CA2147883C - Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor - Google Patents
Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor Download PDFInfo
- Publication number
- CA2147883C CA2147883C CA002147883A CA2147883A CA2147883C CA 2147883 C CA2147883 C CA 2147883C CA 002147883 A CA002147883 A CA 002147883A CA 2147883 A CA2147883 A CA 2147883A CA 2147883 C CA2147883 C CA 2147883C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- cool feeling
- derivative
- methylcyclohexanol
- refrigeration
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 70
- ZYTMANIQRDEHIO-KXUCPTDWSA-N (-)-Isopulegol Natural products C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims description 14
- 239000003507 refrigerant Substances 0.000 claims description 14
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 claims description 10
- LMXFTMYMHGYJEI-IWSPIJDZSA-N (1R,2R,5R)-2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanol Chemical compound C[C@@H]1CC[C@@H](C(C)(C)O)[C@H](O)C1 LMXFTMYMHGYJEI-IWSPIJDZSA-N 0.000 claims description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- IMCZVQCVSSWPCG-UHFFFAOYSA-N cyclohexyloxymethylbenzene Chemical class C=1C=CC=CC=1COC1CCCCC1 IMCZVQCVSSWPCG-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- -1 benzyl halide Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims 1
- 238000005057 refrigeration Methods 0.000 abstract description 50
- 210000002200 mouth mucosa Anatomy 0.000 abstract description 7
- 230000009965 odorless effect Effects 0.000 abstract description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 229940041616 menthol Drugs 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000009472 formulation Methods 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 235000019645 odor Nutrition 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000008213 purified water Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000006071 cream Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical class CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000006210 lotion Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000004949 mass spectrometry Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002537 cosmetic Substances 0.000 description 8
- 235000015961 tonic Nutrition 0.000 description 8
- 230000001256 tonic effect Effects 0.000 description 8
- RMNCXEZCLGGIIN-TVTJGUELSA-N (1r,2s,5r)-2-(1-methoxypropan-2-yl)-5-methylcyclohexan-1-ol Chemical compound COCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O RMNCXEZCLGGIIN-TVTJGUELSA-N 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 7
- 239000000551 dentifrice Substances 0.000 description 7
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 7
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- 244000246386 Mentha pulegium Species 0.000 description 6
- 235000016257 Mentha pulegium Nutrition 0.000 description 6
- 235000004357 Mentha x piperita Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 235000001050 hortel pimenta Nutrition 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- BINZTUGHCIRHLP-JOUUOIQHSA-N (1r,2s,5r)-2-(1-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol Chemical compound OCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O BINZTUGHCIRHLP-JOUUOIQHSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 210000004761 scalp Anatomy 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- QATOZXKGBHJTKH-IBSWDFHHSA-N (1r,2s,5r)-5-methyl-2-(1-propan-2-yloxypropan-2-yl)cyclohexan-1-ol Chemical compound CC(C)OCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O QATOZXKGBHJTKH-IBSWDFHHSA-N 0.000 description 3
- RMNCXEZCLGGIIN-UHFFFAOYSA-N 2-(1-methoxypropan-2-yl)-5-methylcyclohexan-1-ol Chemical compound COCC(C)C1CCC(C)CC1O RMNCXEZCLGGIIN-UHFFFAOYSA-N 0.000 description 3
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- DNTGGZPQPQTDQF-XBXARRHUSA-N crotamiton Chemical compound C/C=C/C(=O)N(CC)C1=CC=CC=C1C DNTGGZPQPQTDQF-XBXARRHUSA-N 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
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- CAYDOSQIOPXLNA-SGUBAKSOSA-N (1r,2s,5r)-2-(1-ethoxypropan-2-yl)-5-methylcyclohexan-1-ol Chemical compound CCOCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O CAYDOSQIOPXLNA-SGUBAKSOSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 2
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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- 229910015900 BF3 Inorganic materials 0.000 description 1
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- 235000019568 aromas Nutrition 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 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
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000005182 tip of the tongue Anatomy 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/188—Unsaturated ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPHEI4-316438 | 1992-10-29 | ||
| JP31643892 | 1992-10-29 | ||
| PCT/JP1993/001562 WO1994010117A1 (en) | 1992-10-29 | 1993-10-28 | Cyclohexanol derivative, agent and composition containing the same for imparting pleasantly cool feeling, process for producing the derivative, and intermediate therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2147883A1 CA2147883A1 (en) | 1994-05-11 |
| CA2147883C true CA2147883C (en) | 2000-06-13 |
Family
ID=18077091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002147883A Expired - Lifetime CA2147883C (en) | 1992-10-29 | 1993-10-28 | Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5756857A (en:Method) |
| EP (1) | EP0667330B1 (en:Method) |
| JP (1) | JP2770081B2 (en:Method) |
| KR (2) | KR950704222A (en:Method) |
| AU (1) | AU5344794A (en:Method) |
| CA (1) | CA2147883C (en:Method) |
| DE (1) | DE69312953T2 (en:Method) |
| DK (1) | DK0667330T3 (en:Method) |
| ES (1) | ES2105338T3 (en:Method) |
| TW (1) | TW255884B (en:Method) |
| WO (1) | WO1994010117A1 (en:Method) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2978043B2 (ja) | 1993-09-16 | 1999-11-15 | 高砂香料工業株式会社 | （２ｓ）−３−｛（１ｒ，２ｓ，５ｒ）−［ ５−メチル−２−（１−メチルエチル）シクロヘキシル ］オキシ｝−１，２−プロパンジオール，その製造方法および用途 |
| US6455080B1 (en) | 1997-12-29 | 2002-09-24 | Wm. Wrigley Jr., Company | Chewing gum containing controlled release acyclic carboxamide and method of making |
| DK1014805T3 (da) | 1997-09-18 | 2009-01-05 | Wrigley W M Jun Co | Tyggegummi indeholdende fysiologisk kölende stoffer |
| US6627233B1 (en) | 1997-09-18 | 2003-09-30 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents |
| US6332042B1 (en) | 1997-10-23 | 2001-12-18 | Sony Corporation | Apparatus and method for encoding and decoding data in a lossy transmission environment |
| US6282684B1 (en) | 1997-10-23 | 2001-08-28 | Sony Corporation | Apparatus and method for recovery of data in a lossy transmission environment |
| US6307560B1 (en) | 1999-02-12 | 2001-10-23 | Sony Corporation | Classified adaptive spatio-temporal format conversion method and apparatus |
| US6170074B1 (en) | 1999-02-12 | 2001-01-02 | Sony Corporation | Source coding to provide for robust error recovery |
| US6591398B1 (en) | 1999-02-12 | 2003-07-08 | Sony Corporation | Multiple processing system |
| US7010737B2 (en) * | 1999-02-12 | 2006-03-07 | Sony Corporation | Method and apparatus for error data recovery |
| US6519369B1 (en) | 1999-02-12 | 2003-02-11 | Sony Corporation | Method and apparatus for filter tap expansion |
| US6549672B1 (en) * | 1999-06-29 | 2003-04-15 | Sony Corporation | Method and apparatus for recovery of encoded data using central value |
| US6389562B1 (en) | 1999-06-29 | 2002-05-14 | Sony Corporation | Source code shuffling to provide for robust error recovery |
| US6384263B1 (en) * | 2000-08-04 | 2002-05-07 | E. I. Du Pont De Nemours And Company | Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane |
| DE10058459A1 (de) * | 2000-11-24 | 2002-06-06 | Haarmann & Reimer Gmbh | Rhinologica |
| US20030229344A1 (en) * | 2002-01-22 | 2003-12-11 | Dycus Sean T. | Vessel sealer and divider and method of manufacturing same |
| US8273367B2 (en) * | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| US6972010B2 (en) * | 2001-04-17 | 2005-12-06 | The Procter & Gamble Company | Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived |
| ATE480211T1 (de) * | 2003-05-19 | 2010-09-15 | Procter & Gamble | Flüchtiges material enthaltender absobierender hygieneartikel mit sperrschichtverpackung |
| JP5335191B2 (ja) | 2003-08-22 | 2013-11-06 | デンドレオン コーポレイション | Ｔｒｐ−ｐ８発現に関連する疾患の処置をするための組成物および方法 |
| US7025997B2 (en) | 2003-09-24 | 2006-04-11 | International Flavors & Fragrances Inc. | Coolant plant extract compositions containing monomenthyl succinate |
| US20070077331A1 (en) | 2005-10-05 | 2007-04-05 | Cadbury Adams Usa Llc. | Cooling compositions |
| ES2488634T3 (es) | 2005-12-23 | 2014-08-28 | Intercontinental Great Brands Llc | Composición que proporciona una sensación refrescante significativamente similar a la que proporciona el mentol |
| ES2441249T3 (es) | 2006-02-15 | 2014-02-03 | Dendreon Corporation | Moduladores de pequeñas moléculas de la actividad de TRP-P8 |
| US7772266B2 (en) | 2006-02-15 | 2010-08-10 | Dendreon Corporation | Small-molecule modulators of TRP-P8 activity |
| JP5371050B2 (ja) * | 2009-11-06 | 2013-12-18 | 住友精化株式会社 | ジボランの製造方法 |
| US8800509B2 (en) | 2010-04-27 | 2014-08-12 | Mitsubishi Heavy Industries, Ltd. | Scavenging passage structure for two-stroke engine |
| DE102012016191A1 (de) | 2012-08-16 | 2014-03-13 | Merck Patent Gmbh | Verwendung von Cyclohexanolethern mit antimikrobiellen Eigenschaften |
| RU2014149076A (ru) | 2012-05-08 | 2016-06-27 | Мерк Патент Гмбх | Применение простых эфиров циклогексанола, обладающих антимикробными свойствами |
| DE102012008892A1 (de) | 2012-05-08 | 2013-11-14 | Merck Patent Gmbh | Verwendung von Cyclohexanolethern mit antimikrobiellen Eigenschaften |
| CN106660934B (zh) | 2014-06-24 | 2020-03-03 | 科思创德国股份有限公司 | 制备硝基苯的方法 |
| FR3029777B1 (fr) | 2014-12-15 | 2019-11-29 | L'oreal | Utilisation de l'association d'un polyether polyurethane non-ionique associatif et d'un derive de cyclohexanol comme agent rafraichissant de la peau |
| US20230120264A1 (en) * | 2020-03-05 | 2023-04-20 | Firmenich Sa | Hydroboration-oxidation process |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656385A (en) * | 1951-02-24 | 1953-10-20 | Upjohn Co | Cyclohexanols |
| GB1315625A (en) * | 1971-02-04 | 1973-05-02 | Wilkinson Sword Ltd | P-menthane diols and compositions containing them |
| BE795751A (fr) * | 1972-02-28 | 1973-08-21 | Unilever Nv | Compositions aromatisees contenant des composes qui donnent une sensation de froid |
| DE3440825A1 (de) * | 1984-11-08 | 1986-05-15 | Basf Ag, 6700 Ludwigshafen | P-alkoxy-cyclohexyl-alkanole und -alkanolester, deren herstellung und verwendung als riechstoffe |
| DE3705299A1 (de) * | 1987-02-19 | 1988-09-01 | Basf Ag | 3-tert-butyl-4-methoxi-cyclohexylmethanol, dessen herstellung und verwendung als riechstoff |
| US4757051A (en) * | 1987-08-11 | 1988-07-12 | Basf Aktiengesellschaft | 2-tert-butyl-4-methylcyclohexanol derivatives, their preparation and their use as scents |
| US5037802A (en) * | 1988-12-16 | 1991-08-06 | Basf K & F Corporation | Sandalwood odorants |
| JPH02290827A (ja) * | 1989-05-01 | 1990-11-30 | Kao Corp | １―アルコキシ―３―ｌ―メントキシプロパン―２―オール並びにこれを含有する冷感剤及び冷感性組成物 |
-
1993
- 1993-10-28 DK DK93923658.4T patent/DK0667330T3/da active
- 1993-10-28 EP EP93923658A patent/EP0667330B1/en not_active Expired - Lifetime
- 1993-10-28 US US08/433,375 patent/US5756857A/en not_active Expired - Lifetime
- 1993-10-28 WO PCT/JP1993/001562 patent/WO1994010117A1/ja active IP Right Grant
- 1993-10-28 CA CA002147883A patent/CA2147883C/en not_active Expired - Lifetime
- 1993-10-28 KR KR1019950701667A patent/KR950704222A/ko active Granted
- 1993-10-28 ES ES93923658T patent/ES2105338T3/es not_active Expired - Lifetime
- 1993-10-28 DE DE69312953T patent/DE69312953T2/de not_active Expired - Lifetime
- 1993-10-28 KR KR1019950701667A patent/KR0152173B1/ko not_active Expired - Lifetime
- 1993-10-28 JP JP6510890A patent/JP2770081B2/ja not_active Expired - Lifetime
- 1993-10-28 AU AU53447/94A patent/AU5344794A/en not_active Abandoned
- 1993-11-15 TW TW082109522A patent/TW255884B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0667330B1 (en) | 1997-08-06 |
| EP0667330A4 (en:Method) | 1995-08-23 |
| CA2147883A1 (en) | 1994-05-11 |
| JP2770081B2 (ja) | 1998-06-25 |
| ES2105338T3 (es) | 1997-10-16 |
| US5756857A (en) | 1998-05-26 |
| DK0667330T3 (da) | 1997-10-27 |
| KR0152173B1 (ko) | 1998-10-15 |
| EP0667330A1 (en) | 1995-08-16 |
| AU5344794A (en) | 1994-05-24 |
| TW255884B (en:Method) | 1995-09-01 |
| DE69312953D1 (de) | 1997-09-11 |
| WO1994010117A1 (en) | 1994-05-11 |
| KR950704222A (ko) | 1995-11-17 |
| DE69312953T2 (de) | 1998-03-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20131028 |