JP5912482B2 - メントール含有混合物 - Google Patents
メントール含有混合物 Download PDFInfo
- Publication number
- JP5912482B2 JP5912482B2 JP2011271709A JP2011271709A JP5912482B2 JP 5912482 B2 JP5912482 B2 JP 5912482B2 JP 2011271709 A JP2011271709 A JP 2011271709A JP 2011271709 A JP2011271709 A JP 2011271709A JP 5912482 B2 JP5912482 B2 JP 5912482B2
- Authority
- JP
- Japan
- Prior art keywords
- menthol
- mixture
- weight
- amount ranging
- isomenthol
- 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.)
- Active
Links
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title claims description 163
- 239000000203 mixture Substances 0.000 title claims description 163
- 229940041616 menthol Drugs 0.000 title claims description 51
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 title description 7
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 146
- -1 alkylene diol Chemical class 0.000 claims description 57
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 34
- 238000002844 melting Methods 0.000 claims description 32
- 230000008018 melting Effects 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 23
- 239000004615 ingredient Substances 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 239000002537 cosmetic Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- NOOLISFMXDJSKH-LPEHRKFASA-N Isomenthol Natural products CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000003205 fragrance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229940051250 hexylene glycol Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 235000016709 nutrition Nutrition 0.000 claims description 3
- 230000035764 nutrition Effects 0.000 claims description 3
- 239000003961 penetration enhancing agent Substances 0.000 claims description 3
- 241001385733 Aesculus indica Species 0.000 claims 2
- 239000000047 product Substances 0.000 description 45
- 239000003795 chemical substances by application Substances 0.000 description 34
- 210000003491 skin Anatomy 0.000 description 19
- 235000015218 chewing gum Nutrition 0.000 description 17
- 229940112822 chewing gum Drugs 0.000 description 14
- 239000000796 flavoring agent Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000006071 cream Substances 0.000 description 11
- 235000019634 flavors Nutrition 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 108010010803 Gelatin Proteins 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000008273 gelatin Substances 0.000 description 9
- 229920000159 gelatin Polymers 0.000 description 9
- 235000019322 gelatine Nutrition 0.000 description 9
- 235000011852 gelatine desserts Nutrition 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- UJNOLBSYLSYIBM-WISYIIOYSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2r)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@@H](C)O UJNOLBSYLSYIBM-WISYIIOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 235000009508 confectionery Nutrition 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 239000002453 shampoo Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
- 230000001953 sensory effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 5
- 229920000615 alginic acid Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011257 shell material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000606 toothpaste Substances 0.000 description 5
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 4
- NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 4
- 229940072056 alginate Drugs 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 4
- 229930007503 menthone Natural products 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 235000019640 taste Nutrition 0.000 description 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
- RCEFMOGVOYEGJN-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one Chemical compound OC1=CC=CC=C1N1C(=O)NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CC1 RCEFMOGVOYEGJN-UHFFFAOYSA-N 0.000 description 3
- 235000007173 Abies balsamea Nutrition 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000005973 Carvone Substances 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- 244000018716 Impatiens biflora Species 0.000 description 3
- 229920002774 Maltodextrin Polymers 0.000 description 3
- BLILOGGUTRWFNI-UHFFFAOYSA-N Monomenthyl succinate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O BLILOGGUTRWFNI-UHFFFAOYSA-N 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 239000003213 antiperspirant Substances 0.000 description 3
- 229960005233 cineole Drugs 0.000 description 3
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 3
- 229940117916 cinnamic aldehyde Drugs 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 239000002781 deodorant agent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000005496 eutectics Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
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- 239000007921 spray Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 2
- KXSDPILWMGFJMM-AEJSXWLSSA-N (1s,4r,5r)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-4-ol Chemical compound C([C@]1(O)C)C[C@]2(C(C)C)[C@H]1C2 KXSDPILWMGFJMM-AEJSXWLSSA-N 0.000 description 2
- YTHRBOFHFYZBRJ-UHFFFAOYSA-N (2-methyl-5-prop-1-en-2-yl-1-cyclohex-2-enyl) acetate Chemical compound CC(=O)OC1CC(C(C)=C)CC=C1C YTHRBOFHFYZBRJ-UHFFFAOYSA-N 0.000 description 2
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 2
- JYOGCCXPANWLJI-UHFFFAOYSA-N 1-(1-methyl-4-propan-2-ylcyclohexyl)oxypropane-1,2-diol Chemical compound CC(C)C1CCC(C)(OC(O)C(C)O)CC1 JYOGCCXPANWLJI-UHFFFAOYSA-N 0.000 description 2
- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 description 2
- OWEMTCOXFULTNW-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanoic acid Chemical class CC(C)C(C)(C(C)C)C(O)=O OWEMTCOXFULTNW-UHFFFAOYSA-N 0.000 description 2
- FLYJSXDJKBHQAU-IBSWDFHHSA-N 2-hydroxypropyl [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] carbonate Chemical compound CC(O)COC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C FLYJSXDJKBHQAU-IBSWDFHHSA-N 0.000 description 2
- ONPCAVOVPFWIRD-UHFFFAOYSA-N 2-methyl-1-(1-methyl-4-propan-2-ylcyclohexyl)oxypropane-1,2-diol Chemical compound CC(C)C1CCC(C)(OC(O)C(C)(C)O)CC1 ONPCAVOVPFWIRD-UHFFFAOYSA-N 0.000 description 2
- JIMGVOCOYZFDKB-UHFFFAOYSA-N 2-phenylethyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OCCC1=CC=CC=C1 JIMGVOCOYZFDKB-UHFFFAOYSA-N 0.000 description 2
- VUVQBYIJRDUVHT-UHFFFAOYSA-N 3,6-dimethyl-5,6,7,7a-tetrahydro-4h-1-benzofuran-2-one Chemical compound C1C(C)CCC2=C(C)C(=O)OC21 VUVQBYIJRDUVHT-UHFFFAOYSA-N 0.000 description 2
- SXIDVHLMAKILQP-UHFFFAOYSA-N 3-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one Chemical compound O=C1CCC(C)=C1N1CCCC1 SXIDVHLMAKILQP-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- WHKRHBLAJFYZKF-UHFFFAOYSA-N 5-(hydroxymethyl)-2-methoxyphenol Chemical compound COC1=CC=C(CO)C=C1O WHKRHBLAJFYZKF-UHFFFAOYSA-N 0.000 description 2
- CTMTYSVTTGVYAW-FRRDWIJNSA-N 5-[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxy-5-oxopentanoic acid Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)CCCC(O)=O CTMTYSVTTGVYAW-FRRDWIJNSA-N 0.000 description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
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- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 2
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- RWAXQWRDVUOOGG-UHFFFAOYSA-N N,2,3-Trimethyl-2-(1-methylethyl)butanamide Chemical compound CNC(=O)C(C)(C(C)C)C(C)C RWAXQWRDVUOOGG-UHFFFAOYSA-N 0.000 description 2
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- UJNOLBSYLSYIBM-NOOOWODRSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2s)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@H](C)O UJNOLBSYLSYIBM-NOOOWODRSA-N 0.000 description 2
- CZNLTCTYLMYLHL-UHFFFAOYSA-N [6]-Paradol Chemical compound CCCCCCCC(=O)CCC1=CC=C(O)C(OC)=C1 CZNLTCTYLMYLHL-UHFFFAOYSA-N 0.000 description 2
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- KVYGGMBOZFWZBQ-UHFFFAOYSA-N benzyl nicotinate Chemical compound C=1C=CN=CC=1C(=O)OCC1=CC=CC=C1 KVYGGMBOZFWZBQ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 2
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- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
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- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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| US41694110P | 2010-11-24 | 2010-11-24 | |
| EP10192468.6 | 2010-11-24 | ||
| EP10192468A EP2457554A1 (de) | 2010-11-24 | 2010-11-24 | Menthol enthaltende Mischung |
| US61/416,941 | 2010-11-24 |
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| JP2012111948A JP2012111948A (ja) | 2012-06-14 |
| JP2012111948A5 JP2012111948A5 (enExample) | 2016-04-07 |
| JP5912482B2 true JP5912482B2 (ja) | 2016-04-27 |
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| US (1) | US8496950B2 (enExample) |
| EP (2) | EP2457554A1 (enExample) |
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| US8646461B2 (en) | 2011-12-14 | 2014-02-11 | Sentiens, Llc | Device and method for simulating chemosensation of smoking |
| EP2934456B1 (en) * | 2012-12-20 | 2016-03-02 | Unilever N.V. | Eutectic mixtures in personal care compositions |
| EA028959B1 (ru) | 2012-12-20 | 2018-01-31 | Юнилевер Н.В. | Эвтектические смеси в композициях для личной гигиены |
| US8697043B1 (en) * | 2013-01-08 | 2014-04-15 | Chattem, Inc. | Odor suppression of volatile organic analgesic compounds and method of use |
| DE102013112065A1 (de) | 2013-11-01 | 2015-05-07 | Minasolve Germany Gmbh | Stabile Lösungen mit physiologischem Kühlreagenz und deren Verwendung |
| JP6718866B2 (ja) * | 2014-10-16 | 2020-07-08 | カーギル インコーポレイテッド | 直接圧縮性のエリスリトールの調製方法及びその使用 |
| EP3093002B1 (de) * | 2015-05-15 | 2018-04-25 | Symrise AG | Flüssige kühlstoffzubereitungen |
| WO2020174340A1 (en) | 2019-02-25 | 2020-09-03 | Universidade Nova De Lisboa | Eutectic menthol-fatty acid combinations for wound healing |
| CA3138194A1 (en) | 2019-04-30 | 2020-11-05 | Bayer Healthcare Llc | Topical analgesic gel compositions |
| WO2020223097A1 (en) | 2019-04-30 | 2020-11-05 | Bayer Healthcare Llc | Topical analgesic compositions |
| WO2020227512A1 (en) | 2019-05-08 | 2020-11-12 | Gamot Global Pte. Ltd. | Use of isothiocyanate in smokeless tobacco products |
| MX2022012569A (es) * | 2020-05-01 | 2022-11-07 | Procter & Gamble | Composicion saborizante de menta. |
| EP4142508B1 (en) * | 2020-05-01 | 2024-10-09 | The Procter & Gamble Company | Mint flavor compositions |
| JP2023523292A (ja) * | 2020-05-01 | 2023-06-02 | ザ プロクター アンド ギャンブル カンパニー | ミント風味組成物 |
| EP3944853A1 (en) * | 2020-07-31 | 2022-02-02 | Basf Se | Liquid l-menthol composition |
| AU2021338763A1 (en) * | 2020-09-09 | 2023-05-25 | Inhale Health Llc | Nicotine-free formulations, devices and methods thereof for cessation of smoking or nicotine replacement |
| WO2024094975A1 (en) * | 2022-10-31 | 2024-05-10 | Reckitt & Colman (Overseas) Hygiene Home Limited | Pest control composition comprising a polymeric ingredient |
| EP4603151A1 (en) * | 2024-02-16 | 2025-08-20 | Solfarcos Soluções Farmaceuticas e Cosmeticas Lda | Stable cosmetic composition, methods and uses thereof |
| WO2025172966A1 (en) * | 2024-02-16 | 2025-08-21 | Solfarcos - Soluções Farmacêuticas E Cosméticas, Lda. | Stable composition, methods and uses thereof |
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| GB9707978D0 (en) | 1997-04-21 | 1997-06-11 | Procter & Gamble | Throat soothing compositions |
| US6214376B1 (en) | 1998-08-25 | 2001-04-10 | Banner Pharmacaps, Inc. | Non-gelatin substitutes for oral delivery capsules, their composition and process of manufacture |
| DE19853562B4 (de) * | 1998-11-20 | 2006-06-08 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von d,l-Menthol |
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| DE10023283A1 (de) * | 2000-05-12 | 2001-11-15 | Bayer Ag | Verfahren zur Herstellung von d,l-Menthol |
| SE0002960D0 (sv) | 2000-08-21 | 2000-08-21 | Eurotube Ab | Engångs-smådjursfälla |
| DE10164110A1 (de) | 2001-12-24 | 2003-07-10 | Dragoco Gerberding Co Ag | Mononuklear gefüllte Mikrokapseln |
| DE10219228A1 (de) | 2002-04-30 | 2003-11-13 | Symrise Gmbh & Co Kg | Aromapartikel |
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| GB0221697D0 (en) | 2002-09-18 | 2002-10-30 | Unilever Plc | Novel compouds and their uses |
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| DE10254872A1 (de) | 2002-11-25 | 2004-06-03 | Symrise Gmbh & Co. Kg | Anthranilsäureamide und deren Derivate als kosmetische und pharmazeutische Wirkstoffe |
| EP1709958A1 (de) | 2002-12-05 | 2006-10-11 | Symrise GmbH & Co. KG | Nahtlose gefüllte Kapseln |
| US20050025795A1 (en) * | 2003-07-30 | 2005-02-03 | The Procter & Gamble Company | Compounds, Compositions and methods for insect control |
| DE102004029239A1 (de) | 2004-05-03 | 2005-12-01 | Symrise Gmbh & Co. Kg | Benyliden-β-dicarbonylverbindungen als neue UV-Absorber |
| US7482378B2 (en) * | 2004-05-28 | 2009-01-27 | Millenium Specialty Chemicals, Inc. | Physiological cooling compositions |
| US9987217B2 (en) | 2004-06-18 | 2018-06-05 | Symrise Ag | Blackberry extract |
| DE102004038485A1 (de) | 2004-08-07 | 2006-02-23 | Symrise Gmbh & Co. Kg | alpha-Benzoyl-zimtsäurenitrile als neue UV-Absorber |
| WO2006039945A1 (en) * | 2004-10-13 | 2006-04-20 | Symrise Gmbh & Co. Kg | Composition of menthyl lactate and a mixture of menthol isomers |
| US20080305054A1 (en) | 2004-10-25 | 2008-12-11 | Symrise Gmbh & Co. Kg | Use of Glycosylated Flavanones for the Browning of Skin or Hair |
| WO2006053912A1 (en) | 2004-11-22 | 2006-05-26 | Symrise Gmbh & Co. Kg | Formulations comprising ceramides and/or pseudoceramides and (alpha-)bisabolol for combating skin damage |
| WO2007042472A1 (en) | 2005-10-14 | 2007-04-19 | Symrise Gmbh & Co. Kg | Synergistic mixtures of bisabolol and ginger extract |
| DE102005056890A1 (de) | 2005-11-28 | 2007-05-31 | Institut für Umweltmedizinische Forschung gGmbH | Kosmetisches Verfahren zur Beeinflussung der Melaninbildung in der Haut |
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| DE102006043587A1 (de) | 2006-09-16 | 2008-03-27 | Symrise Gmbh & Co. Kg | 2-Methyl-2-alkenyl-substituierte 1,3-Dioxane als Riechstoffe |
| EP1923041A1 (de) | 2006-10-20 | 2008-05-21 | Symrise GmbH & Co. KG | Verwendung von C10-C14-Alkandiolen zur Herstellung eines Mittels zur Prophylaxe und/oder Behandlung von Malassezia-induzierter Schuppenbildung, sowie Zubereitungen enthaltend C10-C14-Alkandiole |
| EP1915982A1 (de) | 2006-10-20 | 2008-04-30 | Symrise GmbH & Co. KG | Verwendung von 1,2-Decandiol zur Sebumreduktion bzw. zur Unterstützung des Eindringens von Wirkstoffen in Hautbereiche, sowie kosmetische und/oder dermatologische Zubereitungen umfassend 1,2-Decandiol |
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| EP2036875A1 (de) * | 2007-09-11 | 2009-03-18 | Basf Se | Kontinuierliches Verfahren zur Herstellung von Menthol in reiner oder angereicherter Form |
| DE102008043586A1 (de) * | 2007-11-12 | 2009-05-14 | Symrise Gmbh & Co. Kg | Riechstoffakkorde zur Bekämpfung der Wahrnehmung von Körpergeruch |
| JP4750162B2 (ja) * | 2008-08-28 | 2011-08-17 | 三栄源エフ・エフ・アイ株式会社 | ｌ−メントール含有乳化香料 |
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- 2011-11-24 JP JP2011271709A patent/JP5912482B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012111948A (ja) | 2012-06-14 |
| EP2457555A3 (de) | 2014-04-23 |
| EP2457554A1 (de) | 2012-05-30 |
| US20120128744A1 (en) | 2012-05-24 |
| EP2457555A2 (de) | 2012-05-30 |
| EP2457555B1 (de) | 2016-10-05 |
| US8496950B2 (en) | 2013-07-30 |
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