EP1761618B1 - Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange - Google Patents

Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange Download PDF

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Publication number
EP1761618B1
EP1761618B1 EP05754006A EP05754006A EP1761618B1 EP 1761618 B1 EP1761618 B1 EP 1761618B1 EP 05754006 A EP05754006 A EP 05754006A EP 05754006 A EP05754006 A EP 05754006A EP 1761618 B1 EP1761618 B1 EP 1761618B1
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EP
European Patent Office
Prior art keywords
methyl
cis
decalactone
trans
oil
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Application number
EP05754006A
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German (de)
English (en)
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EP1761618A1 (fr
Inventor
Sabine Widder
Christopher Sabater
Jan Looft
Tobias Vössing
Marcus Eggers
Thomas Obrocki
Johannes Panten
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Symrise AG
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Symrise AG
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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
    • C11B9/0069—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

Definitions

  • the present invention relates to the use of a mixture of cis- and trans-3-methyl- ⁇ -decalactone, perfume compositions containing such a mixture and perfumed articles and a process for the preparation of a fragrance composition.
  • fragrances in the perfume industry continues to have a general need for new fragrances that have beyond their primary, namely odor properties addition secondary positive secondary properties, such.
  • B. a higher stability under certain conditions of use, a higher yielding or better adhesion, or by synergy with other fragrances lead to better sensory profiles.
  • this primary object is achieved by the use of a mixture comprising cis- and trans-3-methyl- ⁇ -decalactone in a molar ratio in the range from 2: 3.5 to 3.5: 2, as a jasmone fragrance.
  • cis- or trans-3-methyl- ⁇ -decalactone encompasses in each case the pure (cis or trans) enantiomers and also their enantiomer mixtures, in particular the racemic mixtures.
  • the invention is based on the surprising finding that a mixture of cis- and trans-3-methyl- ⁇ -decalactone is suitable as a jasmone fragrance, although the individual substances are not jasmone fragrances.
  • JP-A2 2000-086647 describes an enantioselective synthesis for both enantiomers of cis-3-methyl- ⁇ -decalactone. It describes the use in perfume oils and flavors.
  • JP-A2 09-169624 relates to the use of C 11 -C 16 - ⁇ -lactones as antimicrobial agents in toothpaste or mouthwash.
  • the main focus of the synthesizing perfume chemist and composing perfumer is usually to preferentially isolate, analyze, make and use, for compounds with different stereoisomers, that which has the strongest impact or which is most typical of the odor of a structure.
  • the perfumers also classified the strength of the two pure isomers on a scale of 1-6 (see below).
  • the perfumers evaluated neither the pure cis isomer with its coconut aspects nor the pure trans isomer with its fruity peach aspects as the sensory most valuable product, but according to the above table, the mixtures of both isomers with a molar cis / trans Ratio of 60:40 or 40:60 (ie 3: 2 or 2: 3). This applies both in terms of olfactory evaluation, as well as for application criteria such as the adhesion to smelling strips and the charisma.
  • the optimum mixing ratio of the isomers is approximately at a cis content of 36.4-63.6% and a corresponding trans proportion of 63.6-36.4%.
  • Another aspect of the present invention relates to the use of cis-3-methyl- ⁇ -decalactone in a fragrance composition containing trans-3-methyl- ⁇ -decalactone to enhance the trans-3-methyl- ⁇ -decalactone mediated peach odor , Interestingly, by adding cis-3-methyl- ⁇ -decalactone, the peach odor of the trans-3-methyl- ⁇ -decalactone can be enhanced, although the cis compound itself has no such peach odor;
  • the cis connection acts as an enhancer. It follows from the above that at the same time a jasmonic olfactory aspect is added, which is to be determined neither in the pure cis nor in the pure trans connection.
  • the invention also relates to a method for imparting, enhancing or modifying a jasmonic odor in a fragrance composition, the fragrance composition comprising an amount of a mixture of cis- and trans-3-methyl- ⁇ -decalactone in a molar ratio in the range of 2: 3, 5 to 3.5: 2 sufficient to impart, enhance or modify a jasmonic odor.
  • a fragrance composition which initially has no jasmonic odor
  • this fragrance composition can be provided with a jasmonic odor by adding said mixture of cis- and trans-3-methyl- ⁇ -decalactone.
  • an amount of the mixture must be used which is sufficient to mediate the jasmonigen smell within the resulting fragrance composition.
  • Starting from a fragrance composition, which already has a jasmonigen smell can by adding the mixture of cis- and trans-3-methyl- ⁇ -decalactone, an enhancement or modification of the jasmone odor can be effected.
  • a fragrance composition having a strong peach odor is prepared by adding a compound (trans-3-methyl- ⁇ -decalactone) which itself only is able to mediate a weak peach odor and in addition a compound (cis-3-methyl- ⁇ -decalactone) is added as an enhancer which is suitable for the trans-3-methyl- ⁇ -decalactone-mediated peach Reinforce smell.
  • the invention also relates to a method for enhancing a trans-3-methyl- ⁇ -decalactone-mediated peach odor in a fragrance composition, wherein the fragrance composition is added an effective amount of cis-3-methyl- ⁇ -decalactone.
  • the present invention likewise provides a fragrance composition or a perfumed article with a jasmonic odor, comprising an amount of a mixture of cis- and trans-3-methyl- ⁇ -decalactone causing the jasmonic odor in a molar cis / trans ratio in the range of 2 : 3.5 to 3.5: 2, wherein neither the cis-3-methyl- ⁇ -decalactone used alone nor the trans-3-methyl- ⁇ -decalactone used alone causes the jasmonic odor.
  • Such a perfume composition or perfumed article also has a strong peach odor.
  • the amount of the mixture of cis- and trans-3-methyl- ⁇ -decalactone used is preferably in the range from 0.01 to 99.9% by weight, preferably 0.1 to 90% by weight and more preferably 0.5 to 70% by weight, based on the total weight of the perfume oil composition.
  • the olfactory properties, material properties (such as solubility in common cosmetic solvents, compatibility with the common further constituents of such products, etc.), as well as the toxicological safety of the mixtures to be used according to the invention emphasize their particular suitability for the stated purposes.
  • fragrance compositions according to the invention or perfumed articles which contain an amount of a mixture of cis- and trans-3-methyl- ⁇ -decalactone which is not only sufficient to produce a jasmonic odor but also to impart, modify and / or enhance a peach or coconut-like odor note.
  • fragrance fragrance topic (Jenny) vividly demonstrates the olfactory effect of a mixture of cis / trans-3-methyl- ⁇ -decalactone.
  • a perfume oil of the type "Jenny” can be characterized as flowery, modern and transparent.
  • the base perfume oil already contains the trans-3-methyl- ⁇ -decalactone; surprisingly, the addition of cis-3-methyl- ⁇ -decalactone clearly enhances the fruity (peach-like) notes and the fragrance composition also has a jasmonic aspect.
  • a mixture of cis- / trans-3-methyl- ⁇ -decalactone (with a molar ratio in the range of 2: 3.5 to 3.5: 2) is due to its olfactory properties especially suitable for use in perfume compositions.
  • the cis / trans mixture can be combined with a variety of other fragrances and used in numerous products. Particularly advantageously, the compound can be combined with other fragrances in different proportions to novel perfume compositions.
  • a fragrance composition having a peach, coconut and lactone note can be prepared, for example, by mixing the mixture of cis- and trans-3-methyl- ⁇ -decalactone with constituents of a basic fragrance composition, the mixture of cis- and trans- 3-methyl- ⁇ -decalactone is used in an amount sufficient to modify and / or enhance the odor of the basic fragrance composition.
  • fragrances with which the mixture to be used according to the invention can be advantageously combined can be found, for example, in US Pat S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4rd. Ed., Wiley-VCH, Weinheim 2001 ,
  • the perfume oils containing the lactone mixture to be used according to the invention can be used in perfumed form in liquid form, neat or diluted with a solvent.
  • Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerine, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • the perfume oils containing the lactone mixture to be used according to the invention can be adsorbed on a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
  • a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
  • Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as woods and cellulosic based materials.
  • perfume oils containing the lactone mixture to be used according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extruded products and added in this form to the product to be perfumed.
  • the properties of the perfume oils modified in this way can be further optimized by so-called "coats" with suitable materials with a view to a more targeted release of fragrance, to which end preferably wax-like plastics, such as e.g. Polyvinyl alcohol can be used.
  • the microencapsulation of the perfume oils can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be prepared, for example, by spray-drying a perfume oil-containing emulsion or dispersion, it being possible to use as starches modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can e.g. by incorporating dispersions of the perfume oil and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • Extrusion products can be made by fusing the perfume oils with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol, done.
  • the perfume oils containing the lactone mixture to be used according to the invention can be used in concentrated form, in solutions or in modified form described above for the production of, for example, perfume extracts, Eau de perfumes, Eau de Toilettes, shaving waters, Eau de Colognes, Pre-shave Products, splash colognes and perfumed refreshing wipes and the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bath and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents, powder detergents, laundry pretreatment agents such as bleaches, soakers and stain removers, laundry conditioners, laundry soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gelatinous or solid support form, Aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, Shoe creams and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps,
  • the total amount of the lactone mixture to be used according to the invention is from 0.01 to 99.9% by weight, preferably from 0.1 to 90% and particularly preferably from 0.5 to 70%, based on the total fragrance composition.
  • the "Jenny" base perfume oil becomes more floral, hedonic and jasmonic with the addition of cis-3-methyl- ⁇ -decalactone (instead of the sensorially inactive solvent DPG); the fruity (peachy) aspects are enhanced.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (7)

  1. Utilisation d'un mélange qui comprend de la cis- et trans-3-méthyl-γ-décalactone dans un rapport molaire dans le domaine de 2:3,5 à 3,5:2 comme arôme de jasmone.
  2. Utilisation de cis-3-méthyl-γ-décalactone dans une composition de matière odorante contenant de la trans-3-méthyl-γ-décalactone pour renforcer l'odeur de pêche fournie par la trans-3-méthyl-γ-décalactone.
  3. Procédé pour fournir, renforcer ou modifier une odeur de jasmone dans une composition de matière odorante, dans lequel on ajoute à la composition odorante une quantité d'un mélange constitué de cis- et trans-3-méthyl-γ-décalactone dans un rapport molaire dans le domaine de 2:3,5 à 3,5:2, laquelle suffit pour fournir, renforcer ou modifier une odeur de jasmone.
  4. Procédé pour la préparation d'une composition de matière odorante avec une forte odeur de pêche et une odeur de jasmone, présentant les étapes suivantes :
    - de préparation d'une composition de base de matière odorante qui ne possède pas de forte odeur de pêche ;
    - de mélange de la composition de base de matière odorante avec les composés cis-3-méthyl-γ-décalactone et trans-3-méthyl-γ-décalactone avec la mesure consistant en ce que (i) on utilise ces composés dans un rapport molaire cis/trans dans un domaine de 2:3,5 à 3,5:2, (ii) la quantité totale des composés utilisée suffit pour fournir la forte odeur de pêche et l'odeur de jasmone et (iii) la quantité de trans-3-méthyl-γ-décalactone utilisée ne suffit pas en l'absence de cis-3-méthyl-γ-décalactone pour fournir la forte odeur de pêche.
  5. Procédé pour renforcer une odeur de pêche fournie par la trans-3-méthyl-γ-décalactone dans une composition de matière odorante, caractérisé en ce que l'on ajoute à la composition de matière odorante une quantité efficace de cis-3-méthyl-γ-décalactone.
  6. Composition de matière odorante ou article parfumé avec une odeur de jasmone comprenant une quantité d'un mélange de cis- et de trans-3-méthyl-γ-décalactone dans un rapport molaire cis/trans dans le domaine de 2:3,5 à 3,5:2 fournissant l'odeur de jasmone, la cis-3-méthyl-γ-décalactone utilisée seule ainsi que la trans-3-méthyl-γ-décalactone utilisée seule ne fournissant pas l'odeur de jasmone.
  7. Composition de matière odorante avec une odeur de jasmone selon la revendication 6, la composition de matière odorante est une composition d'essence de parfum et la quantité du mélange constitué de cis- et de trans-3-méthyl-γ-décalactone utilisée est de préférence dans le domaine de 0,01 à 99,9 % en poids, de préférence de 0,1 à 90 % en poids et encore mieux de 0,5 à 70 % en poids rapporté au poids total de la composition d'essence de parfum.
EP05754006A 2004-06-19 2005-06-06 Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange Active EP1761618B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004029809A DE102004029809A1 (de) 2004-06-19 2004-06-19 Verwendung eines Gemisches von cis- und trans-3-Methyl-gamma-decalacton sowie Riechstoffkompositionen und parfümierte Artikel umfassend ein solches Gemisch
PCT/EP2005/052581 WO2005123889A1 (fr) 2004-06-19 2005-06-06 Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange

Publications (2)

Publication Number Publication Date
EP1761618A1 EP1761618A1 (fr) 2007-03-14
EP1761618B1 true EP1761618B1 (fr) 2008-09-10

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EP05754006A Active EP1761618B1 (fr) 2004-06-19 2005-06-06 Utilisation d'un melange de cis- et de trans-3-methyl-g-decalactone, compositions de substances odorantes et articles parfumes contenant ledit melange

Country Status (6)

Country Link
US (1) US8034761B2 (fr)
EP (1) EP1761618B1 (fr)
JP (1) JP2008503601A (fr)
AT (1) ATE407994T1 (fr)
DE (2) DE102004029809A1 (fr)
WO (1) WO2005123889A1 (fr)

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Publication number Priority date Publication date Assignee Title
EP2662098B1 (fr) * 2012-05-10 2018-10-24 Symrise AG Utilisation de certaines liaisons pour modifier des odeurs
CN107151684B (zh) * 2017-05-12 2021-06-22 上海应用技术大学 一种天然香料γ-癸内酯的制备方法

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ES2084207T3 (es) * 1991-05-15 1996-05-01 Givaudan Roure Int Derivado tetrahidro-alfa-pirona, metodo para su preparacion y perfume y/o composiciones aromatizantes que lo contienen.
JP2000086647A (ja) * 1998-09-03 2000-03-28 T Hasegawa Co Ltd シス−３−メチル−４−デカノリドの両鏡像体およびその製造方法

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JP2008503601A (ja) 2008-02-07
DE502005005342D1 (de) 2008-10-23
US20080194455A1 (en) 2008-08-14
DE102004029809A1 (de) 2006-06-08
US8034761B2 (en) 2011-10-11
EP1761618A1 (fr) 2007-03-14
ATE407994T1 (de) 2008-09-15
WO2005123889A1 (fr) 2005-12-29

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