DE60315069T2 - Alkylsulfanylbenzole als duftstoffe - Google Patents
Alkylsulfanylbenzole als duftstoffe Download PDFInfo
- Publication number
- DE60315069T2 DE60315069T2 DE60315069T DE60315069T DE60315069T2 DE 60315069 T2 DE60315069 T2 DE 60315069T2 DE 60315069 T DE60315069 T DE 60315069T DE 60315069 T DE60315069 T DE 60315069T DE 60315069 T2 DE60315069 T2 DE 60315069T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- hydrogen
- propyl
- methylsulfanylbenzene
- fragrance
- 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
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- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000000796 flavoring agent Substances 0.000 claims abstract description 12
- 235000019634 flavors Nutrition 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
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- WOBUYSKXJVQBQU-UHFFFAOYSA-N 1-(cyclopentylmethyl)-4-methylsulfanylbenzene Chemical compound C1=CC(SC)=CC=C1CC1CCCC1 WOBUYSKXJVQBQU-UHFFFAOYSA-N 0.000 claims description 4
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- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- WTYGAUXICFETTC-UHFFFAOYSA-N cyclobarbital Chemical compound C=1CCCCC=1C1(CC)C(=O)NC(=O)NC1=O WTYGAUXICFETTC-UHFFFAOYSA-N 0.000 description 1
- 229960004138 cyclobarbital Drugs 0.000 description 1
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 1
- WTLQMMBYEQFMGM-UHFFFAOYSA-N cyclobutyl-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1CCC1 WTLQMMBYEQFMGM-UHFFFAOYSA-N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- BQBFVDZHFJWWEN-UHFFFAOYSA-N cyclopropyl-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1CC1 BQBFVDZHFJWWEN-UHFFFAOYSA-N 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 1
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 1
- HNZUNIKWNYHEJJ-XFXZXTDPSA-N geranylacetone Chemical compound CC(C)=CCC\C(C)=C/CCC(C)=O HNZUNIKWNYHEJJ-XFXZXTDPSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- YAHNYLGSSPTTAG-UHFFFAOYSA-N methyl n-(3,4-dichlorophenyl)carbamodithioate Chemical compound CSC(=S)NC1=CC=C(Cl)C(Cl)=C1 YAHNYLGSSPTTAG-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002324 mouth wash 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
- 239000002088 nanocapsule Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 235000021572 root beer Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000019565 spicy aroma Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0229453 | 2002-12-19 | ||
| GBGB0229453.6A GB0229453D0 (en) | 2002-12-19 | 2002-12-19 | Improvements in or related to organic compounds |
| PCT/CH2003/000814 WO2004056765A1 (en) | 2002-12-19 | 2003-12-12 | Alkylsulfanyl-benzenes as fragrance compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60315069D1 DE60315069D1 (de) | 2007-08-30 |
| DE60315069T2 true DE60315069T2 (de) | 2008-04-03 |
Family
ID=9949891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60315069T Expired - Lifetime DE60315069T2 (de) | 2002-12-19 | 2003-12-12 | Alkylsulfanylbenzole als duftstoffe |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20060014664A1 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1572636B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2006510685A (cg-RX-API-DMAC10.html) |
| CN (1) | CN1307152C (cg-RX-API-DMAC10.html) |
| AT (1) | ATE367375T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU2003303211A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60315069T2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2289366T3 (cg-RX-API-DMAC10.html) |
| GB (1) | GB0229453D0 (cg-RX-API-DMAC10.html) |
| MX (1) | MXPA05006386A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2004056765A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2379721A (en) | 2001-09-12 | 2003-03-19 | Luk Lamellen & Kupplungsbau | Automated transmission system |
| ES2429423T3 (es) * | 2009-11-02 | 2013-11-14 | Firmenich S.A. | Sustancias odorantes con notas anisadas |
| CN105300432A (zh) * | 2015-12-04 | 2016-02-03 | 常熟市裕华计量检测咨询服务有限公司 | 耐压测试仪 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200660A (en) * | 1966-04-18 | 1980-04-29 | Firmenich & Cie. | Aromatic sulfur flavoring agents |
| US5137889A (en) * | 1983-12-02 | 1992-08-11 | Otsuka Pharmaceutical Co., Ltd. | Dihydropyridine derivatives and process for preparing the same |
| JPH01161092A (ja) * | 1987-12-18 | 1989-06-23 | Lion Corp | 香料 |
| JPH04255796A (ja) * | 1991-02-07 | 1992-09-10 | Kao Corp | 香料組成物 |
| DE4126671A1 (de) * | 1991-08-13 | 1993-02-18 | Huels Chemische Werke Ag | Verfahren zur herstellung von alkylphenylalkylethern |
| JP3535210B2 (ja) * | 1994-04-08 | 2004-06-07 | 住友精化株式会社 | アルキルフェニルスルフィドの製造方法 |
| US6222048B1 (en) * | 1995-12-18 | 2001-04-24 | Merck Frosst Canada & Co. | Diaryl-2-(5H)-furanones as Cox-2 inhibitors |
| EP1264547A1 (en) * | 2001-06-06 | 2002-12-11 | Givaudan SA | Flavour and fragrance compositions |
-
2002
- 2002-12-19 GB GBGB0229453.6A patent/GB0229453D0/en not_active Ceased
-
2003
- 2003-12-12 MX MXPA05006386A patent/MXPA05006386A/es active IP Right Grant
- 2003-12-12 US US10/534,338 patent/US20060014664A1/en not_active Abandoned
- 2003-12-12 CN CNB2003801049617A patent/CN1307152C/zh not_active Expired - Fee Related
- 2003-12-12 DE DE60315069T patent/DE60315069T2/de not_active Expired - Lifetime
- 2003-12-12 AT AT03813507T patent/ATE367375T1/de not_active IP Right Cessation
- 2003-12-12 EP EP03813507A patent/EP1572636B1/en not_active Expired - Lifetime
- 2003-12-12 AU AU2003303211A patent/AU2003303211A1/en not_active Abandoned
- 2003-12-12 JP JP2004560977A patent/JP2006510685A/ja active Pending
- 2003-12-12 ES ES03813507T patent/ES2289366T3/es not_active Expired - Lifetime
- 2003-12-12 WO PCT/CH2003/000814 patent/WO2004056765A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE367375T1 (de) | 2007-08-15 |
| GB0229453D0 (en) | 2003-01-22 |
| ES2289366T3 (es) | 2008-02-01 |
| JP2006510685A (ja) | 2006-03-30 |
| CN1720222A (zh) | 2006-01-11 |
| EP1572636B1 (en) | 2007-07-18 |
| DE60315069D1 (de) | 2007-08-30 |
| CN1307152C (zh) | 2007-03-28 |
| MXPA05006386A (es) | 2005-08-29 |
| EP1572636A1 (en) | 2005-09-14 |
| WO2004056765A1 (en) | 2004-07-08 |
| US20060014664A1 (en) | 2006-01-19 |
| AU2003303211A1 (en) | 2004-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: KROHER, STROBEL RECHTS- UND PATENTANWAELTE, 80336 |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: DR. SCHOEN & PARTNER, 80336 MUENCHEN |