CA1040214A - Organoleptic methyl-n-acetyglycinate - Google Patents

Organoleptic methyl-n-acetyglycinate

Info

Publication number: CA1040214A
Authority: CA; Canada
Prior art keywords: ester; menthol; acetylglycine; glycine; sodium
Prior art date: 1973-07-13
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

Application number

CA204,786A

Other languages

English (en)

French (fr)

Inventor

Francoise Humbert

Gerard Guth

Yves T. D'audiffret

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Unilever PLC

Original Assignee

Unilever PLC

Priority date (The priority date 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 date listed.)

1973-07-13

Filing date

1974-07-15

Publication date

1978-10-10

1974-07-15 Application filed by Unilever PLC filed Critical Unilever PLC

1978-10-10 Application granted granted Critical

1978-10-10 Publication of CA1040214A publication Critical patent/CA1040214A/en

Status Expired legal-status Critical Current

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
229940034610 toothpaste Drugs 0.000 description 6
229940051866 mouthwash Drugs 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
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
235000019634 flavors Nutrition 0.000 description 4
238000005498 polishing Methods 0.000 description 4
230000035807 sensation Effects 0.000 description 4
235000019615 sensations Nutrition 0.000 description 4
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
235000003599 food sweetener Nutrition 0.000 description 3
239000003906 humectant Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000003765 sweetening agent Substances 0.000 description 3
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
235000002899 Mentha suaveolens Nutrition 0.000 description 2
235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
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
239000004141 Sodium laurylsulphate Substances 0.000 description 2
235000016639 Syzygium aromaticum Nutrition 0.000 description 2
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229920001615 Tragacanth Polymers 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229940011037 anethole Drugs 0.000 description 2
235000019658 bitter taste Nutrition 0.000 description 2
239000004075 cariostatic agent Substances 0.000 description 2
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
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
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
239000004857 Balsam Substances 0.000 description 1
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
235000009499 Vanilla fragrans Nutrition 0.000 description 1
235000012036 Vanilla tahitensis Nutrition 0.000 description 1
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
230000000397 acetylating effect Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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
230000003115 biocidal effect Effects 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
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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239000010636 coriander oil Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
229960003887 dichlorophen Drugs 0.000 description 1
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
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000006870 function Effects 0.000 description 1
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
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150000002500 ions Chemical class 0.000 description 1
235000010494 karaya gum Nutrition 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
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
239000001923 methylcellulose Substances 0.000 description 1
210000003928 nasal cavity Anatomy 0.000 description 1
210000001640 nerve ending Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
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239000000843 powder Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
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235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 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
239000008107 starch Substances 0.000 description 1
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239000010936 titanium Substances 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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239000000341 volatile oil Substances 0.000 description 1

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)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Oral & Maxillofacial Surgery (AREA)
Birds (AREA)
Epidemiology (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)
Confectionery (AREA)

CA204,786A 1973-07-13 1974-07-15 Organoleptic methyl-n-acetyglycinate Expired CA1040214A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU68016A LU68016A1 (2)	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 (2)
JP (1)	JPS5747904B2 (2)
CA (1)	CA1040214A (2)
CH (1)	CH605669A5 (2)
DE (1)	DE2433165C2 (2)
FR (1)	FR2236844B1 (2)
GB (1)	GB1464985A (2)
IT (1)	IT1050474B (2)
LU (1)	LU68016A1 (2)
NL (1)	NL7409302A (2)

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JP2013535450A (ja)	2010-07-19	2013-09-12	ザプロクターアンドギャンブルカンパニー	精油化合物の誘導体を含む組成物、及びパーソナルケア製品における使用
CN103140209B (zh)	2010-10-01	2017-10-13	宝洁公司	具有改善的风味的口腔护理组合物
US20130042482A1 (en)	2011-08-16	2013-02-21	Valerie Jean Bradford	Skin Engaging Member Comprising An Anti-Irritation Agent
RU2578465C2 (ru)	2011-09-01	2016-03-27	Дзе Проктер Энд Гэмбл Компани	Композиции для ухода за полостью рта с улучшенной реологией
US20130315843A1 (en)	2012-05-25	2013-11-28	The Procter & Gamble Company	Composition for reduction of trpa1 and trpv1 sensations
RU2015105518A (ru)	2012-09-28	2016-11-20	Дзе Жиллетт Компани	Контактирующий с кожей элемент вспомогательного средства для бритья, содержащий, по меньшей мере, одно термоустойчивое вещество, оказывающее сенсорное воздействие
RU2664731C2 (ru)	2012-09-28	2018-08-22	Дзе Жиллетт Компани	Контактирующий с кожей элемент, содержащий по меньшей мере одно термоустойчивое вещество, оказывающее сенсорное воздействие
US9884130B2 (en)	2013-11-13	2018-02-06	The Procter & Gamble Company	Compositions for delivery of oral comfort sensations
EP3110510A1 (en)	2014-02-27	2017-01-04	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
RU2016138746A (ru)	2014-04-23	2018-05-24	Дзе Проктер Энд Гэмбл Компани	Циклогексанкарбоксамид с охлаждающими свойствами
CN106659649A (zh)	2014-08-15	2017-05-10	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
CN114191317A (zh)	2014-08-15	2022-03-18	宝洁公司	感官体验增强的口腔护理组合物
BR112017011022B1 (pt)	2014-11-26	2021-02-17	The Gillette Company Llc	dispositivo de remoção de pelo e processo de formação de um membro de engate à pele
US9951295B2 (en)	2015-02-19	2018-04-24	The Procter & Gamble Company	Compositions for deposition on biological surfaces
EP3381453A3 (en)	2015-04-09	2018-12-12	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
AU2016342264A1 (en)	2015-10-22	2018-04-05	The Procter & Gamble Company	Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products
WO2017106279A1 (en)	2015-12-18	2017-06-22	The Procter & Gamble Company	Synthesis of cyclohexane ester derivatives useful as sensates in consumer products
EP3435960A1 (en)	2016-04-01	2019-02-06	The Procter and Gamble Company	Oral care compositions containing potassium nitrate and peroxide
BR112018069841A2 (pt)	2016-04-01	2019-01-29	Procter & Gamble	composições para tratamento bucal contendo uma fase de rede de gel
WO2017173196A1 (en)	2016-04-01	2017-10-05	The Procter & Gamble Company	Oral care compositions containing gel networks and potassium nitrate
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1973
- 1973-07-13 LU LU68016A patent/LU68016A1/xx unknown
1974
- 1974-07-10 NL NL7409302A patent/NL7409302A/xx not_active Application Discontinuation
- 1974-07-10 DE DE2433165A patent/DE2433165C2/de not_active Expired
- 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
US3991178A (en)	1976-11-09
FR2236844A1 (2)	1975-02-07
DE2433165C2 (de)	1983-05-26
IT1050474B (it)	1981-03-10
NL7409302A (nl)	1975-01-15
LU68016A1 (2)	1975-04-11
GB1464985A (en)	1977-02-16
CH605669A5 (2)	1978-10-13
JPS5032149A (2)	1975-03-28
DE2433165A1 (de)	1975-01-30
FR2236844B1 (2)	1978-02-03
JPS5747904B2 (2)	1982-10-13

Publication	Publication Date	Title
US3991178A (en)	1976-11-09	Menthyl ester of N-acetylglycine and oral compositions containing same
CA1183457A (en)	1985-03-05	Flavoured aqueous oral composition
US3917613A (en)	1975-11-04	Esters of menthol and 2-pyrrolidone or piperidine carboxylic acids
US4071615A (en)	1978-01-31	Flavored dentifrice
DE2205255C3 (de)	1981-06-04	N-substituierte p-Menthan-3-carbonsäureamide und sie enthaltende Mittel zur Stimulierung der Kaltrezeptoren des Nervensystems
EP0498728B1 (fr)	1995-08-16	Amides de la glycyl-sérine et compositions cosmétiques, pharmaceutiques ou alimentaires les contenants
DE2608226A1 (de)	1977-09-08	Mittel mit physiologischer kuehlwirkung
DE69712054T2 (de)	2002-10-24	Zahnpflegemittel gegen zahnsteinbildung enthaltend hochlösliche pyrophosphate
DE2202535A1 (de)	1972-08-17	Substituierte p-Menthane und deren Verwendung
EP0310299A1 (en)	1989-04-05	Beta-amino acid ester derivatives of alcoholic actives having extended duration of activity
US3644613A (en)	1972-02-22	Oral. nasal and labial compositions containing menthyl keto esters
AU2002256299B2 (en)	2007-01-25	Stable herbal dentifrice
JP3884808B2 (ja)	2007-02-21	口腔用組成物
JP4598900B2 (ja)	2010-12-15	口腔歯科分野におけるテルペン類を実質的に含有していないイチョウのフラボノイド抽出物の使用及びかかる抽出物を含有する組成物
AU2002256299A1 (en)	2003-04-17	Stable herbal dentifrice
US20040115138A1 (en)	2004-06-17	Stable herbal dentifrice
US4170635A (en)	1979-10-09	Flavored dentifrice
KR100537834B1 (ko)	2005-12-19	목단피 추출물을 유효성분으로 함유하는 구취 억제용 구강 조성물
JP2001089385A (ja)	2001-04-03	抗う蝕剤
JP2551012B2 (ja)	1996-11-06	口腔用組成物
JP3660717B2 (ja)	2005-06-15	口腔用組成物
WO1992018097A1 (en)	1992-10-29	Perfume bases
JP2619841B2 (ja)	1997-06-11	口腔用組成物
DE69207924T2 (de)	1996-09-19	Dipeptidderivate mit Urethan-Gruppierung, deren Herstellung und Anwendung, insbesondere als hydrierende und tensioaktive Wirkstoffe bei kosmetischen, pharmazeutischen und Nahrungszubereitungen
JP2001089344A (ja)	2001-04-03	抗う蝕剤