WO2009021342A2 - Cyclohexene derivatives and their use as odorants - Google Patents

Cyclohexene derivatives and their use as odorants Download PDF

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Publication number
WO2009021342A2
WO2009021342A2 PCT/CH2008/000337 CH2008000337W WO2009021342A2 WO 2009021342 A2 WO2009021342 A2 WO 2009021342A2 CH 2008000337 W CH2008000337 W CH 2008000337W WO 2009021342 A2 WO2009021342 A2 WO 2009021342A2
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WO
WIPO (PCT)
Prior art keywords
hydrogen
methyl
alkyl
alkenyl
formula
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Ceased
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PCT/CH2008/000337
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English (en)
French (fr)
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WO2009021342A3 (en
Inventor
Andreas Goeke
Yue Zou
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Givaudan SA
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Givaudan SA
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Publication date
Priority to BRPI0815373-6A priority Critical patent/BRPI0815373B1/pt
Priority to MX2010001478A priority patent/MX2010001478A/es
Priority to EP16181761.4A priority patent/EP3112338B1/en
Priority to JP2010519318A priority patent/JP5563454B2/ja
Priority to EP08772908A priority patent/EP2188242A2/en
Priority to US12/672,603 priority patent/US8304380B2/en
Application filed by Givaudan SA filed Critical Givaudan SA
Priority to CN200880102957XA priority patent/CN101796013B/zh
Publication of WO2009021342A2 publication Critical patent/WO2009021342A2/en
Publication of WO2009021342A3 publication Critical patent/WO2009021342A3/en
Anticipated expiration legal-status Critical
Priority to US13/647,161 priority patent/US8691746B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • 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
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • 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
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2026—Hydroxy compounds
    • 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
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • 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
    • A23L27/203—Alicyclic compounds
    • 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/44—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
    • C07C47/445—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic containing a condensed ring system
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/45—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • 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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
    • C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0057—Spiro compounds
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
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    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0088—Spiro compounds
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Definitions

  • the present invention is concerned with a novel process for the production of formyl cyclohexene derivatives which are suitable for use as odorants as such or as intermediates for the preparation of further odorants.
  • the present invention relates to a domino-methylenation-Diels-Alder reaction of ⁇ , ⁇ -unsaturated aldehydes using formaldehyde in the presence of 1 ,3-butadienes.
  • R 10 is hydrogen, linear or branched C 1 -C 5 alkyl (e.g. methyl, ethyl, isopropyl), or linear or branched C 2 -C 5 alkenyl (e.g. prop-2-en-3-yl, prop-1-en-3-yl); and
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently selected from hydrogen, linear or branched
  • R 1 is hydrogen, methyl, or ethyl
  • R 7 and R 8 are independently hydrogen, C 1 -C 6 alkyl (e.g. methyl, tert-butyl, pentyl), or
  • R is hydrogen and R' is selected from hydroxyl or -OCOR 13 , wherein R 13 is hydrogen, or C 1 -C 3 alkyl (e.g. ethyl, isopropyl),
  • alkyl and alkenyl refers to linear and branched alkyls and alkenyls.
  • Example 7 (2,4-Dimethyl-1-vinylcyclohex-3-enyl)but-3-en-1-one Following the general procedure as described in Example 4, (2,4-dimethyl-1- vinylcyclohex-3-enyl)but-3-en-1-one (56 % yield) was prepared starting from (2,4- dimethyl-1-vinylcyclohex-3-enyl)but-3-en-1-ol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/CH2008/000337 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants Ceased WO2009021342A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
MX2010001478A MX2010001478A (es) 2007-08-10 2008-08-07 Derivados de ciclohexeno y su uso como odorantes.
EP16181761.4A EP3112338B1 (en) 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants
JP2010519318A JP5563454B2 (ja) 2007-08-10 2008-08-07 シクロヘキセン誘導体および着臭剤としてのそれらの使用
EP08772908A EP2188242A2 (en) 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants
US12/672,603 US8304380B2 (en) 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants
BRPI0815373-6A BRPI0815373B1 (pt) 2007-08-10 2008-08-07 Compostos derivados de ciclo-hexeno, seu processo de produção, usos dos referidos compostos, métodos para aperfeiçoar, aumentar ou modificar uma base de produto de consumidor e aplicação de fragrância
CN200880102957XA CN101796013B (zh) 2007-08-10 2008-08-07 环己烯衍生物及其作为增香剂的用途
US13/647,161 US8691746B2 (en) 2007-08-10 2012-10-08 Cyclohexene derivatives and their use as odorants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0715496.6 2007-08-10
GBGB0715496.6A GB0715496D0 (en) 2007-08-10 2007-08-10 Novel process

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/672,603 A-371-Of-International US8304380B2 (en) 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants
US13/647,161 Continuation US8691746B2 (en) 2007-08-10 2012-10-08 Cyclohexene derivatives and their use as odorants

Publications (2)

Publication Number Publication Date
WO2009021342A2 true WO2009021342A2 (en) 2009-02-19
WO2009021342A3 WO2009021342A3 (en) 2009-07-30

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Application Number Title Priority Date Filing Date
PCT/CH2008/000337 Ceased WO2009021342A2 (en) 2007-08-10 2008-08-07 Cyclohexene derivatives and their use as odorants

Country Status (9)

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US (2) US8304380B2 (enExample)
EP (2) EP3112338B1 (enExample)
JP (1) JP5563454B2 (enExample)
CN (1) CN101796013B (enExample)
BR (1) BRPI0815373B1 (enExample)
ES (1) ES2900863T3 (enExample)
GB (1) GB0715496D0 (enExample)
MX (1) MX2010001478A (enExample)
WO (1) WO2009021342A2 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012020076A1 (en) * 2010-08-11 2012-02-16 Givaudan Sa Cyclohexene- and cyclopropanated cyclohexene - derivatives as fragrances
WO2012126675A1 (de) * 2011-03-23 2012-09-27 Henkel Ag & Co. Kgaa Diels-alder-addukte als thermisch spaltbare riechstoffvorläufer
WO2013110739A3 (en) * 2012-01-26 2013-10-17 Givaudan Sa 1-vinylcyclohex-3-ene carbaldehyde and 4-vinylcyclohex-1-ene carbaldehyde use in flavour and oral care compositions
CN109651149A (zh) * 2017-10-11 2019-04-19 中国科学院大连化学物理研究所 一种制备1,2-环己烷二甲酸酯或邻苯二甲酸酯的方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0715496D0 (en) * 2007-08-10 2007-09-19 Givauden Sa Novel process
JP2017511402A (ja) * 2014-03-26 2017-04-20 ザ プロクター アンド ギャンブル カンパニー 香料系
CN104433927B (zh) * 2014-10-23 2017-11-10 广东比伦生活用纸有限公司 一种手帕纸的加香工艺及制得的香味手帕纸
GB201613013D0 (en) * 2016-07-27 2016-09-07 Givaudan Sa Organic compound
CN111495289B (zh) * 2020-04-27 2021-01-12 肇庆市高要华新香料有限公司 一种气液两相连续反应装置及山梨醛的制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3067244A (en) * 1958-03-06 1962-12-04 Shell Oil Co Process for the production of dielsalder adducts
US3641156A (en) * 1968-04-29 1972-02-08 Hoffmann La Roche Juvabione and derivatives thereof
NL7304990A (enExample) 1972-05-01 1973-11-05
US4010207A (en) 1976-01-15 1977-03-01 International Flavors & Fragrances Inc. Process for the alkylation of α, β-unsaturated aldehydes
GB1591342A (en) 1976-08-11 1981-06-17 Int Flavors & Fragrances Inc Carbonyl compounds processes for preparing same and uses of such carbonyl compounds in affecting the aroma and taste of foodstuffs robaccos beverages perfumes and perfumed articles
JPH0657120B2 (ja) * 1986-11-18 1994-08-03 長谷川香料株式会社 持続性紫蘇フレーバー剤
DE19961030A1 (de) * 1999-12-16 2001-06-21 Haarmann & Reimer Gmbh Aromen und Aromakompositionen enthaltend 4,8-Dimethyl-3,7-nonadien-2-on und ein Verfahren zu dessen Herstellung
JP2002179509A (ja) * 2000-12-12 2002-06-26 Takasago Internatl Corp 抗カビ香料組成物
US20050191257A1 (en) 2004-02-27 2005-09-01 John Brahms Dry deodorant containing a sesquiterpene alcohol and zinc oxide
GB0715496D0 (en) * 2007-08-10 2007-09-19 Givauden Sa Novel process

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012020076A1 (en) * 2010-08-11 2012-02-16 Givaudan Sa Cyclohexene- and cyclopropanated cyclohexene - derivatives as fragrances
US8999914B2 (en) 2010-08-11 2015-04-07 Givaudan S.A. Cyclohexene- and cyclopropanated cyclohexene- derivatives as fragrances
WO2012126675A1 (de) * 2011-03-23 2012-09-27 Henkel Ag & Co. Kgaa Diels-alder-addukte als thermisch spaltbare riechstoffvorläufer
WO2013110739A3 (en) * 2012-01-26 2013-10-17 Givaudan Sa 1-vinylcyclohex-3-ene carbaldehyde and 4-vinylcyclohex-1-ene carbaldehyde use in flavour and oral care compositions
US9283159B2 (en) 2012-01-26 2016-03-15 Givaudan Sa 1-vinylcyclohex-3-ene carbaldehyde and 4-vinylcyclohex-1-ene carbaldehyde for use in flavour and oral care composition
CN109651149A (zh) * 2017-10-11 2019-04-19 中国科学院大连化学物理研究所 一种制备1,2-环己烷二甲酸酯或邻苯二甲酸酯的方法
CN109651149B (zh) * 2017-10-11 2021-06-01 中国科学院大连化学物理研究所 一种制备1,2-环己烷二甲酸酯或邻苯二甲酸酯的方法

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JP2010535718A (ja) 2010-11-25
BRPI0815373B1 (pt) 2018-01-02
EP3112338A2 (en) 2017-01-04
US20100204084A1 (en) 2010-08-12
EP2188242A2 (en) 2010-05-26
EP3112338B1 (en) 2021-09-29
CN101796013B (zh) 2013-09-04
GB0715496D0 (en) 2007-09-19
EP3112338A3 (en) 2017-03-22
CN101796013A (zh) 2010-08-04
ES2900863T3 (es) 2022-03-18
MX2010001478A (es) 2010-03-01
US8691746B2 (en) 2014-04-08
WO2009021342A3 (en) 2009-07-30
US20130035278A1 (en) 2013-02-07
US8304380B2 (en) 2012-11-06
BRPI0815373A2 (pt) 2015-02-10
JP5563454B2 (ja) 2014-07-30

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