EP1761618B1 - Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture - Google Patents

Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture Download PDF

Info

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
Authority
EP
European Patent Office
Prior art keywords
methyl
cis
decalactone
trans
oil
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.)
Active
Application number
EP05754006A
Other languages
German (de)
French (fr)
Other versions
EP1761618A1 (en
Inventor
Sabine Widder
Christopher Sabater
Jan Looft
Tobias Vössing
Marcus Eggers
Thomas Obrocki
Johannes Panten
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Publication of EP1761618A1 publication Critical patent/EP1761618A1/en
Application granted granted Critical
Publication of EP1761618B1 publication Critical patent/EP1761618B1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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.

Abstract

The use of a mixture which comprises cis- and trans-3-methyl-γ-decalactone in a molar ratio in the range of 2:3 to 3:2, as a jasmone fragrance is described.

Description

Die vorliegende Erfindung betrifft die Verwendung eines Gemisches von cis- und trans-3-Methyl-γ-decalacton, ein solches Gemisch enthaltende Riechstoffkompositionen und parfümierte Artikel sowie ein Verfahren zur Herstellung einer Riechstoffkomposition.The present invention relates to the use of a mixture of cis- and trans-3-methyl-γ-decalactone, perfume compositions containing such a mixture and perfumed articles and a process for the preparation of a fragrance composition.

Trotz einer Vielzahl bereits vorhandener Riechstoffe besteht in der Parfümindustrie auch weiterhin ein genereller Bedarf an neuen Riechstoffen, die über Ihre primären, nämlich geruchlichen Eigenschaften hinaus zusätzliche positive Sekundäreigenschaften besitzen, wie z. B. eine höhere Stabilität unter bestimmten Anwendungsbedingungen, eine höhere Ausgiebigkeit oder ein besseres Haftungsvermögen, oder aber durch Synergieeffekte mit anderen Riechstoffen zu besseren sensorischen Profilen führen.Despite a variety of already existing 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.

So können z.B. durch den Einsatz von Substanzen mit ausgiebigerem Charakter und besserem sensorischem Profil Einsatzmengen und Anzahl von Riechstoffen in Formulierungen minimiert werden, was zu einer nachhaltigen Resourcenschonung beim Parfümieren von Konsum- und Verbrauchsgütern führt.Thus, e.g. Through the use of substances with more extensive character and better sensory profile amounts and number of fragrances in formulations are minimized, resulting in a sustainable resource conservation when perfuming consumer and consumer goods.

Es besteht daher in der Parfümindustrie ein Bedarf an weiteren Riechstoffen mit besseren und ausgiebigeren sensorischen Profilen.There is therefore a need in the perfume industry for other fragrances with better and more extensive sensory profiles.

Insbesondere besteht in der Parfümindustrie ein Bedarf an Riechstoffen mit einem Jasmon-Geruch (Jasmon-Riechstoffe). Hierunter ist im Rahmen des vorliegenden Textes ein Geruch zu verstehen, der ähnlich wie der Geruch des natürlich vorkommenden cis-Jasmon ist. Der Geruch von cis-Jasmon wird in der Literatur wie folgt beschrieben: fruchtiger, sellerieartiger Duft, in Verdünnung süßblumig, an Jasmin und Kirschblüten erinnernd.In particular, there is a need in the perfume industry for fragrances with a jasmone odor (jasmone fragrances). This is to be understood in the context of the present text, a smell that is similar to the smell of the naturally occurring cis-jasmone. The smell of cis-jasmone is described in the literature as follows: fruity, celery-like odor, sweet-flowered in dilution, reminiscent of jasmine and cherry blossoms.

Es war daher die primäre Aufgabe der vorliegenden Erfindung, einen neuen Jasmon-Riechstoff anzugeben.It was therefore the primary object of the present invention to provide a new jasmone fragrance.

Erfindungsgemäß wird diese primäre Aufgabe gelöst durch die Verwendung eines Gemisches, das cis- und trans-3-Methyl-γ-decalacton in einem molaren Verhältnis im Bereich von 2:3,5 bis 3,5:2 umfasst, als Jasmon-Riechstoff.According to the invention, this primary object is achieved by the use of a mixture comprising cis- and trans-3-methyl-γ-decalactone in a molar ratio in the range from 2: 3.5 to 3.5: 2, as a jasmone fragrance.

Dabei umfasst der Begriff cis- bzw. trans-3-Methyl-γ-decalacton jeweils die reinen (cis bzw. trans) Enantiomere sowie deren Enantiomerenmischungen, insbesondere die racemischen Mischungen.The term cis- or trans-3-methyl-γ-decalactone encompasses in each case the pure (cis or trans) enantiomers and also their enantiomer mixtures, in particular the racemic mixtures.

Der Erfindung liegt die überraschende Erkenntnis zugrunde, dass sich ein Gemisch von cis- und trans-3-Methyl-γ-decalacton als Jasmon-Riechstoff eignet, obwohl die Einzelsubstanzen keine Jasmon-Riechstoffe sind.The invention is based on the surprising finding that a mixture of cis- and trans-3-methyl-γ-decalactone is suitable as a jasmone fragrance, although the individual substances are not jasmone fragrances.

Die Strukturformel eines Gemisches von cis- und trans-3-Methyl-γ-decalacton ist nachfolgend wiedergegeben:

Figure imgb0001
The structural formula of a mixture of cis- and trans-3-methyl-γ-decalactone is shown below:
Figure imgb0001

Gemische von cis- und trans-3-Methyl-γ-decalacton sowie die Einzelverbindungen sind aus der Literatur bekannt:

  • Chem. Express 1992, 7, 901 beschreibt die photochemische Synthese des racemischen Gemisches von cis- und trans-3-Methyl-γ-decalacton.
  • In Synlett 2001, 5, 629 wird die Synthese von cis,trans-3-Methyl-γ-decalacton an einem Festphasensystem ausgehend von einem Crotylstannan-Reagenz und Heptanal beschrieben.
  • J. Am. Chem. Soc. 1979, 101, 4752 beschreibt eine elektrochemische Variante zur Herstellung von racemischem cis/trans-3-Methyl-γ-decalacton. Es wird keine Geruchsbeschreibung gegeben.
  • Helv. Chim. Acta 2001, 84, 3428 und auch J. Org. Chem. 2002, 67, 3802 beschreiben enantioselektive Synthesen von cis-3-Methyl-γ-decalacton.
  • In seinem Buch " Vom Duft der Orchideen", Ed.: Editiones Roche, F.Hoffmann-LaRoche AG, Basel, 1993 beschreibt R. Kaiser erstmals die Existenz von cis-3-Methyl-γ-decalacton in der Natur (Aeringis kirkii ).
  • In Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971, 2, 389 ist eine allgemeine Vorschrift für die Darstellung von cis/trans-Lactonen angegeben. Die Substanz cis/trans-3-Methyl-γ-decalacton selber wird nicht explizit erwähnt, kann aber gemäß der allgemeinen Vorschrift dargestellt werden.
  • In J. Essent. Oil Res. 1996, 8, 587 wird beschrieben, daß die Substanz 3-Methyl-4-decanolid in Blutorangen vorkommt und es wird eine Geruchsbeschreibung gegeben: lactonic, peach, coconut.
  • In den Proceedings des 9th Congress of Ess.Oils (Singapur) 1984, Book 3, 69 wird die Substanz als neuer Bestandtteil von Muskatellersalbeiöl (Clary sage oil) erwähnt, mit einer trans-Struktur und typisch lactonischer Note.
  • Nat. Product Lett. 1999, 13, 239 beschreibt die enantioselektive Synthese der cis-Verbindungen (3R,4R)-3-Methyl-4-decanolid und (3S,4S)-3-Methyl-4-decanolid. Spektroskopische Daten werden angegeben, Duftbeschreibungen nicht.
Mixtures of cis- and trans-3-methyl-γ-decalactone and the individual compounds are known from the literature:
  • Chem. Express 1992, 7, 901 describes the photochemical synthesis of the racemic mixture of cis- and trans-3-methyl-γ-decalactone.
  • In Synlett 2001, 5, 629 describes the synthesis of cis, trans-3-methyl-γ-decalactone on a solid phase system starting from a crotylstannane reagent and heptanal.
  • J. Am. Chem. Soc. 1979, 101, 4752 describes an electrochemical variant for the preparation of racemic cis / trans-3-methyl-γ-decalactone. There is no odor description given.
  • Helv. Chim. Acta 2001, 84, 3428 and also J. Org. Chem. 2002, 67, 3802 describe enantioselective syntheses of cis-3-methyl-γ-decalactone.
  • In his book " On the scent of orchids ", Ed .: Editiones Roche, F.Hoffmann-LaRoche AG, Basel, 1993 R. Kaiser describes for the first time the existence of cis-3-methyl-γ-decalactone in nature (Aeringis kirkii ).
  • In Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971, 2, 389 a general procedure for the preparation of cis / trans lactones is given. The substance cis / trans-3-methyl-γ-decalactone itself is not explicitly mentioned, but can be represented according to the general procedure.
  • In J. Essent. Oil Res. 1996, 8, 587 It is described that the substance 3-methyl-4-decanolide occurs in blood oranges and it is given an odor description: lactonic, peach, coconut.
  • In the Proceedings of the 9th Congress of Ess.Oils (Singapore) 1984, Book 3, 69 the substance is mentioned as a new constituent of Clary sage oil, with a trans structure and a typical lactonic note.
  • Nat. Product Lett. 1999, 13, 239 describes the enantioselective synthesis of cis compounds (3R, 4R) -3-methyl-4-decanolide and (3S, 4S) -3-methyl-4-decanolide. Spectroscopic data are given, fragrance descriptions are not.

In JP-A2 2000-086647 ist eine enantioselektive Synthese für beide Enantiomere des cis-3-Methyl-γ-decalacton beschrieben. Es wird der Einsatz in Parfümölen und Aromen beschrieben.In JP-A2 2000-086647 describes an enantioselective synthesis for both enantiomers of cis-3-methyl-γ-decalactone. It describes the use in perfume oils and flavors.

JP-A2 09-169624 betrifft die Anwendung von C11-C16-γ-lactonen als antimikrobielle Wirkstoffe in Zahnpasta bzw. Mundwasser. JP-A2 09-169624 relates to the use of C 11 -C 16 -γ-lactones as antimicrobial agents in toothpaste or mouthwash.

Die Tatsache, daß sich ein Gemisch von zwei Isomeren gegenüber den reinen Isomeren vorzugsweise als Riechstoff eignet, ist überraschend.The fact that a mixture of two isomers is preferable to the pure isomers as a fragrance is surprising.

So ist das Hauptaugenmerk des synthetisierenden Riechstoffchemikers und komponierenden Parfümeurs in der Regel darauf ausgerichtet, bei Verbindungen mit verschiedenen Stereoisomeren dasjenige bevorzugt zu isolieren, zu analysieren, herzustellen und einzusetzen, das den stärksten Impact besitzt bzw. am typischsten für den Geruch einer Struktur ist. In eigenen Untersuchungen ergab sich für cis-3-Methyl-γ-decalacton ein Geruchs-Schwellenwert von 24,6 µg/l (aus Wasser) und für trans-3-Methyl-γ-decalacton ein Schwellenwert von 216 µg/l (aus Wasser). Entsprechend stuften die Parfümeure auch die Stärke der beiden reinen Isomere auf einer Skala von 1-6 ein (s.u.). Den Parfümeuren wurden außerdem verschiedene Mischungen zur Bewertung vorgelegt: Mischung(cis:trans) Stärke Geruch 100 : 0 4 stark, Kokos, Lacton, kein Pfirsich 80 : 20 5 Kokos, weich, cremig, milchig, am trockensten, 60 : 40 6 stark jasmonig, am stärksten, fruchtig, Kokos, Pfirsich 40 : 60 5 jasmonig, fruchtig, frische Kopfnote, lebendig, blumig, stark Pfirsich 20 : 80 3 Fruchtig, Pfirsich, kompakt, schwächer, süßlich 0 : 100 1 am schwächsten, Pfirsich Thus, 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. In our own investigations, there was an odor threshold of 24.6 μg / l (from water) for cis-3-methyl-γ-decalactone and a threshold value of 216 μg / l (out of water) for trans-3-methyl-γ-decalactone Water). Accordingly, the perfumers also classified the strength of the two pure isomers on a scale of 1-6 (see below). The perfumers were also presented with different mixtures for evaluation: Mixture (cis: trans) Strength odor 100: 0 4 strong, coconut, lactone, no peach 80:20 5 Coconut, soft, creamy, milky, driest, 60: 40 6 strong jasmine, strongest, fruity, coconut, peach 40: 60 5 jasmine, fruity, fresh head note, lively, flowery, strong peach 20: 80 3 Fruity, peach, compact, weaker, sweetish 0: 100 1 weakest, peach

Überraschenderweise bewerteten die Parfümeure jedoch weder das reine cis-Isomer mit seinen Kokos-Apekten noch das reine trans-Isomer mit seinen fruchtigen Pfirsich-Aspekten als sensorisch wertvollstes Produkt, sondern gemäß der vorstehenden Tabelle die Mischungen aus beiden Isomeren mit einem molaren cis/trans-Verhältnis von 60:40 bzw. 40:60 (also 3:2 bzw. 2:3). Dieses gilt sowohl hinsichtlich der olfaktorischen Bewertung, als auch für anwendungstechnische Kriterien wie die Haftung auf Riechstreifen und die Ausstrahlung.Surprisingly, however, 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.

Das optimale Mischungsverhältnis der Isomere liegt in etwa bei einem cis-Anteil von 36,4 - 63,6 % und einem entsprechendem trans-Anteil von 63,6 - 36,4%.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%.

Ein weiterer Aspekt der vorliegenden Erfindung betrifft die Verwendung von cis-3-Methyl-γ-decalacton in einer trans-3-Methyl-γ-decalacton enthaltenden Riechstoffkomposition, zur Verstärkung des durch trans-3-Methyl-γ-decalacton vermittelten Pfirsich-Geruchs. Interessanterweise kann durch Zusatz von cis-3-Methyl-γ-decalacton der Pfirsich-Geruch des trans-3-Methyl-γ-decalacton verstärkt werden, obwohl die cis-Verbindung selbst keinen solchen Pfirsich-Geruch besitzt; die cis-Verbindung wirkt als Enhancer (Verstärker). Aus dem Vorgesagten ergibt sich, dass dabei zugleich ein jasmoniger Geruchsaspekt hinzugefügt wird, der weder bei der reinen cis- noch bei der reinen trans-Verbindung festzustellen ist.Another aspect of the present invention relates to the use of cis-3-methyl-γ-decalactone in a fragrance composition containing trans-3-methyl-γ-decalactone to enhance the trans-3-methyl-γ-decalactone mediated peach odor , Interestingly, by adding cis-3-methyl-γ-decalactone, the peach odor of the trans-3-methyl-γ-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.

Die Erfindung betrifft auch ein Verfahren zum Vermitteln, Verstärken oder Modifizieren eines jasmonigen Geruchs in einer Riechstoffkomposition, wobei der Riechstoffkomposition eine Menge eines Gemisches aus cis- und trans-3-Methyl-γ-decalacton in einem molaren Verhältnis im Bereich von 2:3,5 bis 3,5:2 zugesetzt wird, die ausreicht, einen jasmonigen Geruch zu vermitteln, zu verstärken oder zu modifizieren. Wird also beispielsweise von einer Riechstoffkomposition ausgegangen, welche zunächst keinen jasmonigen Geruch besitzt, so kann diese Riechstoffkomposition mit einem jasmonigen Geruch versehen werden, indem das besagte Gemisch aus cis- und trans-3-Methyl-γ-decalacton zugesetzt wird. Selbstverständlich muss hierbei eine Menge des Gemisches eingesetzt werden, die ausreicht, innerhalb der entstehenden Riechstoffkomposition den jasmonigen Geruch zu vermitteln. Ausgehend von einer Riechstoffkomposition, welche bereits einen jasmonigen Geruch besitzt, kann durch Zusatz des Gemisches aus cis- und trans-3-Methyl-γ-decalacton eine Verstärkung oder Modifizierung des Jasmon-Geruches bewirkt werden.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-γ-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. If, for example, a fragrance composition is used which initially has no jasmonic odor, then this fragrance composition can be provided with a jasmonic odor by adding said mixture of cis- and trans-3-methyl-γ-decalactone. Of course, 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-γ-decalactone, an enhancement or modification of the jasmone odor can be effected.

Die Erfindung betrifft ferner ein Verfahren zum Herstellen einer Riechstoffkomposition mit einem starken Pfirsich-Geruch und einem Jasmon-Geruch, mit folgenden Schritten:

  • Bereitstellen einer Riechstoff-Basiskomposition, die keinen starken Pfirsich-Geruch besitzt
  • Vermischen der Riechstoff-Basiskomposition mit den Verbindungen cis-3-Methyl-γ-decalacton und trans-3-Methyl-γ-decalacton, mit der Maßgabe dass (i) diese Verbindungen in einem molaren cis/trans-Verhältnis im Bereich von 2:3,5 bis 3,5:2 eingesetzt werden, (ii) die eingesetzte Gesamtmenge der Verbindungen ausreicht, um den starken Pfirsichgeruch und den Jasmon-Geruch zu vermitteln und (iii) die eingesetzte Menge an trans-3-Methyl-γ-decalacton in Abwesenheit von cis-3-Methyl-γ-decalacton nicht ausreicht, um den starken Pfirsich-Geruch zu vermitteln.
The invention further relates to a process for producing a fragrance composition having a strong peach odor and a jasmone odor, comprising the following steps:
  • Providing a fragrance base composition that does not have a strong peach odor
  • Mixing the fragrance base composition with the compounds cis-3-methyl-γ-decalactone and trans-3-methyl-γ-decalactone, with the proviso that (i) these compounds in a molar cis / trans ratio in the range of 2: (Ii) the total amount of compounds used is sufficient to mediate the strong peach odor and jasmone odor, and (iii) the amount of trans-3-methyl-γ-decalactone used in the absence of cis-3-methyl-γ-decalactone is insufficient to mediate the strong peach odor.

Mit diesem erfindungsgemäßen Verfahren wird ausgehend von einer Riechstoff-Basiskomposition, die keinen starken Pfirsich -Geruch besitzt, eine Riechstoffkomposition mit einem starken Pfirsich-Geruch hergestellt, indem eine Verbindung (trans-3-Methyl-γ-decalacton) zugesetzt wird, welche selbst nur in der Lage ist, einen schwachen Pfirsich-Geruch zu vermitteln und zusätzlich eine Verbindung (cis-3-Methyl-γ-decalacton) als Enhancer zugesetzt wird, die geeignet ist, den durch trans-3-Methyl-γ-decalacton vermittelten Pfirsich-Geruch zu verstärken.With this inventive method, starting from a fragrance base composition which does not possess a strong peach odor, a fragrance composition having a strong peach odor is prepared by adding a compound (trans-3-methyl-γ-decalactone) which itself only is able to mediate a weak peach odor and in addition a compound (cis-3-methyl-γ-decalactone) is added as an enhancer which is suitable for the trans-3-methyl-γ-decalactone-mediated peach Reinforce smell.

Die Erfindung betrifft auch ein Verfahren zum Verstärken eines durch trans-3-Methyl-γ-decalacton vermittelten Pfirsichgeruchs in einer Riechstoffkomposition, wobei der Riechstoffkomposition eine wirksame Menge an cis-3-Methyl-γ decalacton zugesetzt wird.The invention also relates to a method for enhancing a trans-3-methyl-γ-decalactone-mediated peach odor in a fragrance composition, wherein the fragrance composition is added an effective amount of cis-3-methyl-γ-decalactone.

Ebenfalls Gegenstand der vorliegenden Erfindung ist eine Riechstoffkomposition oder ein parfümierter Artikel mit jasmonigem Geruch, umfassend eine den jasmonigen Geruch bewirkende Menge eines Gemisches aus cis- und trans-3-Methyl-γ-decalacton in einem molaren cis/trans-Verhältnis im Bereich von 2:3,5 bis 3,5:2, wobei weder das eingesetzte cis-3-Methyl-γ-decalacton für sich alleine noch das eingesetzte trans-3-Methyl-γ-decalacton für sich alleine den jasmonigen Geruch bewirkt.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-γ-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-γ-decalactone used alone nor the trans-3-methyl-γ-decalactone used alone causes the jasmonic odor.

Eine solche Riechstoffkomposition bzw. ein solcher parfümierter Artikel besitzt dabei auch einen starken Pfirsich-Geruch.Such a perfume composition or perfumed article also has a strong peach odor.

Ist die Riechstoffkomposition mit jasmonigem Geruch eine Parfümöl-Komposition, so liegt die eingesetzte Menge des Gemisches aus cis- und trans-3-Methyl-γ-decalacton vorzugsweise im Bereich von 0,01 bis 99,9 Gew.%, vorzugsweise 0,1 bis 90 Gew.% und besonders bevorzugt 0,5 bis 70 Gew.%, bezogen auf das Gesamtgewicht der Parfümöl-Komposition.If the fragrance composition having a jasmonic odor is a perfume oil composition, the amount of the mixture of cis- and trans-3-methyl-γ-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.

Die olfaktorischen Eigenschaften, stofflichen Eigenschaften, (wie Löslichkeit in gängigen kosmetischen Lösungsmitteln, Kompatibilität mit den gängigen weiteren Bestandteilen derartiger Produkte, etc.), sowie die toxikologische Unbedenklichkeit der erfindungsgemäß einzusetzenden Gemische unterstreichen deren besondere Eignung für die genannten Einsatzzwecke.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.

Besonders bevorzugt sind erfindungsgemäße Riechstoffkompositionen oder parfümierte Artikel, die eine Menge an einem Gemisch aus cis- und trans-3-Methyl-γ-decalacton enthalten, die nicht nur ausreicht, einen jasmonigen Geruch zu vermitteln, sondern auch um eine pfirsichartige oder cocosartige Geruchsnote zu vermitteln, zu modifizieren und/oder zu verstärken.Particular preference is given to fragrance compositions according to the invention or perfumed articles which contain an amount of a mixture of cis- and trans-3-methyl-γ-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.

Bei der Herstellung erfindungsgemäßer Riechstoffkompositionen können jasmonige bzw. pfirsich-, cocos- und lactonartige Geruchsnoten in vielfältigen Variationen eingesetzt werden. Das untenstehende Beispiel eines Parfüm-Duftthemas ("Jenny") demonstriert in anschaulicher Weise den olfaktorischen Effekt eines Gemisches von cis/trans-3-Methyl-γ-decalacton. Ein Parfümöl vom Typ "Jenny" läßt sich charakterisieren als blumig, modern und transparent. Das Basis-Parfümöl enthält bereits das trans-3-Methyl-γ-decalacton; durch den Zusatz des cis-3-Methyl-γ-decalacton werden die fruchtigen (pfirsichartigen) Noten überraschenderweise eindeutig verstärkt und die Riechstoffkomposition bekommt auch einen jasmonigen Aspekt.In the preparation of fragrance compositions according to the invention, jasmone or peach, coconut and lactone-like odor notes can be used in a wide variety of variations. The below example of a fragrance fragrance topic ("Jenny") vividly demonstrates the olfactory effect of a mixture of cis / trans-3-methyl-γ-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-γ-decalactone; surprisingly, the addition of cis-3-methyl-γ-decalactone clearly enhances the fruity (peach-like) notes and the fragrance composition also has a jasmonic aspect.

Ein Gemisch aus cis-/trans-3-Methyl-γ-decalacton (mit einem molaren Verhältnis im Bereich 2:3,5 bis 3,5:2) eignet sich wegen seiner olfaktorischen Eigenschaften vorzüglich für den Einsatz in Parfümkompositionen. Das cis/trans-Gemisch kann mit einer Vielzahl weiterer Riechstoffe kombiniert und in zahlreichen Produkten verwendet werden. Besonders vorteilhaft lässt sich die Verbindung mit anderen Riechstoffen in unterschiedlichen Mengenverhältnissen zu neuartigen Parfümkompositionen kombinieren.A mixture of cis- / trans-3-methyl-γ-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.

Eine Riechstoffkomposition mit einer Pfirsich-, Cocos- und Lactonnote kann beispielsweise hergestellt werden, indem das Gemisch aus cis- und trans-3-Methyl-γ-decalacton mit Bestandteilen einer Basis-Riechstoffkomposition vermischt wird, wobei das Gemisch aus cis- und trans-3-Methyl-γ-decalacton in einer Menge eingesetzt wird, die ausreicht, um den Geruch der Basis-Riechstoffkomposition zu modifizieren und/oder zu verstärken.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-γ-decalactone with constituents of a basic fragrance composition, the mixture of cis- and trans- 3-methyl-γ-decalactone is used in an amount sufficient to modify and / or enhance the odor of the basic fragrance composition.

Beispiele für Riechstoffe, mit denen das erfindungsgemäß einzusetzende Gemisch vorteilhaft kombiniert werden können, finden sich z.B. in S. Arctander, Perfume and Flavor Chemicals, Vol. I und II, Montclair, N. J., 1969, Selbstverlag oder K. Bauer, D. Garbe und H. Surburg, Common Fragrance and Flavor Materials, 4rd. Ed., Wiley-VCH, Weinheim 2001 .Examples of 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 ,

Im einzelnen seien genannt:

  • Extrakte aus natürlichen Rohstoffen wie Etherische Öle, Concretes, Absolues, Resine, Resinoide, Balsame, Tinkturen wie z. B.
    Ambratinktur; Amyrisöl; Angelicasamenöl; Angelicawurzelöl; Anisöl; Baldrianöl; Basilikumöl; Baummoos -Absolue; Bayöl; Beifußöl; Benzoeresin; Bergamotteöl; Bienenwachs-Absolue; Birkenteeröl; Bittermandelöl; Bohnenkrautöl; Buccoblätteröl; Cabreuvaöl; Cadeöl; Calmusöl; Campheröl; Canangaöl; Cardamomenöl; Cascarillaöl; Cassiaöl; Cassie-Absolue; Castoreum-absolue; Cedernblätteröl; Cedernholzöl; Cistusöl; Citronellöl; Citronenöl; Copaivabalsam; Copaivabalsamöl; Corianderöl; Costuswurzelöl; Cuminöl; Cypressenöl; Davanaöl; Dillkrautöl; Dillsamenöl; Eau de brouts-Absolue; Eichenmoos-Absolue; Elemiöl; Estragonöl; Eucalyptus-citriodora-Öl; Eucalyptusöl; Fenchelöl ; Fichtennadelöl; Galbanumöl; Galbanumresin; Geraniumöl; Grapefruitöl; Guajakholzöl; Gurjunbalsam; Gurjunbalsamöl; Helichrysum-Absolue; Helichrysumöl; Ingweröl; Iriswurzel-Absolue; Iriswurzelöl; Jasmin -Absolue; Kalmusöl; Kamillenöl blau; Kamillenöl römisch; Karottensamenöl; Kaskarillaöl; Kiefernadelöl; Krauseminzöl; Kümmelöl; Labdanumöl; Labdanum-Absolue; Labdanumresin; Lavandin-Absolue; Lavandinöl ; Lavendel-Absolue; Lavendelöl; Lemongrasöl; Liebstocköl; Limetteöl destilliert; Limetteöl gepreßt; Linaloeöl; Litsea-cubeba-Öl; Lorbeerblätteröl; Macisöl; Majoranöl; Mandarinenöl; Massoirindenöl; Mimosa-Absolue; Moschuskörneröl; Moschustinktur; Muskateller-Salbei-Öl; Muskatnußöl; Myrrhen-Absolue; Myrrhenöl; Myrtenöl; Nelkenblätteröl; Nelkenblütenöl; Neroliöl; Olibanum-Absolue; Olibanumöl; Opopanaxöl; Orangenblüten-Absolue; Orangenöl; Origanumöl; Palmarosaöl; Patchouliöl; Perillaöl; Perubalsamöl; Petersilienblätteröl; Petersiliensamenöl; Petitgrainöl; Pfefferminzöl; Pfefferöl; Pimentöl; Pineöl; Poleyöl; Rosen-Absolue; Rosenholzöl; Rosenöl; Rosmarinöl; Salbeiöl dalmatinisch; Salbeiöl spanisch; Sandelholzöl; Selleriesamenöl; Spiklavendelöl; Sternanisöl; Styraxöl; Tagetesöl; Tannennadelöl; Tea-tree-Öl; Terpentinöl; Thymianöl; Tolubalsam; Tonka-Absolue; Tuberosen-Absolue; Vanilleextrakt; Veilchenblätter-Absolue; Verbenaöl; Vetiveröl; Wacholderbeeröl; Weinhefenöl; Wermutöl; Wintergrünöl; Ylangöl; Y-sopöl; Zibet-Absolue; Zimtblätteröl; Zimtrindenöl sowie Fraktionen davon, bzw. daraus isolierten Inhaltsstoffen;
  • Einzel-Riechstoffe aus der Gruppe der Kohlenwasserstoffe, wie z.B. 3 - Caren; α-Pinen; β-Pinen; α-Terpinen; γ-Terpinen; p-Cymol; Bisabolen; Camphen; Caryophyllen; Cedren; Farnesen; Limonen; Longifolen; Myrcen; Ocimen; Valencen; (E,Z)-1,3,5-Undecatrien; Styrol; Diphenylmethan;
  • der aliphatischen Alkohole wie z.B. Hexanol; Octanol; 3-Octanol; 2,6-Dimethylheptanol; 2-Methyl-2-heptanol; 2-Methyl-2-octanol; (E)-2-Hexenol; (E)-und (Z)-3-Hexenol; 1-Octen-3-ol; Gemisch von 3,4,5,6,6-Pentamethyl-3/4-hepten-2-ol und 3,5,6,6-Tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-Nonadienol; 3,7-Dimethyl-7-methoxyoctan-2-ol; 9-Decenol; 10-Undecenol; 4-Methyl-3-decen-5-ol;
  • der aliphatischen Aldehyde und deren Acetale wie z.B. Hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-Methyloctanal; 2-Methylnonanal; (E)-2-Hexenal; (Z)-4-Heptenal; 2,6-Dimethyl-5-heptenal; 10-Undecenal; (E)-4-Decenal; 2-Dodecenal;2,6,10-Trimethyl-9-undecenal; 2,6,10-Trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-Dimethoxy-2,2,5-trimethyl-4-hexen; Citronellyloxyacetaldehyd;1-(1-Methoxypropoxy)-(E/Z)-3-hexen;
  • der aliphatischen Ketone und deren Oxime wie z.B. 2-Heptanon; 2-Octanon; 3-Octanon; 2-Nonanon; 5-Methyl-3-heptanon ; 5-Methyl-3-heptanonoxim; 2,4,4,7-Tetramethyl-6-octen-3-on; 6-Methyl-5-hepten-2-on;
  • der aliphatischen schwefelhaltigen Verbindungen wie z.B. 3-Methylthiohexanol; 3-Methylthiohexylacetat; 3-Mercaptohexanol; 3-Mercaptohexylacetat; 3-Mercaptohexylbutyrat; 3-Acetylthiohexylacetat; 1-Menthen-8-thiol;
  • der aliphatischen Nitrile wie z.B. 2-Nonensäurenitril; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-Dimethyl-2,6-octadiensäurenitril; 3,7-Dimethyl-6-octensäurenitril;
  • der Ester von aliphatischen Carbonsäuren wie z.B. (E)- und (Z)-3-Hexenylformiat; Ethylacetoacetat; Isoamylacetat; Hexylacetat; 3,5,5-Trimethylhexylacetat; 3-Methyl-2-butenylacetat; (E)-2-Hexenylacetat; (E)- und (Z)-3-Hexenylacetat; Octylacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat, ; Isoamylbutyrat; Hexylbutyrat; (E)- und (Z)-3-Hexenylisobutyrat; Hexylcrotonat; Ethylisovalerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat; Allylheptanoat; Ethyloctanoat; Ethyl-(E,Z)-2,4-decadienoat; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoat;4-Methyl-2-pentylcrotonat;
  • der acyclischen Terpenalkohole wie z. B. Citronellol; Geraniol; Nerol; Linalool; Lavandulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylen-7-octen-2-ol; 2,6-Dimethyl-5,7-octadien-2-ol; 2,6-Dimethyl-3,5-octadien-2-ol; 3,7-Dimethyl-4,6-octadien-3-ol; 3,7-Dimethyl-1,5,7-octatrien-3-ol 2,6-Dimethyl-2,5,7-octatrien-1-ol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
  • der acyclischen Terpenaldehyde und -ketone wie z. B. Geranial; Neral; Citronellal; 7-Hydroxy-3,7-dimethyloctanal; 7-Methoxy-3,7-dimethyloctanal; 2,6,10-Trimethyl-9-undecenal; Geranylaceton; sowie die Dimethyl- und Diethylacetale von Geranial, Neral, 7-Hydroxy-3,7-dimethyloctanal;
  • der cyclischen Terpenalkohole wie z. B. Menthol; Isopulegol; alpha-Terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalooloxid; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
  • der cyclischen Terpenaldehyde und -ketone wie z. B. Menthon; Isomenthon ; 8-Mercaptomenthan-3-on ; Carvon; Campher; Fenchon; alpha-lonon; beta-lonon; alpha-n-Methylionon; beta-n-Methylionon; alpha-Isomethylionon; beta-Isomethylionon; alpha-Iron; alpha-Damascon; beta-Damascon; beta-Damascenon; delta-Damascon; gamma-Damascon; 1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-on; 1,3,4,6,7,8a-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-on;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; Nootkaton ; Dihydronootkaton ; 4,6,8-Megastigmatrien-3-on; alpha-Sinensal ; beta-Sinensal ; acetyliertes Cedernholzöl (Methylcedrylketon);
  • der cyclischen Alkohole wie z.B. 4-tert.-Butylcyclohexanol ; 3,3,5-Trimethylcyclohexanol; 3-Isocamphylcyclohexanol; 2,6,9-Trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-Isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
  • der cycloaliphatischen Alkohole wie z.B. alpha,3,3-Trimethylcyclohexylmethanol;1-(4-Isopropylcyclohexyl)ethanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 2-Ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-Trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-Trimethylcyclohexyl)hexan-3-ol;
  • der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether;1,1-Dimethoxycyclododecan; (Ethoxymetho-xy)cyclododecan; alpha-Cedrenepoxid; 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan; 3a-Ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-Trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxan;
  • der cyclischen und makrocyclischen Ketone wie z.B. 4-tert-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Pentylcyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2-penten-1-yl-2-cyclopenten-1-on, 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl-4-cyclopentadecenon; 3-Methyl-5-cyclopentadecenon; 3-Methylcyclopentadecanon; 4-(1-Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanon; 4-tert.-Pentylcyclohexanon; 5-Cyclohexadecen-1-on; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanon; 8-Cyclohexadecen-1-on; 9-Cycloheptadecen-1-on; Cyclopentadecanon; Cyclohexadecanon;
  • der cycloaliphatischen Aldehyde wie z.B. 2,4-Dimethyl-3-cyclohexencarbaldehyd; 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd;
  • der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1-on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert.-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton;
  • der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4-tert-Butylcyclohexylacetat; 2-tert-Pentylcyclohexylacetat; 4-tert-Pentylcyclohexylacetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthylacetat;2-Cyclopentylcyclopentylcrotonat; 3-Pentyltetrahydro-2H-pyran-4-ylacetat; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylpropionat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylisobutyrat; 4,7-Methanooctahydro-5, bzw. 6-indenylacetat;
  • der Ester cycloaliphatischer Alkohole wie z.B.1-Cyclohexylethylcrotonat;;
  • der Ester cycloaliphatischer Carbonsäuren wie z. B. Allyl-3-cyclohexylpropionat; Allylcyclohexyloxyacetat; cis- und trans-Methyldihydrojasmonat; cis- und trans-Methyljasmonat; Methyl-2-hexyl-3-oxocyclopentancarboxylat; Ethyl-2-ethyl-6,6-dimethyl-2-cyclohexencarboxylat; Ethyl-2,3,6,6-tetramethyl-2-cyclohexencarboxylat; Ethyl-2-methyl-1,3-dioxolan-2-acetat;
  • der araliphatischen Alkohole wie z.B. Benzylalkohol; 1-Phenylethylalkohol; 2-Phenylethylalkohol; 3-Phenylpropanol; 2-Phenylpropanol; 2-Phenoxyethanol; 2,2-Dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1,1-Dimethyl-2-phenylethylalkohol; 1,1-Dimethyl-3-phenylpropanol; 1-Ethyl-1-methyl-3-phenylpropanol; 2-Methyl-5-phenylpentanol; 3-Methyl-5-phenylpentanol; 3-Phenyl-2-propen-1-ol; 4-Methoxybenzylalkohol; 1-(4-Isopropylphenyl)ethanol;
  • der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B. Benzylacetat; Benzylpropionat; Benzylisobutyrat; Benzylisovalerianat; 2-Phenylethylacetat; 2-Phenylethylpropionat; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-Phenylethylacetat; alpha-Trichlormethylbenzylacetat; alpha,alpha-Dimethylphenylethylacetat; alpha,alpha-Dimethylphenylethylbutyrat; Cinnamylacetat; 2-Phenoxyethylisobutyrat; 4-Methoxybenzylacetat;
  • der araliphatischen Ether wie z.B. 2-Phenylethylmethylether; 2-Phenylethylisoamylether; 2-Phenylethyl-1-ethoxyethylether; Phenylacetaldehyddimethylacetal; Phenylacetaldehyddiethylacetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-Trimethyl-4-phenyl-1,3-dioxan; 4,4a,5,9b-Tetrahydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;
  • der aromatischen und araliphatischen Aldehyde wie z. B. Benzaldehyd; Phenylacetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4-Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4-isopropylphenyl)propanal; 2-Methyl-3-(4-tert.-butylphenyl)propanal; 2-Methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert.-Butylphenyl)propanal; Zimtaldehyd; alpha-Butylzimtaldehyd; alpha-Amylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5-phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenzaldehyd; 4-Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4-methylendioxyphenyl)propanal;
  • der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4-Methylacetophenon; 4-Methoxyacetophenon; 4-tert.-Butyl-2,6-dimethylacetophenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1-(2-Naphthalenyl)ethanon;2-Benzofuranylethanon;(3-Methyl-2-benzofuranyl)ethanon; Benzophenon; 1,1,2,3,3,6-Hexamethyl-5-indanylmethylketon; 6-tert.-Butyl-1,1-dimethyl-4-indanylmethylketon; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanon; 5',6',7',8'-Tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetonaphthon;
  • der aromatischen und araliphatischen Carbonsäuren und deren Ester wie z.B. Benzoesäure; Phenylessigsäure; Methylbenzoat; Ethylbenzoat; Hexylbenzoat; Benzyl-benzoat; Methylphenylacetat; Ethylphenylacetat; Geranylphenylacetat; Phenylethyl-phenylacetat; Methylcinnmat; Ethylcinnamat; Benzylcinnamat; Phenylethylcinnamat; Cinnamylcinnamat; Allylphenoxyacetat; Methylsalicylat; Isoamylsalicylat; Hexylsalicylat; Cyclohexylsalicylat; Cis-3-Hexenylsalicylat; Benzylsalicylat; Phenylethylsalicylat; Methyl-2,4-dihydroxy-3,6-dimethylbenzoat; Ethyl-3-phenylglycidat; Ethyl-3-methyl-3-phenylglycidat;
  • der stickstoffhaltigen aromatischen Verbindungen wie z.B. 2,4,6-Trinitro-1,3-dimethyl-5-tert.-butylbenzol; 3,5-Dinitro-2,6-dimethyl-4-tert.-butylacetophenon; Zimtsäurenitril; 3-Methyl-5-phenyl-2-pentensäurenitril; 3-Methyl-5-phenylpentansäurenitril; Methylanthranilat; Methy-N-methylanthranilat; Schiffsche Basen von Methylanthranilat mit 7-Hydroxy-3,7-dimethyloctanal, 2-Methyl-3-(4-tert.-butylphenyl)propanal oder 2,4-Dimethyl-3-cyclohexencarbaldehyd; 6-Isopropylchinolin; 6-Isobutylchinolin; 6-sec.-Butylchinolin;2-(3-Phenylpropyl)pyridin; Indol; Skatol; 2-Methoxy-3-isopropylpyrazin; 2-Isobutyl-3-methoxypyrazin;
  • der Phenole, Phenylether und Phenylester wie z.B. Estragol; Anethol; Eugenol; Eugenylmethylether; Isoeugenol; Isoeugenylmethylether; Thymol; Carvacrol; Diphenylether; beta-Naphthylmethylether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-Dimethoxybenzol; Eugenylacetat; 2-Methoxy-4-methylphenol; 2-Ethoxy-5-(1-propenyl)phenol; p-Kresylphenylacetat;
  • der heterocyclischen Verbindungen wie z.B. 2,5-Dimethyl-4-hydroxy-2H-furan-3-on; 2-Ethyl-4-hydroxy-5-methyl-2H-furan-3-on; 3-Hydroxy-2-methyl-4H-pyran-4-on; 2-Ethyl-3-hydroxy-4H-pyran-4-on;
  • der Lactone wie z.B. 1,4-Octanolid; 3-Methyl-1,4-octanolid; 1,4-Nonanolid; 1,4-Decanolid; 8-Decen-1,4-olid; 1,4-Undecanolid; 1,4-Dodecanolid; 1,5-Decanolid; 1,5-Dodecanolid;4-Methyl-1,4-decanolid; 1,15-Pentadecanolid; cis- und trans-11-Pentadecen-1,15-olid; cis- und trans-12-Pentadecen-1,15-olid; 1,16-Hexadecanolid; 9-Hexadecen-1,16-olid; 10-Oxa-1,16-hexadecanolid; 11-Oxa-1,16-hexadecanolid; 12-Oxa-1,16-hexadecanolid; Ethylen-1,12-dodecandioat; Ethylen-1,13-tridecandioat; Cumarin; 2,3-Dihydrocumarin; Octahydrocumarin.
Specifically, may be mentioned:
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balms, tinctures such. B.
    ambergris tincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree Moss -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccoblätteröl; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cedernblätteröl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; Fennel oil; Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil; guaiac wood; gurjun balsam; gurjun balsam oil; Helichrysum absolute; Helichrysumöl; Ginger oil; Iris root absolute; Orris root oil; Jasmine -Absolue; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; linaloe; Litsea cubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Clary sage oil; nutmeg; Myrrh absolute; Myrrh oil; myrtle; Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; olibanum; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree oil; turpentine; Thyme oil; Tolu; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; verbena; vetiver; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; ylang oil; Y sopöl; Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
  • Individual fragrances from the group of hydrocarbons, such as 3 - carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1,3,5-undecatriene; styrene; diphenylmethane;
  • the aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) and (Z) -3-hexenol; 1-octene-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-Nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
  • the aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; Citronellyloxyacetaldehyde; 1- (1-methoxypropoxy) - 3-ene (E / Z);
  • the aliphatic ketones and their oximes such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
  • the aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
  • the aliphatic nitriles such as 2-nonenitrile; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-dimethyl-2,6-octadiensäurenitril; 3,7-dimethyl-6-octensäurenitril;
  • the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate, isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentylcrotonat;
  • the acyclic terpene alcohols such. For example, citronellol; geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadiene-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
  • the acyclic terpene aldehydes and ketones such. B. Geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
  • the cyclic terpene alcohols such. For example, menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; soborneol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
  • the cyclic terpene aldehydes and ketones such. Eg menthone; Isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-irone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; Nootkatone; Dihydronootkaton; 4,6,8-Mega stigma triene-3-one; alpha-sinensal; beta-Sinensal; acetylated cedarwood oil (methyl cedryl ketone);
  • the cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
  • the cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-Dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hexan-3-ol;
  • the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl; 1,1-Dimethoxycyclododecan; (Ethoxymetho-xy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-tetramethyl-dodecahydronaphtho [2,1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1,5,9-trimethyl-13-oxabicyclo [10.1.0] trideca-4,8-diene; rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;
  • the cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one, 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanon; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
  • the cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexene carbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
  • the cycloaliphatic ketones such. B. 1- (3,3-dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1- (2,4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
  • the ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate, 2-Cyclopentylcyclopentylcrotonat; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenylpropionate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl isobutyrate, respectively; 4,7-Methanooctahydro-5, or 6-indenyl acetate;
  • the ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate;
  • the esters of cycloaliphatic carboxylic acids such as. For example, allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; cis- and trans-methyldihydrojasmonate; cis- and trans-methyl jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl-2-methyl-1,3-dioxolan-2-acetate;
  • the araliphatic alcohols such as benzyl alcohol; 1-phenylethyl; 2-phenylethyl; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl; 1- (4-isopropylphenyl) ethanol;
  • the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-Dimethylphenylethylacetat; alpha, alpha-Dimethylphenylethylbutyrat; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • the araliphatic ethers such as 2-phenylethyl methyl ether ; 2-Phenylethylisoamylether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; phenylacetaldehyde; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;
  • the aromatic and araliphatic aldehydes such. B. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; propanal, 2-methyl-3- (4-tert-butylphenyl); 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-Butylzimtaldehyd; alpha amyl cinnamic aldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-Hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;
  • the aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-Benzofuranylethanon; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 8'-hexamethyl-2-acetonaphthone, 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8';
  • the aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl-3-methyl-3-phenylglycidate;
  • the nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-pentensäurenitril; 3-methyl-5-phenylpentansäurenitril; methyl anthranilate; Methyl N-methylanthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-Isopropyl; 6-Isobutylchinolin; 6-sec.-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;
  • the phenols, phenyl ethers and phenyl esters such as estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
  • heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide, 4-methyl-1,4-decanolide; 1.15 pentadecanolide; cis- and trans-11-pentadecene-1,15-olide; cis and trans-12-pentadecene-1,15-olide; 1,16-hexadecanolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedioate; Ethylene-1,13-tridecandioat; coumarin; 2,3-dihydrocoumarin; Octahydrocoumarin.

Die das erfindungsgemäß zu verwendende Lactongemisch enthaltenden Parfümöle können in flüssiger Form, unverdünnt oder mit einem Lösungmittel verdünnt für Parfümierungen eingesetzt werden. Geeignete Lösungsmittel hierfür sind z.B. Ethanol, Isopropanol, Diethylenglycolmonoethylether, Glycerin, Propylenglycol, 1,2-Butylenglycol, Dipropylenglycol, Diethylphthalat, Triethylcitrat, Isopropylmyristat usw.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.

Des weiteren können die das erfindungsgemäß zu verwendende Lactongemisch enthaltenden Parfümöle an einem Trägerstoff adsorbiert sein, der sowohl für eine feine Verteilung der Riechstoffe im Produkt als auch für eine kontrollierte Freisetzung bei der Anwendung sorgt. Derartige Träger können poröse anorganische Materialien wie Leichtsulfat, Kieselgele, Zeolithe, Gipse, Tone, Tongranulate, Gasbeton usw. oder organische Materialien wie Hölzer und Cellulose-basierende Stoffe sein.Furthermore, 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. 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.

Die das erfindungsgemäß zu verwendende Lactongemisch enthaltenden Parfümöle können auch mikroverkapselt, sprühgetrocknet, als Einschluß-Komplexe oder als Extrusions-Produkte vorliegen und in dieser Form dem zu parfümierenden Produkt hinzugefügt werden.The 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.

Gegebenenfalls können die Eigenschaften der derart modifizierten Parfümöle durch sog "Coaten" mit geeigneten Materialien im Hinblick auf eine gezieltere Duftfreisetzung weiter optimiert werden, wozu vorzugsweise wachsartige Kunststoffe wie z.B. Polyvinylalkohol verwendet werden.Optionally, 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.

Die Mikroverkapselung der Parfümöle kann beispielsweise durch das sogenannte Koazervationsverfahren mit Hilfe von Kapselmaterialien z.B. aus polyurethanartigen Stoffen oder Weichgelatine, erfolgen. Die sprühgetrockneten Parfümöle können beispielsweise durch Sprühtrocknung einer das Parfümöl enthaltenden Emulsion, bzw. Dispersion hergestellt werden, wobei als Trägerstoffe modifizierte Stärken, Proteine, Dextrin und pflanzliche Gummen verwendet werden können. Einschluß-Komplexe können z.B. durch Eintragen von Dispersionen von dem Parfümöl und Cyclodextrinen oder Harnstoffderivaten in ein geeignetes Lösungsmittel, z.B. Wasser, hergestellt werden. Extrusions-Produkte können durch Verschmelzen der Parfümöle mit einem geeigneten wachsartigen Stoff und durch Extrusion mit nachfolgender Erstarrung, ggf. in einem geeigneten Lösungsmittel, z.B. Isopropanol, erfolgen.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.

Die das erfindungsgemäß zu verwendende Lactongemisch enthaltenden Parfümöle können in konzentrierter Form, in Lösungen oder in oben beschriebener modifizierter Form verwendet werden für die Herstellung von z.B. Parfüm-Extraits, Eau de Parfums, Eau de Toilettes, Rasierwässer, Eau de Colognes, Pre-shave-Produkte, Splash-Colognes und parfümierten Erfrischungstüchern sowie die Parfümierung von sauren, alkalischen und neutralen Reinigungsmitteln, wie z.B. Fußbodenreinigern, Fensterglasreinigern, Geschirrspülmittel, Bad- und Sanitärreinigern, Scheuermilch, festen und flüssigen WC-Reinigern, pulver- und schaumförmigen Teppichreinigern, flüssigen Waschmitteln, pulver förmigen Waschmitteln, Wäschevorbehandlungsmitteln wie Bleichmittel, Einweichmittel und Fleckenentfernern, Wäscheweichspülern, Waschseifen, Waschtabletten, Desinfektionsmitteln, Oberflächendesinfektionsmitteln sowie von Luftverbesserern in flüssiger, gelartiger oder auf einem festen Träger aufgebrachter Form, Aerosolsprays, Wachsen und Polituren wie Möbelpolituren, Fußbodenwachsen, Schuhcremes sowie Körperpflegemitteln wie z.B. festen und flüssigen Seifen, Duschgelen, Shampoos, Rasierseifen, Rasierschäumen, Badeölen, kosmetischen Emulsionen vom Öl-in-Wasser-, vom Wasser-in-Öl- und vom Wasser-in-Öl-in-Wasser-Typ wie z.B. Hautcremes- und -lotionen, Gesichtscremes und - lotionen, Sonnenschutzcremes-und -lotionen, After-sun-cremes und -lotionen, Handcremes und -lotionen, Fußcremes und -lotionen, Enthaarungscremes und -lotionen, After-shave-Cremes und -lotionen, Bräunungscremes und -lotionen, Haarpflegeprodukten wie z.B. Haarsprays, Haargelen, festigen Haarlotionen, Haarspülungen, permanenten und semipermanenten Haarfärbemitteln, Haarverformungsmitteln wie kaltwellen und Haarglättungsmitteln, Haarwässern, Haarcremes und -lotionen, Deodorantien und Antiperspirantien wie z.B. Achselsprays, Roll-ons, Deosticks, Deocremes, Produkten der dekorativen Kosmetik wie z.B. Lidschatten, Nagellacke, Make-ups, Lippenstifte, Mascara sowie von Kerzen, Lampenölen, Räucherstäbchen, Insektiziden, Repellentien, Treibstoffen.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 Parfums, 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, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products such as hair sprays, hair gels, firm hair lotions, hair rinses, permanent and semipermanent hair dyes, hair styling agents such as cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorants, Deocremes, products of decorative cosmetics such as eyeshadows, nail polishes, make-ups, lipsticks, mascara and candles, lamp oils, incense sticks n, insecticides, repellents, fuels.

In Riechstoffkompositionen beträgt die eingesetzte Gesamtmenge des erfindungsgemäß zu verwendenden Lacton-Gemisches 0,01 bis 99,9 Gew.-%, vorzugsweise 0,1 bis 90 % und besonders bevorzugt 0,5 bis 70 %, bezogen auf die gesamte Riechstoffkomposition.In fragrance compositions, 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.

Beispiele:Examples: 1. Parfümkompositionen:1. perfume compositions:

Vergleichsbeispiel für ein Parfümöl vom Typ "Jenny" : Zusatz von cis-3-Methyl-γ decalacton zu einer Basisformulierung: Basis-Parfümöl modifiziertes Parfümöl Benzylacetate 5.00 5.00 Bergamote Oil Colorless 20.00 20.00 7-Methyl-2H-1,5-Benzodioxepin-3(4H)-one 10% DPG 5.00 5.00 Citronellol Inactive 10.00 10.00 2,4,4,7-Tetramethyl-oct-6-en-3-one 5.00 5.00 Dimethylbenzylcarbinylacetate 10.00 10.00 Ethyl acetoacetat 5.00 5.00 Ethyl Linalool 60.00 60.00 Cyclohexadec-8-enone 100P. 255.00 255.00 Methyl dihydrojasmonate 280.00 280.00 Helional 5.00 5.00 Hexenol cis-3 10% DPG 10.00 10.00 Hexyl cinnamic aldehyde 40.00 40.00 lonone Beta 15.00 15.00 Isodamascone 1 % DPG 10.00 10.00 2-Methyl-4-phenyl-[1,3]dioxolane 10% DPG 5.00 5.00 Lemon Oil Clear 15.00 15.00 4-tert.-Butyl-α-methyldihydrocinnamaldehyde 20.00 20.00 Linalool Synth. 30.00 30.00 2,2-Dimethyl-3-(3-methylphenyl)propanol 10.00 10.00 Mandarine Oil Clear 10.00 10.00 Nerolidol 20.00 20.00 Patchouli Oil Indo. 10% DPG 10.00 10.00 3-Methyl-5-phenylpentanol 40.00 40.00 Phenylethylalcohol 10.00 10.00 Rosewood Oil Bras. 10.00 10.00 Sandelwood Oil East India 5.00 5.00 3-(5,5,6-Trimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohexanol 20.00 20.00 Tagette Oil 10% DPG 10.00 10.00 2,4,6-Trimethyl-4-phenyl-1,3-dioxane coeur 10%DPG 5.00 5.00 Ylang Ylang Oil Extra 10% DPG 5.00 5.00 Trans-3-Methyl-γ-decalacton 20.00 20.00 DPG (Dipropylenglykol) 20.00 - Cis-3-Methyl-γ-decalacton - 20.00 1000.00 1000.00 Comparative Example of a "Jenny" Perfume Oil: Addition of cis-3-methyl-γ-decalactone to a base formulation: Base perfume oil modified perfume oil Benzylacetate 5:00 5:00 Bergamot Oil Colorless 8:00 pm 8:00 pm 7-methyl-2H-1,5-benzodioxepin-3 (4H) -one 10% DPG 5:00 5:00 Citronellol Inactive 10:00 10:00 2,4,4,7-Tetramethyl-oct-6-en-3-one 5:00 5:00 Dimethylbenzylcarbinylacetate 10:00 10:00 Ethyl acetoacetate 5:00 5:00 Ethyl Linalool 60.00 60.00 Cyclohexadec-8-enone 100P. 255.00 255.00 Methyl dihydrojasmonate 280.00 280.00 helional 5:00 5:00 Hexenol cis-3 10% DPG 10:00 10:00 Hexyl cinnamic aldehydes 40.00 40.00 lonone beta 15:00 15:00 Isodamascone 1% DPG 10:00 10:00 2-Methyl-4-phenyl- [1,3] dioxolane 10% DPG 5:00 5:00 Lemon Oil Clear 15:00 15:00 4-tert-butyl-α-methyldihydrocinnamaldehyde 8:00 pm 8:00 pm Linalool synth. 30.00 30.00 2,2-dimethyl-3- (3-methylphenyl) propanol 10:00 10:00 Mandarin Oil Clear 10:00 10:00 nerolidol 8:00 pm 8:00 pm Patchouli Oil Indo. 10% DPG 10:00 10:00 3-methyl-5-phenylpentanol 40.00 40.00 Phenylethylalcohol 10:00 10:00 Rosewood Oil Bras. 10:00 10:00 Sandelwood Oil East India 5:00 5:00 3- (5,5,6-trimethyl-bicyclo [2.2.1] hept-2-yl) cyclohexanol 8:00 pm 8:00 pm Tagette Oil 10% DPG 10:00 10:00 2,4,6-trimethyl-4-phenyl-1,3-dioxane coeur 10% DPG 5:00 5:00 Ylang Ylang Oil Extra 10% DPG 5:00 5:00 Trans-3-methyl-γ-decalactone 8:00 pm 8:00 pm DPG (dipropylene glycol) 8:00 pm - Cis-3-methyl-γ-decalactone - 8:00 pm 1000.00 1000.00

Das Basis-Parfumöl vom Typ "Jenny" wird durch den Zusatz von cis-3-Methyl-γ-decalacton (anstelle des sensorisch unwirksamen Lösungsmittels DPG) blumiger, hedionartiger und jasmoniger; die fruchtigen (pfirsichartigen) Aspekte werden verstärkt.The "Jenny" base perfume oil becomes more floral, hedonic and jasmonic with the addition of cis-3-methyl-γ-decalactone (instead of the sensorially inactive solvent DPG); the fruity (peachy) aspects are enhanced.

2. Herstellung:2. Production:

Die Herstellung von cis- und trans-3-Methyl-γ-decalacton erfolgt in bekannter Weise gemäß der Verfahrensgestaltung aus folgender Lit.-Stelle: Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971, 2 , 389 .The preparation of cis- and trans-3-methyl-γ-decalactone is carried out in a known manner according to the process design of the following Ref .: Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1971, 2, 389 ,

Claims (7)

  1. The use of a mixture which comprises cis- and trans-3-methyl-γ-decalactone in a molar ratio in the range from 2:3.5 to 3.5:2 as a jasmone fragrance.
  2. The use of cis-3-methyl-γ-decalactone in a fragrance composition containing trans-3-methyl-γ-decalactone to intensify the peach odour imparted by trans-3-methyl-γ-decalactone.
  3. A process for imparting, intensifying or modifying a jasmone odour in a fragrance composition, wherein a quantity of a mixture of cis- and trans-3-methyl-γ-decalactone in a molar ratio in the range from 2:3.5 to 3.5:2 which is sufficient to impart, to intensify or to modify a jasmone odour is added to the fragrance composition.
  4. A process for the production of a fragrance composition with a strong peach odour and a jasmone odour, with the following steps:
    - preparation of a fragrance base composition which does not possess a strong peach odour
    - blending of the fragrance base composition with the compounds cis-3-methyl-γ-decalactone and trans-3-methyl-γ-decalactone, with the proviso that (i) these compounds are used in a molar cis/trans ratio in the range from 2:3.5 to 3.5:2, (ii) the total quantity of the compounds used is sufficient to impart the strong peach odour and the jasmone odour and (iii) the quantity of trans-3-methyl-γ-decalactone used is not sufficient to impart the strong peach odour in the absence of cis-3-methyl-γ-decalactone.
  5. A process for intensifying a peach odour imparted by trans-3-methyl-γ-decalactone in a fragrance composition, characterised in that an effective quantity of cis-3-methyl-γ-decalactone is added to the fragrance composition.
  6. A fragrance composition or perfumed article with a jasmone odour, comprising a mixture of cis- and trans-3-methyl-γ-decalactone in a molar cis/trans ratio in the range from 2:3.5 to 3.5:2 in a quantity creating the jasmone odour, wherein neither the cis-3-methyl-γ-decalactone used nor the trans-3-methyl-γ-decalactone used creates the jasmone odour by itself individually.
  7. The fragrance composition with a jasmone odour according to claim 6, wherein the fragrance composition is a perfume oil composition and the quantity of the mixture of cis- and trans-3-methyl-γ-decalactone used is in the range from 0.01 to 99.9 wt.%, preferably 0.1 to 90 wt.% and particularly preferably 0.5 to 70 wt.%, based on the total weight of the perfume oil composition.
EP05754006A 2004-06-19 2005-06-06 Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture Active EP1761618B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004029809A DE102004029809A1 (en) 2004-06-19 2004-06-19 Use of a mixture of cis- and trans-3-methyl-gamma-decalactone and fragrance compositions and perfumed articles comprising such a mixture
PCT/EP2005/052581 WO2005123889A1 (en) 2004-06-19 2005-06-06 Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture

Publications (2)

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

Family

ID=34970755

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05754006A Active EP1761618B1 (en) 2004-06-19 2005-06-06 Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture

Country Status (6)

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

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2662098B1 (en) * 2012-05-10 2018-10-24 Symrise AG Use of specific compounds for changing odours
CN107151684B (en) * 2017-05-12 2021-06-22 上海应用技术大学 Preparation method of natural perfume gamma-decalactone

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0513627B1 (en) * 1991-05-15 1996-02-28 Givaudan-Roure (International) S.A. Tetrahydro-alpha-pyrone derivative, method for its preparation and perfume and/or flavouring compositions containing it
JP2000086647A (en) * 1998-09-03 2000-03-28 T Hasegawa Co Ltd Both enantiomers of cis-3-methyl-4-decanolide and their production

Also Published As

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

Similar Documents

Publication Publication Date Title
EP3206756B1 (en) Use of hexadeca-8,15-dienal as an aroma chemical
EP3197987B1 (en) Use of isomerically pure or highly isomerically enriched cis- or trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate
EP2065360B1 (en) Use of 3-methylbenzyl isobutyrate as a fragrance compound
EP2966158B1 (en) Isomers mixtures of unsaturated macrocyclic musk compounds
EP1111029A2 (en) Perfume compositions containing 4,8-dimethyl-3,7-nonadien-2-one
DE10330865A1 (en) 4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one as fragrances
EP2948534B1 (en) Use of 4,8-dimethyl-3,7-nonadien-2-ol as a perfume
EP1797025B1 (en) 4-isoamylcyclohexanol as odiferant
EP1654246B1 (en) Acetals, use thereof as fragrances and methods for production thereof
EP2072083B1 (en) Utilisation of 2.4'-dimethyl-propiophenon as an aroma
EP1215189A1 (en) Process for the preparation of isolongifolanol
EP1599434B1 (en) 4-cyclohexyl-2-butanol as an odiferous substance
EP1761618B1 (en) Use of a mixture of cis- and trans-3-methyl-g-decalactone and compositions of odoriferous substances and perfumed articles comprising said mixture
EP1067126B1 (en) Tetracyclic acetals
EP3112448B1 (en) Derivatives of 1- (4-methylcyclohexyl) ethanol
EP2966159B1 (en) Mixtures with enriched e-isomers of unsaturated macrocyclic musk compounds
EP1992606A1 (en) Alkene acetals and their use as odorous substances
EP1648526B1 (en) Cis-3,3,5-trimethylcyclohexyl esters
DE10229474A1 (en) New fragrances and processes for their manufacture
DE10222025A1 (en) Novel unsaturated oxalactone compounds where the double bond may be cis- or trans are useful as fragrances
DE10325628A1 (en) Use of 2-methyl-5-phenylpentanal in perfumery, to impart, modify or intensify rose scents in e.g. cosmetics and domestic cleaning compositions, also its preparation by hydrogenating 5-phenyl-2-methyl-2,4-pentenedienal
DE10324018A1 (en) Use of 2-methyl-5-phenylpentanal in perfumery, to impart, modify or intensify rose scents in e.g. cosmetics and domestic cleaning compositions, also its preparation by hydrogenating 5-phenyl-2-methyl-2,4-pentenedienal

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20070119

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: LOOFT, JAN

Inventor name: VOESSING, TOBIAS

Inventor name: EGGERS, MARCUS

Inventor name: WIDDER, SABINE

Inventor name: SABATER, CHRISTOPHER

Inventor name: PANTEN, JOHANNES

Inventor name: OBROCKI, THOMAS

DAX Request for extension of the european patent (deleted)
GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: LANGUAGE OF EP DOCUMENT: GERMAN

REF Corresponds to:

Ref document number: 502005005342

Country of ref document: DE

Date of ref document: 20081023

Kind code of ref document: P

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081221

Ref country code: IE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081210

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20090110

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20090210

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

26N No opposition filed

Effective date: 20090611

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

BERE Be: lapsed

Owner name: SYMRISE G.M.B.H. & CO. KG

Effective date: 20090630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081210

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090630

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090630

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090606

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081211

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090606

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20090311

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080910

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20130620

Year of fee payment: 9

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

Owner name: SYMRISE AG, DE

Effective date: 20131022

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20140606

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20140606

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 12

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 13

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20230622

Year of fee payment: 19

Ref country code: DE

Payment date: 20230620

Year of fee payment: 19