CA1055772A - Flavour modifiers - Google Patents
Flavour modifiersInfo
- Publication number
- CA1055772A CA1055772A CA218,377A CA218377A CA1055772A CA 1055772 A CA1055772 A CA 1055772A CA 218377 A CA218377 A CA 218377A CA 1055772 A CA1055772 A CA 1055772A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- compound
- carbon atoms
- flavour
- 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
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 165
- 235000019634 flavors Nutrition 0.000 title claims abstract description 163
- 239000003607 modifier Substances 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 238000002360 preparation method Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 25
- 230000000051 modifying effect Effects 0.000 claims abstract description 13
- 210000000653 nervous system Anatomy 0.000 claims abstract description 7
- 230000004936 stimulating effect Effects 0.000 claims abstract description 4
- -1 hydroxyalkoxyalkyl Chemical class 0.000 claims description 99
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- 230000000694 effects Effects 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000001816 cooling Methods 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000002768 hydroxyalkyl group Chemical class 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004181 carboxyalkyl group Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 241000208125 Nicotiana Species 0.000 claims description 15
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 230000001965 increasing effect Effects 0.000 description 81
- 235000009508 confectionery Nutrition 0.000 description 33
- 206010013911 Dysgeusia Diseases 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 239000002253 acid Substances 0.000 description 25
- 244000299461 Theobroma cacao Species 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
- 235000019640 taste Nutrition 0.000 description 21
- 235000019219 chocolate Nutrition 0.000 description 20
- 150000001408 amides Chemical class 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 150000001721 carbon Chemical group 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- 235000005979 Citrus limon Nutrition 0.000 description 13
- 244000131522 Citrus pyriformis Species 0.000 description 13
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 13
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 12
- 235000013361 beverage Nutrition 0.000 description 12
- 238000001802 infusion Methods 0.000 description 11
- 150000003456 sulfonamides Chemical class 0.000 description 10
- 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 9
- 229930006000 Sucrose Natural products 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000005720 sucrose Substances 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000008267 milk Substances 0.000 description 8
- 229940081974 saccharin Drugs 0.000 description 8
- 235000019204 saccharin Nutrition 0.000 description 8
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000002015 acyclic group Chemical group 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 235000019658 bitter taste Nutrition 0.000 description 7
- 239000008370 chocolate flavor Substances 0.000 description 7
- 235000013336 milk Nutrition 0.000 description 7
- 210000004080 milk Anatomy 0.000 description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 7
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 7
- NNPFZDMSNIETII-UHFFFAOYSA-N 2-hydroxyethyl 5-methyl-2-propan-2-ylcyclohexane-1-carboxylate Chemical group CC(C)C1CCC(C)CC1C(=O)OCCO NNPFZDMSNIETII-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 244000269722 Thea sinensis Species 0.000 description 6
- 239000013068 control sample Substances 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 235000011962 puddings Nutrition 0.000 description 6
- 235000018553 tannin Nutrition 0.000 description 6
- 229920001864 tannin Polymers 0.000 description 6
- 239000001648 tannin Substances 0.000 description 6
- 235000013616 tea Nutrition 0.000 description 6
- MNVSUVYRIVXDBK-UHFFFAOYSA-N 5-methyl-2-propan-2-ylcyclohexane-1-carboxylic acid Chemical compound CC(C)C1CCC(C)CC1C(O)=O MNVSUVYRIVXDBK-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 235000019504 cigarettes Nutrition 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 150000003950 cyclic amides Chemical class 0.000 description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 5
- 229940041616 menthol Drugs 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 5
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- 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 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 244000290333 Vanilla fragrans Species 0.000 description 4
- 235000009499 Vanilla fragrans Nutrition 0.000 description 4
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 235000021539 instant coffee Nutrition 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- 229940113083 morpholine Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000007968 orange flavor Substances 0.000 description 4
- 235000020365 orange squash Nutrition 0.000 description 4
- 230000008447 perception Effects 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
- 229940080818 propionamide Drugs 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 235000019600 saltiness Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 235000020354 squash Nutrition 0.000 description 4
- 125000001174 sulfone group Chemical group 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FVESDCZDESZGHA-URLMMPGGSA-N 1-[4-[(2s,3r)-2-(2,3-dihydro-1h-inden-2-yloxy)-3-(3,5-dimethoxy-4-methylphenyl)-3-hydroxypropoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound COC1=C(C)C(OC)=CC([C@@H](O)[C@H](COC=2C=CC(=CC=2)C2(CC2)C(O)=O)OC2CC3=CC=CC=C3C2)=C1 FVESDCZDESZGHA-URLMMPGGSA-N 0.000 description 3
- RYLFWQILVNWPEL-UHFFFAOYSA-N 1-methyl-4-propan-2-ylcyclohexane-1,2-diol Chemical class CC(C)C1CCC(C)(O)C(O)C1 RYLFWQILVNWPEL-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 240000007154 Coffea arabica Species 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 235000015218 chewing gum Nutrition 0.000 description 3
- 229940112822 chewing gum Drugs 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 235000016213 coffee Nutrition 0.000 description 3
- 235000013353 coffee beverage Nutrition 0.000 description 3
- 238000010411 cooking Methods 0.000 description 3
- 206010013781 dry mouth Diseases 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000020278 hot chocolate Nutrition 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 235000015110 jellies Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- HNSGVPAAXJJOPQ-UHFFFAOYSA-N n-(4-methoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1C(C(C)C)CCC(C)C1 HNSGVPAAXJJOPQ-UHFFFAOYSA-N 0.000 description 3
- ZVKDZYPEJXGLJG-UHFFFAOYSA-N n-tert-butyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC(C)(C)C ZVKDZYPEJXGLJG-UHFFFAOYSA-N 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000019605 sweet taste sensations Nutrition 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- PJQKYFARRHBMHL-UHFFFAOYSA-N 1,2,6,6-tetramethylcycloheptan-1-ol Chemical compound CC1CCCC(C)(C)CC1(C)O PJQKYFARRHBMHL-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DYCABLGCXHCEMN-UHFFFAOYSA-N 1-ethyl-5-methyl-2-propan-2-ylcyclohexan-1-ol Chemical compound CCC1(O)CC(C)CCC1C(C)C DYCABLGCXHCEMN-UHFFFAOYSA-N 0.000 description 2
- QIXDCVATINBRLV-UHFFFAOYSA-N 2,4,4-trimethylcyclopentan-1-ol Chemical compound CC1CC(C)(C)CC1O QIXDCVATINBRLV-UHFFFAOYSA-N 0.000 description 2
- UCRUTNJGISGZMY-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyl-6-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(C)C(CO)C1O UCRUTNJGISGZMY-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 description 2
- YOYCWCRNFVYCKY-UHFFFAOYSA-N 3-ethyl-2,4-dimethylhexan-3-ol Chemical compound CCC(C)C(O)(CC)C(C)C YOYCWCRNFVYCKY-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- ZFVYZHDDIOBINE-UHFFFAOYSA-N 6-ethyldecan-3-ol Chemical compound CCCCC(CC)CCC(O)CC ZFVYZHDDIOBINE-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 241000219104 Cucurbitaceae Species 0.000 description 2
- VUNOFAIHSALQQH-UHFFFAOYSA-N Ethyl menthane carboxamide Chemical compound CCNC(=O)C1CC(C)CCC1C(C)C VUNOFAIHSALQQH-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000008122 artificial sweetener Substances 0.000 description 2
- 235000021311 artificial sweeteners Nutrition 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 108091005708 gustatory receptors Proteins 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 235000020344 instant tea Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 235000020094 liqueur Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- 239000004223 monosodium glutamate Substances 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- ZQMPWXFHAUDENN-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
- MCDKWCMKCJAFSZ-UHFFFAOYSA-N n,n-di(butan-2-yl)acetamide Chemical compound CCC(C)N(C(C)=O)C(C)CC MCDKWCMKCJAFSZ-UHFFFAOYSA-N 0.000 description 2
- 229930004008 p-menthane Natural products 0.000 description 2
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 230000009967 tasteless effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WIYBEAHUAVVOHR-UHFFFAOYSA-N (2,2,6-trimethylcyclohexyl)methanol Chemical compound CC1CCCC(C)(C)C1CO WIYBEAHUAVVOHR-UHFFFAOYSA-N 0.000 description 1
- HRCWGGKKJJMGHD-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl)-morpholin-4-ylmethanone Chemical compound CC(C)C1CCC(C)CC1C(=O)N1CCOCC1 HRCWGGKKJJMGHD-UHFFFAOYSA-N 0.000 description 1
- GMOXAINVEINILR-UHFFFAOYSA-N 1,1-dimethyl-3,3-bis(2-methylpropyl)urea Chemical compound CC(C)CN(CC(C)C)C(=O)N(C)C GMOXAINVEINILR-UHFFFAOYSA-N 0.000 description 1
- FHPIIUUMMWHNFC-UHFFFAOYSA-N 1,2-diethylcyclohexan-1-ol Chemical compound CCC1CCCCC1(O)CC FHPIIUUMMWHNFC-UHFFFAOYSA-N 0.000 description 1
- JQRBSTOKUUWTJN-UHFFFAOYSA-N 1,4,4-trimethylcycloheptane-1-carboxylic acid Chemical compound CC1(C)CCCC(C)(C(O)=O)CC1 JQRBSTOKUUWTJN-UHFFFAOYSA-N 0.000 description 1
- DTSZTPPMUGNHKT-UHFFFAOYSA-N 1,5-dimethyl-2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(C)CC1(C)O DTSZTPPMUGNHKT-UHFFFAOYSA-N 0.000 description 1
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-
- 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
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
- A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
- A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
-
- 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
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Jellies, Jams, And Syrups (AREA)
- Manufacture Of Tobacco Products (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Dairy Products (AREA)
- Confectionery (AREA)
- Tea And Coffee (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB458774A GB1457671A (en) | 1974-01-31 | 1974-01-31 | Flavour |
| GB1708874 | 1974-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055772A true CA1055772A (en) | 1979-06-05 |
Family
ID=26239244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,377A Expired CA1055772A (en) | 1974-01-31 | 1975-01-21 | Flavour modifiers |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS50111264A (show.php) |
| AU (1) | AU7754875A (show.php) |
| CA (1) | CA1055772A (show.php) |
| DE (1) | DE2503555A1 (show.php) |
| DK (1) | DK31575A (show.php) |
| FR (1) | FR2272610B3 (show.php) |
| GB (1) | GB1457671A (show.php) |
| IL (1) | IL46502A0 (show.php) |
| NL (1) | NL7501135A (show.php) |
Families Citing this family (50)
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|---|---|---|---|---|
| DE3724900C2 (de) * | 1986-08-08 | 2000-04-06 | Colgate Palmolive Co | N-Alkylneoalkanamide sowie deren Verwendung |
| DE60031025T2 (de) | 1999-03-31 | 2007-05-24 | Firmenich S.A. | Verwendung von Cubebol als Aromastoff |
| US8512718B2 (en) | 2000-07-03 | 2013-08-20 | Foamix Ltd. | Pharmaceutical composition for topical application |
| IL152486A0 (en) | 2002-10-25 | 2003-05-29 | Meir Eini | Alcohol-free cosmetic and pharmaceutical foam carrier |
| US20060140984A1 (en) | 2002-10-25 | 2006-06-29 | Foamix Ltd. | Cosmetic and pharmaceutical foam |
| US7700076B2 (en) | 2002-10-25 | 2010-04-20 | Foamix, Ltd. | Penetrating pharmaceutical foam |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| US7820145B2 (en) | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
| US20080138296A1 (en) | 2002-10-25 | 2008-06-12 | Foamix Ltd. | Foam prepared from nanoemulsions and uses |
| US9265725B2 (en) | 2002-10-25 | 2016-02-23 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
| US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
| US10117812B2 (en) | 2002-10-25 | 2018-11-06 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
| US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
| US8486376B2 (en) | 2002-10-25 | 2013-07-16 | Foamix Ltd. | Moisturizing foam containing lanolin |
| US7575739B2 (en) | 2003-04-28 | 2009-08-18 | Foamix Ltd. | Foamable iodine composition |
| CA2530884C (en) * | 2003-07-02 | 2016-01-12 | Genentech, Inc. | Trp-p8 active compounds and therapeutic treatment methods |
| US8795693B2 (en) | 2003-08-04 | 2014-08-05 | Foamix Ltd. | Compositions with modulating agents |
| US8486374B2 (en) | 2003-08-04 | 2013-07-16 | Foamix Ltd. | Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses |
| EP1659881B1 (en) | 2003-08-06 | 2019-04-03 | Senomyx Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| CN100582089C (zh) | 2003-11-21 | 2010-01-20 | 吉万奥丹股份有限公司 | N-取代的对-薄荷烷甲酰胺 |
| US7417048B2 (en) | 2003-12-31 | 2008-08-26 | Wei Edward T | Aryl-substituted derivatives of cycloalkyl and branched chain alkyl carboxylic acids useful as antinociceptive drugs for peripheral targets |
| US7189760B2 (en) | 2004-04-02 | 2007-03-13 | Millennium Specialty Chemicals | Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl) cyclohexyl] carbonyl]glycine |
| GB0425661D0 (en) * | 2004-11-23 | 2004-12-22 | Givaudan Sa | Organic compounds |
| CN101384183B (zh) | 2005-02-04 | 2012-07-04 | 西诺米克斯公司 | 包含连接有杂芳基部分的化合物及其作为用于食物组合物的新型鲜味调节剂、促味剂和味觉增强剂的应用 |
| JP2008530017A (ja) * | 2005-02-04 | 2008-08-07 | セノミックス インコーポレイテッド | 食料用組成物のための風味調整剤として連結された有機部分を含む分子 |
| TW200715993A (en) | 2005-06-15 | 2007-05-01 | Senomyx Inc | Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers |
| DK3235811T3 (en) | 2006-04-21 | 2018-11-12 | Senomyx Inc | PROCEDURE FOR THE PREPARATION OF OXALAMIDS |
| US20080260655A1 (en) | 2006-11-14 | 2008-10-23 | Dov Tamarkin | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
| CN101677930A (zh) * | 2007-05-23 | 2010-03-24 | 吉万奥丹股份有限公司 | 用作清凉剂的丁酮衍生物 |
| US8636982B2 (en) | 2007-08-07 | 2014-01-28 | Foamix Ltd. | Wax foamable vehicle and pharmaceutical compositions thereof |
| WO2009069006A2 (en) | 2007-11-30 | 2009-06-04 | Foamix Ltd. | Foam containing benzoyl peroxide |
| US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives having cooling properties |
| WO2010041141A2 (en) | 2008-10-07 | 2010-04-15 | Foamix Ltd. | Oil-based foamable carriers and formulations |
| WO2009072007A2 (en) | 2007-12-07 | 2009-06-11 | Foamix Ltd. | Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof |
| AU2009205314A1 (en) | 2008-01-14 | 2009-07-23 | Foamix Ltd. | Poloxamer foamable pharmaceutical compositions with active agents and/or therapeutic cells and uses |
| US20120087872A1 (en) | 2009-04-28 | 2012-04-12 | Foamix Ltd. | Foamable Vehicles and Pharmaceutical Compositions Comprising Aprotic Polar Solvents and Uses Thereof |
| WO2010128026A2 (en) | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
| CA2769677A1 (en) | 2009-07-29 | 2011-02-03 | Foamix Ltd. | Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses |
| WO2011013009A2 (en) | 2009-07-29 | 2011-02-03 | Foamix Ltd. | Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses |
| AU2010302350B2 (en) | 2009-10-02 | 2015-06-18 | Journey Medical Corporation | Surfactant-free water-free foamable compositions, breakable foams and gels and their uses |
| US9849142B2 (en) | 2009-10-02 | 2017-12-26 | Foamix Pharmaceuticals Ltd. | Methods for accelerated return of skin integrity and for the treatment of impetigo |
| EP2364689B1 (de) * | 2009-10-06 | 2019-12-11 | Symrise AG | Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung |
| US9446267B2 (en) | 2009-10-06 | 2016-09-20 | Symrise Ag | Products comprising a flavoring agent composition |
| US12661407B2 (en) | 2010-04-08 | 2026-06-23 | Journey Medical Corporation | Compositions, gels and foams with rheology modulators and uses thereof |
| GB201103103D0 (en) | 2011-02-23 | 2011-04-06 | Givaudan Sa | Organic compounds |
| AU2013403622B2 (en) * | 2013-10-22 | 2019-05-16 | Edward Tak Wei | Di-isopropyl-phosphinoyl-alkane (DAPA) compounds as topical agents for the treatment of sensory discomfort |
| US10173966B2 (en) * | 2015-06-04 | 2019-01-08 | Symrise, Inc. | Physiological cooling compounds |
| MX2020012139A (es) | 2016-09-08 | 2021-01-29 | Vyne Pharmaceuticals Inc | Composiciones y metodos para tratar rosacea y acne. |
| JP6564498B2 (ja) * | 2018-06-06 | 2019-08-21 | エドワード タク ウェイＷＥＩ， Ｅｄｗａｒｄ Ｔａｋ | 感覚的不快感の治療向け局所薬としてのジ−イソプロピル−アルカン（ｄａｐａ）化合物 |
-
1974
- 1974-01-31 GB GB458774A patent/GB1457671A/en not_active Expired
-
1975
- 1975-01-21 CA CA218,377A patent/CA1055772A/en not_active Expired
- 1975-01-23 AU AU77548/75A patent/AU7754875A/en not_active Expired
- 1975-01-24 IL IL46502A patent/IL46502A0/xx unknown
- 1975-01-29 JP JP50012289A patent/JPS50111264A/ja active Pending
- 1975-01-29 DE DE19752503555 patent/DE2503555A1/de active Pending
- 1975-01-30 NL NL7501135A patent/NL7501135A/xx unknown
- 1975-01-30 FR FR7502883A patent/FR2272610B3/fr not_active Expired
- 1975-01-30 DK DK31575*#A patent/DK31575A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50111264A (show.php) | 1975-09-01 |
| GB1457671A (en) | 1976-12-08 |
| IL46502A0 (en) | 1975-04-25 |
| NL7501135A (nl) | 1975-08-04 |
| FR2272610B3 (show.php) | 1977-10-21 |
| FR2272610A1 (show.php) | 1975-12-26 |
| DK31575A (show.php) | 1975-09-22 |
| DE2503555A1 (de) | 1975-08-14 |
| AU7754875A (en) | 1976-07-29 |
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