EP0073984B1 - Compositions parfumantes et/ou aromatisantes comprenant des acides insaturés - Google Patents

Compositions parfumantes et/ou aromatisantes comprenant des acides insaturés Download PDF

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Publication number
EP0073984B1
EP0073984B1 EP82107607A EP82107607A EP0073984B1 EP 0073984 B1 EP0073984 B1 EP 0073984B1 EP 82107607 A EP82107607 A EP 82107607A EP 82107607 A EP82107607 A EP 82107607A EP 0073984 B1 EP0073984 B1 EP 0073984B1
Authority
EP
European Patent Office
Prior art keywords
acid
tobacco
oil
cis
compositions
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
EP82107607A
Other languages
German (de)
English (en)
Other versions
EP0073984A3 (en
EP0073984A2 (fr
Inventor
Peter Dr. Naegeli
Martin Dr. Rohr
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
Application filed by L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of EP0073984A2 publication Critical patent/EP0073984A2/fr
Publication of EP0073984A3 publication Critical patent/EP0073984A3/de
Application granted granted Critical
Publication of EP0073984B1 publication Critical patent/EP0073984B1/fr
Expired legal-status Critical Current

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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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • 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
    • 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
    • A24B15/32—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
    • 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

Definitions

  • the invention relates to fragrance and / or flavoring compositions which are characterized by the addition of cis-3,7-dimethylocta-3,8-dienoic acid.
  • the invention further relates to methods for improving the smell of fragrance compositions or the taste of flavoring compositions, which are characterized in that an amount of cis-3,7-dimethylocta-3,6-diene acid which is effective in terms of smell or taste is used.
  • the invention relates to the use of cis-3,7-dimethylocta-3,6-dienoic acid as a fragrance and / or flavoring.
  • I was very good with the 2,2,4-trimethyl-cyclohex-3 (or 4) -en-carboxylic acid, ie the compound of the formula can be combined.
  • the combination I + II shows surprising organoleptic properties.
  • II supports the natural notes of I; II also rounds off in such compositions, and I can support the resinous note of I.
  • the compound of formula II is also known, see e.g. B. J. Org. Chem. 34 (1968) 2196-2203.
  • the compound of the formula I, or the mixtures I + II, are particularly suitable for modifying known compositions owing to their natural odor notes.
  • Threshold value determinations have shown that I is almost 2 powers of ten more intense than I 'or I ". I is therefore a typical" impact chemical ".
  • fruit bases e.g. B. of the apricot type I or I + II can be successfully used to achieve a stronger and more naturally fruity and rounding effect.
  • the compound of the formula I (or the mixture I + II) can be used within wide limits, which can range, for example, from 0.01 (detergents) -10% (alcoholic solutions) in compositions, without these values, however, being intended to represent limit values , because the experienced perfumer can achieve effects with even lower concentrations or build up new complexes with even higher doses.
  • the preferred concentrations are between 0.1 and 5%.
  • the compositions made with I. can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, Extraits, lotions, creams, shampoos, soaps, ointments, powders, toothpastes, mouthwashes, deodorants, detergents, tobacco, etc.).
  • the compound I (or the mixture I + II) can accordingly be used in the production of compositions and - as the above composition shows - using a wide range of known fragrances or mixtures of fragrances.
  • the above-mentioned known fragrances or mixtures of fragrances can be used in a manner known to the perfumer, such as, for example, B. from W.A. Poucher, Perfumes, Cosmetics, Soaps 2, 7th edition, Chapman and Hall, London 1974.
  • the compound of formula 1 or their mixtures with II are also excellently suitable for use in flavors, in particular in fruit flavors of all kinds, but in particular also for flavoring tobacco.
  • the compounds I can be used, for example, to improve, reinforce, increase or modify fruit flavors of all kinds, e.g. B. raspberry or apricot flavors can be used.
  • Foods yogurt, confectionery, etc.
  • luxury foods tea, tobacco, etc.
  • drinks lemonade, etc.
  • a suitable dosage includes, for example, the range of 0.01 ppm - 100 ppm, preferably the range of 0.1 ppm - 20 ppm in the finished product, i.e. the flavored food, luxury food or drink.
  • the dosage for example in the case of a top flavor, can range from 0.1 to 2 ppm in the end product.
  • the compounds can be mixed in a conventional manner with the constituents used for flavoring compositions or added to such flavors.
  • the aromas used according to the invention are understood to mean flavoring compositions which can be diluted in a manner known per se or distributed in edible materials. They contain, for example, about 0.1-10, in particular 0.5-3,% by weight. 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.
  • yeast alginates, carrageenan or similar absorbents
  • Cloves diacetyl, sodium citrate
  • IMP disodium aminosin 5'-
  • acid I (or the mixture of I + II) can serve in particular to improve the organoleptic properties of tobacco products.
  • tobacco product is a common term in the industry, which not only includes tobacco itself, but also tobacco by-products such as reconstituted and homogenized leaves and stems, tobacco surrogates (e.g. lettuce and cabbage leaves, etc.), materials, used in tobacco processing, such as paper, filters etc. and flavor compositions used for tobacco products.
  • tobacco product includes cigarette tobacco, cigar tobacco, chewing tobacco and pipe tobacco, etc.
  • the differences between the treated and untreated tobacco are even more noticeable when smoking.
  • the untreated cigarettes have an undesirable tartness when smoking, an effect that is reduced by the addition of I or I + II.
  • the treated cigarettes give a smoother, lighter and more rounded taste when smoking, which is why they are clearly preferred to the untreated ones.
  • the amount of acid 1 or mixture of I + II that is expediently added can depend on various factors, including the desired effect, the type and amount of other additives used at the same time and / or the personal preference of the aromatist. Even quantities of 0.01 ppm, based on the weight of the tobacco, have proven to be effective, but quantities of 10 ppm can still be used. However, amounts of 0.1 ppm to 2 ppm are preferably used.
  • the compounds I and II can the tobacco product (cigarette paper, etc.) according to the expert known methods, e.g. B. atomization, immersion, coating, etc. can be added or mixed.
  • ratio of I: II this can vary within wide ranges.
  • a suitable range is, for example, that from 90: 1 to 1:90.
  • the freshness effect of the base is significantly increased by adding 2 parts I.
  • geranium acid does not fit into the base at all.
  • the composition on the freshly dipped smelling strip appears stronger and, above all, more balanced than when the same amount of geranic acid is added. This strength and harmony remain in the base note after 24, 48 and 96 hours.
  • the base base woody, woody
  • incense olibanum, encens, frankincense
  • composition A By adding I to composition A, the existing fruity note is significantly enhanced.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Claims (6)

1. Composition parfumante et/ou aromatisante, caractérisée en ce qu'elle a été additionnée d'acide cis-3,7-diméthylocta-3,6-diénoïque.
2. Composition parfumante et/ou aromatisante, selon la revendication 1, caractérisée en ce qu'elle contient de l'acide cis-3,7-diméthylocta-3,6-diénoique en combinaison avec de l'acide 2,2,4-triméthylcyclohexa-3 (ou 4)-ène-carboxylique.
3. Utilisation de l'acide cis-3,7-diméthylocta-3,6-diénoïque en tent que matière parfumante et/ou aromatisante ou en tant qu'agent modifiant de compositions parfumantes et/ou aromatisantes.
4. Utilisation de l'acide cis-3,7-diméthylocta-3,6-diénoïque en combineison avec l'acide 2,2,4-trimé- thylcyclohexe-3 (ou 4)-ène-carboxylique en tant que matière odorante et/ou arôme ou en tent qu'agent modifient de compositions de parfums et/ou d'arômes, selon le revendication 3.
5. Procédé pour améliorer l'odeur de compositions parfumées ou le goût de compositions aromatisées, caractérisé en ce que l'on ajoute une quantité efficace à cet effet d'acide cis-3,7-diméthylocte-3,6-diénoïque.
6. Procédé pour améliorer l'odeur de compositions parfumées ou le goût de compositions aromatisées selon la revendication 5, caractérisé en ce que l'on ajoute une quantité efficace à cet effet d'acide cis-3,7-diméthylocta-3,6-diénoique en combinaison avec de l'acide 2,2,4-triméthylcyclohexa-3 (ou 4)-ène-carboxylique.
EP82107607A 1981-09-09 1982-08-20 Compositions parfumantes et/ou aromatisantes comprenant des acides insaturés Expired EP0073984B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH5823/81 1981-09-09
CH582381 1981-09-09

Publications (3)

Publication Number Publication Date
EP0073984A2 EP0073984A2 (fr) 1983-03-16
EP0073984A3 EP0073984A3 (en) 1985-01-09
EP0073984B1 true EP0073984B1 (fr) 1988-04-27

Family

ID=4299891

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82107607A Expired EP0073984B1 (fr) 1981-09-09 1982-08-20 Compositions parfumantes et/ou aromatisantes comprenant des acides insaturés

Country Status (4)

Country Link
US (2) US4496476A (fr)
EP (1) EP0073984B1 (fr)
JP (1) JPS5857314A (fr)
DE (1) DE3278403D1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4832059A (en) * 1987-12-08 1989-05-23 Lorillard, Inc. Citrus-flavored tobacco articles
US5024847A (en) * 1989-09-18 1991-06-18 Basf K&F Corporation Sulfur containing acyclic terpenes
ATE140723T1 (de) * 1992-12-11 1996-08-15 Quest Int Demethyl-cyclohexanecarbonsäureestern in der parfümerie
US6127450A (en) 1998-06-09 2000-10-03 Kerr Corporation Dental restorative composite
DE60136090D1 (de) * 2000-11-06 2008-11-20 Japan Tobacco Inc Desodorisierungszusammensetzung für tabakgeruch, desodorisierungsmittel für tabakgeruch und zigaretten- und tabakpackung mit vermindertem sekundärrauchgeruch
EP1336345B2 (fr) * 2000-11-06 2014-01-22 Japan Tobacco Inc. Utilisation de compositions parfumees permettant de reduire l'odeur secondaire de fumee dans une cigarette
WO2008119197A1 (fr) * 2007-03-30 2008-10-09 Givaudan Sa Acide 4-(2, 2, 3-triméthylcyclopentyle) butanoïque utilisé comme agent de masquage de notes atypiques dans des produits consommables
ATE555670T1 (de) 2007-03-30 2012-05-15 Givaudan Sa Off-note-blockierende sensorische organische verbindungen
CN106235396A (zh) * 2016-08-17 2016-12-21 广西中烟工业有限责任公司 一种桃金娘提取物的制备方法及其在卷烟中的应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3553110A (en) * 1967-02-02 1971-01-05 Int Flavors & Fragrances Inc Perfume compositions containing unconjugated octanitriles
NL7500220A (nl) * 1975-01-08 1976-07-12 Naarden International Nv Vertakte carbonzuren.

Also Published As

Publication number Publication date
JPS5857314A (ja) 1983-04-05
EP0073984A3 (en) 1985-01-09
US4669490A (en) 1987-06-02
EP0073984A2 (fr) 1983-03-16
JPH0221440B2 (fr) 1990-05-14
US4496476A (en) 1985-01-29
DE3278403D1 (en) 1988-06-01

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