CA1040214A - Organoleptic methyl-n-acetyglycinate - Google Patents
Organoleptic methyl-n-acetyglycinateInfo
- Publication number
- CA1040214A CA1040214A CA204,786A CA204786A CA1040214A CA 1040214 A CA1040214 A CA 1040214A CA 204786 A CA204786 A CA 204786A CA 1040214 A CA1040214 A CA 1040214A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- menthol
- acetylglycine
- glycine
- sodium
- 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
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000002148 esters Chemical class 0.000 claims abstract description 29
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940041616 menthol Drugs 0.000 claims abstract description 18
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract description 16
- 239000004471 Glycine Substances 0.000 claims abstract description 14
- 230000032050 esterification Effects 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- -1 menthol ester Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 9
- 239000000551 dentifrice Substances 0.000 abstract description 5
- 230000021736 acetylation Effects 0.000 abstract description 4
- 238000006640 acetylation reaction Methods 0.000 abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000796 flavoring agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 210000000214 mouth Anatomy 0.000 description 6
- 239000002324 mouth wash Substances 0.000 description 6
- 239000000606 toothpaste Substances 0.000 description 6
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- 239000006072 paste Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
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- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
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- MCNJOIMMYWLFBA-UHFFFAOYSA-N 2-dodecoxy-2-oxoethanesulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCOC(=O)CS(O)(=O)=O MCNJOIMMYWLFBA-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 206010006784 Burning sensation Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
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- 240000004760 Pimpinella anisum Species 0.000 description 2
- 235000012550 Pimpinella anisum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- 229940011037 anethole Drugs 0.000 description 2
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- 235000017803 cinnamon Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000001 dental powder Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
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- 241000206575 Chondrus crispus Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 229920000569 Gum karaya Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
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- 239000003082 abrasive agent Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 239000003212 astringent agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
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- 239000004202 carbamide Substances 0.000 description 1
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- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
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- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
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- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000010494 karaya gum Nutrition 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229960000414 sodium fluoride Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU68016A LU68016A1 (enExample) | 1973-07-13 | 1973-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040214A true CA1040214A (en) | 1978-10-10 |
Family
ID=19727400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA204,786A Expired CA1040214A (en) | 1973-07-13 | 1974-07-15 | Organoleptic methyl-n-acetyglycinate |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3991178A (enExample) |
| JP (1) | JPS5747904B2 (enExample) |
| CA (1) | CA1040214A (enExample) |
| CH (1) | CH605669A5 (enExample) |
| DE (1) | DE2433165C2 (enExample) |
| FR (1) | FR2236844B1 (enExample) |
| GB (1) | GB1464985A (enExample) |
| IT (1) | IT1050474B (enExample) |
| LU (1) | LU68016A1 (enExample) |
| NL (1) | NL7409302A (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582229B2 (ja) * | 1977-04-11 | 1983-01-14 | 住友化学工業株式会社 | グリシンエステルの製法 |
| GB2114481B (en) * | 1982-02-16 | 1985-08-29 | Standard Telephones Cables Ltd | Improvements in hand tools |
| JPS59110521A (ja) * | 1982-12-17 | 1984-06-26 | Matsushita Electric Ind Co Ltd | ねじ締め機 |
| JPS59116177U (ja) * | 1983-01-28 | 1984-08-06 | 古河電気工業株式会社 | 締付箇所数計数装置付トルクレンチ |
| JPS59148273U (ja) * | 1983-03-25 | 1984-10-03 | 松下電器産業株式会社 | 動作回数カウント機構を備えた電動ドライバ− |
| DE3502830A1 (de) * | 1984-02-09 | 1985-08-14 | Colgate Palmolive Co | Zahnpflegemittelzusammensetzung |
| JPS62124081U (enExample) * | 1986-01-31 | 1987-08-06 | ||
| JPS6310074U (enExample) * | 1986-07-04 | 1988-01-22 | ||
| JPS63116275U (enExample) * | 1986-07-18 | 1988-07-27 | ||
| FR2603888B1 (fr) * | 1986-09-16 | 1990-12-21 | Panmedica Sa | Esters d'amino acides du trimethyl cyclohexanol, procede de preparation et utilisation comme medicaments |
| US5236946A (en) * | 1986-09-16 | 1993-08-17 | Panmedica S.A. | Amino acid esters of cycloaliphatic alcohols and their use in treating lipemic disorders |
| EP0310299A1 (en) * | 1987-09-28 | 1989-04-05 | The Procter & Gamble Company | Beta-amino acid ester derivatives of alcoholic actives having extended duration of activity |
| US4945347A (en) * | 1988-03-17 | 1990-07-31 | Perry John C | Motion and orientation responsive device for seismic, intrusion, and tilt alarms and the like |
| AU636516B2 (en) * | 1990-11-06 | 1993-04-29 | Wm. Wrigley Jr. Company | Enhanced flavors using menthone ketals |
| US5629013A (en) * | 1991-04-04 | 1997-05-13 | The Procter & Gamble Company | Chewable calcium carbonate antacid tablet compositions |
| US5244670A (en) * | 1991-04-04 | 1993-09-14 | The Procter & Gamble Company | Ingestible pharmaceutical compositions for treating upper gastrointestinal tract distress |
| DE4110973A1 (de) * | 1991-04-05 | 1992-10-08 | Haarmann & Reimer Gmbh | Mittel mit physiologischem kuehleffekt und fuer diese mittel geeignete wirksame verbindungen |
| US5286480A (en) * | 1992-06-29 | 1994-02-15 | The Procter & Gamble Company | Use of N-acetylated amino acid complexes in oral care compositions |
| AU5134893A (en) * | 1992-10-09 | 1994-05-09 | Procter & Gamble Company, The | Anaesthetic compositions |
| JPH08509725A (ja) * | 1993-04-30 | 1996-10-15 | ザ、プロクター、エンド、ギャンブル、カンパニー | コートされた医薬組成物 |
| JPH0720267U (ja) * | 1993-09-17 | 1995-04-11 | 株式会社東日製作所 | トルクレンチ |
| US6455080B1 (en) | 1997-12-29 | 2002-09-24 | Wm. Wrigley Jr., Company | Chewing gum containing controlled release acyclic carboxamide and method of making |
| US6627233B1 (en) | 1997-09-18 | 2003-09-30 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents |
| CA2303828C (en) | 1997-09-18 | 2005-08-09 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents |
| ES2272209T3 (es) | 1999-03-31 | 2007-05-01 | Firmenich Sa | Utilizacion de cubebol como ingrediente aromatizante. |
| EP1318761B1 (en) * | 2000-09-21 | 2011-01-19 | Align Technology, Inc. | System for concurrent tooth repositioning and substance delivery |
| KR100411205B1 (ko) * | 2001-08-27 | 2003-12-18 | 주식회사 태평양 | 멘톨 유도체 및 그의 제조방법 |
| US20040185093A1 (en) * | 2003-03-18 | 2004-09-23 | Szymczak Christopher E. | Compositions containing sucralose |
| US7025997B2 (en) * | 2003-09-24 | 2006-04-11 | International Flavors & Fragrances Inc. | Coolant plant extract compositions containing monomenthyl succinate |
| DE102004043945A1 (de) * | 2004-09-11 | 2006-03-30 | Henkel Kgaa | Mund-, Zahn- und Zahnprotesenpflegemittel enthaltend die Plaquebildung inhibierende Substanzen |
| US8899976B2 (en) | 2004-09-24 | 2014-12-02 | Align Technology, Inc. | Release agent receptacle |
| EP2559424A1 (en) | 2005-10-05 | 2013-02-20 | Kraft Foods Global Brands LLC | Cooling composition comprising trimethyl isopropyl butanamide |
| US20070148283A1 (en) | 2005-12-23 | 2007-06-28 | Cadbury Adams Usa Llc | Compositions providing a sensation substantially similar to that provided by menthol |
| CN102123982B (zh) | 2008-08-15 | 2014-08-06 | 宝洁公司 | 在消费品中可用作感觉剂的环己烷衍生物的合成 |
| EP2313070A1 (en) * | 2008-08-15 | 2011-04-27 | The Procter & Gamble Company | Solution of menthane carboxamides for use in consumer products |
| PL2346475T3 (pl) | 2008-11-20 | 2017-08-31 | The Procter & Gamble Company | Kompozycje do higieny osobistej zapewniające intensywniejsze uczucie chłodzenia |
| RU2012158245A (ru) | 2010-07-19 | 2014-08-27 | Дзе Проктер Энд Гэмбл Компани | Композиции, содержащие производные эфирно-масличных соединений, и их применение в средствах личной гигиены |
| EP2621462B1 (en) | 2010-10-01 | 2020-02-12 | The Procter and Gamble Company | Oral care compositions with improved flavor |
| US20130042482A1 (en) | 2011-08-16 | 2013-02-21 | Valerie Jean Bradford | Skin Engaging Member Comprising An Anti-Irritation Agent |
| CA2847249C (en) | 2011-09-01 | 2016-10-18 | The Procter & Gamble Company | Oral care compositions with improved rheology |
| US20130315843A1 (en) | 2012-05-25 | 2013-11-28 | The Procter & Gamble Company | Composition for reduction of trpa1 and trpv1 sensations |
| CA2882090C (en) | 2012-09-28 | 2018-07-10 | The Gillette Company | A skin engaging member comprising at least one thermally resilient sensate |
| CN104703658B (zh) | 2012-09-28 | 2017-11-07 | 吉列有限公司 | 包含至少一种热弹性感觉剂的皮肤接合剃刮助剂构件 |
| US9884130B2 (en) | 2013-11-13 | 2018-02-06 | The Procter & Gamble Company | Compositions for delivery of oral comfort sensations |
| WO2015131002A1 (en) | 2014-02-27 | 2015-09-03 | The Procter & Gamble Company | Oral care compositions with a reduced bitter taste perception |
| US20150272847A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Skin Engaging Shaving Aid Comprising A Thermally Resilient Sensate And A TRPA1 Receptor Inhibitor |
| US20150273711A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Razor Comprising A Molded Shaving Aid Composition Comprising A Thermally Resilient Sensate |
| EP3134080A1 (en) | 2014-04-23 | 2017-03-01 | The Procter & Gamble Company | Cyclohexanecarboxamide with cooling properties |
| AU2015301623B2 (en) | 2014-08-15 | 2018-10-18 | The Procter & Gamble Company | Oral care compositions with an enhanced sensory experience |
| CN111939090A (zh) | 2014-08-15 | 2020-11-17 | 宝洁公司 | 具有增量化学物质的牙粉 |
| WO2016025414A1 (en) | 2014-08-15 | 2016-02-18 | The Procter & Gamble Company | Oral care compositions and regimens |
| WO2016085729A1 (en) | 2014-11-26 | 2016-06-02 | The Gillette Company | A skin engaging member comprising ethylene vinyl acetate |
| US9951295B2 (en) | 2015-02-19 | 2018-04-24 | The Procter & Gamble Company | Compositions for deposition on biological surfaces |
| AU2016245865B2 (en) | 2015-04-09 | 2019-04-11 | The Procter & Gamble Company | Reduction in CPC taste aversion by reducing CPC activation of TRPA1 receptors, TPRV1 receptors, or both |
| JP2018533567A (ja) | 2015-10-22 | 2018-11-15 | ザ プロクター アンド ギャンブル カンパニー | クロマトグラフィー分離方法 |
| CA3000022A1 (en) | 2015-10-22 | 2017-04-27 | The Procter & Gamble Company | Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products |
| CA3007767A1 (en) | 2015-12-18 | 2017-06-22 | The Procter & Gamble Company | Synthesis of cyclohexane ester derivatives useful as sensates in consumer products |
| CA3018559A1 (en) | 2016-04-01 | 2017-10-05 | The Procter & Gamble Company | Oral care compositions with an effective flavor display |
| WO2017173272A1 (en) | 2016-04-01 | 2017-10-05 | The Procter & Gamble Company | Oral care compositions containing potassium nitrate and peroxide |
| US10758461B2 (en) | 2016-04-01 | 2020-09-01 | The Procter & Gamble Company | Oral care compositions containing a gel network phase and potassium nitrate |
| MX371216B (es) | 2016-04-01 | 2020-01-08 | Procter & Gamble | Composiciones para el cuidado bucal que contienen redes de gel y nitrato de potasio. |
| MX2018011989A (es) | 2016-04-01 | 2019-02-13 | Procter & Gamble | Composiciones para el cuidado bucal que contienen una fase de red de gel. |
| US20170334082A1 (en) | 2016-05-18 | 2017-11-23 | The Gillette Company Llc | Skin Engaging Member Comprising Ethylene Vinyl Acetate |
| CA3037098C (en) | 2016-10-25 | 2023-01-17 | The Procter & Gamble Company | Differential pillow height fibrous structures |
| WO2018081189A1 (en) | 2016-10-25 | 2018-05-03 | The Procter & Gamble Company | Fibrous structures |
| WO2018085479A1 (en) | 2016-11-03 | 2018-05-11 | The Gillette Company Llc | Skin engaging member comprising ethylene vinyl acetate |
| BR112019009754B1 (pt) | 2016-11-17 | 2022-11-22 | The Gillette Company Llc | Membro de contato com a pele compreendendo etileno-acetato de vinila e uma fragrância |
| AU2021350111B2 (en) | 2020-09-28 | 2025-02-27 | The Procter & Gamble Company | Oral care composition comprising hops and flavor |
| CA3219441A1 (en) | 2021-05-11 | 2022-11-17 | The Procter & Gamble Company | Oral care compositions comprising block copolymer |
| CN115872881B (zh) * | 2022-11-14 | 2025-02-14 | 云南中烟工业有限责任公司 | 一种薄荷醇胺类化合物的合成方法及其在卷烟中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793446A (en) * | 1969-05-14 | 1974-02-19 | Nickstadt Moeller Inc | Oral,nasal and labial compositions containing menthyl keto esters |
-
1973
- 1973-07-13 LU LU68016A patent/LU68016A1/xx unknown
-
1974
- 1974-07-10 DE DE2433165A patent/DE2433165C2/de not_active Expired
- 1974-07-10 NL NL7409302A patent/NL7409302A/xx not_active Application Discontinuation
- 1974-07-11 FR FR7424109A patent/FR2236844B1/fr not_active Expired
- 1974-07-11 GB GB3080674A patent/GB1464985A/en not_active Expired
- 1974-07-12 IT IT69234/74A patent/IT1050474B/it active
- 1974-07-12 CH CH965274A patent/CH605669A5/xx not_active IP Right Cessation
- 1974-07-12 JP JP49080056A patent/JPS5747904B2/ja not_active Expired
- 1974-07-15 US US05/488,856 patent/US3991178A/en not_active Expired - Lifetime
- 1974-07-15 CA CA204,786A patent/CA1040214A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5032149A (enExample) | 1975-03-28 |
| DE2433165C2 (de) | 1983-05-26 |
| LU68016A1 (enExample) | 1975-04-11 |
| JPS5747904B2 (enExample) | 1982-10-13 |
| FR2236844A1 (enExample) | 1975-02-07 |
| US3991178A (en) | 1976-11-09 |
| DE2433165A1 (de) | 1975-01-30 |
| NL7409302A (nl) | 1975-01-15 |
| CH605669A5 (enExample) | 1978-10-13 |
| GB1464985A (en) | 1977-02-16 |
| IT1050474B (it) | 1981-03-10 |
| FR2236844B1 (enExample) | 1978-02-03 |
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