FR2422616A1 - TRANS, TRANS-D-DAMASCONE, AS WELL AS MIXTURES CONTAINING SIGNIFICANT PROPORTIONS OF THIS COMPOUND, THE PROCESSES FOR PREPARING THE SAME AND THE ORGANOLEPTIC USES OF THE LATTER - Google Patents

TRANS, TRANS-D-DAMASCONE, AS WELL AS MIXTURES CONTAINING SIGNIFICANT PROPORTIONS OF THIS COMPOUND, THE PROCESSES FOR PREPARING THE SAME AND THE ORGANOLEPTIC USES OF THE LATTER

Info

Publication number
FR2422616A1
FR2422616A1 FR7832072A FR7832072A FR2422616A1 FR 2422616 A1 FR2422616 A1 FR 2422616A1 FR 7832072 A FR7832072 A FR 7832072A FR 7832072 A FR7832072 A FR 7832072A FR 2422616 A1 FR2422616 A1 FR 2422616A1
Authority
FR
France
Prior art keywords
trans
damascone
preparing
processes
compound
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.)
Granted
Application number
FR7832072A
Other languages
French (fr)
Other versions
FR2422616B1 (en
Inventor
Braja Dulal Mookherjee
Robert Walter Trenkle
Richard A Wilson
Frederic Louis Schmitt
Manfred Hugo Vock
Edward J Granda
Joaquin Vinals
Jacob Kiwala
William L Schreiber
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances 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
Priority claimed from US05/851,727 external-priority patent/US4211242A/en
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Publication of FR2422616A1 publication Critical patent/FR2422616A1/en
Application granted granted Critical
Publication of FR2422616B1 publication Critical patent/FR2422616B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
    • 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
    • C07C403/14—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 substituted by doubly-bound oxygen atoms
    • C07C403/16—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 substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • 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
    • 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
    • C07C45/69—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 addition to carbon-to-carbon double or triple bonds
    • 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
    • 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
    • C07C49/543—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a six-membered ring
    • 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
    • C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
    • 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
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compositions caractérisées en ce qu'elles comprennent une proportion importante de trans, trans- DELTA -damascone et une faible proportion de cis,trans- DELTA -damascone. Ce procédé de préparation de ces compositions, par réaction du 1- alpha -acétyl-2, alpha ,6,6-triméthyl-cyclohexène avec une base forte, puis condensation par aldolisation de l'acétaldéhyde avec le produit de cette réaction, suivie d'une déshydratation de l'hydroxycétone obtenue. Application de ces compositions à l'augmentation ou à l'exaltation des propriétés organolesptiques d'une substance consommable à laquelle elles sont ajoutées.Compositions characterized in that they comprise a large proportion of trans, trans-DELTA -damascone and a small proportion of cis, trans-DELTA -damascone. This method of preparing these compositions, by reaction of 1- alpha -acetyl-2, alpha, 6,6-trimethyl-cyclohexene with a strong base, then condensation by aldolization of acetaldehyde with the product of this reaction, followed by 'dehydration of the hydroxy ketone obtained. Application of these compositions to the increase or enhancement of the organolesptic properties of a consumable substance to which they are added.

FR7832072A 1977-11-15 1978-11-14 TRANS, TRANS-D-DAMASCONE, AS WELL AS MIXTURES CONTAINING SIGNIFICANT PROPORTIONS OF THIS COMPOUND, THE PROCESSES FOR PREPARING THE SAME AND THE ORGANOLEPTIC USES OF THE LATTER Granted FR2422616A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/851,727 US4211242A (en) 1977-11-15 1977-11-15 Composition of matter comprising more than 50% trans, trans-Δ-damascone for augmenting or enhancing the aroma and taste of a smoking tobacco
US92871878A 1978-07-27 1978-07-27

Publications (2)

Publication Number Publication Date
FR2422616A1 true FR2422616A1 (en) 1979-11-09
FR2422616B1 FR2422616B1 (en) 1982-10-29

Family

ID=27127018

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7832072A Granted FR2422616A1 (en) 1977-11-15 1978-11-14 TRANS, TRANS-D-DAMASCONE, AS WELL AS MIXTURES CONTAINING SIGNIFICANT PROPORTIONS OF THIS COMPOUND, THE PROCESSES FOR PREPARING THE SAME AND THE ORGANOLEPTIC USES OF THE LATTER

Country Status (2)

Country Link
FR (1) FR2422616A1 (en)
GB (1) GB2008115B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056109A2 (en) * 1981-01-13 1982-07-21 Firmenich Sa Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4206090A (en) * 1978-10-06 1980-06-03 International Flavors & Fragrances Inc. 3-Methyl-1-phenyl-pentanol-5 or its isomer and butanoyl cyclohexane derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056109A2 (en) * 1981-01-13 1982-07-21 Firmenich Sa Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent
EP0056109A3 (en) * 1981-01-13 1983-08-31 Firmenich Sa Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent

Also Published As

Publication number Publication date
GB2008115A (en) 1979-05-31
GB2008115B (en) 1982-06-09
FR2422616B1 (en) 1982-10-29

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