CA2634869C - Compositions providing a sensation substantially similar to that provided by menthol - Google Patents
Compositions providing a sensation substantially similar to that provided by menthol Download PDFInfo
- Publication number
- CA2634869C CA2634869C CA2634869A CA2634869A CA2634869C CA 2634869 C CA2634869 C CA 2634869C CA 2634869 A CA2634869 A CA 2634869A CA 2634869 A CA2634869 A CA 2634869A CA 2634869 C CA2634869 C CA 2634869C
- Authority
- CA
- Canada
- Prior art keywords
- menthol
- amount
- composition
- cooling
- compositions
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 258
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 title claims abstract description 169
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title claims abstract description 169
- 229940041616 menthol Drugs 0.000 title claims abstract description 167
- 230000035807 sensation Effects 0.000 title claims abstract description 76
- 235000015218 chewing gum Nutrition 0.000 claims abstract description 73
- 235000009508 confectionery Nutrition 0.000 claims abstract description 69
- 210000004400 mucous membrane Anatomy 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims description 115
- NFLGAXVYCFJBMK-UHFFFAOYSA-N isomenthone Natural products CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 claims description 78
- 235000019615 sensations Nutrition 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 68
- 229940112822 chewing gum Drugs 0.000 claims description 62
- 239000002826 coolant Substances 0.000 claims description 56
- -1 phellendrene Chemical compound 0.000 claims description 54
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims description 48
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 claims description 46
- 229930007503 menthone Natural products 0.000 claims description 46
- 230000000694 effects Effects 0.000 claims description 38
- NFLGAXVYCFJBMK-IUCAKERBSA-N (-)-isomenthone Chemical compound CC(C)[C@@H]1CC[C@H](C)CC1=O NFLGAXVYCFJBMK-IUCAKERBSA-N 0.000 claims description 32
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 claims description 26
- BLILOGGUTRWFNI-UHFFFAOYSA-N Monomenthyl succinate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O BLILOGGUTRWFNI-UHFFFAOYSA-N 0.000 claims description 25
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims description 24
- 229940095045 isopulegol Drugs 0.000 claims description 24
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 22
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 22
- 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 claims description 22
- 229960005233 cineole Drugs 0.000 claims description 22
- 230000009471 action Effects 0.000 claims description 21
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 20
- 241000723346 Cinnamomum camphora Species 0.000 claims description 20
- 229930008380 camphor Natural products 0.000 claims description 20
- 229960000846 camphor Drugs 0.000 claims description 20
- 235000019640 taste Nutrition 0.000 claims description 18
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 10
- KRCZYMFUWVJCLI-UHFFFAOYSA-N Dihydrocarveol Chemical compound CC1CCC(C(C)=C)CC1O KRCZYMFUWVJCLI-UHFFFAOYSA-N 0.000 claims description 10
- OMSUIQOIVADKIM-UHFFFAOYSA-N ethyl 3-hydroxybutyrate Chemical compound CCOC(=O)CC(C)O OMSUIQOIVADKIM-UHFFFAOYSA-N 0.000 claims description 10
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 8
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 8
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 8
- 229940116229 borneol Drugs 0.000 claims description 8
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 8
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 8
- 229930006735 fenchone Natural products 0.000 claims description 8
- 239000000834 fixative Substances 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 6
- HTHKKWZMEVJWQF-UHFFFAOYSA-N 2-amino-4-methyl-n-naphthalen-2-ylpentanamide;hydron;chloride Chemical compound Cl.C1=CC=CC2=CC(NC(=O)C(N)CC(C)C)=CC=C21 HTHKKWZMEVJWQF-UHFFFAOYSA-N 0.000 claims description 5
- CKZXONNJVHXSQM-UHFFFAOYSA-N Ledol Natural products CC(C)C1CCC(C)(O)C2C3CC(C)CC123 CKZXONNJVHXSQM-UHFFFAOYSA-N 0.000 claims description 5
- 244000178231 Rosmarinus officinalis Species 0.000 claims description 5
- TUWWTQRJWLLWJE-UHFFFAOYSA-N Viridiflorol Natural products CC1CCC2C1C3C(CCC2(O)O)C3(C)C TUWWTQRJWLLWJE-UHFFFAOYSA-N 0.000 claims description 5
- 229940062909 amyl salicylate Drugs 0.000 claims description 5
- 235000005687 corn oil Nutrition 0.000 claims description 5
- 229930007024 dihydrocarveol Natural products 0.000 claims description 5
- WGTRJVCFDUCKCM-UHFFFAOYSA-N ent-ledene Natural products C1CC2C(C)(C)C2C2C(C)CCC2=C1C WGTRJVCFDUCKCM-UHFFFAOYSA-N 0.000 claims description 5
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 claims description 5
- YERFHJZYNMRVLO-UHFFFAOYSA-N hexyl pentanoate Chemical compound CCCCCCOC(=O)CCCC YERFHJZYNMRVLO-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001699 mentha arvensis leaf oil Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000010670 sage oil Substances 0.000 claims description 5
- AYXPYQRXGNDJFU-IMNVLQEYSA-N viridiflorol Chemical group [C@@H]1([C@@](CC[C@@H]2[C@H]3C2(C)C)(C)O)[C@H]3[C@H](C)CC1 AYXPYQRXGNDJFU-IMNVLQEYSA-N 0.000 claims description 5
- 229930006731 (1S,4R)-fenchone Natural products 0.000 claims description 4
- HSCVIIISAAEVQT-UHFFFAOYSA-N Propyl 2-furoate Chemical compound CCCOC(=O)C1=CC=CO1 HSCVIIISAAEVQT-UHFFFAOYSA-N 0.000 claims description 4
- 244000182022 Salvia sclarea Species 0.000 claims description 4
- 235000002911 Salvia sclarea Nutrition 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000005770 Eugenol Substances 0.000 claims description 3
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 3
- 229960002217 eugenol Drugs 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 244000166124 Eucalyptus globulus Species 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 230000001766 physiological effect Effects 0.000 abstract description 15
- 239000000796 flavoring agent Substances 0.000 description 65
- 239000003765 sweetening agent Substances 0.000 description 55
- 235000003599 food sweetener Nutrition 0.000 description 48
- 235000019634 flavors Nutrition 0.000 description 45
- 239000000047 product Substances 0.000 description 41
- 235000000346 sugar Nutrition 0.000 description 34
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 32
- 239000006188 syrup Substances 0.000 description 30
- 235000020357 syrup Nutrition 0.000 description 29
- 239000011248 coating agent Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 21
- 239000003086 colorant Substances 0.000 description 18
- 235000013355 food flavoring agent Nutrition 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 239000000654 additive Substances 0.000 description 16
- 239000004615 ingredient Substances 0.000 description 16
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 14
- 235000019477 peppermint oil Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- 235000011187 glycerol Nutrition 0.000 description 13
- VUNOFAIHSALQQH-UHFFFAOYSA-N Ethyl menthane carboxamide Chemical compound CCNC(=O)C1CC(C)CCC1C(C)C VUNOFAIHSALQQH-UHFFFAOYSA-N 0.000 description 12
- 235000013336 milk Nutrition 0.000 description 12
- 239000008267 milk Substances 0.000 description 12
- 210000004080 milk Anatomy 0.000 description 12
- 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 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 239000000806 elastomer Substances 0.000 description 11
- 210000003491 skin Anatomy 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 235000013305 food Nutrition 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000001993 wax Substances 0.000 description 10
- 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 9
- 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 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229920001908 Hydrogenated starch hydrolysate Polymers 0.000 description 8
- 244000299461 Theobroma cacao Species 0.000 description 8
- 230000035597 cooling sensation Effects 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 235000015110 jellies Nutrition 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
- 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 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
- 244000246386 Mentha pulegium Species 0.000 description 7
- 235000016257 Mentha pulegium Nutrition 0.000 description 7
- 235000004357 Mentha x piperita Nutrition 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 235000001727 glucose Nutrition 0.000 description 7
- 235000001050 hortel pimenta Nutrition 0.000 description 7
- 210000000214 mouth Anatomy 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000600 sorbitol Substances 0.000 description 7
- 235000010356 sorbitol Nutrition 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- 235000021092 sugar substitutes Nutrition 0.000 description 7
- 235000019220 whole milk chocolate Nutrition 0.000 description 7
- 244000061176 Nicotiana tabacum Species 0.000 description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical class NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000008274 jelly Substances 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 235000010449 maltitol Nutrition 0.000 description 6
- 239000000845 maltitol Substances 0.000 description 6
- 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 6
- 229940035436 maltitol Drugs 0.000 description 6
- 239000002324 mouth wash Substances 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 150000005846 sugar alcohols Chemical class 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 5
- 239000013543 active substance Substances 0.000 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 description 5
- YZXZAUAIVAZWFN-UHFFFAOYSA-N bis(5-methyl-2-propan-2-ylcyclohexyl) butanedioate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(=O)OC1C(C(C)C)CCC(C)C1 YZXZAUAIVAZWFN-UHFFFAOYSA-N 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 4
- MDVYIGJINBYKOM-IBSWDFHHSA-N 3-[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxypropane-1,2-diol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OCC(O)CO MDVYIGJINBYKOM-IBSWDFHHSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 244000004281 Eucalyptus maculata Species 0.000 description 4
- ZBJCYZPANVLBRK-UHFFFAOYSA-N Menthone 1,2-glyceryl ketal Chemical compound CC(C)C1CCC(C)CC11OC(CO)CO1 ZBJCYZPANVLBRK-UHFFFAOYSA-N 0.000 description 4
- 108010009736 Protein Hydrolysates Proteins 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 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 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 4
- 239000002535 acidifier Substances 0.000 description 4
- 229940095602 acidifiers Drugs 0.000 description 4
- 235000010357 aspartame Nutrition 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000004067 bulking agent Substances 0.000 description 4
- 239000001506 calcium phosphate Substances 0.000 description 4
- 235000013736 caramel Nutrition 0.000 description 4
- 230000001055 chewing effect Effects 0.000 description 4
- 235000019219 chocolate Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 4
- 235000015145 nougat Nutrition 0.000 description 4
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane group Chemical class C1(CCC(CC1)C(C)C)C CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- 235000019222 white chocolate Nutrition 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L27/203—Alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Confectionery (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Seasonings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75352405P | 2005-12-23 | 2005-12-23 | |
| US60/753,524 | 2005-12-23 | ||
| PCT/US2006/049058 WO2007076025A2 (en) | 2005-12-23 | 2006-12-21 | Compositions providing a sensation substantially similar to that provided by menthol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2634869A1 CA2634869A1 (en) | 2007-07-05 |
| CA2634869C true CA2634869C (en) | 2012-03-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2634869A Expired - Fee Related CA2634869C (en) | 2005-12-23 | 2006-12-21 | Compositions providing a sensation substantially similar to that provided by menthol |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20070148283A1 (enExample) |
| EP (2) | EP2478777B1 (enExample) |
| JP (2) | JP5203965B2 (enExample) |
| CN (1) | CN101346073B (enExample) |
| AU (2) | AU2006330915B2 (enExample) |
| BR (1) | BRPI0620328A2 (enExample) |
| CA (1) | CA2634869C (enExample) |
| ES (1) | ES2488634T3 (enExample) |
| PL (1) | PL2478777T3 (enExample) |
| RU (1) | RU2398476C2 (enExample) |
| WO (1) | WO2007076025A2 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8337296B2 (en) | 2001-09-28 | 2012-12-25 | SHFL entertaiment, Inc. | Method and apparatus for using upstream communication in a card shuffler |
| US7764836B2 (en) | 2005-06-13 | 2010-07-27 | Shuffle Master, Inc. | Card shuffler with card rank and value reading capability using CMOS sensor |
| US20070221236A1 (en) * | 2005-10-05 | 2007-09-27 | Cadbury Adams Usa Llc. | Cooling compositions including menthyl esters |
| US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| US7556266B2 (en) | 2006-03-24 | 2009-07-07 | Shuffle Master Gmbh & Co Kg | Card shuffler with gravity feed system for playing cards |
| US8342525B2 (en) * | 2006-07-05 | 2013-01-01 | Shfl Entertainment, Inc. | Card shuffler with adjacent card infeed and card output compartments |
| US8579289B2 (en) | 2006-05-31 | 2013-11-12 | Shfl Entertainment, Inc. | Automatic system and methods for accurate card handling |
| US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| BRPI0819819A2 (pt) * | 2007-11-21 | 2015-05-26 | Procter & Gamble | Preparações, método e kits ùteis para o tratamento de tosse |
| EP2355665A1 (en) * | 2008-11-12 | 2011-08-17 | Kraft Foods Global Brands LLC | Sensate- plated sanding composition and products made therefrom |
| EP2378883B1 (en) * | 2008-12-04 | 2015-12-23 | Intec Pharma Ltd. | Zaleplon gastroretentive drug delivery system |
| AU2010204909B9 (en) * | 2009-01-15 | 2014-02-06 | Intercontinental Great Brands Llc | Compositions and methods for the treatment of throat discomfort |
| US8967621B2 (en) | 2009-04-07 | 2015-03-03 | Bally Gaming, Inc. | Card shuffling apparatuses and related methods |
| WO2010133645A2 (en) * | 2009-05-20 | 2010-11-25 | Givaudan Sa | Menthol replacement |
| WO2010137938A1 (en) * | 2009-05-28 | 2010-12-02 | Yee Cheng Kong | Anti mosquito confectionary |
| US9446267B2 (en) * | 2009-10-06 | 2016-09-20 | Symrise Ag | Products comprising a flavoring agent composition |
| US20110189366A1 (en) * | 2010-01-29 | 2011-08-04 | PepsiCo North America | Method for modifying taste with essential oil fractions |
| AU2011268274A1 (en) * | 2010-06-18 | 2013-01-10 | Wm. Wrigley Jr. Company | Chewing gum containing combinations of physiological cooling agents |
| CA2805411C (en) * | 2010-06-18 | 2016-05-17 | Wm. Wrigley Jr. Company | Chewing gum products containing ethyl ester of n-[[5-methyl-2-(1-methylethyl)-cyclohexyl] carbonyl] glycine |
| JP5828658B2 (ja) * | 2011-03-31 | 2015-12-09 | 小林製薬株式会社 | 経口消臭組成物 |
| US8485527B2 (en) | 2011-07-29 | 2013-07-16 | Savant Shuffler LLC | Card shuffler |
| BR102012033020A2 (pt) | 2011-12-22 | 2015-10-20 | Int Flavors & Fragrances Inc | composições para aumento da sensação de frescor |
| GB2499218A (en) | 2012-02-08 | 2013-08-14 | Rumenco Ltd | Production of animal feed supplement using a thin film processor |
| CN111084419B (zh) | 2012-04-30 | 2023-03-17 | 菲利普莫里斯生产公司 | 具有凉爽剂包络物的吸烟制品烟嘴 |
| US8960674B2 (en) | 2012-07-27 | 2015-02-24 | Bally Gaming, Inc. | Batch card shuffling apparatuses including multi-card storage compartments, and related methods |
| US9511274B2 (en) | 2012-09-28 | 2016-12-06 | Bally Gaming Inc. | Methods for automatically generating a card deck library and master images for a deck of cards, and a related card processing apparatus |
| WO2014054737A1 (ja) * | 2012-10-05 | 2014-04-10 | 小川香料株式会社 | 粉末状清涼剤組成物 |
| US20150126464A1 (en) * | 2013-01-21 | 2015-05-07 | Resilio Company Limited | Therapeutic drug and therapeutic method for neurological diseases including alzheimer's disease associated with 1,25d3-marrs |
| BR112015019347B1 (pt) | 2013-02-13 | 2022-12-20 | The Procter & Gamble Company | Medicamento com sabor de anis |
| US20160015053A1 (en) * | 2013-03-14 | 2016-01-21 | Intercontinental Great Brands Llc | Chewing gum snacks; and methods of making thereof |
| EP2801263B1 (de) * | 2013-05-09 | 2021-04-14 | Symrise AG | Verfahren zur Herstellung einer kühlende Zusammensetzung in Form eines Granulats |
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- 2006-12-21 JP JP2008547615A patent/JP5203965B2/ja not_active Expired - Fee Related
- 2006-12-21 BR BRPI0620328-0A patent/BRPI0620328A2/pt not_active IP Right Cessation
- 2006-12-21 CN CN2006800489276A patent/CN101346073B/zh not_active Expired - Fee Related
- 2006-12-21 WO PCT/US2006/049058 patent/WO2007076025A2/en not_active Ceased
- 2006-12-21 EP EP12157450.3A patent/EP2478777B1/en not_active Not-in-force
- 2006-12-21 ES ES12157450.3T patent/ES2488634T3/es active Active
- 2006-12-21 US US11/643,575 patent/US20070148283A1/en not_active Abandoned
- 2006-12-21 RU RU2008124701/13A patent/RU2398476C2/ru not_active IP Right Cessation
- 2006-12-21 EP EP06846008A patent/EP1973421A2/en not_active Withdrawn
- 2006-12-21 AU AU2006330915A patent/AU2006330915B2/en not_active Ceased
- 2006-12-21 PL PL12157450T patent/PL2478777T3/pl unknown
- 2006-12-21 CA CA2634869A patent/CA2634869C/en not_active Expired - Fee Related
-
2011
- 2011-05-02 AU AU2011201997A patent/AU2011201997B2/en not_active Ceased
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2012
- 2012-01-18 JP JP2012007872A patent/JP5547757B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012117074A (ja) | 2012-06-21 |
| CA2634869A1 (en) | 2007-07-05 |
| EP1973421A2 (en) | 2008-10-01 |
| EP2478777A1 (en) | 2012-07-25 |
| RU2008124701A (ru) | 2010-01-27 |
| JP5203965B2 (ja) | 2013-06-05 |
| AU2006330915B2 (en) | 2011-02-03 |
| AU2011201997A1 (en) | 2011-05-26 |
| JP5547757B2 (ja) | 2014-07-16 |
| RU2398476C2 (ru) | 2010-09-10 |
| US20070148283A1 (en) | 2007-06-28 |
| PL2478777T3 (pl) | 2014-10-31 |
| BRPI0620328A2 (pt) | 2011-11-08 |
| CN101346073A (zh) | 2009-01-14 |
| EP2478777B1 (en) | 2014-07-09 |
| JP2009523181A (ja) | 2009-06-18 |
| WO2007076025A3 (en) | 2007-09-07 |
| WO2007076025A2 (en) | 2007-07-05 |
| CN101346073B (zh) | 2013-02-13 |
| ES2488634T3 (es) | 2014-08-28 |
| AU2006330915A1 (en) | 2007-07-05 |
| AU2011201997B2 (en) | 2011-07-14 |
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