DE2503555A1 - Verfahren zur abwandlung des geschmackes einnehmbarer stoffe - Google Patents
Verfahren zur abwandlung des geschmackes einnehmbarer stoffeInfo
- Publication number
- DE2503555A1 DE2503555A1 DE19752503555 DE2503555A DE2503555A1 DE 2503555 A1 DE2503555 A1 DE 2503555A1 DE 19752503555 DE19752503555 DE 19752503555 DE 2503555 A DE2503555 A DE 2503555A DE 2503555 A1 DE2503555 A1 DE 2503555A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- groups
- alkyl
- carbon atoms
- taste
- 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.)
- Pending
Links
- 235000019640 taste Nutrition 0.000 title claims description 160
- 238000000034 method Methods 0.000 title claims description 37
- 239000000126 substance Substances 0.000 title claims description 14
- 230000000051 modifying effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 128
- -1 hydroxyalkoxyalkyl Chemical group 0.000 claims description 110
- 230000000694 effects Effects 0.000 claims description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- 239000003607 modifier Substances 0.000 claims description 53
- 238000001816 cooling Methods 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 239000000796 flavoring agent Substances 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 235000019634 flavors Nutrition 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 241000208125 Nicotiana Species 0.000 claims description 16
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229940041616 menthol Drugs 0.000 claims description 8
- 210000000653 nervous system Anatomy 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 206010013911 Dysgeusia Diseases 0.000 description 35
- 238000012360 testing method Methods 0.000 description 33
- 244000299461 Theobroma cacao Species 0.000 description 32
- 235000019219 chocolate Nutrition 0.000 description 30
- 229940124530 sulfonamide Drugs 0.000 description 24
- 239000000523 sample Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000001408 amides Chemical class 0.000 description 20
- 150000003456 sulfonamides Chemical class 0.000 description 16
- 235000019605 sweet taste sensations Nutrition 0.000 description 16
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000013068 control sample Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 11
- 235000009508 confectionery Nutrition 0.000 description 11
- 238000001802 infusion Methods 0.000 description 11
- 235000013305 food Nutrition 0.000 description 10
- 230000006872 improvement Effects 0.000 description 10
- 235000019614 sour taste Nutrition 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 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 8
- 229930006000 Sucrose Natural products 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 235000013336 milk Nutrition 0.000 description 8
- 239000008267 milk Substances 0.000 description 8
- 210000004080 milk Anatomy 0.000 description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 8
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
- 229960004793 sucrose Drugs 0.000 description 8
- 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 7
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 7
- 235000011941 Tilia x europaea Nutrition 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 239000004571 lime Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 240000007154 Coffea arabica Species 0.000 description 6
- 244000269722 Thea sinensis Species 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 235000016213 coffee Nutrition 0.000 description 6
- 235000013353 coffee beverage Nutrition 0.000 description 6
- 150000003950 cyclic amides Chemical class 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 235000011962 puddings Nutrition 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 6
- 150000003457 sulfones Chemical class 0.000 description 6
- 235000013616 tea Nutrition 0.000 description 6
- 235000013361 beverage Nutrition 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
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 4
- 244000131522 Citrus pyriformis Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 150000001412 amines Chemical class 0.000 description 4
- 235000013405 beer Nutrition 0.000 description 4
- 235000019658 bitter taste Nutrition 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 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 4
- 230000003287 optical effect Effects 0.000 description 4
- 235000015205 orange juice Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003509 tertiary alcohols Chemical class 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WIYBEAHUAVVOHR-UHFFFAOYSA-N (2,2,6-trimethylcyclohexyl)methanol Chemical compound CC1CCCC(C)(C)C1CO WIYBEAHUAVVOHR-UHFFFAOYSA-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
- QIXDCVATINBRLV-UHFFFAOYSA-N 2,4,4-trimethylcyclopentan-1-ol Chemical compound CC1CC(C)(C)CC1O QIXDCVATINBRLV-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
- 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 3
- 241000207199 Citrus 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
- 230000009471 action Effects 0.000 description 3
- 150000001260 acyclic compounds Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
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- 235000015218 chewing gum Nutrition 0.000 description 3
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- 235000020971 citrus fruits Nutrition 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- 235000015110 jellies Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- HEGMIMMSZBAFJC-UHFFFAOYSA-N (1-propan-2-ylcycloheptyl)methanol Chemical compound CC(C)C1(CO)CCCCCC1 HEGMIMMSZBAFJC-UHFFFAOYSA-N 0.000 description 2
- 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
- LLJOUPIOKXFIFJ-UHFFFAOYSA-N 1-[bis(2-methylpropyl)phosphoryl]nonane Chemical compound C(C(C)C)P(CCCCCCCCC)(CC(C)C)=O LLJOUPIOKXFIFJ-UHFFFAOYSA-N 0.000 description 2
- WRLIIBLDYPFTLG-UHFFFAOYSA-N 1-[bis(3-methylbutyl)phosphoryl]-3-methylbutane Chemical compound CC(C)CCP(=O)(CCC(C)C)CCC(C)C WRLIIBLDYPFTLG-UHFFFAOYSA-N 0.000 description 2
- QXMUYPHHLVIBTB-UHFFFAOYSA-N 1-propan-2-ylcycloheptan-1-ol Chemical compound CC(C)C1(O)CCCCCC1 QXMUYPHHLVIBTB-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
- HMDZEJHWEZOBKG-UHFFFAOYSA-N 2-butan-2-yl-2,3-dimethylpentan-1-ol Chemical compound CCC(C)C(C)(CO)C(C)CC HMDZEJHWEZOBKG-UHFFFAOYSA-N 0.000 description 2
- SQITZQXJIFQULD-UHFFFAOYSA-N 2-butan-2-ylcyclopentan-1-ol Chemical compound CCC(C)C1CCCC1O SQITZQXJIFQULD-UHFFFAOYSA-N 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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- 238000000586 desensitisation Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- PVBRXXAAPNGWGE-LGVAUZIVSA-L disodium 5'-guanylate Chemical compound [Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O PVBRXXAAPNGWGE-LGVAUZIVSA-L 0.000 description 1
- 239000004193 disodium 5'-ribonucleotide Substances 0.000 description 1
- 235000013896 disodium guanylate Nutrition 0.000 description 1
- 235000013890 disodium inosinate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- FOLFMQFDEHZBRV-UHFFFAOYSA-N ethyl 2-[(2-propan-2-ylcycloheptanecarbonyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1CCCCCC1C(C)C FOLFMQFDEHZBRV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 235000019581 fat taste sensations Nutrition 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 235000014080 ginger ale Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 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 description 1
- 238000013101 initial test Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019223 lemon-lime Nutrition 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 235000019656 metallic taste Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- VFBMWIIOKYPCAI-UHFFFAOYSA-N n,2-diethylcyclooctane-1-carboxamide Chemical compound CCNC(=O)C1CCCCCCC1CC VFBMWIIOKYPCAI-UHFFFAOYSA-N 0.000 description 1
- VSFJWEKZFXXWFP-UHFFFAOYSA-N n-(2,4,4-trimethylpentan-2-yl)pentanamide Chemical compound CCCCC(=O)NC(C)(C)CC(C)(C)C VSFJWEKZFXXWFP-UHFFFAOYSA-N 0.000 description 1
- BQTWORMKLQVDGL-UHFFFAOYSA-N n-(2,4-dimethylpentan-3-yl)-2-methylpropanamide Chemical compound CC(C)C(C(C)C)NC(=O)C(C)C BQTWORMKLQVDGL-UHFFFAOYSA-N 0.000 description 1
- XQABCMPKRIMGIC-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-methyl-2-propan-2-ylcyclohexane-1-sulfinamide Chemical compound CC(C)C1CCC(C)CC1S(=O)NCCO XQABCMPKRIMGIC-UHFFFAOYSA-N 0.000 description 1
- LNQLZUNVNYEKDQ-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)C1C(C(C)C)CCC(C)C1 LNQLZUNVNYEKDQ-UHFFFAOYSA-N 0.000 description 1
- CKDFENXIYVCLOO-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(C)C(C)=C1 CKDFENXIYVCLOO-UHFFFAOYSA-N 0.000 description 1
- LAZPRGNKUJIIEB-UHFFFAOYSA-N n-(3-hydroxy-4-methylphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(C)C(O)=C1 LAZPRGNKUJIIEB-UHFFFAOYSA-N 0.000 description 1
- ZLUVOIPGFFLPMO-UHFFFAOYSA-N n-(5-hydroxypentyl)-2-methyl-1-propan-2-ylcyclopentane-1-carboxamide Chemical compound OCCCCCNC(=O)C1(C(C)C)CCCC1C ZLUVOIPGFFLPMO-UHFFFAOYSA-N 0.000 description 1
- GZUUJHZWINXBDB-UHFFFAOYSA-N n-benzyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NCC1=CC=CC=C1 GZUUJHZWINXBDB-UHFFFAOYSA-N 0.000 description 1
- DEUXMJFFGDETDN-UHFFFAOYSA-N n-ethyl-1-(3-methylbutyl)cyclopentane-1-carboxamide Chemical compound CCNC(=O)C1(CCC(C)C)CCCC1 DEUXMJFFGDETDN-UHFFFAOYSA-N 0.000 description 1
- SIXMZXVQNHSLMO-UHFFFAOYSA-N n-ethyl-1-propan-2-ylcycloheptane-1-carboxamide Chemical compound CCNC(=O)C1(C(C)C)CCCCCC1 SIXMZXVQNHSLMO-UHFFFAOYSA-N 0.000 description 1
- ZPWOHLYYRKICAA-UHFFFAOYSA-N n-ethyl-2,4-dimethyl-2-(2-methylpropyl)pentanamide Chemical compound CCNC(=O)C(C)(CC(C)C)CC(C)C ZPWOHLYYRKICAA-UHFFFAOYSA-N 0.000 description 1
- XUHIEWKUIPNAQF-UHFFFAOYSA-N n-tert-butyl-2-propan-2-ylcycloheptane-1-carboxamide Chemical compound CC(C)C1CCCCCC1C(=O)NC(C)(C)C XUHIEWKUIPNAQF-UHFFFAOYSA-N 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000021565 orange beverage Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000007967 peppermint flavor Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- NOHWSHIQJRPKOC-UHFFFAOYSA-N propyl 2-[(5-methyl-2-propan-2-ylcyclohexanecarbonyl)amino]acetate Chemical compound CCCOC(=O)CNC(=O)C1CC(C)CCC1C(C)C NOHWSHIQJRPKOC-UHFFFAOYSA-N 0.000 description 1
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000019643 salty taste Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical group C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019220 whole milk chocolate Nutrition 0.000 description 1
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
- 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)
- Non-Alcoholic Beverages (AREA)
- Dairy Products (AREA)
- Confectionery (AREA)
- Tea And Coffee (AREA)
- Jellies, Jams, And Syrups (AREA)
- Manufacture Of Tobacco 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 |
|---|---|
| DE2503555A1 true DE2503555A1 (de) | 1975-08-14 |
Family
ID=26239244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752503555 Pending DE2503555A1 (de) | 1974-01-31 | 1975-01-29 | Verfahren zur abwandlung des geschmackes einnehmbarer stoffe |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS50111264A (enExample) |
| AU (1) | AU7754875A (enExample) |
| CA (1) | CA1055772A (enExample) |
| DE (1) | DE2503555A1 (enExample) |
| DK (1) | DK31575A (enExample) |
| FR (1) | FR2272610B3 (enExample) |
| GB (1) | GB1457671A (enExample) |
| IL (1) | IL46502A0 (enExample) |
| NL (1) | NL7501135A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2602506A1 (fr) * | 1986-08-08 | 1988-02-12 | Colgate Palmolive Co | N-alkyl-neoalcanamides insectifuges, composition detergente, produit detergent, composition insectifuge, produit a usage domestique et parfum en contenant et procede les utilisant |
| US6214788B1 (en) | 1999-03-31 | 2001-04-10 | Firmenich Sa | Use of cubebol as a flavoring ingredient |
| 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 |
| EP2186506A1 (de) | 2009-10-06 | 2010-05-19 | Symrise GmbH & Co. KG | Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung |
| US9446267B2 (en) | 2009-10-06 | 2016-09-20 | Symrise Ag | Products comprising a flavoring agent composition |
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|---|---|---|---|---|
| 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 |
| US8486376B2 (en) | 2002-10-25 | 2013-07-16 | Foamix Ltd. | Moisturizing foam containing lanolin |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
| US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
| US7820145B2 (en) | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| ES2532906T5 (es) | 2002-10-25 | 2022-03-23 | Foamix Pharmaceuticals Ltd | Espuma cosmética y farmacéutica |
| 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 |
| US20080138296A1 (en) | 2002-10-25 | 2008-06-12 | Foamix Ltd. | Foam prepared from nanoemulsions and uses |
| US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| US7700076B2 (en) | 2002-10-25 | 2010-04-20 | Foamix, Ltd. | Penetrating pharmaceutical foam |
| US7575739B2 (en) | 2003-04-28 | 2009-08-18 | Foamix Ltd. | Foamable iodine composition |
| AU2004253582B2 (en) * | 2003-07-02 | 2011-02-10 | Genentech, Inc. | TRP-P8 active compounds and therapeutic treatment methods |
| 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 |
| JP2007512227A (ja) | 2003-08-06 | 2007-05-17 | セノミックス、インコーポレイテッド | Ｔ１ｒヘテロオリゴマー味覚受容体、この受容体を発現する細胞株、および味覚化合物 |
| 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 |
| GB0425661D0 (en) * | 2004-11-23 | 2004-12-22 | Givaudan Sa | Organic compounds |
| MX2007009388A (es) | 2005-02-04 | 2007-09-25 | Senomyx Inc | Compuestos que comprenden porciones heteroarilo unidas y su uso como modificadores del sabor unami, saborizantes y mejoradores del sabor para composiciones comestibles. |
| WO2006084184A2 (en) * | 2005-02-04 | 2006-08-10 | Senomyx, Inc. | Molecules comprising linked organic moieties as flavor modifiers for comestible compositions |
| AR055329A1 (es) | 2005-06-15 | 2007-08-15 | Senomyx Inc | Amidas bis-aromaticas y sus usos como modificadores de sabor dulce, saborizantes, y realzadores de sabor |
| EP3235811B1 (en) | 2006-04-21 | 2018-07-25 | Senomyx, Inc. | Process of preparing oxalamides |
| US20080260655A1 (en) | 2006-11-14 | 2008-10-23 | Dov Tamarkin | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
| WO2008141469A2 (en) * | 2007-05-23 | 2008-11-27 | Givaudan Sa | Butone derivatives useful as cooling agents |
| US8636982B2 (en) | 2007-08-07 | 2014-01-28 | Foamix Ltd. | Wax foamable vehicle and pharmaceutical compositions thereof |
| US9439857B2 (en) | 2007-11-30 | 2016-09-13 | Foamix Pharmaceuticals Ltd. | Foam containing benzoyl peroxide |
| WO2009090495A2 (en) | 2007-12-07 | 2009-07-23 | Foamix Ltd. | Oil and liquid silicone foamable carriers and formulations |
| US8518376B2 (en) | 2007-12-07 | 2013-08-27 | Foamix Ltd. | Oil-based foamable carriers and formulations |
| US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives having cooling properties |
| EP2242476A2 (en) | 2008-01-14 | 2010-10-27 | 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 |
| EP2482788B1 (en) | 2009-10-02 | 2022-12-14 | Journey Medical Corporation | Topical tetracycline compositions |
| US9849142B2 (en) | 2009-10-02 | 2017-12-26 | Foamix Pharmaceuticals Ltd. | Methods for accelerated return of skin integrity and for the treatment of impetigo |
| 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 |
| CA2978573A1 (en) | 2016-09-08 | 2018-03-08 | 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 FR FR7502883A patent/FR2272610B3/fr not_active Expired
- 1975-01-30 NL NL7501135A patent/NL7501135A/xx unknown
- 1975-01-30 DK DK31575*#A patent/DK31575A/da unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2602506A1 (fr) * | 1986-08-08 | 1988-02-12 | Colgate Palmolive Co | N-alkyl-neoalcanamides insectifuges, composition detergente, produit detergent, composition insectifuge, produit a usage domestique et parfum en contenant et procede les utilisant |
| DE3724900A1 (de) * | 1986-08-08 | 1988-03-10 | Colgate Palmolive Co | N-alkylneoalkanamide sowie diese enthaltenden zubereitungen |
| GB2194787A (en) * | 1986-08-08 | 1988-03-16 | Colgate Palmolive Co | N-alkyl neoalkanamides |
| GB2194787B (en) * | 1986-08-08 | 1991-05-15 | Colgate Palmolive Co | N-alkyl neoalkanoamides |
| DE3724900C2 (de) * | 1986-08-08 | 2000-04-06 | Colgate Palmolive Co | N-Alkylneoalkanamide sowie deren Verwendung |
| US6214788B1 (en) | 1999-03-31 | 2001-04-10 | Firmenich Sa | Use of cubebol as a flavoring ingredient |
| 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 |
| EP2186506A1 (de) | 2009-10-06 | 2010-05-19 | Symrise GmbH & Co. KG | Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung |
| EP2364689A2 (de) | 2009-10-06 | 2011-09-14 | Symrise AG | Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung |
| US9446267B2 (en) | 2009-10-06 | 2016-09-20 | Symrise Ag | Products comprising a flavoring agent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2272610B3 (enExample) | 1977-10-21 |
| IL46502A0 (en) | 1975-04-25 |
| JPS50111264A (enExample) | 1975-09-01 |
| FR2272610A1 (enExample) | 1975-12-26 |
| CA1055772A (en) | 1979-06-05 |
| AU7754875A (en) | 1976-07-29 |
| GB1457671A (en) | 1976-12-08 |
| DK31575A (enExample) | 1975-09-22 |
| NL7501135A (nl) | 1975-08-04 |
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