EP0073984A2 - 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
EP0073984A2
EP0073984A2 EP82107607A EP82107607A EP0073984A2 EP 0073984 A2 EP0073984 A2 EP 0073984A2 EP 82107607 A EP82107607 A EP 82107607A EP 82107607 A EP82107607 A EP 82107607A EP 0073984 A2 EP0073984 A2 EP 0073984A2
Authority
EP
European Patent Office
Prior art keywords
acid
cis
fragrance
tobacco
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.)
Granted
Application number
EP82107607A
Other languages
German (de)
English (en)
Other versions
EP0073984B1 (fr
EP0073984A3 (en
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

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
    • C11B9/0007Aliphatic compounds
    • C11B9/0015Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/32Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
    • 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
    • C11B9/0034Essential 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 a content of cis-3,7-dimethylocta-3,6-dienoic acid.
  • the invention further relates to processes 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-dienoic acid which is effective in terms of smell or taste is characterized 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 2,2,4-trimethylcyclohex-3 (or 4) -enecarboxylic acid, ie the compound of the formula can be combined.
  • the combination I + II shows surprising organoleptic properties.
  • II supports the natural notes of Ir II in such compositions also rounds off, and Ir can support the resinous note of I.
  • the compound of formula II is also known, see e.g. 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.
  • Remarkable is the way in which the compound I (or I + II) gives the olfactory notes of known compositions, e.g. oriental (i.e. heavier, sweeter) notes, amber, powdery notes, citrus notes rounded off in colognes and harmonized, even embossed. in perfume bases, e.g. in flowery, like rose bases the sought-after character of the heavy, sweet and somewhat fruity Bulgarian rose.
  • 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 ".
  • 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 Perfumers can achieve effects with even lower concentrations or can build up new complexes with even higher doses.
  • the preferred concentrations are between 0.1 and 5%.
  • the compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powder, 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 from W.A. Poucher, Perfumes, Cosmetics, Soaps 2, 7th edition, Chapman and Hall, London 1974.
  • the new compound of formula I 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, enhance, increase or modify a wide variety of fruit flavors, e.g. Raspberry or apricot flavors can be used.
  • Food yogurt, confectionery, etc.
  • luxury foods tea, tobacco, etc.
  • beverages lemonade, etc.
  • a suitable dosage includes, for example, the range from 0.01 ppm to 100 ppm, preferably the range from 0.1 pp m - 2 0 ppm in the finished product, ie 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.
  • 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 the Tobacco processing are used, 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 I or the mixture of I + II which is expediently added can depend on various factors, including the desired effect, the type and amount of other additives used simultaneously 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 be added to the tobacco product (cigarette paper, etc.) by the methods known to the person skilled in the art, e.g. Atomize, immerse, coat, etc. can be added or mixed in.
  • ratio of I: II this can vary within wide ranges.
  • a suitable range is, for example, 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 animal note becomes even more pronounced, which effect cannot be achieved with the same additions of geranic acid.
  • the base note in the former case has the warmest, most voluminous and, in a typical way, the most animalistic effect on the smell strip.
  • the composition on the freshly dipped scent strip is 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.
  • a tobacco aroma (so-called top flavor towards apricot)
  • composition A By adding I to composition A, the existing fruity note is significantly enhanced.
  • a significantly more pronounced fruit note is noticeable, and the tobacco note is also 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)
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 true EP0073984A2 (fr) 1983-03-16
EP0073984A3 EP0073984A3 (en) 1985-01-09
EP0073984B1 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)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5024847A (en) * 1989-09-18 1991-06-18 Basf K&F Corporation Sulfur containing acyclic terpenes
WO1994013766A3 (fr) * 1992-12-11 1996-02-01 Quest Int Esters d'acide dimethyl-cyclohexanecarboxylique en parfumerie
WO2008119196A1 (fr) * 2007-03-30 2008-10-09 Givaudan Sa Composés organiques bloquant les notes atypiques sensorielles
CN101652342A (zh) * 2007-03-30 2010-02-17 吉万奥丹股份有限公司 遮蔽不适感感觉的有机化合物

Families Citing this family (5)

* 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
US6127450A (en) 1998-06-09 2000-10-03 Kerr Corporation Dental restorative composite
ES2310562T3 (es) * 2000-11-06 2009-01-16 Japan Tobacco Inc. Composicion desodorante contra el olor a tabaco, desodorante contra el olor a tabaco y paquete de tabaco y cigarrillos con olor a humo secundario reducido.
AU2002210998A1 (en) * 2000-11-06 2002-05-15 Japan Tobacco Inc. Perfume compositions for deodorizing tobacco, tobacco deodorizing agents and cigarette and tobacco packages with little side smoke flow odor
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.

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5024847A (en) * 1989-09-18 1991-06-18 Basf K&F Corporation Sulfur containing acyclic terpenes
WO1994013766A3 (fr) * 1992-12-11 1996-02-01 Quest Int Esters d'acide dimethyl-cyclohexanecarboxylique en parfumerie
WO2008119196A1 (fr) * 2007-03-30 2008-10-09 Givaudan Sa Composés organiques bloquant les notes atypiques sensorielles
CN101652342A (zh) * 2007-03-30 2010-02-17 吉万奥丹股份有限公司 遮蔽不适感感觉的有机化合物
US8409649B2 (en) 2007-03-30 2013-04-02 Givaudan S.A. Off-note blocking sensory organic compounds
CN101652342B (zh) * 2007-03-30 2014-01-29 奇华顿股份有限公司 遮蔽不适感感觉的有机化合物
US9451784B2 (en) 2007-03-30 2016-09-27 Givaudan S.A. Off-note blocking sensory organic compounds

Also Published As

Publication number Publication date
EP0073984B1 (fr) 1988-04-27
JPH0221440B2 (fr) 1990-05-14
US4669490A (en) 1987-06-02
DE3278403D1 (en) 1988-06-01
JPS5857314A (ja) 1983-04-05
US4496476A (en) 1985-01-29
EP0073984A3 (en) 1985-01-09

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