GB2383327B - Improved citral derivatives - Google Patents

Improved citral derivatives

Info

Publication number
GB2383327B
GB2383327B GB0219381A GB0219381A GB2383327B GB 2383327 B GB2383327 B GB 2383327B GB 0219381 A GB0219381 A GB 0219381A GB 0219381 A GB0219381 A GB 0219381A GB 2383327 B GB2383327 B GB 2383327B
Authority
GB
United Kingdom
Prior art keywords
groups
derivatives
citral
group
acetal
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 - Fee Related
Application number
GB0219381A
Other languages
English (en)
Other versions
GB0219381D0 (en
GB2383327A (en
Inventor
Luca Turin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Flexitral Inc
Original Assignee
Flexitral Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Flexitral Inc filed Critical Flexitral Inc
Publication of GB0219381D0 publication Critical patent/GB0219381D0/en
Publication of GB2383327A publication Critical patent/GB2383327A/en
Application granted granted Critical
Publication of GB2383327B publication Critical patent/GB2383327B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/0026Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/203Alicyclic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/205Heterocyclic compounds
    • A23L27/2052Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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
    • C07C45/69Preparation 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 addition to carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/02Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/105Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
    • C07C47/11Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/28Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/293Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with three- or four-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/28Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/34Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/38Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/45Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/0069Heterocyclic compounds
    • C11B9/0073Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Confectionery (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Seasonings (AREA)
GB0219381A 2001-12-19 2002-08-20 Improved citral derivatives Expired - Fee Related GB2383327B (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US34215001P 2001-12-19 2001-12-19
US34858002P 2002-01-15 2002-01-15
US35505202P 2002-02-07 2002-02-07
US37791402P 2002-05-03 2002-05-03
US38929802P 2002-06-17 2002-06-17
PCT/US2002/022120 WO2003053902A1 (en) 2001-12-19 2002-07-12 Improved aromachemicals
PCT/US2002/022441 WO2003053903A1 (en) 2001-12-19 2002-07-12 Improved citral derivatives

Publications (3)

Publication Number Publication Date
GB0219381D0 GB0219381D0 (en) 2002-09-25
GB2383327A GB2383327A (en) 2003-06-25
GB2383327B true GB2383327B (en) 2004-12-08

Family

ID=27541172

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0219381A Expired - Fee Related GB2383327B (en) 2001-12-19 2002-08-20 Improved citral derivatives

Country Status (10)

Country Link
EP (2) EP1458666B1 (enExample)
JP (2) JP2006506316A (enExample)
AT (1) ATE338017T1 (enExample)
AU (5) AU2002318237A1 (enExample)
CA (2) CA2469602A1 (enExample)
DE (1) DE60214427T2 (enExample)
DK (1) DK1458666T3 (enExample)
ES (1) ES2274985T3 (enExample)
GB (1) GB2383327B (enExample)
WO (4) WO2003053902A1 (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7309795B2 (en) 2001-12-19 2007-12-18 Luca Turin Citral derivatives
US7342042B2 (en) 2001-12-19 2008-03-11 Flexitral, Inc. Lily of the valley aromachemicals
WO2003053902A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved aromachemicals
MX2007007467A (es) * 2004-12-22 2007-10-15 Flexitral Inc Derivados mejorados de citral y citronelal.
GB0428306D0 (en) * 2004-12-24 2005-01-26 Givaudan Sa Compound
WO2006087571A2 (en) * 2005-02-17 2006-08-24 Flexitral Inc. Aromachemicals
JP2008532947A (ja) * 2005-03-02 2008-08-21 フレクシトラル・インコーポレーテッド 大環状チイラン
US7485668B2 (en) 2005-04-14 2009-02-03 International Flavors & Fragrances Inc. Cyclopropanated macrocyclic ketones and lactones
CN101258140A (zh) * 2005-04-19 2008-09-03 佛莱克特瑞尔公司 苯并(b)环丙(d)吡喃-2-(1h)-酮衍生物
JP4745914B2 (ja) * 2005-12-01 2011-08-10 花王株式会社 毛髪洗浄剤
WO2007117462A1 (en) * 2006-04-03 2007-10-18 Flexitral, Inc. Cyclopropanated aromachemicals
EP2041062A1 (en) * 2006-04-03 2009-04-01 Flexitral, Inc. Aromachemicals
ES2396126T3 (es) 2008-04-15 2013-02-19 Eisai R&D Management Co., Ltd. Compuesto de 3-fenilpirazol[5,1-b]tiazol
CN105073698B (zh) * 2013-03-12 2017-03-15 高砂香料工业株式会社 具有环丙烷环的化合物及包含其的香料组合物和/或芳香组合物
JP6356431B2 (ja) * 2014-02-20 2018-07-11 アサヒビール株式会社 発酵麦芽飲料
JP6356432B2 (ja) * 2014-02-20 2018-07-11 アサヒビール株式会社 発酵麦芽飲料
US20170275262A1 (en) * 2014-09-19 2017-09-28 Tingwei Cai Cyclopropane derivatives in flavor and fragrance compositions
JP6487685B2 (ja) * 2014-12-03 2019-03-20 アサヒビール株式会社 容器詰めアルコール飲料
JP6091028B1 (ja) * 2015-11-11 2017-03-08 花王株式会社 シクロプロパン化合物
WO2019037862A1 (de) * 2017-08-24 2019-02-28 Symrise Ag Organoschwefelverbindungen als riech- und geschmackstoffe
CN109453091B (zh) * 2019-01-02 2021-08-24 广东美宝化妆品有限公司 一种基于复合鲜花提取液的香水及其制备方法
JP6744937B2 (ja) * 2019-02-22 2020-08-19 アサヒビール株式会社 容器詰めアルコール飲料
CN114989057B (zh) * 2022-07-25 2023-06-02 江西农业大学 一种柠檬醛基酰基硫脲衍生物及其制备方法和应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2938040A (en) * 1957-09-09 1960-05-24 Shell Oil Co Epoxidation of unsaturated aldehydes
GB1082364A (en) * 1964-03-18 1967-09-06 Unilever Ltd Method for the preparation of linalool
GB1108268A (en) * 1964-12-17 1968-04-03 Unilever Ltd Preparation of linalool oxide
US3470241A (en) * 1968-02-05 1969-09-30 Firmenich & Cie Cyclopropane intermediates for irones
GB1237972A (enExample) * 1968-03-11 1971-07-07
US3926860A (en) * 1974-01-28 1975-12-16 Int Flavors & Fragrances Inc Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid
WO2001006853A2 (en) * 1999-07-23 2001-02-01 Bioparken As Novel juvenile hormone analogues and their use as antifouling agents

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US1061732A (en) * 1912-08-07 1913-05-13 Julius Hirsh Union suit.
CH424765A (de) * 1963-02-11 1966-11-30 Firmenich & Cie Verfahren zur Herstellung von ungesättigten Ketonen
BE754374A (fr) * 1969-08-05 1971-02-04 Hoffmann La Roche Derives de propargyle
US3950429A (en) * 1969-09-10 1976-04-13 Givaudan Corporation 2-Methylthio-myrtanal
US3770836A (en) * 1970-06-15 1973-11-06 Philip Morris Inc Cyclopropyl cyclohexanes
DE2617816A1 (de) * 1976-04-23 1977-11-10 Henkel & Cie Gmbh Verwendung von epoxynitrilen als riechstoffe sowie diese enthaltende riechstoffkompositionen
US4097531A (en) * 1976-06-04 1978-06-27 Scm Corporation Substituted cyclopropane process and product
US4151103A (en) * 1977-07-28 1979-04-24 Int Flavors & Fragrances Inc {60 -Oxy(oxo) sulfides and uses thereof in perfumery and in perfumed articles
FR2543134B2 (fr) * 1981-11-10 1986-08-08 Roussel Uclaf Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes
FR2516076B1 (fr) * 1981-11-10 1986-05-16 Roussel Uclaf Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes
US4435428A (en) * 1982-09-23 1984-03-06 International Flavors & Fragrances Inc. Use in augmenting or enhancing the aroma or taste of foodstuff or chewing gum with the methyl carbonate of 1-hydroxymethyl-2-heptanoyl cyclopropane
US4536583A (en) * 1983-08-01 1985-08-20 International Flavors & Fragrances Inc. Process for preparing mixtures containing 8,9-epithio-1-p-menthene
US4658067A (en) * 1985-05-08 1987-04-14 International Flavors & Fragrances Inc. Dialkylthioalkenes, dialkylthioalkylcycloalkenes and monoalkylthioalkenylcycloalkenes and organoleptic uses thereof
NL8502530A (nl) * 1985-09-16 1987-04-16 Naarden International Nv Aroma- en parfumcomposities, gearomatiseerde voedings- en genotmiddelen, resp. geparfumeerde produkten die een of meer gesubstitueerde thiofenen als grondstof bevatten, alsmede gesubstitueerde thiofenen.
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US6051548A (en) * 1998-11-05 2000-04-18 International Flavors & Fragrances Inc. Trimethylcyclohexenylcyclopropyl ketones perfume composition
WO2003053902A1 (en) * 2001-12-19 2003-07-03 Flexitral, Inc. Improved aromachemicals
JP2003252812A (ja) * 2002-02-28 2003-09-10 Nippon Zeon Co Ltd シクロプロパン化合物および香料組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2938040A (en) * 1957-09-09 1960-05-24 Shell Oil Co Epoxidation of unsaturated aldehydes
GB1082364A (en) * 1964-03-18 1967-09-06 Unilever Ltd Method for the preparation of linalool
GB1108268A (en) * 1964-12-17 1968-04-03 Unilever Ltd Preparation of linalool oxide
US3470241A (en) * 1968-02-05 1969-09-30 Firmenich & Cie Cyclopropane intermediates for irones
GB1237972A (enExample) * 1968-03-11 1971-07-07
US3926860A (en) * 1974-01-28 1975-12-16 Int Flavors & Fragrances Inc Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid
WO2001006853A2 (en) * 1999-07-23 2001-02-01 Bioparken As Novel juvenile hormone analogues and their use as antifouling agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
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(ARMSTRONG) Journal of the Chemical Society, Perkin Transactions 1 (2001), vol. 21, pages 2861-2873 *
(ROCHAT) Helvetica Chimica Acta (2000), vol. 83(7), pages 1645-1671 *
CAS abstract AN 1977:533807 of Bulletin de la Societe Chimique de France (1970), vol. 5, pages 1822-33; in particular compounds with reference numbers RN: 29845-42-9; 29975-49-3; 29975-50-6; 29975-54-0; and 29975-53-9 *

Also Published As

Publication number Publication date
AU2002323273A1 (en) 2003-07-09
WO2003053901A1 (en) 2003-07-03
DE60214427T2 (de) 2007-04-26
CA2469602A1 (en) 2003-07-03
AU2002332586A2 (en) 2003-07-09
WO2003053902A1 (en) 2003-07-03
DK1458666T3 (da) 2006-11-27
GB0219381D0 (en) 2002-09-25
CA2469604A1 (en) 2003-07-03
AU2002366778A2 (en) 2003-07-09
WO2003053903A1 (en) 2003-07-03
GB2383327A (en) 2003-06-25
DE60214427D1 (de) 2006-10-12
JP2006506316A (ja) 2006-02-23
ES2274985T3 (es) 2007-06-01
EP1458665A1 (en) 2004-09-22
JP2005513119A (ja) 2005-05-12
EP1458666B1 (en) 2006-08-30
AU2009200217A1 (en) 2009-02-12
EP1458666A1 (en) 2004-09-22
WO2003053887A1 (en) 2003-07-03
AU2002366778A1 (en) 2003-07-09
AU2002318237A1 (en) 2003-07-09
ATE338017T1 (de) 2006-09-15
AU2002332586B2 (en) 2006-07-13
AU2002332586A1 (en) 2003-07-09

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PCNP Patent ceased through non-payment of renewal fee

Effective date: 20100820