969 for C14H16O8 6-[(3-hydroperoxy-4- hydroxyphenyl)-methyl]- 3,6,6a-trihydroxy-3,3a- dihydro-2H-furo[3,2-b]furan-5- one* 3 3.98 found 313.0920 calc. 312.083969 for C14H16O8 2-hydroxy-3-(4-hydroxy-3- methoxyphenyl)-2-(3-hydroxy- 2-oxo-tetrahydrofuran-3-yl) propanoic acid 4 4.66 found 251.0924 calc. 250.083575 for C13H14O5 2-hydroxy-3-(4-hydroxy-3- methoxyphenyl)-4- (hydroxymethyl) cyclopent-2- en-1-one* 5 6.12 found 387.1449 calc. 386.136004 for C21H22O7 2-hydroxy-3-[4-hydroxy-2-[(4- hydroxy-3- methoxyphenyl)methyl]-5- methoxyphenyl]-4- (hydroxymethyl) cyclopent-2- en-1-one 6 6.33 found 251.0925 calc. 250.083575 for C13H14O5 2-[(4-hydroxy-3- methoxyphenyl)-methylene]- 5-(hydroxymethyl) tetrahydrofuran-3-one 7 6.34 found 251.0921 calc. 250.083575 for C13H14O5 5-hydroxy-6-[(4-hydroxy-3- methoxyphenyl)methyl]-2,3- dihydropyran-4-one 8 6.98 found 341.1251 calc. 340.115269 for C16H20O8 Ethyl-2-hydroxy-3-(4-hydroxy- 3-methoxyphenyl)-2-(3- hydroxy-2-oxo-tetrahydro- furan-3-yl) propanoate 9 7.68 found 233.0842 calc. 232.073010 for C13H12O4 1-(2-furyl)-2-(4-hydroxy-3- methoxyphenyl) ethanone 10 7.71 found 387.1457 calc. 386.136004 for C21H22O7 2-hydroxy-3-[4-hydroxy-3-[(4- hydroxy-3- methoxyphenyl)methyl]-5- methoxyphenyl]-4- (hydroxymethyl) cyclopent-2- en-1-one 11 7.93 found 233.0821 calc. 233.073010 for C13H12O4 2-[(4-hydroxy-3- methoxyphenyl)methylene]-5- methyl furan-3-one 12 8.22 found 297.1347 calc. 296.125440 for C15H20O6 Ethyl-3-[3-(4-hydroxy-3- methoxyphenyl)-2-oxo- propoxy] propanoate 14 8.82 found 465.1606 calc. 464.146569 for C26H24O8 2-[3-(2-furyl)-1,2-bis(4- hydroxy-3-methoxyphenyl)-3- oxo-propyl]-5-methyl furan-3-one one 15 9.52 found 369.1346 calc. 368.125440 for C21H20O6 1-(2-furyl)-2-[4-hydroxy-2-[(4- hydroxy-3- methoxyphenyl)methyl]-5- methoxy-phenyl] ethanone *cf. Preobrazhenskaya, M.N. et al. Tetrahedron 1997, 53, 6971-6976 - The primary reaction mixture can be purified by one or several of the following methods:
- a) If applicable, concentrating the primary reaction mixture, preferably by one or several evaporative or pervaporative processes,
- b) If applicable, treating the primary reaction mixture (optionally concentrated in step a), if applicable) by partition chromatographic (e.g. countercurrent distribution processes such as FCPC, SCLC, Craig process) or adsorption chromatographic processes with or at adsorbents, preferably selected from the group consisting of silica gel, modified silica gel, activated carbon, zeolite, bentonite, diatomaceous earth, alumina, basic or acidic or neutral, optionally macroporous, ion exchanger, preferably by batch or column process, with the aid of further extracting agents, if applicable, whereby a purified flavour composition is obtained,
- c) If applicable, drying the purified flavour composition obtained in step b), preferably by an evaporative or pervaporative process,
- d) If applicable, repeating the steps b) and c) once or several times
- e) If applicable, mixing the purified flavour composition obtained in the preceding steps with a suitable diluent or a mixture of two or several diluents, preferably selected from the group consisting of ethanol, isopropanol, 1,2-propylene glycol, vegetable oil triglycerides, diacetin, triacetin and glycerin, wherein preferably the flavour composition is obtained in the form of a solution.
- According to a another preferred embodiment, compounds of formula (I) or their salts or an aroma composition according to the invention in particular, the primary reaction mixture (as described above by way of example) or the purified flavour composition (as described above by way of example) and other components of the preparation according to the invention in the form of emulsions, in liposomes, e.g. starting from phosphatidyl choline, in microspheres, in nanospheres, or also in capsules, granules or extrudates from a matrix suitable for standard and luxury food, e.g. from starch, starch derivatives, cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. alginate), natural fats, natural waxes (e.g. beeswax, carnauba wax), or from proteins, e.g. gelatin, to be used according to the invention are incorporated for producing preparations according to the invention. In a preferred preparation process, the compounds of formula (I) or their salts are complexed with one or several suitable complexing agents, for example with cycloglycans, e.g. cyclofructans, cyclodextrins or cyclodextrin derivatives, preferably alpha, beta and gamma cyclodextrin, and are used in this complexed form.
- The present invention is further described below by means of selected, specific examples. The examples only serve the purpose of illustrating the invention, without any limitation. Unless specified otherwise, all details provided relate to the weight.
- 3 mmol ascorbic acid and 3 mmol vanillyl alcohol were dissolved in 10 ml water/ethanol (1/1; v/v). The solution was heated to 100° C. with constant stirring in the microwave (Mars Synthesis, CEM) for 7 minutes. The reaction mixture was subsequently heated in the microwave with constant stirring for further 6 h at 100° C. The LC-MS/QTOF chromatogram illustrated below shows the substances that are listed in Table 1 and form after 6 h as well as ethyl homovanillate (EHV, 17). Ethyl homovanillate (17) is contained in the primary reaction mixture at a quantity of 1.2%.
- Carrying out the above reaction with the indicated ratios of ascorbic acid and vanillyl alcohol with a boiling time of 4 h also leads to the formation of EHV.
- In this regard, refer to
FIG. 1 (LC-MS/QTOF chromatogram of the primary reaction mixture after 6 h at 100° C.; upper chromatogram mass trace ESI positive, lower chromatogram UV-VIS totalled; the numbers represent the compounds according to Table 1 and EHV stands for ethyl homovanillate (17)). - The primary reaction mixture is pre-fractionated using medium-pressure liquid chromatography (MPLC) (column material: Lewatit VP OC 1064; water/
ethanol 3/1; v/v). Subsequently, further separation is carried out via preparative high-pressure liquid chromatography (pHPLC) (column: Phenomenex Luna C18 5μ 150×21.2 mm,flow rate 30 ml/min, detection 210 nm) in the isocratic mode (63% H2O, 37% MeOH). Final isolation of ethyl homovanillate (17) is carried out via semi-preparative high-pressure liquid chromatography (sPHPLC) in the gradient mode (column: YMC Triart 018 5μ 250×10 mm; A: H2O; B: MeOH; 0 min 65% A, 35% B; 25min 40% A, 60% B; 30min 100% B; flowrate 3 ml/min; detection: 250 nm). The obtained ethyl homovanillate (17) was subsequently freeze-dried and tasted and sensorially assessed at a dosage of 100 ppm in 5% sugar solution, 0.5% salt solution, 500 ppm caffeine solution and water. -
Medium Taste description Water Pungent, stinging, slightly warming 5% sugar solution Pungent, warming 0.5% salt solution Pungent - The primary reaction mixture is divided into 12 fractions using LC-Taste® (according to WO 2006 111,476) in the gradient mode (Hamilton PRP-1 10μ 250×21.5 mm; A: H2O, B: EtOH; 0
min 100% A; 25 min 75% A, 25% B; 40min 100% B; flow rate: 10 ml/min, oven temperature: 80° C.), wherein the fractions were divided based on the UV trace at 210 nm. Following the narrowing of the fractions to 0.5 ml on the Bũchi Syncore at 40° C., the residue was dissolved in 10 ml water. 2 ml of each one of these solutions wasmixed mit 18 ml 3.33% sugar solution (corresponds to a final dose of 96 mg/kg ethyl homovanillate (17) forfraction fraction 11 in 3% sugar solution) and subjected to sensorial assessment. - To this end, see
FIG. 2 (LC Taste Chromatogram of the primary reaction mixture;Fraction -
TABLE 2 Sensory taste profile of the fractions separation (see FIG. 2) Fraction Taste Intensity 10 Warming 5-6 Medical 4-5 Pepper 3-4 Smoked ham (smoky) 3 Pungent 5 11 Warming 2-3 Smoked ham 4-5 Smoky 4 Grilled, BBQ 4 Phenolic 3 Vanilla 2 - Method A:
- Homovanillic acid (1.5-3 g) was provided with the respective alcohol (equimolar) in toluene (100 ml), conc. sulphuric acid was added to it and heated to the boiling point at the water separator for 5 h. It was washed once with saturated aqueous NaHCO3 solution, twice with water or alternately with saturated aqueous NaCl solution and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a yield of about 70%.
- Method B:
- Homovanillinic acid (1.5-3 g) was stirred with the respective alcohol (100 ml) and 0.2-0.5 equivalent of sulphuric acid for 7 h at 90° C. (heating block temperature). Majority of the alcohol was removed under vacuum, saturated aqueous NaHCO3 solution and EtOAc were added, the organic phase separated and the aqueous phase extracted once with EtOAc. The combined organic phases were washed once with saturated aqueous NaHCO3 solution and with water or alternately with saturated aqueous NaCl solution, dried over NaSO4 and the solvent was removed under vacuum. The product was obtained by column chromatography on silica gel with a 90% to quantitative yield.
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.1 Hz, 1H), 6.81 (dd, J=2.0, 0.5 Hz, 1H), 6.76 (ddt, J=8.0, 2.0, 0.6 Hz, 1H), 5.60 (s, 1H), 5.01 (hept, J=6.3 Hz, 1H), 3.88 (s, 3H), 3.496 (t, J=0.5 Hz, 2H), 1.23 (d, J=6.3 Hz, 6H).
- 13C-NMR (100 MHz, CDCl3): δ=171.5, 146.4, 144.7, 126.1, 122.1, 114.3, 111.7, 68.1, 55.9, 41.3, 21.8 (2C).
- GCMS: m/z (%)=224 [M+] (30), 137 (100), 122 (10), 107 (2), 94 (6), 77 (3), 66 (5), 51 (3), 43 (15).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.1 Hz, 1H), 6.82 (d, J=1.9 Hz, 1H), 6.79-6.74 (m, 1H), 5.57 (s, 1H), 4.92-4.78 (m, 1H), 3.88 (s, 3H), 3.51 (t, J=0.5 Hz, 2H), 1.62-1.46 (m, 2H), 1.19 (d, J=6.3 Hz, 3H), 0.85 (t, J=7.5 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=171.6, 146.4, 144.7, 126.2, 122.1, 114.3, 111.7, 72.7, 55.9, 41.4, 28.8, 19.4, 9.6.
- GCMS: m/z (%)=238 [M+] (30), 137 (100), 122 (8), 107 (2), 94 (5), 77 (2), 66 (3), 57 (20), 51 (2), 41 (8), 29 (8).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (dd, J=8.1, 0.3 Hz, 1H), 6.82-6.81 (m, 1H), 6.77 (ddt, J=8.1, 2.0, 0.6 Hz, 1H), 5.60 (s, 1H), 3.87 (d, J=0.3 Hz, 3H), 3.86 (d, J=6.6 Hz, 2H), 3.54 (t, J=0.5 Hz, 2H), 1.91 (dq, J=6.7 Hz, 1H), 0.90 (d, J=6.7 Hz, 6H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.1, 114.3, 111.7, 70.9, 55.9, 41.1, 27.7, 19.0 (2C).
- GCMS: m/z (%)=238 [M+] (30), 182 (5), 137 (100), 122 (9), 107 (2), 94 (6), 77 (2), 66 (3), 57 (11), 51 (2), 41 (8), 29 (7).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.1 Hz, 1H), 6.81 (dd, J=2.0, 0.5 Hz, 1H), 6.76 (ddt, J=8.1, 1.9, 0.6 Hz, 1H), 5.60 (s, 1H), 4.09 (t, J=6.7 Hz, 2H), 3.87 (d, J=0.3 Hz, 3H), 3.53 (t, J=0.5 Hz, 2H), 1.67-1.55 (m, 2H), 1.42-1.29 (m, 2H), 0.91 (t, J=7.4 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.1, 114.3, 111.7, 64.7, 55.9, 41.1, 30.6, 19.1, 13.7.
- GCMS: m/z (%)=238 [M+] (27), 182 (2), 137 (100), 122 (9), 107 (2), 94 (5), 77 (2), 66 (2), 57 (4), 41 (5), 29 (8).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.0 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.76 (dd, J=8.1, 2.0 Hz, 1H), 5.61-5.58 (m, 1H), 4.05 (t, J=6.7 Hz, 2H), 3.88 (s, 3H), 3.54 (s, 2H), 1.71-1.52 (m, 2H), 0.91 (t, J=7.4 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.2, 144.3, 111.7, 66.4, 55.9, 41.1, 22.0, 10.4.
- GCMS: m/z (%)=224 [M+] (30), 137 (100), 122 (10), 107 (2), 94 (8), 77 (2), 66 (3), 51 (2) 43 (8).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.05 Hz, 1H), 6.81 (d, J=1.94 Hz, 1H), 6.76 (ddd, J=8.01, 1.99, 0.50 Hz, 1H), 5.61 (d, J=0.36 Hz, 1H), 4.15 (q, J=7.13 Hz, 2H), 3.88 (s, 3H), 3.53 (d, J=0.57 Hz, 2H), 1.25 (t, J=7.13 Hz, 1H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 125.9, 122.1, 114.4, 111.7, 60.8, 55.9, 41.0, 14.2.
- GCMS: m/z (%)=210 [M+] (30), 137 (100), 122 (11), 107 (2), 94 (8), 77 (2), 66 (3), 51 (3), 39 (3), 29 (8).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (dd, J=8.1, 0.3 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.76 (ddq, J=8.1, 2.0, 0.5 Hz, 1H), 5.58 (s, 1H), 4.08 (t, J=6.7 Hz, 2H), 3.88 (s, 3H), 3.53 (s, 2H), 1.65-1.56 (m, 2H), 1.36-1.20 (m, 6H), 0.87 (t, J=7.0 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.1, 114.3, 111.7, 65.0, 55.9, 41.1, 31.4, 28.6, 25.5, 22.5, 14.0.
- GCMS: m/z (%)=266 [M+] (30), 182 (8), 137 (100), 122 (8), 107 (2), 94 (4), 77 (2), 66 (2), 55 (3), 43 (13).
-
- 1H NMR (600 MHz, CDCl3): δ=7.29-7.24 (m, 2H), 7.20-7.16 (m, 1H), 7.14-7.10 (m, 2H), 6.87 (d, J=8.0 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.78 (dd, J=8.1, 2.0 Hz, 1H), 5.57 (s, 1H), 4.10 (t, J=6.5 Hz, 2H), 3.88 (s, 3H), 3.54 (s, 2H), 2.64 (dd, J=8.5, 6.8 Hz, 2H), 1.98-1.90 (m, 2H).
- 13C NMR (151 MHz, CDCl3): δ=171.91, 146.46, 144.75, 141.09, 128.42, 128.37, 126.00, 125.88, 122.13, 114.36, 111.68, 64.10, 55.90, 41.08, 32.06, 30.16.
- GCMS: m/z (%)=300 [M+] (28), 182 (62), 137 (100), 122 (16), 118 (20), 91 (34), 77 (6), 65 (6), 51 (4), 28 (4).
-
- 1H NMR (600 MHz, CDCl3): δ=7.29-7.25 (m, 2H), 7.20-7.16 (m, 1H), 7.15-7.11 (m, 2H), 6.85 (d, J=8.1 Hz, 1H), 6.79 (d, J=2.0 Hz, 1H), 6.75 (dd, J=8.0, 2.0 Hz, 1H), 5.60 (s, 1H), 4.10 (t, J=6.1 Hz, 2H), 3.83 (s, 3H), 3.52 (s, 2H), 2.60 (t, J=7.1 Hz, 2H), 1.69-1.60 (m, 4H).
- 13C NMR (151 MHz, CDCl3): δ=171.97, 146.45, 144.72, 141.97, 128.33, 128.32, 125.86, 125.81, 122.09, 114.35, 111.67, 64.67, 55.84, 41.06, 35.38, 28.17, 27.68.
- GCMS: m/z (%)=314 [M+] (48), 182 (36), 137 (100), 122 (10), 104 (20), 91 (44), 65 (4), 51 (2).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.1 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 6.76 (dd, J=8.0, 2.0 Hz, 1H), 5.58 (s, 1H), 5.49 (ddt, J=10.9, 7.3, 1.6 Hz, 1H), 5.29 (ddt, J=10.7, 7.3, 1.5 Hz, 1H), 4.08 (t, J=7.0 Hz, 2H), 3.88 (s, 3H), 3.53 (s, 2H), 2.43-2.32 (m, 2H), 2.03 (pd, J=7.5, 1.6 Hz, 2H), 0.96 (t, J=7.5 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=171.9, 146.5, 144.7, 134.6, 125.8, 123.6, 122.1, 114.3, 111.7, 64.4, 55.9, 41.0, 26.7, 20.6, 14.2.
- GCMS: m/z (%)=264 [M+] (30), 182 (55), 137 (100), 122 (15), 94 (10), 82 (8), 67 (15), 55 (20), 41 (15).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.86 (d, J=8.1 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.77 (dd, J=8.0, 2.0 Hz, 1H), 5.55 (s, 1H), 3.97 (dd, J=10.7, 6.0 Hz, 1H), 3.90 (dd, J=10.8, 6.7 Hz, 1H), 3.88 (s, 3H), 3.54 (s, 2H), 1.69 (dddd, J=12.4, 7.8, 6.8, 5.8 Hz, 1H), 1.38 (dtd, J=13.1, 7.5, 5.6 Hz, 1H), 1.23-1.08 (m, 1H), 0.88 (d, J=6.8 Hz, 3H), 0.88 (t, J=7.5 Hz, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.4, 144.7, 126.0, 122.1, 114.3, 111.7, 69.4, 55.9, 41.1, 34.1, 26.0, 16.3, 11.2.
- GCMS: m/z (%)=252 [M+] (30), 182 (10), 137 (100), 122 (8), 94 (7), 71 (5), 55 (4), 43 (18), 29 (10).
-
- 1H-NMR (400 MHz, CDCl3): δ=7.29-7.24 (m, 2H), 7.24-7.19 (m, 1H), 7.16-7.12 (m, 2H), 6.85 (d, J=7.9 Hz, 1H), 6.74 (d, J=1.9 Hz, 1H), 6.72 (dd, J=8.0, 1.9 Hz, 1H), 5.57 (s, 1H), 4.30 (t, J=6.9 Hz, 2H), 3.84 (s, 3H), 3.51 (s, 2H), 2.91 (t, J=6.9 Hz, 2H).
- 13C-NMR (100 MHz, CDCl3): δ=171.8, 146.4, 144.7, 137.7, 128.9 (2C), 128.4 (2C), 126.5, 125.7, 122.2, 114.3, 111.7, 65.3, 55.87, 41.1, 35.0.
- GCMS: m/z (%)=286 [M+] (30), 182 (48), 137 (100), 122 (12), 105 (30), 94 (11), 77 (12), 65 (8), 51 (7), 39 (5).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (d, J=8.0 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.76 (dd, J=8.1, 2.0 Hz, 1H), 5.58 (s, 1H), 4.08 (t, J=6.7 Hz, 2H), 3.88 (s, 3H), 3.53 (s, 2H), 1.61 (q, J=6.7 Hz, 2H), 1.37-1.24 (m, 4H), 0.94-0.83 (m, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.1, 114.3, 111.7, 65.0, 55.9, 41.1, 28.3, 28.0, 22.3, 14.0.
- GCMS: m/z (%)=252 [M+] (28), 182 (5), 137 (100), 122 (10), 94 (5), 66 (3), 43 (13), 29 (4).
-
- 1H-NMR (400 MHz, CDCl3): δ=6.85 (dd, J=8.1, 1.1 Hz, 1H), 6.81 (t, J=1.4 Hz, 1H), 6.76 (dt, J=8.2, 1.4 Hz, 1H), 5.59 (d, J=1.1 Hz, 1H), 4.08 (td, J=6.8, 1.1 Hz, 2H), 3.88 (d, J=1.2 Hz, 3H), 3.53 (s, 2H), 1.68-1.55 (m, 2H), 1.28 (td, J=9.8, 9.3, 4.0 Hz, 8H), 0.94-0.82 (m, 3H).
- 13C-NMR (100 MHz, CDCl3): δ=172.0, 146.5, 144.7, 126.0, 122.1, 114.3, 111.7, 65.0, 55.9, 41.1, 31.7, 28.9, 28.6, 25.8, 22.6, 14.1.
- GCMS: m/z (%)=280 [M+] (34), 182 (12), 137 (100), 122 (8), 94 (5), 57 (11), 41 (8).
- Alternatively, esters of homovanillic acid can also be obtained by transesterification, as shown by way of example on substance 2:
- Ethyl homovanillate (5 g) was mixed with cinnamyl alcohol (7.5 g) and 25% sodium methylate solution (0.52 g) and heated to 150-170° C., vacuum applied above approximately 130° C. and MeOH/EtOH distilled from the reaction mixture for 1-3 h. It was diluted with MTBE, the organic phase was washed once with saturated aqueous NH4Cl solution and once with water and the solvent was removed under vacuum. Excess cinnamyl alcohol was then removed by distillation and the product was obtained by column chromatographic purification on silica gel or fractionated distillation with a yield of 40-50%.
- 1H NMR (400 MHz, CDCl3): δ=7.38-7.35 (m, 2H), 7.35-7.29 (m, 2H), 7.29-7.23 (m, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.82 (d, J=2.0 Hz, 1H), 6.79 (dd, J=8.0, 2.0 Hz, 1H), 6.60 (dt, J=15.9, 1.5 Hz, 1H), 6.27 (dt, J=15.9, 6.4 Hz, 1H), 5.56 (s, 1H), 4.75 (dd, J=6.4, 1.4 Hz, 2H), 3.86 (s, 3H), 3.59 (s, 2H).
- 13C NMR (100 MHz, CDCl3): δ=171.64, 146.48, 144.80, 136.15, 134.17, 128.60, 128.08, 126.58, 125.69, 123.02, 122.19, 114.38, 111.71, 65.34, 55.89, 40.99.
- GCMS: m/z (%)=298 [M+] (12), 137 (100), 122 (8), 117 (68), 94 (8), 91 (12), 77 (4), 65 (4), 51 (4), 39 (6).
- The substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 25 ppm). For the tasting, the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the sugar solution. The pungency was assessed on a scale of 1 (very weak)-9 (very strong) and the profile was assessed.
- a) Profile of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21): clearly pungent, slightly delayed effect, warming, relatively fast decrease in pungency; pungency assessed at 9.
- b) Profile of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19): immediate pungency, quick decrease; pungency assessed at 7.
- c) Profile of isobutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (9): quick onset of pungency, warming, slightly biting pungency; pungency assessed at 4-5.
- d) Profile of propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18): weak and delayed pungency, gradually warming, tingling; pungency assessed at 4-5.
- e) Profile of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17): slightly warming, somewhat pungent; pungency assessed at 1-2.
- f) Profile of isopropyl-2-(4-hydroxy-3-methoxyphenyl) acetate (7): Late onset, tingling, warming, pungent, somewhat delayed, not long-lasting, pleasant; pungency assessed at 3.
- g) Profile of sec-butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (8): very delayed onset, tingling, mainly warming, gradually increasing pungency, pungency assessed at 3.
- h) Profile of octyl-2-(4-hydroxy-3-methoxy-phenyl) acetate (not according to the invention): slow onset of pungency, late, delayed, greasy-pulpy secondary effect, burning; pungency assessed at 7.
- i) Profile of decyl-2-(4-hydroxy-3-methoxyphenyl) acetate (not according to the invention): weakly pungent, delayed, pear-like and greasy-pulpy secondary effect, throat burns more than the tongue; pungency assessed at 2.
- k) 3-Phenylpropyl-2-(4-hydroxy-3-methoxyphenyl) acetate (22): 2 ppm*: delayed effect, pungent, warming, slightly tingling; pungency assessed at 5.
- l) 4-Phenylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (23): 2.5 ppm*: delayed effect, pungent, delayed warming, burning, slightly tingling; pungency assessed at 4-5.
- m) [(E)-Cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2): 1.5 ppm*: delayed effect, very pungent, slightly warming, somewhat mouthwatering; pungency assessed at 5-6.
- n) Heptyl-2-(4-hydroxy-3-methoxyphenyl) acetate (14): 1.5 ppm*: slightly delayed effect, burning, pungent, warming, pungency assessed at 3.
- “Owing to their strong pungency, these compounds were only tasted at final concentrations of 1.5-2.5 ppm.
- The substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 10 ppm). As reference, Capsicum extract with 1,000,000 SHU (0.3-10 ppm) and nonivamide (0.1-1 ppm) were prepared in 5% sugar solution in increasing concentration. For the tasting, the oral cavity was rinsed and spat out by 4 tasters with approx. 5 ml of the solution to be tasted and assessed against the reference series.
- The pungency of 10 ppm of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) is comparable to the one of 0.5 ppm nonivamide.
- The pungency of 10 ppm of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) is comparable to the one of 0.3 ppm nonivamide.
- The pungency of 10 ppm of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) is comparable to the one of 4.5 ppm Capsicum extract with 1,000,000 SHU.
- The pungency of 10 ppm of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) is comparable to the one of 8.5 ppm Capsicum extract with 1,000,000 SHU.
- The thresholds were determined according to ASTM E 679-91 (“Standard Practice for Determination of Odor and Taste Thresholds By a Forced-Choice Ascending Concentration Series Method of Limits1”). It is the respective flavour stimulus threshold to Vittel® water.
- For example, the threshold of hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) in water is at 1.7 ppm (1700 ppb).
- For example, the threshold of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in water is at 29.5 ppm (29460 ppb).
- For example, the threshold of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) in water is at 3.5 ppm (3540 ppb).
- To obtain a time vs. intensity profile, trained panelists (n=8-10) rinsed their oral cavity with a gulp of a sample solution (5 ml of a 5% sugar solution). Then, the intensity of the characteristic pungency was assessed at defined time intervals on the basis of a scale without fixed graduation. The two solutions to be tasted (butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) with 25 ppm and nonivamide with 0.5 ppm of the corresponding substance were coded and placed in a mixed sequence. Between the two samples to be tasted, the oral cavity was neutralised with bread and water and pre-rinsing with 5 ml of 5% sugar solution. The data was analysed and graphically displayed as a time vs. intensity curve (see
FIG. 3 (Pungency profile of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) compared with nonivamide). - The faster onset of the pungency of butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) compared with nonivamide at identical total intensity as well as the considerably faster decrease in pungency could be clearly observed.
- Different combinations of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) and butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) with grains of paradise extract (PN 300953, Symrise), nonivamide and Capsicum extract 1,000,000 SHU were subjected to sensorial assessment. The tasting solutions containing an ester of homovanillic acid at an increasing concentration (ppm) in combination with a trigeminal substance of a certain concentration, based on a 5% sugar solution (Tab. 3) were assessed by 3 testers. To this end, the oral cavity was rinsed with approx. 5 ml of the specific solution to be tasted and the solution was spat out again.
-
TABLE 3 Combinations of esters of homovanillic acid (HVE) with grains of paradise extract (PN 300953, Symrise), nonivamide and a capsicum extract (basis: 5% sugar solution, specifications in ppm). Example 1* 2 3 4 5 6* 7 8 9 10 11* 12 13 14 15 Grains of 30 30 30 30 30 — — — — — — — — — — paradise extract Noni- — — — — — 0.2 0.2 0.2 0.2 0.2 0.5 0.5 0.5 0.5 0.5 vamide Capsicum — — — — — — — — — — — — — — — extract HVE 17 — 10 25 — — — 50 100 — — — 50 100 HVE 19— — — 3 7 — — — 15 30 — — — 15 30 Combinations of esters of homovanillic acid (HVE) with grains of paradise extract (PN 300953, Symrise), nonivamide and a capsicum extract (basis: 5% sugar solution, specifications in ppm). Example 16* 17 18 19 20 21* 22 23 24 25 26* 27 28* 29 Grains of — — — — — — — — — — — — — — paradise extract Noni- — — — — — — — — — — 0.1 0.1 0.2 0.2 vamide Capsicum 2 2 2 2 2 5 5 5 5 5 5 5 2 2 extract HVE 17 — 50 100 — — — 50 100 — — — — — 50 HVE 19— — — 10 25 — — — 10 25 — 10 — — *not according to the invention - Esters of homovanillic acid have an intensifying effect on the used compounds. A faster onset of the pungency was detected for the combination of grains of paradise extract (PN 300953, Symrise) with ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, examples 2 and 3). In the combination of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) with nonivamide (examples 7 and 8 as well as 12 and 13), the pungency of nonivamide was intensified at both of the tested concentrations, wherein this intensification corresponded to more than just the additive effect. Furthermore, a faster onset of the pungency was detected. The same intensifying and faster onsetting effect was also detected in the combination of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) with 2 ppm Capsicum extract with 1,000,000 SHU (examples 17 and 18), wherein the pungency sensation was assessed as being pleasant and not long-lasting. In the absence of combination with a homovanillyl ester, the onset of the pungency of the Capsicum extract with 1,000,000 SHU was perceived only with a delay (examples 16* and 21*). The intensification of the pungency was significantly higher with 2 ppm Capsicum extract with 1,000,000 SHU than with 5 ppm. In the combination of 5 ppm Capsicum extract with 1,000,000 SHU with different amounts of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, examples 22 and 23), quick decline in the pungency was apparent. In addition, the pungency of Capsicum extract with 1,000,000 SHU in the combination with ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) at all concentrations was complemented by a pleasantly warming effect, which remained even after the pungency sensation receded. For butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19), the same effects were detected even at lower concentrations (examples 19 and 20 as well as 24 and 25), wherein the intensifications were more significant than just an additive effect. Also a combination of nonivamide, Capsicum extract with 1,000,000 SHU and ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, example 27) or butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19, example 29) also showed quicker decline in the pungency sensation as well as a warming effect for the combinations without esters of homovanillic acid (examples 26* and 28*).
- On the basis of a 5% sugar solution with 20% ethanol (example 1), different concentrations (10-100 ppm) of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17), polymethoxylated flavone PMF 60 (Miritz) and combinations (10-50 ppm) of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) with polymethoxylated flavone PMF 60 (Miritz) (20 ppm) were compared with a second base solution (5% sugar solution with 40% ethanol) (Tab. 4). To this end, 5 testers rinsed their mouth with about 5 ml of the relevant solution to be tasted, spat out the solution and assessed the taste sensation.
-
TABLE 4 Combinations of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) and polymethoxylated flavone PMF 60 (Miritz) in a 5% sugar solution with 20% ethanol (specifications in ppm). Ingredient 1* 2 3 4 5 6* 7 8 9 Ethyl-2-(4- — 10 20 50 100 — 10 20 50 hydroxy-3- methoxyphenyl) acetate (17) Polymethoxylated — — — — — 20 20 20 20 flavone PMF 60*not according to the invention - The base solution (5% sugar solution with 20% ethanol, example 1) was described as alcoholic, burning. The addition of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, example 2) led to an increase and an extension of the burning sensation in the mouth. Further increase to 20 ppm and 50 ppm (examples 2-5) resulted in an additional pungency effect.
Polymethoxylated flavone PMF 60 on its own (example 6) resulted in an increase of the alcoholic taste in the tasting solution, but not a burning sensation in the mouth compared to example 1. This taste was increased by means of the combination with ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17, examples 7-9), an increase of the burning sensation was additionally generated, and an extension of these effects was also achieved, whereby the use of 20-50 ppm ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) was sensorially preferred. Compared to the second base solution (5% sugar solution with 40% ethanol) with a higher alcohol content and a high nasal effect, this combination did not show any nasal effect. - Test solutions with 4-10 ppm ester of homovanillic acid were sensorially evaluated in a 5% sugar solution and were compared to a test solution of 10 ppm vanillyl butyl ether. Ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) had a milder warming effect compared to vanillyl butyl ether. Butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) had a more marked warming effect than vanillyl butyl ether. Isobutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (9) showed a warming effect similar to vanillyl butyl ether, but which lasted for a longer period. Propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18) also showed a long-lasting warming effect, but which occurred at a comparatively later time.
- The following were mixed (all specifications in % w/w, unless specified otherwise):
-
Ingredient A B C D E F G H 10% w/w pellitorine in 1,2- 0.25 0.25 0.25 0.25 0.25 0.25 0.25 0.25 propylene glycol/diethyl malonate Hesperetin 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 Phloretin 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Ethyl-2-(4-hydroxy-3- 3.00 — 1.50 100 — — — — methoxyphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — 0.50 0.25 — — — — — methoxyphenyl) acetate (19) Propyl-2-(4-hydroxy-3- — — — 1.50 — — 100 — methoxyphenyl) acetate (18) 3-phenylpropyl 2-(4-hydroxy-3- — — — — 0.05 — — — methoxyphenyl) acetate (22) 4-phenylbutyl 2-(4-hydroxy-3- — — — — — 0.07 — — methoxyphenyl) acetate (23) Heptyl-2-(4-hydroxy-3- — — — — — — 0.10 — methoxyphenyl) acetate (14) [(E)-cinnamyl]-2-(4-hydroxy-3- — — — — — — — 0.06 methoxyphenyl) acetate (2) Propylene glycol ad ad ad ad ad ad ad ad 100 100 100 100 100 100 100 100 - The ingredients (substances or solutions) are mixed in the above-specified quantity ratios and then taken up in propylene glycol and dissolved completely by slight warming.
- The following were mixed (all specifications in % w/w, unless specified otherwise):
-
Ingredient A B C D E F G H Ethyl-2-(4-hydroxy-3- 10.00 — — — — — — — methoxphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — 3.50 — — — — — — methoxphenyl) acetate (19) Propyl-2-(4-hydroxy-3- — — 5.00 — — — — — methoxphenyl) acetate (18) Hexyl-2-(4-hydroxy-3- — — — 2.50 — — — — methoxphenyl) acetate (21) 3-phenylpropyl 2-(4-hydroxy-3- — — — — 0.20 — — — methoxphenyl) acetate (22) 4-phenylbutyl 2-(4-hydroxy-3- — — — — — 0.22 — — methoxphenyl) acetate (23) Heptyl-2-(4-hydroxy-3- — — — — — — 0.25 — methoxphenyl) acetate (14) [(E)-cinnamyl]-2-(4-hydroxy-3- — — — — — — — 0.21 methoxphenyl) acetate (2) Maltodextrin ad ad ad ad ad ad ad ad 100 100 100 100 100 100 100 100 - The two components are dissolved in a mixture of ethanol and demineralised water and are spray-dried afterwards.
- The following were mixed (all specifications in % w/w, unless specified otherwise):
-
Ingredient A B C D E F G H I Anethole 30 30 30 30 30 30 30 30 30 Eucalyptol 25 25 25 25 25 25 25 25 25 L-Menthol 36.00 36.00 38.00 36.20 36.00 36.90 39.85 34.90 39.90 Optacool A — 8 — 8 — 8 — 8 — Coolact 10 5 — 5 — 5 — 5 — 5 Ethyl-2-(4-hydroxy-3- 4.00 — — — 3.00 — — 2.00 — methoxyphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — 1.00 — — — — — — — methoxphenyl) acetate (19) Propyl-2-(4-hydroxy-3- — — 2.00 — 1.00 — — — — methoxphenyl) acetate (18) Hexyl-2-(4-hydroxy-3- — — — 0.80 — — — — — methoxphenyl) acetate (21) 3-phenylpropyl 2-(4-hydroxy- — — — — — 0.10 — — — 3-methoxyphenyl) acetate (22) 4-phenylbutyl 2-(4-hydroxy-3- — — — — — — 0.15 — — methoxphenyl) acetate (23) Heptyl-2-(4-hydroxy-3- — — — — — — — 0.10 — methoxphenyl) acetate (14) [(E)-cinnamyl]-2-(4-hydroxy-3- — — — — — — — — 0.10 methoxphenyl) acetate (2) Total 100 100 100 100 100 100 100 100 100 - The following were mixed (all specifications in % w/w, unless specified otherwise):
-
Ingredient A B C D E F G H I K Peppermint oil 56 59.00 58.50 58.80 56 59 60 60 59.5 60 Mentha arvensis L-Menthone 20 20 20 20 20 20 20 20 20 20 L-Menthol 20 20 20 20 20 20 20 20 20 20 Ethyl-2-(4-hydroxy-3- 4.00 — — — 3.00 — — — — — methoxyphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — 1.00 — — — 0.50 — — 0.50 — methoxyphenyl) acetate (19) Propyl-2-(4-hydroxy-3- — — 1.50 — 1.00 0.50 — — — — methoxyphenyl) acetate (18) Pentyl-2-(4-hydroxy-3- — — — 1.20 — — — — — — methoxyphenyl) acetate (20) 3-phenylpropyl 2-(4- — — — — — — 0.20 — — — hydroxy-3-methoxyphenyl) acetate (22) 4-phenylbutyl 2-(4-hydroxy- — — — — — — — 0.22 — — 3-methoxyphenyl) acetate (23) Heptyl-2-(4-hydroxy-3- — — — — — — — — 0.25 — methoxyphenyl) acetate (14) [(E)-cinnamyl]-2-(4- — — — — — — — — — 0.21 hydroxy-3-methoxyphenyl) acetate (2) Total 100 100 100 100 100 100 100 100 100 100 - The flavour compositions were used in the below-described application examples.
- Production of a beer mixed drink with reduced alcohol content or without alcohol. All specifications are in % w/w.
-
Ingredient A* B C D E F G H I Sugar syrup 4 4 4 4 4 4 4 4 4 Beer (4.9% v/v) 50 — — — — — — — — Beer (with reduced — — 50 — 50 — 50 — 50 alcohol and calories, 2.8% v/v) Beer (alcohol-free, 0%) — 50 — 50 — 50 — 50 — Citric acid 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Ascorbic acid 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 Grapefruit juice 6 6 6 6 6 6 6 6 6 Grapefruit flavour 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Flavour preparation — 0.20 0.20 — — — — — — (application example 1A) Flavour preparation — — — 0.20 0.20 — — — — (application example 1B) Flavour preparation — — — — — 0.20 0.20 — — (application example 1E) Flavour preparation — — — — — — — 0.20 0.20 (application example 1H) Water ad ad ad ad ad ad ad ad ad 100 100 100 100 100 100 100 100 100 Carbon dioxide 0.70 0.70 0.70 0.70 0.70 0.70 0.70 0.70 0.70 *not according to the invention - All specifications in % w/w, unless specified otherwise.
-
Ingredient A B C D E F G H I K Deionised water 26.53 26.53 26.53 26.53 26.53 26.53 26.53 26.53 26.53 26.53 Sorbitol 70% 45 44.975 45 44.975 45 44.975 45 44.975 45 44.975 Solbrol M sodium 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 salt Trisodium 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 phosphate Saccharin 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Sodium 1.12 1.12 1.12 1.12 1.12 1.12 1.12 1.12 1.12 1.12 monofluorophosphate PEG 1500 5 5 5 5 5 5 5 5 5 5 Sident 9 (abrasive 10 10 10 10 10 10 10 10 10 10 silica) Sident 22 S 8 8 8 8 8 8 8 8 8 8 (thickening silica) Sodium 0.90 0.90 0.90 0.90 0.90 0.90 0.90 0.90 0.90 0.90 carboxymethyl cellulose Titanium (IV) oxide 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 Sodium lauryl 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 sulphate (SLS) Pellitorine solution — 0.025 — 0.025 — 0.025 — 0.025 — 0.025 PLM (containing 10% pellitorine) Peppermint flavour 1.00 1.00 — — — — — — — — type (application example 4A) Peppermint flavour — — 1.00 1.00 — — — — — — type (application example 4B) Peppermint flavour — — — — 1.00 1.00 — — — — type (application example 4C) Peppermint flavour — — — — — — 1.00 1.00 — — type (application example 4G) Peppermint flavour — — — — — — — — 1.00 1.00 type (application example 4K) Total 100 100 100 100 100 100 100 100 100 100 - All specifications in % w/w, unless specified otherwise.
-
Ingredient A B C D E F G H I K Deionised water 27.5 27.48 27.5 27.48 27.5 27.48 27.5 27.48 27.5 27.48 Saccharin 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Solbrol M sodium salt 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Sodium 0.80 0.80 0.80 0.80 0.80 0.80 0.80 0.80 0.80 0.80 monofluorophosphate Sorbitol 70% 29 29 29 29 29 29 29 29 29 29 Calcium carbonate 35 35 35 35 35 35 35 35 35 35 Sident 22 S (thickening 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 silica) Sodium carboxymethyl 1.30 1.30 1.30 1.30 1.30 1.30 1.30 1.30 1.30 1.30 cellulose Titanium dioxide 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 Sodium lauryl sulphate 2 2 2 2 2 2 2 2 2 2 Pellitorine solution — 0.02 — 0.02 — 0.02 — 0.02 — 0.02 PLM (containing 10% pellitorine) Peppermint flavour 1.00 1.00 — — — — — — — — type (application example 4D) Peppermint flavour — — 1.00 1.00 — — — — — — type (application example 4E) Peppermint flavour — — — — 1.00 1.00 — — — — type (application example 4F) Peppermint flavour — — — — — — 1.00 1.00 — — type (application example 4H) Peppermint flavour — — — — — — — — 1.00 1.00 type (application example 4I) Total 100 100 100 100 100 100 100 100 100 100 - By means of using the substances according to the invention, a quickly onsetting pleasant feeling of pungency with warming aspects is achieved. Additionally, an increased mouthwatering effect is achieved.
-
-
Part Ingredient wt % A Chewing gum, company “Jagum T” 30.00 B Sorbitol, pulverised 39.00 Isomalt ® (Palatinit GmbH) 9.50 Xylitol 2.00 Mannitol 3.00 Aspartame ® 0.10 Acesulfam ® K 0.10 Emulgum ® (Colloides Naturels, Inc.) 0.30 C Sorbitol 70% 14.00 Glycerine 1.00 D Flavour compositions according to example 4) 1.00 - Parts A to D are mixed and kneaded intensively. The obtained raw mass can then be processed to ready-to-eat chewing gums, e.g. in the form of thin strips.
- All specifications in % w/w, unless specified otherwise.
-
Ingredient A B C D E F G H I K Cremophor 1.80 1.80 1.80 1.80 1.80 1.80 1.80 1.80 1.80 1.80 RH 455 Deionised 87.57 87.5575 87.57 87.5575 87.57 87.5575 87.57 87.5575 87.57 87.5575 water Sorbitol 10 10 10 10 10 10 10 10 10 10 70% Sodium 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.18 fluoride Sodium 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 saccharin 450 Solbrol M 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 sodium salt Pellitorine — 0.0125 — 0.0125 — 0.0125 0.0125 0.0125 solution PLM (containing 10% pellitorine) Mouthwash 0.20 0.20 — — — — — — — — flavour (application example 3A) Mouthwash — — 0.20 0.20 — — — — — — flavour (application example 3B) Mouthwash — — — — 0.20 0.20 — — — — flavour (application example 30) Mouthwash — — — — — — 0.20 0.20 — — flavour (application example 3F) Mouthwash — — — — — — — — 0.20 0.20 flavour (application example 3D) Total 100 100 100 100 100 100 100 100 100 100 - All specifications are in % w/w.
-
Ingredient A B C D E F G Ethanol, 96% 5 5 5 5 5 5 5 Sorbitol, 70% in water 40 40 40 40 40 40 40 Glycerin 20 20 20 20 20 20 20 Saccharin 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Sodium monofluorophosphate 0.76 0.76 0.76 0.76 0.76 0.76 0.76 Solbrol M, sodium salt 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Abrasive silica (Sident 9) 20 20 20 20 20 20 20 Thickening silica (Sident 22S) 2 2 2 2 2 2 2 Sodium carboxymethyl cellulose 0.30 0.30 0.30 0.30 0.30 0.30 0.30 Sodium lauryl sulphate 1.20 1.20 1.20 1.20 1.20 1.20 1.20 Green dye (1% in water) 0.50 0.50 0.50 0.50 0.50 0.50 0.50 Distilled water 9.39 9.39 9.39 9.39 8.89 8.89 8.89 Flavour preparation 0.50 — — — — — — (Application example 3A) Flavour preparation — 0.50 — — — — — (Application example 3B) Flavour preparation — — 0.50 — — — — (Application example 3C) Flavour preparation — — — 0.50 — — — (Application example 3D) Flavour preparation — — — — 1.00 — — (Application example 3F) Flavour preparation — — — — — 1.00 — (Application example 3H) Flavour preparation — — — — — — 1.00 (Application example 3I) Total 100 100 100 100 100 100 100 -
-
7.39 kg alcohol, p.A. 20 kg inverted sugar syrup, 66.5% dry mass 72.61 kg water Total 100 kg -
-
4.06 kg alcohol, p.A. 20 kg inverted sugar syrup, 66.5% dry mass 75.94 kg water Total 100 kg - Version A: liqueur base 5.5% v/v+0.3% of a 10% solution of an extract of grains of paradise in ethanol
- Version B: liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.2% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 20 ppm).
- Version C: liqueur base 5.5% v/v+0.075% of a 10% solution of an extract of grains of paradise in ethanol+0.01% of a solution of 1% ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) in ethanol (corresponds to 1 ppm).
- In the versions B and C, the alcohol pungency of the reference sample is sensorially imitated better than in version A. Version A and the reference sample are sensorially evaluated as being very similar.
-
-
% w/w Ingredient (INCI) A 2.00 Ceteareth-6, stearyl alcohol 2.00 Ceteareth-25 5.00 Cetearyl ethyl hexanoate 4.00 Cetyl alcohol 4.00 Glyceryl stearate 5.00 Mineral oil 0.20 Menthol 0.50 Camphor B 69.30 Demineralised water q.s. Preservative C 1.00 Bisabolol 1.00 Tocopheryl acetate D 1.00 Aqueous solution with 1-1.5% pentyl-2-(4-hydroxy-3- methoxyphenyl) acetate (20) 5.00 Witch hazel extract 100 Total - Preparation: Heat the components of phases A and B separately to about 80° C. Stir phase B intro phase A while homogenising. Cool to about 40° C. while stirring, add the phases C and D and shortly homogenise again. Cool to room temperature while stirring.
-
-
Ingredient Content [% w/w] Palatinite, type M 75.47 Water 24.03 Peppermint flavour 0.10 Flavour preparation (example 1) 0.40 Total 100 - At first, palatinite was mixed with water. The mixture was then melted at 165° C. and subsequently cooled to 115° C. The peppermint flavour and the flavour preparation (example 1) were then added. The mixtures were poured into moulds after mixing, removed from the moulds after solidifying, and then packaged individually.
- A=Reference preparation
- B, C, D, E=Preparations according to the invention
- All specifications are in % w/w.
-
Ingredient A* B C D E F G Milk protein 0.80 0.80 0.80 0.80 0.80 0.80 0.80 Locust bean gum 2.00 2.00 2.00 2.00 2.00 2.00 2.00 powder Corn starch 24.00 23.00 23.00 23.00 23.00 23.00 23.00 Cooking salt 14.00 14.00 14.00 14.00 14.00 14.00 14.00 Bell pepper powder 12.00 12.00 12.00 12.00 12.00 12.00 12.00 Tomato powder 12.00 12.00 12.00 12.00 12.00 12.00 12.00 Sucrose 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Garlic powder 0.50 0.50 0.50 0.50 0.50 0.50 0.50 Hardened vegetable fat 8.00 8.00 8.00 8.00 8.00 8.00 8.00 Fat powder 11.00 11.00 11.00 11.00 11.00 11.00 11.00 Sodium glutamate 6.00 6.00 6.00 6.00 6.00 6.00 6.00 Food dye beetroot and 2.00 2.00 2.00 2.00 2.00 2.00 2.00 bell pepper Flavour type “pepper” 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Flavour type “pizza” 1.20 1.20 1.20 1.20 1.20 1.20 1.20 Flavour type “tomato” 0.40 0.40 0.40 0.40 0.40 0.40 0.40 Extract from black 0.10 0.10 0.10 0.10 0.10 0.10 0.10 pepper Flavour preparation — 1.00 — — — — — (application example 1A) Flavour preparation — — 1.00 — — — — (application example 1B) Flavour preparation — — — 1.00 — — — (application example 1C) Flavour preparation — — — — 1.00 — — (application example 1D) Flavour preparation — — — — — 1.00 — (application example 1E) Flavour preparation — — — — — — 1.00 (application example 1G) Total 100 100 100 100 100 100 100 *not according to the invention - A=Reference preparation
- B, C, D, E=Preparations according to the invention
- All specifications are in % w/w.
-
Ingredient A* B C D E F G Sodium glutamate 3.50 3.50 3.50 3.50 3.50 3.50 3.50 Cheese powder 10.00 10.00 10.00 10.00 10.00 10.00 10.00 Garlic powder 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Whey powder 38.86 36.86 36.86 36.86 36.86 36.86 36.86 Spice extract oil 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Bell pepper powder 9.80 9.80 9.80 9.80 9.80 9.80 9.80 Cooking salt 21.00 21.00 21.00 21.00 21.00 21.00 21.00 Tomato powder 9.00 9.00 9.00 9.00 9.00 9.00 9.00 Dry flavouring 2.50 2.50 2.50 2.50 2.50 2.50 2.50 Silicon dioxide 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Vegetable oil 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Onion powder 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Cream flavour concentrate 0.03 0.03 0.03 0.03 0.03 0.03 0.03 Cheese flavouring 0.03 0.03 0.03 0.03 0.03 0.03 0.03 Tomato flavour concentrate 0.04 0.04 0.04 0.04 0.04 0.04 0.04 Spray-dried composition according to — 2.00 — — — application example 2A Spray-dried composition according to — — 2.00 — — application example 2B Spray-dried composition according to — — — 2.00 — application example 2C Spray-dried composition according to — — — — 2.00 application example 2D Spray-dried composition according to 2.00 application example 2E Spray-dried composition according to 2.00 application example 2H Total 100 100 100 100 100 100 100 *not according to the invention - 6 g of the spice mix was sprinkled on 94 g of potato crisps.
-
-
Usage in % w/w Ingredient A B Green tea concentrate 18.00 18.00 1% solution 0.40 — Ethyl-2-(4-hydroxy-3- methoxyphenyl) acetate (17) 1% solution — 0.015 3-phenylpropyl 2-(4-hydroxy- 3-methoxyphenyl) acetate (22) Demineralised water 81.60 81.985 Total 100 100 - The green tea concentrate is mixed with the 1% solution of ethyl-2-(4-hydroxy-3-methoxy-phenyl)acetate (17) in propylene glycol in the case of drink A, and with the 1% solution 3-phenylpropyl-2-(4-hydroxy-3-methoxyphenyl) acetate (22) in propylene glycol in the case of drink B. Subsequently, it is filled with demineralised water and mixed again thoroughly. The product is filtered afterwards, packaged ready-to-use, and sterilised at 118° C. The taste of the drinks A and B is evaluated by a panel of educated testers as clearly preferred to the non-flavoured green tea concentrate. The bitterness and the astringency is reduced by the addition of the compounds according to the invention.
- The esters of homovanillic acid were pre-dissolved in 10% or 1% ethanol, respectively. Black tea extract was dissolved in water and stirred together with sugar, a flavour preparation (peach taste), as well as the ethanol solutions of the esters of homovanillic acid in a beaker.
-
Usage in % w/w Ingredient A B C D Black tea extract 1.40 1.40 1.40 1.40 Water 89.5 89.51 89.51 89.515 Flavour preparation (peach 0.67 0.67 0.67 0.67 type) Sugar 7 7 7 7 Citric acid (crystalline) 1.20 1.20 1.20 1.20 Ascorbic acid 0.20 0.20 0.20 0.20 10% in ethanol 0.03 — — — Ethyl-2-(4-hydroxy-3- methoxphenyl) acetate (17) 10% in ethanol — 0.02 — — Propyl-2-(4-hydroxy-3- methoxphenyl) acetate (18) 1% in ethanol — — 0.02 — 3-phenylpropyl 2-(4- hydroxy-3-methoxyphenyl) acetate (22) 1% in ethanol — — — 0.015 [(E)-cinnamyl]-2-(4- hydroxy-3-methoxyphenyl) acetate (2) Total 100 100 100 100 - A=Reference preparation
- B, C, D=Preparations according to the invention
- All specifications are in % w/w.
-
Ingredient A* B C D E F Fat powder 8.77 8.77 8.77 8.77 8.77 8.77 Sodium glutamate 8.77 8.77 8.77 8.77 8.77 8.77 Yeast extract powder 12.28 12.28 12.28 12.28 12.28 12.28 Cooking salt 29.83 29.83 29.83 29.83 29.83 29.83 Maltodextrin 37.28 36.68 36.98 36.88 37.265 37.27 Natural vegetable extract 3.07 3.07 3.07 3.07 3.07 3.07 Ethyl-2-(4-hydroxy-3- — 0.60 — — — — methoxphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — — 0.30 — . — methoxphenyl) acetate (19) Isobutyl-2-(4-hydroxy-3- — — — 0.40 — — methoxy-phenyl) acetate (9) 3-phenylpropyl 2-(4- — — — — 0.015 — hydroxy- 3-methoxphenyl) acetate (22) [(E)-cinnamyl]-2-(4- — — — — — 0.01 hydroxy-3- methoxphenyl) acetate (2) Total 100 100 100 100 100 100 *not according to the invention - 1,000 ml of hot water was poured onto 15 g of the respective powder mixture.
- A=Reference preparation
- B, C, D, E=Preparations according to the invention
- All specifications are in % w/w.
-
Ingredient A* B C D E F G Potato starch 20.00 20.00 20.00 20.00 20.00 20.00 20.00 Fat powder 25.00 25.00 25.00 25.00 25.00 25.00 25.00 Lactose 20.00 20.00 20.00 20.00 20.00 20.00 20.00 Maltodextrin 11.73 11.65 11.68 11.67 11.66 11.727 11.725 Cooking salt 8.00 8.00 8.00 8.00 8.00 8.00 8.00 Sodium glutamate 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Spinach powder 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Green leek powder 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Citric acid in powder 0.30 0.30 0.30 0.30 0.30 0.30 0.30 form Hardened vegetable fat 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Freeze-dried leek 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Chicken flavouring 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Spice mix of “green leek 2.00 2.00 2.00 2.00 2.00 2.00 2.00 powder” type Spice mix of “cooked 0.60 0.60 0.60 0.60 0.60 0.60 0.60 onion” type Yeast spice mix of 0.30 0.30 0.30 0.30 0.30 0.30 0.30 “vegetable stock powder” type 0.07 0.07 0.07 0.07 0.07 0.07 0.07 Turmeric extract Ethyl-2-(4-hydroxy-3- — 0.08 — — 0.06 methoxphenyl) acetate (17) Propyl-2-(4-hydroxy-3- — — 0.05 — — methoxphenyl) acetate (18) Isobutyl-2-(4-hydroxy-3- — — — 0.06 0.01 methoxphenyl) acetate (8) 3-phenylpropyl 2-(4- 0.003 hydroxy-3- methoxyphenyl) acetate (22) [(E)-cinnamyl]-2-(4- 0.005 hydroxy-3- methoxyphenyl) acetate (2) Total 100 100 100 100 100 100 100 - 100 ml of hot water was poured onto 5 g of the respective powder mixture to obtain a ready-to-eat soup.
- A=Reference preparation
- B, C, D, E=Preparations according to the invention
- All specifications are in % w/w.
-
Ingredient A* B C D E F G Starch 16.16 16.06 16.12 16.13 16.11 16.155 16.157 Cooking salt 7.00 7.00 7.00 7.00 7.00 7.00 7.00 Refined saccharose 3.20 3.20 3.20 3.20 3.20 3.20 3.20 Sodium glutamate 3.20 3.20 3.20 3.20 3.20 3.20 3.20 Sodium inosinate/ 0.80 0.80 0.80 0.80 0.80 0.80 0.80 sodium guanylate in a ratio of 1:1 Acid-hydrolysed 8.00 8.00 8.00 8.00 8.00 8.00 8.00 vegetable protein Fat powder 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Spray-dried vegetable 1.00 1.00 1.00 1.00 1.00 1.00 1.00 fat Freeze-dried chicken 2.00 2.00 2.00 2.00 2.00 2.00 2.00 meat in pieces Soup noodles 32.00 32.00 32.00 32.00 32.00 32.00 32.00 Maltodextrin 12.00 12.00 12.00 12.00 12.00 12.00 12.00 Freeze-dried Chinese 4.60 4.60 4.60 4.60 4.60 4.60 4.60 vegetables Chicken flavouring 8.00 8.00 8.00 8.00 8.00 8.00 8.00 Food dye riboflavin 0.04 0.04 0.04 0.04 0.04 0.04 0.04 Ethyl-2-(4-hydroxy-3- — 0.10 — — 0.04 — — methoxyphenyl) acetate (17) Butyl-2-(4-hydroxy-3- — — 0.04 — 0.01 — — methoxyphenyl) acetate (19) Hexyl-2-(4-hydroxy-3- — — — 0.031 — — — methoxyphenyl) acetate (21) 3-phenylpropyl 2-(4- — — — — — 0.005 — hydroxy-3- methoxyphenyl) acetate (22) [(E)-cinnamyl]-2-(4- — — — — — — 0.003 hydroxy-3- methoxyphenyl) acetate (2) Total 100 100 100 100 100 100 100 *not according to the invention - 4.60 g of the respective powder mixture was boiled in 100 ml of water for 10 minutes to obtain a ready-to-eat soup.
- All specifications in % w/w, unless specified otherwise.
- A=Dark chocolate reference preparation
- B=Calorie-reduced dark chocolate
- C=Calorie-reduced dark chocolate
- D=Calorie-reduced dark chocolate
- E=Calorie-reduced whole milk chocolate
- F=Dark chocolate
- G=Dark chocolate
-
Ingredient A* B C D E F G Cocoa butter 14.49 12.99 13.49 9.48 14.00 14.49 14.50 Cocoa paste 41.00 39.00 42.00 44.00 23.00 41.00 41.00 Erythritol — 47.45 — — — — — Crystalline maltitol — — — 23.00 — — Inulin — — — 23.00 — — Sorbitol — — 44.00 — — — — Lactitol — — — — 38.55 — — Polydextrose — — — — 9.70 — — Whole milk powder — — — — 14.00 — — Sucrose 43.98 — — — — 44.00 44.00 Lecithin 0.48 0.48 0.40 0.48 0.50 0.48 0.48 Vanillin 0.02 0.02 0.02 0.02 0.20 0.02 0.02 Aspartame — 0.03 0.06 — 0.03 — — Capsicum extract (1,000,000 0.03 0.02 0.02 0.01 — 0.01 — SHU) Hexyl-2-(4-hydroxy-3- — 0.01 — 0.01 0.01 — — methoxphenyl) acetate (21) Butyl-2-(4-hydroxy-3- — — 0.01 — 0.01 — — methoxphenyl) acetate (19) 3-phenylpropyl 2-(4-hydroxy-3- — — — — — 0.001 — methoxphenyl) acetate (22) [(E)-cinnamyl]-2-(4-hydroxy-3- — — — — — — 0.002 methoxphenyl) acetate (2) Total 100 100 100 100 100 100 100 *not according to the invention - The effects found in the above application examples can be transferred to all products of the respective product category, i.e. particulary to toothpastes, chewing gums, mouthwashes, lozenges, gelatine capsules, chewing sweets and tea in bags, if applicable by modifications which can be easily carried out by a person skilled in the art. For the person skilled in the art, it is readily apparent on the basis of the present description that the compounds and mixtures according to the invention can easily be interchanged with one another maybe with minor modifications. This means that the compound according to the invention used in the products of the application examples must also be regarded as a placeholder for the other compounds and mixtures according to the invention. Also the concentration of the used compound or mixture according to the invention is adjustable as can be easily recognised by a person skilled in the art. In addition, the other product-specific components in the respective application example can also easily be interchanged with or supplemented by further product-specific components as can be easily understood by the person skilled in the art. A variety of such product-specific components are disclosed in the above description.
Claims (20)
1. A composition comprising one or more compounds, or physiologically acceptable salts thereof, having a structure represented by formula (I):
wherein
(i) R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms, and
R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue;
or
(ii) R1 and R3 along with the carbon atoms linking them form a cyclohexyl ring,
R2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
R4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue,
wherein the compounds of formula (I) are one or several different compounds of formula and/or physiologically acceptable salts thereof, where the phenolic hydroxy group in formula (I) is deprotonated, respectively.
2. The composition of claim 1 , wherein the one or more compounds are:
a flavouring and/or pungent substance that creates a warm and/or pungent effect, and/or
a flavouring for reducing or masking an unpleasant taste sensation,
and/or
a flavouring for increasing a pleasant taste sensation.
3. The composition of claim 1 , wherein one, several or all of the compounds of formula (I), independently of each other, have:
(i) R1 and R2 being, independently of each other, a hydrogen atom or methyl group,
R3 and R4 being, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue; or
(ii) Formula (I) corresponds to the following formula (Ia)
4. The composition of claim 1 , wherein one, several or all of the one or more compounds of formula (I), independently of each other, have:
R1 and R2 being a hydrogen atom, respectively,
R3 being a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue,
R4 being a hydrogen atom.
5. The composition of claim 1 , wherein one or several or all the compounds of formula (I) is or are selected from the group consisting of:
2-phenylethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (1)
6. The composition of claim 1 formulated in a pharmaceutical preparation, a preparation serving nutrition, oral hygiene, wherein the total quantity of the one or more compound(s) of formula (I), and/or salt(s) thereof in the preparation is sufficient to:
(a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation is used or consumed, and/or
(b) reduce or mask an unpleasant taste sensation, and/or
(c) increase a pleasant taste sensation.
7. The composition of claim 6 , wherein the total amount of the compound(s) of formula (I), and/or salt(s) thereof in the preparation is not sufficient to create a warm or pungent effect on the tongue or in the oral cavity, but is sufficient to mask or reduce an unpleasant taste sensation of an unpleasantly tasting substance or mixture of substances.
8. A composition comprising one or more compounds in accordance with formula (I), or a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or a mixture comprising one or several different compounds of formula (I) and/or one or several physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or a plurality of different compounds of formula (I) and/or physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively,
wherein
(i) R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue,
or
(ii) R1 and R3 along with the carbon atoms linking them form a cyclohexyl ring, which optionally is substituted with an additional residue R5, wherein R5 is an alkyl residue with 1-2 carbon atoms,
R2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
R4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue,
wherein
R1, R2, R3 and R4 do not all represent hydrogen atoms,
and
in case R1, R2 and R4 represent hydrogen, R3 neither represents a linear alkyl residue with 1, 2, 4 or 5 carbon atoms nor 2-propyl or phenyl, methylphenyl,
and
in case R2, R3 and R4 represent hydrogen, R1 does not represent a linear alkyl residue with 1 or 2 carbon atoms,
R3 and R4 do not represent methyl, if R1 and R2 represent hydrogen,
and
R1 and R2 do not represent methyl, if R3 and R4 represent hydrogen.
9. The composition of claim 8 , wherein one or several or all of the one or more compounds of formula (I) in the mixture is or are selected from:
[(E)-cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2)
pentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (20)
10. A flavour composition comprising the composition of claim 1 , wherein
the total quantity of the compound(s) of formula and/or salt(s) thereof, in the flavour composition is in the range of 100-100,000 mg/kg, based on the total weight of the flavour composition.
11. The flavour composition of claim 10 , additionally comprising one or several further flavours, which do not correspond to formula (I) selected from:
a) warming or pungent substances;
b) substances perceivable as pungent or biting;
c) alkamides described as causing a tingling sensation;
d) substances with physiological cooling effect;
e) substances having astringent effect.
12. The flavour composition of claim 10 , additionally comprising one or several substances which do not correspond to formula (I), with an unpleasant, in particular, bitter taste, or an astringent, bitter, dry, dusty, floury, chalky and/or metallic touch, selected from:
f) xanthin alkaloids, xanthines, caffeine, theobromine, theophylline and methylxanthine, alkaloids, quinine, brucine, strychnine, nicotine, phenolic glycosides, salicin, arbutin, flavonoid glycosides neohespereidin, hesperidin, naringin, quercitrin, rutin, hyperosid, quercetin 3-O-glucoside, myricetin-3-O-glycosides, chalcones or chalcone glycosides, phloridzine, phloridzinxyloside, hydrolyzable tannins, gallic or ellagic acid esters of carbohydrates, pentagalloyl glucose, tannic acids, non-hydrolyzable tannins, flavones, quercetin, taxifolin, myricetin, phenols, salicin, polyphenols, gamma-oryzanol, caffeic acid or esters thereof, chlorogenic acid and isomers, terpenoid bitter and tanning agents, limonoides, limonin or nomilin from citrus fruits, lupolones and humulones from hops, iridoids, secoiridoids, absinthin from wormwood, amarogentin from gentian, metallic salts, potassium, magnesium and calcium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, sodium sulphate, magnesium sulphate, aluminium salts, zinc salts, tin salts, iron (II) salts, iron (III) salts, chromium (II) picolinate), active pharmaceutical ingredients, fluoroquinolone antibiotics, paracetamol, aspirin, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], guaifenesin, vitamins, vitamin H, vitamins from the B-series, such as vitamin B1, B2, B6, B12, niacin, pantothenic acid, denatonium benzoate, sucralose octaacetate, iron salts, aluminium salts, zinc salts, urea, unsaturated fatty acids, especially unsaturated fatty acids in emulsions, amino acids with a bitter/astringent taste, leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine and peptides or proteins with a bitter/astringent taste, peptides with an amino acid from the group of leucine, isoleucine, valine, tryptophan, proline or phenylalanine at the N- or C-terminus, saponins, soya saponins, isoflavonoids, genistein, daidzein, genistein, daidzin, their glycosides and acylated glycosides;
g) substances with a non-unpleasant primary taste, sweet, salty, spicy, sour and/or smell selected from the group of sweeteners or sugar substitutes, potassium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, aspartame, acesulfame K, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, stevioside, rebaudiosides, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside X, rubusoside, hernandulcin, thaumatin, miculin, glycyrrhizin, glycyrrhetinic acid, balansin A or balansin B, or derivatives thereof, cyclamate or the pharmaceutically acceptable salts of the above-mentioned compounds.
13. A pharmaceutical preparation, preparation serving nutrition, oral hygiene, comprising the favour composition of claim 12 wherein,
the total quantity of the one or more compound(s) in accordance with formula (I), and/or salt(s), thereof in the preparation is in the range of 0.1-1,000 mg/kg, based on the total weight of the preparation.
14. A pharmaceutical preparation, preparation serving nutrition, oral hygiene of claim 13 , additionally comprising
one or several usual base materials, auxiliaries and additives in a quantity of 10-80% w/w, based on the total weight of the preparation,
and/or
water in a quantity of 5-80% w/w, based on the total weight of the preparation.
15. A pharmaceutical preparation, preparation serving nutrition, oral hygiene of claim 13 , wherein the total quantity of the compound(s) of formula (I), and/or salt(s), thereof in the preparation is sufficient to:
(a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation is used or consumed,
and/or
(b) reduce or mask an unpleasant taste sensation,
and/or
(c) increase a pleasant taste sensation.
16. A method for producing a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, comprising:
i) providing
a mixture that includes the composition of claim 8 ,
wherein
the total quantity of compound(s) of formula (I) and/or salt(s) thereof is selected such that the total quantity in the preparation to be made is in the range of 0.1-1,000 mg/kg, based on the total weight of the preparation,
ii) providing of one or several further components of the preparation to be made, and
iii) contacting or mixing the further components provided in step ii) with the component(s) provided in step i) in a sensorially effective quantity.
17. A method for imparting a warm and/or pungent effect, for reducing or masking an unpleasant taste sensation, and/or for increasing a pleasant taste sensation, the method comprising:
adding a sufficient amount of one or more compounds of formula (I), or physiologically acceptable salt thereof, to a preparation that comes into contact with an oral cavity, wherein the compounds of formula (I) are represented by the following structure:
wherein
(i) R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms, and
R3 and R4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue; or
(ii) R1 and R3 along with the carbon atoms linking them form a cyclohexyl ring,
R2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
R4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue,
wherein the one or more compounds in accordance with formula I being one or several different compounds of formula (I), and/or physiologically acceptable salts thereof, where the phenolic hydroxy group in formula (I) is deprotonated, respectively.
18. The method of claim 17 , wherein one or more of the compounds of formula (I), independently of each other, have R1 and R2 being, independently of each other, a hydrogen atom or methyl group, R3 and R4 being, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue.
20. The method of claim 17 , wherein one or more of the compounds of formula (I), independently of each other, have:
R1 and R2 being a hydrogen atom, respectively,
R3 being a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue,
R4 being a hydrogen atom.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14165020.0A EP2932858A1 (en) | 2014-04-16 | 2014-04-16 | Homovanillic acid esters, in particular for achieving an impression of heat and/or spiciness |
EP14165020.0 | 2014-04-16 | ||
PCT/EP2015/058004 WO2015158677A1 (en) | 2014-04-16 | 2015-04-14 | Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2015/058004 A-371-Of-International WO2015158677A1 (en) | 2014-04-16 | 2015-04-14 | Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US17/077,133 Continuation US11535584B2 (en) | 2014-04-16 | 2020-10-22 | Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation |
Publications (1)
Publication Number | Publication Date |
---|---|
US20190276386A1 true US20190276386A1 (en) | 2019-09-12 |
Family
ID=50479146
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/345,921 Abandoned US20190276386A1 (en) | 2014-04-16 | 2015-04-14 | Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness |
US17/077,133 Active 2035-04-16 US11535584B2 (en) | 2014-04-16 | 2020-10-22 | Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US17/077,133 Active 2035-04-16 US11535584B2 (en) | 2014-04-16 | 2020-10-22 | Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation |
Country Status (7)
Country | Link |
---|---|
US (2) | US20190276386A1 (en) |
EP (2) | EP2932858A1 (en) |
JP (1) | JP6712549B2 (en) |
KR (1) | KR102498596B1 (en) |
AU (1) | AU2015248962B2 (en) |
PH (1) | PH12016502050B1 (en) |
WO (1) | WO2015158677A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190169111A1 (en) * | 2016-08-04 | 2019-06-06 | Takasago International Corporation | Warming sensation compounds |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6794758B2 (en) * | 2015-10-21 | 2020-12-02 | 大正製薬株式会社 | Oral liquid pharmaceutical composition |
CN105779217A (en) * | 2016-02-01 | 2016-07-20 | 李滋星 | Gingerol biological beverage and preparation method thereof |
US20190127314A1 (en) * | 2016-03-23 | 2019-05-02 | Symrise Ag | Homovanillic acid ester for reducing or inhibiting fatty acid absorption in the small intestine |
EP3687311A1 (en) * | 2017-09-27 | 2020-08-05 | Symrise AG | Amides for generating a trigeminal effect |
WO2020015816A1 (en) | 2018-07-16 | 2020-01-23 | Symrise Ag | Composition for substituting sugar in baked goods |
US20220071933A1 (en) | 2019-01-18 | 2022-03-10 | Symrise Ag | Combination remedy |
KR20220024533A (en) * | 2019-06-13 | 2022-03-03 | 시므라이즈 아게 | Cooling Preparation |
US20230167045A1 (en) | 2020-04-27 | 2023-06-01 | Symrise Ag | Method for producing esters of homovanillic acid |
CN114601743B (en) * | 2022-03-22 | 2022-09-13 | 宝萃生物科技有限公司 | Dihydromyricetin liposome and preparation and application thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090258128A1 (en) * | 2006-09-14 | 2009-10-15 | Tsukasa Saito | Hydrogenated oil flavor-imparting agent |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2168974A (en) * | 1984-12-20 | 1986-07-02 | Procter & Gamble | Compounds and compositions having anti-inflammatory activity |
DE10226942A1 (en) | 2002-06-17 | 2003-12-24 | Symrise Gmbh & Co Kg | Use of mandelic acid alkyl amides as flavorings |
DE10227462A1 (en) | 2002-06-20 | 2004-01-08 | Symrise Gmbh & Co. Kg | Production of cis-pellitor and use as a flavoring |
GB0221697D0 (en) | 2002-09-18 | 2002-10-30 | Unilever Plc | Novel compouds and their uses |
DE10253331A1 (en) | 2002-11-14 | 2004-06-03 | Symrise Gmbh & Co. Kg | Use of trans-pellitori as a flavoring |
WO2006111476A1 (en) | 2005-04-21 | 2006-10-26 | Symrise Gmbh & Co. Kg | Process for the separation and sensory evaluation of flavours |
WO2007111276A1 (en) | 2006-03-24 | 2007-10-04 | Ajinomoto Co., Inc. | Novel ester derivative and use thereof |
US8778987B2 (en) | 2007-03-13 | 2014-07-15 | Symrise Ag | Use of 4-hydroxychalcone derivatives for masking an unpleasant taste |
WO2009065239A1 (en) | 2007-11-19 | 2009-05-28 | Givaudan Sa | Compositions and their use |
GB0911000D0 (en) | 2009-06-25 | 2009-08-12 | Givaudan Sa | Compounds |
DE102010002558A1 (en) | 2009-11-20 | 2011-06-01 | Symrise Ag | Use of physiological cooling agents and agents containing such agents |
-
2014
- 2014-04-16 EP EP14165020.0A patent/EP2932858A1/en not_active Withdrawn
-
2015
- 2015-04-14 AU AU2015248962A patent/AU2015248962B2/en active Active
- 2015-04-14 KR KR1020167032034A patent/KR102498596B1/en active IP Right Grant
- 2015-04-14 WO PCT/EP2015/058004 patent/WO2015158677A1/en active Application Filing
- 2015-04-14 EP EP15718467.2A patent/EP3142499B1/en active Active
- 2015-04-14 JP JP2016563026A patent/JP6712549B2/en not_active Expired - Fee Related
- 2015-04-14 US US16/345,921 patent/US20190276386A1/en not_active Abandoned
-
2016
- 2016-10-14 PH PH12016502050A patent/PH12016502050B1/en unknown
-
2020
- 2020-10-22 US US17/077,133 patent/US11535584B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090258128A1 (en) * | 2006-09-14 | 2009-10-15 | Tsukasa Saito | Hydrogenated oil flavor-imparting agent |
Non-Patent Citations (1)
Title |
---|
Delgado de la Torre et al J Sci Food Agric 94 504-514 (published 6/21/2013); of record * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190169111A1 (en) * | 2016-08-04 | 2019-06-06 | Takasago International Corporation | Warming sensation compounds |
US11059771B2 (en) * | 2016-08-04 | 2021-07-13 | Takasago International Corporation | Warming sensation compounds |
Also Published As
Publication number | Publication date |
---|---|
JP6712549B2 (en) | 2020-06-24 |
PH12016502050A1 (en) | 2017-01-09 |
KR20160145734A (en) | 2016-12-20 |
US20210040028A1 (en) | 2021-02-11 |
AU2015248962A1 (en) | 2016-11-03 |
US11535584B2 (en) | 2022-12-27 |
EP3142499B1 (en) | 2019-10-30 |
EP2932858A1 (en) | 2015-10-21 |
JP2017514468A (en) | 2017-06-08 |
KR102498596B1 (en) | 2023-02-10 |
WO2015158677A1 (en) | 2015-10-22 |
AU2015248962B2 (en) | 2019-03-21 |
PH12016502050B1 (en) | 2017-01-09 |
EP3142499A1 (en) | 2017-03-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11535584B2 (en) | Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation | |
US10165791B2 (en) | Use of rubusoside for reducing or suppressing certain unpleasant taste impressions | |
EP2008530B1 (en) | Aroma composition for reducing or suppressing unwanted bitter and astringent impressions | |
US8063107B2 (en) | Use of trans-pellitorin as flavor substance | |
US9131719B2 (en) | Use of certain neoflavonoids for intensifying and/or producing a sensory impression of sweetness | |
EP1868452B1 (en) | Hydroxydeoxybenzoins and the use thereof to mask a bitter taste | |
EP1901618B1 (en) | Hydroxyphenylalkadiones and their use for masking bitter taste and/or for intensifying sweet taste | |
US8828469B2 (en) | Use of alkamides for masking an unpleasant flavor | |
US20070202188A1 (en) | Use of alkene carboxlic acid n alkylamides as flavouring agents | |
US20080214675A1 (en) | Hydroxybenzoic Acid Amides and the Use Thereof For Masking Bitter Taste | |
US20100292175A1 (en) | Use of hydroxyflavan derivatives for taste modification | |
JP2017514468A5 (en) | ||
JP2008505868A (en) | Use of alkoxyalkanoic acid amides and in particular novel alkoxyalkanoic acid amides as flavoring agents | |
EP3687311A1 (en) | Amides for generating a trigeminal effect | |
EP3510010B1 (en) | Taste modulating aldehyde | |
DE102006006123A1 (en) | Use of alk-2-en-4-acidamide compounds e.g. as aroma materials, for producing tingling sensation or cooling effect and/or stimulation of saliva in mouth, for mouth hygiene and in oral pharmaceutical preparation | |
DE202004021058U1 (en) | Use of N-alkyl alkenoamides as sharp-tasting substances, for inducing a temperature-independent feeling of warmth, for enhancing or imitating the flavor of ethanol or for inducing salivation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: FINAL REJECTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: ADVISORY ACTION MAILED |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |