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)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Inorganic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Non-Alcoholic Beverages (AREA)
- Confectionery (AREA)
- Tea And Coffee (AREA)
- Jellies, Jams, And Syrups (AREA)
- Manufacture Of Tobacco Products (AREA)
- Dairy Products (AREA)
- Seasonings (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 (enrdf_load_stackoverflow) |
| AU (1) | AU7754875A (enrdf_load_stackoverflow) |
| CA (1) | CA1055772A (enrdf_load_stackoverflow) |
| DE (1) | DE2503555A1 (enrdf_load_stackoverflow) |
| DK (1) | DK31575A (enrdf_load_stackoverflow) |
| FR (1) | FR2272610B3 (enrdf_load_stackoverflow) |
| GB (1) | GB1457671A (enrdf_load_stackoverflow) |
| IL (1) | IL46502A0 (enrdf_load_stackoverflow) |
| NL (1) | NL7501135A (enrdf_load_stackoverflow) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3724900C2 (de) * | 1986-08-08 | 2000-04-06 | Colgate Palmolive Co | N-Alkylneoalkanamide sowie deren Verwendung |
| ES2272209T3 (es) | 1999-03-31 | 2007-05-01 | Firmenich Sa | Utilizacion de cubebol como ingrediente aromatizante. |
| 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 |
| MXPA05004278A (es) | 2002-10-25 | 2005-10-05 | Foamix Ltd | Espuma cosmetica y farmaceutica. |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
| US20080138296A1 (en) | 2002-10-25 | 2008-06-12 | Foamix Ltd. | Foam prepared from nanoemulsions and uses |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic 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 |
| 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 |
| US8486376B2 (en) | 2002-10-25 | 2013-07-16 | Foamix Ltd. | Moisturizing foam containing lanolin |
| US7700076B2 (en) | 2002-10-25 | 2010-04-20 | Foamix, Ltd. | Penetrating pharmaceutical foam |
| US7820145B2 (en) | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| US7575739B2 (en) | 2003-04-28 | 2009-08-18 | Foamix Ltd. | Foamable iodine composition |
| ES2476902T5 (es) * | 2003-07-02 | 2018-04-03 | Genentech, Inc. | Compuestos activadores de TRP-P8 y métodos de tratamiento terapéuticos |
| US8486374B2 (en) | 2003-08-04 | 2013-07-16 | Foamix Ltd. | Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses |
| US8795693B2 (en) | 2003-08-04 | 2014-08-05 | Foamix Ltd. | Compositions with modulating agents |
| CL2004002015A1 (es) | 2003-08-06 | 2005-05-13 | Senomyx Inc | Derivados de amida, productos que las contienen, utiles para modificar el sabor de alimentos y medicamentos. |
| WO2005049553A1 (en) * | 2003-11-21 | 2005-06-02 | Givaudan Sa | N-substituted p-menthane carbosamided |
| 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 |
| US20060257543A1 (en) * | 2005-02-04 | 2006-11-16 | Catherine Tachdjian | Molecules comprising linked organic moieties as flavor modifiers for comestible compositions |
| US8968708B2 (en) | 2005-02-04 | 2015-03-03 | Senomyx, Inc. | Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions |
| TW200715993A (en) | 2005-06-15 | 2007-05-01 | Senomyx Inc | Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers |
| DK2010009T3 (en) | 2006-04-21 | 2017-10-02 | Senomyx Inc | PROCEDURES FOR THE PREPARATION OF SOLID FLAVOR COMPOSITIONS |
| US20080260655A1 (en) | 2006-11-14 | 2008-10-23 | Dov Tamarkin | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
| BRPI0811924A2 (pt) * | 2007-05-23 | 2014-11-25 | Givaudan Sa | Derivados de butona úteis como agentes refrigerantes |
| 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 |
| US8518376B2 (en) | 2007-12-07 | 2013-08-27 | Foamix Ltd. | Oil-based foamable carriers and formulations |
| WO2009070910A2 (en) | 2007-12-07 | 2009-06-11 | Givaudan Sa | Carboxamide derivatieves having cooling properties |
| WO2009072007A2 (en) | 2007-12-07 | 2009-06-11 | Foamix Ltd. | Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof |
| WO2009090558A2 (en) | 2008-01-14 | 2009-07-23 | Foamix Ltd. | Poloxamer foamable pharmaceutical compositions with active agents and/or therapeutic cells and uses |
| WO2010125470A2 (en) | 2009-04-28 | 2010-11-04 | Foamix Ltd. | Foamable vehicle and pharmaceutical compositions comprising aprotic polar solvents and uses thereof |
| WO2010128026A2 (en) | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
| WO2011013008A2 (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 |
| CA2769625C (en) | 2009-07-29 | 2017-04-11 | Foamix Ltd. | Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses |
| MX359879B (es) | 2009-10-02 | 2018-10-12 | Foamix Pharmaceuticals Ltd | Composiciones tópicas de tetraciclina. |
| US9849142B2 (en) | 2009-10-02 | 2017-12-26 | Foamix Pharmaceuticals Ltd. | Methods for accelerated return of skin integrity and for the treatment of impetigo |
| US9446267B2 (en) | 2009-10-06 | 2016-09-20 | Symrise Ag | Products comprising a flavoring agent composition |
| EP2186506B1 (de) * | 2009-10-06 | 2015-09-30 | Symrise AG | Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung |
| 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 |
| US10398641B2 (en) | 2016-09-08 | 2019-09-03 | Foamix Pharmaceuticals Ltd. | Compositions and methods for treating rosacea and 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 DE DE19752503555 patent/DE2503555A1/de active Pending
- 1975-01-29 JP JP50012289A patent/JPS50111264A/ja active Pending
- 1975-01-30 DK DK31575*#A patent/DK31575A/da unknown
- 1975-01-30 FR FR7502883A patent/FR2272610B3/fr not_active Expired
- 1975-01-30 NL NL7501135A patent/NL7501135A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1457671A (en) | 1976-12-08 |
| DE2503555A1 (de) | 1975-08-14 |
| JPS50111264A (enrdf_load_stackoverflow) | 1975-09-01 |
| FR2272610A1 (enrdf_load_stackoverflow) | 1975-12-26 |
| NL7501135A (nl) | 1975-08-04 |
| DK31575A (enrdf_load_stackoverflow) | 1975-09-22 |
| AU7754875A (en) | 1976-07-29 |
| IL46502A0 (en) | 1975-04-25 |
| FR2272610B3 (enrdf_load_stackoverflow) | 1977-10-21 |
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