EP0000719B1 - Neue 1,4-Epoxy-trimethyl-butenyliden-cyclohexane (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe, Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an den neuen Cyclohexanen - Google Patents

Neue 1,4-Epoxy-trimethyl-butenyliden-cyclohexane (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe, Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an den neuen Cyclohexanen Download PDF

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Publication number
EP0000719B1
EP0000719B1 EP78100472A EP78100472A EP0000719B1 EP 0000719 B1 EP0000719 B1 EP 0000719B1 EP 78100472 A EP78100472 A EP 78100472A EP 78100472 A EP78100472 A EP 78100472A EP 0000719 B1 EP0000719 B1 EP 0000719B1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
trans
fragrance
trimethyl
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
Application number
EP78100472A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000719A2 (de
EP0000719A3 (en
Inventor
Roman Kaiser
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.)
Givaudan SA
Original Assignee
L Givaudan and Co SA
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 LU77834A external-priority patent/LU77834A1/de
Application filed by L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of EP0000719A2 publication Critical patent/EP0000719A2/de
Publication of EP0000719A3 publication Critical patent/EP0000719A3/xx
Application granted granted Critical
Publication of EP0000719B1 publication Critical patent/EP0000719B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • 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
    • C07C403/06—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 singly-bound oxygen atoms
    • C07C403/08—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 singly-bound oxygen atoms by hydroxy groups
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
    • 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
    • C07C47/46—Unsaturated compounds having —CHO groups bound to carbon atoms of 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
    • C11B9/0069—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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
    • C07C2601/14—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

Definitions

  • the invention relates to new fragrances and / or flavors. These are the compounds of the formula wherein R represents the 2-cis or the 2-trans-buten-1-ylidene radical.
  • the formula accordingly comprises the compounds of the formula -1,4-epoxy-1,3,3-trimethyl-2- (2-buten-1-ylidene) cyclohexane
  • the invention further relates to a method for producing the compounds of the formula
  • This process is characterized in that 1,3,3-trimethyl-2- (3-hydroxybutylidene) -6-cyclohexen-4-ol is reacted in an acidic medium.
  • the acidic medium with the aid of mineral acids such as sulfuric acid or hydrochloric acid
  • acidic salts such as bisulfates, for example KHS0 4
  • acidic earths such as diatomaceous earth, for. B. Filtrol.
  • Suitable organic acids such as medium to strong acids of this type, are also suitable. Examples include alkanesulfonic acids, such as methanesulfonic acid, p-toluenesulfonic acid or picric acid.
  • the reaction temperature is not critical. It is expediently 20-200 ° C, preferably 60-130 ° C. It is expediently higher when using weaker acids and lower when using stronger acids.
  • the reaction is preferably carried out with the aid of an organic solvent, in particular an aromatic solvent.
  • organic solvent in particular an aromatic solvent. Examples are benzene, toluene and xylene.
  • a mixture of la: Ib is obtained in an approximate ratio of 15:85. Traces of the cis / cis and trans / cis isomers can also be detected in the mixture.
  • the separation of the isomer mixture can be carried out in a conventional manner, e.g. B. by means of column chromatography or preparative gas chromatography. As can be seen further below, the isomers do not differ fundamentally in their organoleptic properties, so that the isomer mixture can be used for economic reasons.
  • the 1,3,3-trimethy) 2- (3 hydroxylbutylidene) -6-cyclohexen-4-ol referred to below and in Example 1 as compound 14 is a new compound. It can - as shown there - from the known 2-hydroxy-ß-ionon can be obtained.
  • this 2-hydroxy- ⁇ -ionone is advantageously reacted with an enol acylate in the presence of one of the acids specified above; so z. B. dissolved in (an excess of) acetonenol acetate, mixed with a catalytic amount of p-toluenesulfonic acid and the reaction mixture kept at reflux temperature for 1-2 hours.
  • the diacetate 13 obtained after working up can be converted directly into the diol 14 by treatment with a strong reducing agent, such as lithium aluminum hydride.
  • Connection 13 is new.
  • the compounds I have special organoleptic properties which make them particularly suitable as fragrances and / or flavors.
  • the invention accordingly also relates to the use of the compounds I, in particular in practically pure form or in the form of mixtures (with the exception of natural mixtures containing 1) as fragrances and / or flavorings.
  • Practically pure 1 should in particular be understood to mean those I which are free of accompanying substances, such as are present in addition to I in natural extracts.
  • Practically pure I in the sense of the present invention should be understood to mean in particular synthetically produced I.
  • the compounds I used according to the invention as fragrances and / or flavorings - in particular Ib [because of its greater diffusion and intensity] - are distinguished by fresh, green, spicy, very natural-looking, certain aspects of cassis buds and exotic fruits - such as mango, passion fruit , Guanabana - reminiscent of smells.
  • the compounds can accordingly serve, for example, for perfuming or aromatizing products, such as cosmetics (soaps, salves, powders, toothpastes, mouthwashes, deodorants, shampoos, lotions, etc.), detergents or foods, luxury foods and beverages, the compounds preferably not used alone, but in the form of compositions with other fragrances or flavors.
  • fragrance or flavoring compositions with a content of compounds I and their preparation in a manner known per se (addition of I to known fragrance or flavoring compositions or mixing of I with natural or suitable components of fragrance or flavoring positions synthetic compounds or mixtures) also forms the subject of the invention.
  • fragrance compositions produced using compounds 1, in particular of the Chypre, Cologne, Muguet or generally floral and woody direction, are particularly spectacular due to their spectacular freshness and originality.
  • fragrances can be used in a manner known to the perfumer, such as, for example, B. from W. A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall, London, 1974.
  • the concentration of the compounds I can vary within wide limits, for example between about 0.01 (detergents) and about 15% by weight (alcoholic solutions).
  • concentrations in perfume bases or concentrates can of course also be higher.
  • the perfume bases can be used in the usual way for perfuming Eaux de Cologne, Eaux de toilette, lotions, creams, shampoos, soaps and detergents, etc.
  • the compounds 1 can be used, for example, to produce or improve, enhance, increase or modify fruit or berry flavors in foods (yogurt, confectionery, etc.); be used in luxury foods (tea, etc.) and beverages (lemonades, etc.).
  • a suitable dosage includes, for example, the range 0.1 ppm-100 ppm, preferably 1 ppm -20 ppm in the finished product, i. H. the flavored food, stimulant or drink.
  • the compounds can be mixed in a customary manner with the constituents used for flavoring compositions or added to such flavors.
  • the flavors used according to the invention are understood to mean flavoring compositions which can be diluted in a manner known per se or can be distributed in edible materials. They can be converted into the usual forms of use, such as solutions, pastes or powders, using methods known per se.
  • the products can be spray dried, vacuum dried or lyophilized.
  • Perfume composition (towards grapefruit, lemon peel)
  • Perfumery composition (masculine chypre note)
  • the two yoghurts were presented to the test panel (10 people) and evaluated in terms of their senses in comparison to a fresh mango fruit.
  • test persons (6) found significantly more character of the fresh mango fruit in the additionally flavored yoghurt.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Seasonings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Cosmetics (AREA)
EP78100472A 1977-07-25 1978-07-21 Neue 1,4-Epoxy-trimethyl-butenyliden-cyclohexane (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe, Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an den neuen Cyclohexanen Expired EP0000719B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
LU77834 1977-07-25
LU77834A LU77834A1 (de) 1977-07-25 1977-07-25 Verfahren zur herstellung von neuen riech-und/oder geschmackstoffen
CH546478 1978-05-19
CH5464/78 1978-05-19

Publications (3)

Publication Number Publication Date
EP0000719A2 EP0000719A2 (de) 1979-02-21
EP0000719A3 EP0000719A3 (en) 1979-06-27
EP0000719B1 true EP0000719B1 (de) 1981-05-20

Family

ID=25697750

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100472A Expired EP0000719B1 (de) 1977-07-25 1978-07-21 Neue 1,4-Epoxy-trimethyl-butenyliden-cyclohexane (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe, Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an den neuen Cyclohexanen

Country Status (7)

Country Link
US (3) US4225501A (ja)
EP (1) EP0000719B1 (ja)
JP (1) JPS5424893A (ja)
DE (2) DE2832137A1 (ja)
FR (1) FR2398751A1 (ja)
GB (1) GB2002364B (ja)
NL (1) NL7807609A (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168882A1 (en) * 1984-07-13 1986-01-22 The Procter & Gamble Company Oxa-fenchols and oxa-fenchyl amines useful for preparing high intensity sweeteners
EP0312412A1 (fr) * 1987-10-16 1989-04-19 L'oreal Nouveaux dérivés du norbornane, leur procédé de préparation et compositions cosmétique et médicamenteuse les contenant

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS591415A (ja) * 1982-06-28 1984-01-06 Mochida Pharmaceut Co Ltd 循環系疾患治療剤
DE3470032D1 (en) * 1983-01-20 1988-04-28 Basf Ag Racemic and optically actif 3-hydroxy-alpha-cyclocitral, their acetals and optically actif 3-oxo-alpha-cyclocitralacetals, and also the preparation and use of these compounds
US4868901A (en) * 1987-10-13 1989-09-19 Sci-Agra, Inc. Reflected light detecting apparatus and method
FR2707630B1 (fr) * 1993-07-13 1995-09-29 Centre Nat Rech Scient Dérivé du cyclohexèneméthanol, sa préparation et son emploi dans la synthèse de taxoïdes.
US6166371A (en) * 1999-04-30 2000-12-26 Beckman Coulter, Inc. Diffuse reflective light curtain system
KR101962561B1 (ko) 2015-03-06 2019-03-26 미쓰이 가가쿠 가부시키가이샤 가교체 및 제진재

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168882A1 (en) * 1984-07-13 1986-01-22 The Procter & Gamble Company Oxa-fenchols and oxa-fenchyl amines useful for preparing high intensity sweeteners
EP0312412A1 (fr) * 1987-10-16 1989-04-19 L'oreal Nouveaux dérivés du norbornane, leur procédé de préparation et compositions cosmétique et médicamenteuse les contenant
FR2621912A1 (fr) * 1987-10-16 1989-04-21 Oreal Nouveaux derives du norbornane, leur procede de preparation et compositions cosmetique et medicamenteuse les contenant
US5047575A (en) * 1987-10-16 1991-09-10 L'oreal Norbornene carboxylic acids and esters

Also Published As

Publication number Publication date
EP0000719A2 (de) 1979-02-21
US4250062A (en) 1981-02-10
JPS6159317B2 (ja) 1986-12-16
GB2002364A (en) 1979-02-21
DE2860714D1 (en) 1981-08-27
FR2398751A1 (fr) 1979-02-23
GB2002364B (en) 1982-02-17
EP0000719A3 (en) 1979-06-27
US4258071A (en) 1981-03-24
DE2832137A1 (de) 1979-02-08
JPS5424893A (en) 1979-02-24
NL7807609A (nl) 1979-01-29
US4225501A (en) 1980-09-30

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