US20130090390A1 - Fragrances with note of lily of the valley - Google Patents

Fragrances with note of lily of the valley Download PDF

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Publication number
US20130090390A1
US20130090390A1 US13/645,871 US201213645871A US2013090390A1 US 20130090390 A1 US20130090390 A1 US 20130090390A1 US 201213645871 A US201213645871 A US 201213645871A US 2013090390 A1 US2013090390 A1 US 2013090390A1
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Prior art keywords
formula
compound
oil
fragrance
lily
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US13/645,871
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Emilie Singer
Bernd Holscher
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Symrise AG
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Symrise AG
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Priority to US13/645,871 priority Critical patent/US20130090390A1/en
Assigned to SYMRISE AG reassignment SYMRISE AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HOLSCHER, BERND, SINGER, EMILIE
Publication of US20130090390A1 publication Critical patent/US20130090390A1/en
Priority to US18/231,957 priority patent/US20240084216A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C5/00—Candles
    • C11C5/002—Ingredients
    • C11C5/004—Ingredients dyes, pigments; products giving a coloured flame
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention primarily relates to novel compounds selected from the group consisting of the compound of formula (1a)
  • fragrance especially as lily-of-the-valley fragrance, and fragrance preparations and perfumed products comprising a (preferably sensorially effective) amount of the compound of formula (I) as defined above and methods of producing a compound of formula (I) as defined above.
  • fragrances have a structure comprising a 4-alkyl-phenylpropanal as skeleton structure, for example 3-(4-tert-butylphenyl)-2-methylpropanal (formula (A); Lilial®, manufacturer: Givaudan S.
  • 3-(4-tert-Butylphenyl)-2-methylpropanal (A) a synthetic fragrance, was for a long time one of the most important industrially used fragrances for floral fragrance compositions, especially with an odor note of lily of the valley, and was used in large quantities in the cosmetics and soaps industry. Then, however, results of animal tests showed that 3-(4-tert-butylphenyl)-2-methylpropanal could be reprotoxic. In addition, it was found that this compound is possibly an allergen and might cause contact dermatitis in sensitive persons.
  • patent document US 6,376,458 discloses compounds represented by the following general formula (E), which in contrast to the compounds described above of formulas (A) to (D) have a saturated or unsaturated cyclohexyl group instead of a phenyl group:
  • the endocyclic dashed line denotes a single bond or a double bond
  • the group R is a methyl group or a hydrogen atom.
  • the compound 3-(4-tert-butyl-1-cyclohexen-1-yl)-2-methylpropanal specifically disclosed in patent document U.S. Pat. No. 6,376,458 has an odor comprising the odor notes lily of the valley, almost white flowers and freesias.
  • the compound 3-(4-tert-butyl-1-cyclohexen-1-yl)propanal preferred according to US 6,376,458 shows an odor of the aldehyde-like, floral lily of the valley-like, fatty type with a side note of Lilial®/Bourgeonal®, but this fragrance is more floral and the note of white flowers is more pronounced than with Lilian®.
  • the odor notes of the compounds of formula (F) disclosed in U.S. Pat. No. 7,834,219 have a strong floral note and a note of lily of the valley.
  • the compounds differ from compounds (A) to (D) in that they comprise a cyclohexyl group instead of a phenyl group.
  • the group R denotes an ethyl, isopropyl, or sec-butyl group.
  • the odor of this molecule is described as persistent, very fresh, pungent, floral, woody and ozone-like.
  • the compound 3-(4-isopropyl-1-cyclohexen-1-yl)-2-methylpropanal (formula (H) also does not show any odor note of lily of the valley, despite structural similarity to compounds (A) to (F). Rather, the odor profile of this compound is aldehyde-like, sweet, watery and floral (cyclamen tendency).
  • fragrances which in addition to their primary, namely olfactory, properties, also possess positive secondary properties, for example greater stability in particular conditions of use, greater substantivity and/or diffusivity or better adherence, or which, through synergy effects with other fragrances, lead to better sensory profiles.
  • Fragrances that are characterized by the aforementioned positive secondary properties allow for increased efficiency in the production of fragrance preparations and perfumed products. For example, by using fragrances with a better sensory profile, higher substantivity and/or better adherence, the number and the amounts of fragrances used in corresponding formulations can be optimized and/or minimized, which leads to a saving of sustainable resources in the production of perfumed products.
  • the primary problem to be solved by the present invention was to provide a fragrance with a floral, especially lily-of-the-valley odor note, whose olfactory properties are comparable to 3-(4-tert-butylphenyl)-2-methylpropanal (Lilial®), i.e. the fragrance should impart an odor impression that largely corresponds to the complexity of the natural odor of lily of the valley blossom. Furthermore, this fragrance should preferably be superior with respect to the sum of its secondary properties or at least some of its secondary properties to the lily of the valley fragrances known from the prior art.
  • a fragrance is, in the context of the present text, any substance that is suitable for being used for bringing about an olfactory impression, i.e. for imparting an olfactory impression, or for altering (modifying or intensifying) the olfactory perception of another substance.
  • said substance should preferably have no undesirable side-effects, e.g. effects that are injurious to health or to the environment, or have no adverse effects on the proper use of a product that contains this fragrance.
  • the figure shows:
  • FIG. 1 Assessment of the substantivity of the compound of formula (Ia) and of the compound of formula (Ib) compared to Lilial® (A) as a function of time
  • a compound of formula (I) imparts an odor impression that comes very close to the complexity of the natural odor of lily of the valley blossom. That is, the odor impression imparted by the compound of formula (I) is characterized by outstanding naturalness and complexity, especially with respect to the odor note of lily of the valley.
  • Such a complex odor impression largely corresponding to the natural odor of lily of the valley blossom, has not previously been achieved with the fragrances with an odor note of lily of the valley known from the prior art.
  • the compound of formula (I) to be used according to the invention is characterized by high building-up capacity (Intrinsic adhesion on a substrate) and high substantivity (capacity for being absorbed from a, generally aqueous, phase onto a substrate or also to remain on a substrate after a washing or rinsing process). This effect is observed in particular on substrates such as the skin, the hair and textile fibers (e.g. wool, cotton, linen, synthetic fibers).
  • fragrances and fragrance preparations are their substantivity with respect to the substrate or retention on the substrate, especially on the hair or on textile fibers.
  • substantially and retention are for example explained in detail in EP 1 201 738 A1, cf. sections [0004]-[0005]. Fragrances are generally required to have high substantivity and/or retention.
  • another aspect of the invention relates in particular to the use of the compound of formula (I) to be used according to the invention as an agent for increasing the substantivity and/or retention of a fragrance preparation (especially with respect to or on hair or textile fibers), preferably a fragrance preparation with an odor note of lily of the valley, preferably a fragrance preparation according to the invention as described below.
  • a fragrance preparation especially with respect to or on hair or textile fibers
  • a fragrance preparation with an odor note of lily of the valley preferably a fragrance preparation according to the invention as described below.
  • the compound of formula (I) to be used according to the invention is characterized by its fixing properties, i.e. it is a fixative.
  • the compound of formula (I) according to the invention increases the adherence of other fragrances, either by lowering their vapor pressure or by olfactory intensification (e.g. lowering of the threshold value).
  • the invention therefore also relates—as mentioned above—to the use of the compound of formula (I) as a fixative.
  • the compound of formula (I) has indeed already been mentioned in the prior art, but its suitability as a fragrance, especially its particular suitability for imparting an odor note of lily of the valley, had not been recognized.
  • R in each case is selected from the group consisting of hydrogen, methyl and ethyl.
  • the present invention also relates to a compound selected from the group consisting of the compound of formula (Ia)
  • compound of formula (Ia) or formula (Ib) means in each case the corresponding special enantiomer (as defined above), whereas the term “compound of formula (I)” comprises both the individual compounds selected from the group consisting of the compound of formula (Ia) and the compound of formula (Ib) and all mixtures (enantiomeric mixtures) consisting of these two compounds (in any mixture ratio). That is, statements relating to the “compound of formula (I)” always apply to the compound of formula (Ia) and the compound of formula (Ib) as well as to mixtures consisting of the compound of formula (Ia) and the compound of formula (Ib) in any mixture ratio.
  • the mass ratio of the compound of formula (Ia) to the compound of formula (Ib) is preferably selected in such a way that the amount of rotation of the mixture is not ⁇ 54.2°.
  • the mass ratio of the compound of formula (Ia) to the compound of formula (Ib) is selected so as to give an amount of rotation greater than ⁇ 54.2°, more preferably greater than ⁇ 54°, even more preferably greater than ⁇ 50°.
  • Mixtures that comprise the compounds of formula (Ia) as defined above and (ii) the compound of formula (Ib) as defined above or consist of these two compounds, are according to the invention mixtures preferably with
  • the odor profile of the compound of formula (Ia) as defined above is described as follows: odor note of lily of the valley, floral, sweet, watery, powdery and ozone-like, natural, caring, complex and radiant.
  • complex odor impression largely corresponding to the natural odor of lily of the valley blossom, is noteworthy.
  • the compound of formula (Ia) is therefore similar to 3-(4-tert-butylphenyl)-2-methylpropanal (formula (A)).
  • odor profile of the compound of formula (Ib) as defined above is described as follows: odor note of lily of the valley, fruity, green, watery and aldehyde-like.
  • the compound of formula (Ia) is, owing to its odor profile, especially suitable for imparting, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like and/or one, several or all impressions selected from the group consisting of natural, caring, complex and radiant.
  • the compound of formula (Ia), in conjunction with one or more further fragrances, is able to produce or to intensify further odor notes that are desirable for perfumery purposes, especially the odor notes creamy (cf. examples 10 and 14), cosmetic (see example 10), rounded aldehyde-like (see example 12), green (see example 13) and watery-fruity (see example 15).
  • the compound of formula (Ib) is, owing to its odor profile, especially suitable for imparting, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of fruity, green, watery and aldehyde-like.
  • the compound of formula (Ia) as defined above according to the invention is preferably used for imparting, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like and/or one, several or all impressions selected from the group consisting of natural, caring, complex and radiant.
  • the compound of formula (Ib) as defined above is preferably used according to the invention for imparting, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of fruity, green, watery and aldehyde-like.
  • a fragrance preparation is, in the context of the present text, a mixture of various substances, which is produced by a prescribed method from the corresponding substances according to a recipe or a formulation. Said preparations are produced and used specifically for the purpose of imparting, modifying or intensifying a desired odor impression, usually perceived as pleasant or positive in some other way. Preparations such as are used in preparative organic chemistry, especially the preparations known from the prior art described above for radical addition on ⁇ -pinene, therefore are not fragrance preparations in the sense of the present invention. Respective mixtures described in the publications Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157, Comptes Rendus des Séances de I'Académie des Sciences, Series C: Sciences
  • fragrance preparations are therefore preferably also not fragrance preparations according to the invention:
  • a fragrance preparation according to the invention is preferably not a mixture containing
  • a fragrance preparation according to the invention is not a mixture containing
  • the fragrance preparation according to the invention is not a mixture containing the compound of formula (I) as defined above and one or more substances selected from the group consisting of heptane, acetic acid, ⁇ -pinene, ethanal, manganese salts, copper salts, compound of formula (Ia) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), compound of formula (IIa) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), compound of formula (IIIa) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), dimethylsulfoxide, (p-menthen-1-yl-7)-2-ethanol tosylate, di-tert-butyl peroxide, benzoyl peroxide, the compound (4b) described in Bulletin de la describes Chimique de France 1973, 4, 1368-1372 (as defined there)
  • extracts of natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, for example:
  • fragrances from the hydrocarbons group for example 3-carene; ⁇ -pinene; ⁇ -pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;
  • aliphatic aldehydes and acetals thereof for example hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 2-methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,1 0-trimethyl-9-undecenal; 2,6,1 0-trimethyl-5,9-undecadienal; heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citron ellyloxyacetaldehyde; 1-(1-methoxy-propoxy)-(E/Z)-3-hexene;
  • ketones and oximes thereof for example 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;
  • aliphatic sulfur-containing compounds for example 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
  • aliphatic nitriles for example 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;
  • esters of aliphatic carboxylic acids for example (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3-hexenyl-isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl-2-methylpentanoate; ethyl hexanoate; allyl hexano
  • acyclic terpene alcohols for example geraniol; nerol; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-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; and formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hex
  • cyclic terpene aldehydes and ketones for example menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-irone; beta-damascenone; 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-methano-naphthalen-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-s
  • cyclic alcohols for example 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;
  • cyclic and cycloaliphatic ethers for example cineol; cedryl methyl ether; cyclododecylmethyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclo-dodecane; alpha-cedrene-epoxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1 b]furan; 1 ,5,9-trimethyl-1 3-oxabicyclo[1 0.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;
  • cyclic and macrocyclic ketones for example 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentyl-cyclopentanone; 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)-indanone; 8-cyclohexadecen-1-one;
  • cycloaliphatic aldehydes for example 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;
  • cycloaliphatic ketones for example 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-naphthalenylmethyl ketone; methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl) ketone;
  • esters of cycloaliphatic alcohols for example 1-cyclohexylethyl crotonate
  • esters of cycloaliphatic carboxylic acids for example allyl-3-cyclohexyl propionate; allylcyclohexyloxyacetate; cis- and trans-methyldihydrojasmonate; cis- and trans-methyljasmonate; methyl-2-hexyl-3-oxocyclopentane carboxylate; ethyl-2-ethyl-6,6-dimethyl-2-cyclohexene-carboxylate; ethyl-2,3,6,6-tetramethyl-2-cyclohexene-carboxylate; ethyl-2-methyl-1,3-dioxolan-2-acetate;
  • araliphatic alcohols for example benzyl alcohol; 1-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenulpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4-isopropylphenyl)ethanol;
  • esters of araliphatic alcohols and aliphatic carboxylic acids for example benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha,alpha-dimethylphenylethyl acetate; alpha,alpha-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • araliphatic ethers for example 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; phenyl acetaldehyde dimethylacetal; phenylacetaldehyde diethylacetal; hydratropa aldehyde dimethylacetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetra-hydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;
  • aromatic and araliphatic aldehydes for example benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropa aldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butyl-phenyl)propanal; cinnamaldehyde; alpha-butyl cinnamaldehyde; alpha-hexyl cinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylene dioxybenz
  • aromatic and araliphatic ketones for example 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-benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1 ,1-di-methyl-4-indanylmethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5′,6′,7′,8′-tetrahydro-3′,5′,5′,6′,8′,8′-hexamethyl-2-
  • aromatic and araliphatic carboxylic acids and esters thereof for example benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methylphenyl acetate; ethylphenyl acetate; geranylphenyl acetate; phenylethyl-phenyl acetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allylphenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl-2,4-dihydroxy-3,6-dimethyl benzoate; ethyl
  • nitrogen-containing aromatic compounds for example 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentanoic acid nitrile; methylanthranilate; methy-N-methylanthranilate; Schiff's bases of methylanthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butyl-phenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy
  • estragole for example estragole; anethole; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthylmethyl ether; beta-naphthylethyl ether; beta-naphthylisobutyl ether; 1,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresylphenyl acetate;
  • heterocyclic compounds for example 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;
  • lactones for example 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; 1,16-hexadecanolide; 9-hexadecen-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-tridecandioate; 2,3-dihydrocoumarin; octahydrocoumarin.
  • the amount of the compound of formula (Ia) as defined above and/or of the compound of formula (Ib) as defined above is preferably in the range from 0.0001 to 40 wt %, preferably in the range from 0.001 to 25 wt %, in each case relative to the total weight of the fragrance preparation.
  • a fragrance preparation according to the invention optionally contains further constituents, which are not themselves fragrances in the sense of the above definition, for example solvents, solubilizers, emulsifiers, stabilizers, radical traps.
  • a fragrance preparation according to the invention especially in the form of a perfume oil, comprises one, 2, 3 or more further fragrances with an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, ozone-like, woody, ambery, musky, fruity, animal.
  • odor notes selected from the group consisting of floral, sweet, watery, ozone-like, woody, ambery, musky, fruity, animal.
  • Corresponding fragrances are known by a person skilled in the art.
  • a fragrance preparation according to the invention is especially preferred in which
  • Fragrance preparations according to the invention are for example obtainable by a method comprising the step of mixing
  • the compound of formula (I) to be used as fragrance according to the invention, mixtures according to the invention as defined above and fragrance preparations according to the invention as defined above are used in particular for producing perfumed products (perfumed articles).
  • a perfumed product according to the invention comprises the compound of formula (I) as defined above, preferably in a sensorially effective amount.
  • a perfumed product comprises a mixture or fragrance preparation according to the invention, and a carrier or a substrate, wherein the carrier or the substrate is in direct contact with said mixture or fragrance preparation.
  • the substrate is for example a solid substrate or the carrier is for example a solid carrier.
  • Preferred perfumed products according to the invention are detergents and cleaning products, hygiene or care products, especially products from the area of body and hair care, cosmetics and household products.
  • a perfumed product according to the invention is especially preferred in which the amount of the compound of formula (Ia) as defined above and/or of the compound of formula (Ib) as defined above is in the range from 0.0001 to 5 wt %, preferably in the range from 0.001 to 2.5 wt %, in each case relative to the total weight of the product.
  • Preferred perfumed products according to the invention are selected from the group consisting of:
  • Fragrance preparations according to the invention containing the compound of formula (I) or a mixture according to the invention as defined above can generally be used (e.g. in concentrated form, in solutions or in the modified form described below) for the production of e.g. perfume extracts, eaux de perfume, eaux de toilette, shaving lotions, eaux de cologne, pre-shave products, splash-Colognes and perfumed tissue wipes and the perfuming of acidic, alkaline and neutral cleaning agents, for example floor cleaners, window cleaners, dishwasher agents, bath and sanitary cleaners, scouring products, solid and liquid lavatory cleaners, powder and foam carpet cleaners, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in the form of liquid or gel or applied on a solid carrier, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe cream
  • Preferred perfumed products according to the invention are products selected from the group consisting of washing and cleaning products, hygiene or care products, especially from the area of body and hair care, cosmetics and household products, fine fragrance (perfume), air care (especially candles), air fresheners.
  • fragrance preparations according to the invention or the fragrance preparations to be used according to the invention in the corresponding products can be used for perfuming in liquid form, undiluted or diluted with a solvent.
  • Suitable solvents for this are e.g. ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate etc.
  • solvents it applies that in the context of the present text, in the case of the presence of their own olfactory properties, they are to be classified exclusively as the constituent “solvent” and not the “fragrances”.
  • the compound of formula (I) contained in the perfumed products according to the invention, a mixture according to the invention as defined above or a fragrance preparation according to the invention as defined above can, in a preferred embodiment, be absorbed on a carrier, which ensures both a fine distribution of the fragrances in the product and controlled release during use.
  • Said carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsums, clays, clay granules, porous concrete etc. or organic materials such as wood and cellulose-based materials.
  • the compound of formula (I) contained in the perfumed products according to the invention, a mixture according to the invention as defined above or a fragrance preparation according to the invention as defined above can also be microencapsulated, spray-dried, as inclusion complexes or as extrusion products and can be added in this form to the product or article to be perfumed.
  • the properties of the fragrance preparations modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted release of fragrance, for which preferably wax-like plastics, e.g. polyvinyl alcohol, are used.
  • suitable materials e.g. wax-like plastics, e.g. polyvinyl alcohol, are used.
  • the microencapsulation of the fragrance preparations can be carried out for example by the so-called coacervation process using capsule materials, e.g. of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be produced for example by spray-drying an emulsion or dispersion containing the perfume oil, wherein modified starches, proteins, dextrin and vegetable gums can be used as carriers.
  • Inclusion complexes can be produced for example by feeding dispersions of the fragrance preparation and cyclodextrins or urea derivatives into a suitable solvent, e.g. water.
  • Extrusion products can be produced by melting the fragrance preparation with a suitable wax-like substance and by extrusion and subsequent solidification, optionally in a suitable solvent, e.g. isopropanol.
  • fragrance preparations according to the invention can then, as already mentioned, be used in concentrated form, in solutions or in the modified form described above for the production of the corresponding perfumed articles according to the invention.
  • ingredients with which the compound of formula (I) according to the invention, a mixture according to the invention as defined above or a fragrance preparation according to the invention as defined above can preferably be combined are for example: preservatives, abrasives, antiacne agents, agents against skin aging, antibacterial agents, anticellulitis agents, antidandruff agents, anti-inflammatory agents, agents for preventing irritation, agents that inhibit irritation, antimicrobial agents, antioxidants, astringents, agents inhibiting sweating, antiseptics, antistatic agents, binders, buffers, carriers, chelating agents, cell stimulants, cleaning agents, care agents, depilatory agents, surface active substances, deodorants, antiperspirants, plasticizers, emulsifiers, enzymes, essential oils, fibers, film-forming agents, fixatives, foam formers, foam stabilizers, antifoaming agents, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair straightening agents, hydrat
  • a perfumed product according to the invention is preferably not a mixture containing
  • a perfumed product according to the invention is not a mixture containing
  • the perfumed product according to the invention is not a mixture containing the compound of formula (I) as defined above and one or more substances selected from the group consisting of heptane, acetic acid, ⁇ -pinene, ethanal, manganese salts, copper salts, compound of formula (Ia) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), compound of formula (IIa) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), compound of formula (IIIa) from the publication Zhurnal Organicheskoi Khimii 1974, 10, 1153-1157 (as defined there), dimethylsulfoxide, (p-menthen-1-yl-7)-2-ethanol tosylate, di-tert-butyl peroxide, benzoyl peroxide, the compound (4b) described in Bulletin de la describes Chimique de France 1973, 4, 1368-1372 (as defined there
  • a further aspect of the present invention relates to a method of imparting, intensifying and/or modifying odor notes, especially an odor note of lily of the valley.
  • a method according to the invention of imparting, intensifying and/or modifying odor notes, especially an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like comprising the following step:
  • the perfumed product according to the invention is formed.
  • “Product” is in this case to be understood as the totality of the ingredients of the perfumed product according to the invention with the exception of the compound of formula (I) that is used, the mixture used according to the invention or the fragrance preparation used according to the invention.
  • the high substantivity of the compounds (Ia) and (Ib) according to the invention proves advantageous, since the higher the substantivity of a fragrance, the smaller is the amount of the fragrance required to be used for maintaining an odor for a specified time.
  • Another aspect of the present invention relates to a method of providing skin, hair, surfaces or textile fibers with an odor note, especially an odor note of lily of the valley.
  • a method according to the invention of providing skin, hair, surfaces or textile fibers with an odor note, especially an odor note of lily of the valley comprises the following steps:
  • the fragrance preparation can be a constituent of a perfumed product according to the invention, for example a body, hair or textile care product.
  • the compound of formula (I) to be used as fragrance according to the invention is obtainable inter alia by radical addition of ethanal onto (+)- ⁇ -pinene.
  • the compounds according to the invention selected from the group consisting of the compound of formula (Ia) and of the compound of formula (Ib) are obtainable inter alia by radical addition of ethanal on (+)- ⁇ -pinene or ( ⁇ )- ⁇ -pinene.
  • Another problem to be solved by the present invention was to provide novel methods for the production of the compound of formula (I) to be used as fragrance according to the invention and the compounds according to the invention selected from the group consisting of the compound of formula (Ia).
  • a method according to the invention for producing the compound of formula (I) as defined above comprises the step
  • group R in the acetal of formula (II) is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, preferably a butyl group.
  • acetal of formula (II) is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, preferably a butyl group, is novel and is also an object of the present invention.
  • the designation “acetal of formula (II)” comprises both the individual enantiomers (acetal of formula (IIa) as defined below and acetal of formula (IIb) as defined below) and all mixtures (enantiomeric mixtures) consisting of these two compounds (in any mixture ratio).
  • d-(+)-limonene and/or I-( ⁇ )-limonene as educt is that they are easily accessible, i.e. commercially available, low-cost educts from renewable raw materials.
  • the compound of formula (Ia) or of formula (Ib) are in each case accessible selectively.
  • the educt limonene (VI) (d-(+)-limonene and/or I-( ⁇ )-limonene) is first monohydrogenated catalytically in a manner known per se to p-menth-1-ene (formula (V)). This is epoxidized with a peracid in a manner known per se.
  • the epoxide of formula (IV) obtained is heated in the presence of aluminum isopropylate, so that ring opening to the allyl alcohol of formula (III) takes place.
  • the first stage of synthesis route (i) according to the invention the selective hydrogenation of the exocyclic double bond of limonene (formula (VIa), (VIb)), has often been described in the literature.
  • Typical reagents for this reaction are platinum(IV) oxide, as published for example in the react J. Chem. Soc., Chem. Commun. 1994, 24, 2759-2760 or W-4 Raney nickel as published in J. Org. Chem. 1982, 10, 1824-1831.
  • platinum(IV) oxide platinum(IV) oxide
  • the use of ruthenium on carbon is easier to manage than the combustible Raney nickel and is less expensive than platinum(IV) oxide.
  • the next step is selective ring opening of the epoxide of formula (IVa), (Vlb) to the allyl alcohol of formula (IIIa), (IIIb).
  • Various products may form in this reaction, namely the desired allyl alcohol with the exocyclic double bond and the corresponding allyl alcohol with endocyclic double bond.
  • lithium diisopropylamide or tert-butanolate, among others, are described as base for this reaction [ Roczniki Chemii Ann. Soc. Chim. Polonorum 1976, 50, 1709-1717 and Helv. Chim. Acta 1984, 67, 1249-1253].
  • the intermediate 4-isopropyl-1-methylene-2-vinyloxy-cyclohexane can, as is known by a person skilled in the art, be produced selectively from the allyl alcohol of formula (IIIa) or (IIIb) and acetylene.
  • a method preferred according to the invention for producing the compound of formula (Ia) as above and/or the compound of formula (Ib) as defined above accordingly comprises the following steps
  • limonene (formula (VIa), (VIb)) is first hydrogenated as described above to p-menth-1-ene (formula (Va), (Vb)).
  • P-Menth-1-ene (formula (Va), (Vb)) is then submitted in a solvent, e.g. methanol, in the presence of a sensitizer, e.g. Bengal pink at room temperature to photo-oxidation and the hydroperoxides that have formed (not shown in the following scheme)) are reduced with a suitable reducing agent, e.g.
  • An alternative method according to the invention for producing the compound of formula (I) as defined above comprises the step
  • cerium-containing catalyst especially cerium(III) acetate hydrate.
  • 8-Isopropyl-1-oxaspiro[4.5]decan-2-one is obtainable by a radical reaction of 4-isopropylcyclohexanol (formula (IX)) with methyl acrylate in the presence of di-tert-butyl peroxide.
  • 4-Isopropylcyclohexanol (formula (IX)) is in its turn obtainable by hydrogenation of 4-isopropylphenol (formula (X)):
  • a preferred method according to the invention for production of the compound of formula (I) as defined above or the compound of formula (Ia) according to the invention as defined above and/or the compound of formula (Ib) according to the invention as defined above to be used as fragrance according to the invention comprises or consists of the following steps
  • a method of production of the compound of formula (Ia) according to the invention as defined above and/or of the compound of formula (Ib) according to the invention as defined above comprises the following steps or consists of the following steps
  • a mixture of 2 g of 8-isopropyl-4-oxaspiro[4.5]decan-3-one (93%, 9.5 mmol, formula (VIII) as defined above) and 18 g of formic acid is fed into the equipment with the catalyst described above at 440° C. and in the space of 2 hours with a nitrogen flow of 16 L/h.
  • the pyrolysis product is captured in a cold trap, then diluted with MTBE and neutralized with saturated sodium hydrogen carbonate solution.
  • the phases are separated, and after removal of the solvent, 1.5 g of crude product is obtained at a purity of 32%. This io corresponds to a raw yield of 28%.
  • Perfume oil A2 (according Perfume oil A1 to the Fragrances (comparison) invention) ETHYL ACETOACETATE 4.0 4.0 HEXENOL CIS-3 10% DPG 3.0 3.0 HEXENYL ACETATE CIS-3 10% DPG 3.0 3.0 HEXENYL BENZOATE CIS-3 10% DPG 3.0 3.0 VERTOCITRAL 10% DPG 5.0 5.0 CYCLOGALBANAT ® 10% DPG 3.0 3.0 STYRALYL ACETATE 10% DPG 6.0 6.0 BERGAMOT OIL BERGAPTEN FREE FF 6.0 6.0 MANDARY OIL DIST. DECOL.
  • 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal endows the composition with perfume oil A2 more power and fullness than the composition with perfume oil A1; on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of the perfume oil B1 or B2 is a composition of the perfume oil B1 or B2:
  • Perfume oil B2 Perfume oil (according B1 to the Fragrances (comparison) invention) NONADIENAL TRANS, CIS-2.6 5% TEC 2.0 2.0 20% DPG ETHYL ACETOACETATE 3.0 3.0 FARENAL ® 10% DPG 5.0 5.0 VERTOCITRAL 3.0 3.0 CYCLOGALBANAT ® 10% DPG 2.0 2.0 STYRALYL ACETATE 3.0 3.0 MELONAL ® 0.5 0.5 DIHYDROMYRCENOL 15.0 15.0 LINALYL ACETATE 20.0 20.0 LEMON OIL TERPENE FLAVOR WONF 8.0 8.0 EUCALYPTOL NATURAL.
  • the findings are as follows: due to the proportion of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal, the body lotion containing perfume oil B2 has a stronger and more natural floral note than the body lotion that contains perfume oil B1 (without 3-[(4R)-4-isopropylcyclohexen-1-yl] propanal).
  • the body lotion with perfume oil B2 displays a more cosmetic top note and a creamier bottom note than the body lotion with perfume oil B1; on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of perfume oil C1 or C2 Composition of perfume oil C1 or C2:
  • Perfume oil C2 Perfume oil (according C1 to the Fragrances (comparison) invention)
  • ALDEHYDE C10 0.5 0.5 ALDEHYDE C11 ISO 2.0 2.0 ALDEHYDE C11 UNDECYLENIC 12.0 12.0 ALDEHYDE C12 MNA 6.0 6.0 FARENAL ® 1.0 1.0 VERTOCITRAL 8.0 8.0 ALLYL AMYL GLYCOLATE 1.0 1.0 STYRALYL ACETATE 1.5 1.5 DIHYDROMYRCENOL 65.0 65.0 AGRUNITRIL 1.0 1.0 PEONILE 15.0 15.0 METHYL ANTHRANILATE 10.0 10.0 NEROLIONE 10% DPG 1.5 1.5 ROSEMARY OIL BM 7.0 7.0 SAGE OFFICINALE OIL DALM.
  • the findings are as follows: due to the proportion of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal, the fabric softener containing perfume oil C2 has a more natural, fresher floral note than the fabric softener that contains perfume oil C1 (without 3-[(4R)-4-isopropylcyclohexen-1-yl] propanal); on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of perfume oil D1 or D2 Composition of perfume oil D1 or D2:
  • Perfume oil D2 Perfume oil (according D1 to the Fragrances (comparison) invention)
  • ALDEHYDE C 8 10.0 10.0 ALDEHYDE C10 14.0 14.0 ALDEHYDE C11 UNDECYLIC 5.0 5.0 ALDEHYDE C12 MNA 4.0 4.0 ISOAMYL ALCOHOL 6.0 6.0 VERTOCITRAL 4.0 4.0 ALLYL AMYL GLYCOLATE 4.0 4.0 DIHYDROMYRCENOL 120.0 120.0 CITRAL 95 30.0 30.0 AGRUNITRIL 80.0 80.0 CITRONITRILE 40.0 40.0 CITRYLAL 4.0 4.0 ORANGE OIL TERPENES 250.0 250.0 METHYL ANTHRANILATE 1.5 1.5 TERPINEOL HEAD FRACTION 10.0 10.0 EUCALYPTOL NAT.
  • the findings are as follows: due to the proportion of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal, the soap containing perfume oil D2 has a round, aldehyde note, in contrast to the soap that contains perfume oil D1 (without 3-[(4R)-4-isopropylcyclohexen-1-yl] propanal).
  • the soap with perfume oil D2 radiates more naturalness and fullness than the soap with perfume oil D1; on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of perfume oil E1 or E2 Composition of perfume oil E1 or E2:
  • Perfume oil (according E1 to the Fragrances (comparison) invention) ALDEHYDE C 8 0.5 0.5 HEXENOL CIS-3 3.5 3.5 VERTOCITRAL 15.0 15.0 STYRALYL ACETATE 3.0 3.0 MELONAL ® 2.0 2.0 DIHYDROMYRCENOL 60.0 60.0 CITRAL 95 6.0 6.0 ORANGE OIL TERPENES 20.0 20.0 EUCALYPTUS OIL GLOBULUS 80/85% 10.0 10.0 MENTHONE L/ISOMENTHONE D 82/18 1.5 1.5 HEXYL ACETATE 10% DPG 5.0 5.0 ISOPENTYRATE 4.0 4.0 ETHYL CAPROATE 1.0 1.0 ETHYL METHYL BUTYRATE-2 6.0 6.0 LINALOOL 10.0 10.0 DIMETHYL BENZYL CARBINYL 15.0 15.0 BUTYRATE PHENYLETHYL ALCOHOL 15.0 15.0 CITRONELLOL
  • composition of the washing powder with perfume oil E2 radiates altogether more freshness than the washing powder with perfume oil E1; on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of perfume oil F1 or F2 Composition of perfume oil F1 or F2:
  • Perfume oil (according F1 to the Fragrances (comparison) invention)
  • ALDEHYDE C10 0.5 0.5 ALCOHOL C10 6.0 6.0 HEXENOL CIS-3 1.0 1.0 LIMONENAL 4.0 4.0 VERTOCITRAL 8.0 8.0 PHENYLACETALDEHYDE 50% DPG 1.0 1.0 MINTONAT 15.5 15.5 METHYL ANTHRANILATE 1.0 1.0 HEXYL ACETATE 20.0 20.0 ALLYL HEPTOATE 1.0 1.0 LINALOOL 30.0 30.0 DIMETHYL BENZYL CARBINYL 2.0 2.0 ACETATE PHENYLETHYL ALCOHOL 150.0 150.0 CITRONELLOL 950 130.0 130.0 GERANIOL SUPER 35.0 35.0 GERANYL ACETATE PURE 10.0 10.0 BENZYL ACETATE 55.0 55.0 HEDIONE 15.0 15.0 HEXYL CINNAMIC ALDEHYDE A
  • the findings are as follows: the proportion of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal produces, in the general-purpose cleaner containing perfume oil F2, an intensification of the floral note relative to the general-purpose cleaner that contains perfume oil F1 (without 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal).
  • composition of the general-purpose cleaner with perfume oil F2 seems much creamier and fresher than that of the general-purpose cleaner with perfume oil F1; on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • composition of perfume oil G1 or G2 Composition of perfume oil G1 or G2:
  • Perfume oil (according G1 to the Fragrances (comparison) invention) FARENAL ® 3.0 3.0 FLORAZON 0.5 0.5 HEXENYL ACETATE CIS-3 3.0 3.0 VERTOCITRAL 1.0 1.0 DYNASCONE 10% DPG 2.0 2.0 CYCLOGALBANAT ® 2.0 2.0 STYRALYL ACETATE 1.5 1.5 DIHYDROMYRCENOL 6.0 6.0 OXANTHIA 50% IN TEC 10% DPG 10.0 10.0 LEMON OIL ITAL.
  • the findings are as follows: the addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal endows the shower gel containing perfume oil G2 with a more natural and caring note relative to the shower gel that contains perfume oil G1 (without 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal); on the whole, addition of 3-[(4R)-4-isopropylcyclohexen-1-yl]propanal results in an odor impression reminiscent of lily of the valley.
  • a B C D Component wt % wt % wt % wt % wt % Aluminum zirconium 25.00 20.00 25.00 20.00 tetrachlorohydrate - glycine complex Dimethicone (10 cst) — — 5.00 5.00 Cyclopentasiloxane — 0.50 1.00 0.50 Petroleum jelly 5.00 4.70 5.00 5.00 Ozokerite 1.00 1.50 — — Stearyl alcohol 12.00 12.00 — — 2-Butyloctanoic acid 0.50 — 0.50 — Wax — — 1.25 1.25 PPG-14 butyl ether 9.00 9.00 — — Hardened rapeseed oil — — 5.00 5.00 Silicon dioxide — — 1.00 — Farnesol 0.25 — 0.25 — Paraffin oil 0.50 0.50 — — Hydrogenated castor oil (castor 3.50 3.50 — — wax) Talc 4.00 4.00 — — Beheny
  • composition of perfume oil H1 or H2 Composition of perfume oil H1 or H2
  • Perfume oil H2 Perfume oil (according H1 to the Fragrances (comparison) invention) ALDEHYDE C10 0.5 0.5 ALDEHYDE C12 MNA 10% DPG 2.0 2.0 MINTONAT 40.0 40.0 MELOZONE 0.5 0.5 VERTOCITRAL 6.0 6.0 DIHYDRO MYRCENOL 120.0 120.0 TETRAHYDRO MYRCENOL 10.0 10.0 AGRUNITRIL 1.0 1.0 ORANGE OIL BRASIL 10.0 10.0 TAMARINE TYPE BASE 10.0 10.0 HEXYL ACETATE 6.0 6.0 ALDEHYDE C14 SO-CALLED 1.0 1.0 TETRAHYDRO LINALOOL 40.0 40.0 DIMETHYL BENZYL CARBINYL 5.0 5.0 BUTYRATE ORANGE FLOWER ETHER 5.0 5.0 PHENYLETHYL ACETATE 6.5 6.5 PHENYLETHYL ALCOHOL 15.0 15.0 GERANIOL SUPER 30.0 30.0
  • the mixture obtained after mixing the components given in each case is filled with a propane-butane mixture (2:7) in the weight ratio 2:3 in an aerosol container.
  • Sunscreen Soft Cream W/O
  • Sun Protection Factor SPF
  • the hair coloring basis according to the invention (part A) and the developer according to the invention (part B) are stirred together in a 1:1 weight ratio and applied to the hair.
  • Method of production Mix together all the raw materials in the order given.
  • Method of production Mix together all the raw materials in the order given. Adjust the pH.
  • Method of production Mix together materials of Part A in the order given. Mix together materials of Part B. When Part A is clear, add Part B. Then add Part C and stir until the mixture is homogeneous.
  • Method of production Melt the candle wax and stir. Add the perfume oil, stir well. Cast into the desired shape.
  • Method of production Melt Part A. Mix in Part B in a mixer-kneader. Form in the extruder at 35-40° C. to a WC block.
  • the aldehyde 3-[(4S)-4-isopropylcyclohexen-1-yl]propanal (formula (Ib) as defined above) is produced starting from I-( ⁇ )-limonene (79.5% ee, formula (VIb) as defined above) similarly to the synthesis of 3-[(4R)-4-isopropylcyclohexen-1-yl] propanal (Ia) (examples 4 to 8).
  • the product is obtained with a purity of 97% and with 78% ee.
  • the substantivity test is a test for determining the sensory adherence of a substance on smelling strips.
  • the fragrances to be investigated (compound of formula (Ia), compound of formula (Ib) and Lilial® as benchmark) are each applied in the form of a 10% solution in triethyl citrate (TEC) on a coded smelling strip by dipping and are assessed for intensity at specified time intervals by 15 testers.
  • the results (odor intensity I as a function of the time elapsed t in days d since dipping of the smelling strips) are in shown FIG. 1 .
  • the odor intensity is assessed at the following time intervals after dipping of the smelling strips: 1 hour or less (shown in FIG. 1 as time point “0 days”); 1 day; 2 days; 3 days; 4 days; 7 days; 8 days; 9 days. To ensure that the testers are not influenced, the coded smelling strips are not arranged in a chronological order on the smelling strip stand.
  • the odor intensity of the compound of formula (Ia) (black filled bar) is assessed in the fresh state and for a period of up to 3 days by the testers in comparison with Lilial® (black cross-hatched bar) as stronger, and after 4 to 7 days at least comparable to Lilial®. After 9 days, a higher odor intensity of the compound of formula (Ia) compared to Lilial® is observed again.
  • the odor intensity of compound (Ib) (black dotted bar) is, in the fresh state, stronger than that of Lilial® (black cross-hatched bar) and after one day is comparable to Lilial®. After that, the odor intensity of the compound of formula (Ib) at first decreases more than for Lilial® and the compound of formula (Ia), but after 7 to 9 days the values are comparable or slightly higher than with Lilial®.

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US20150225677A1 (en) * 2014-02-12 2015-08-13 Sanflor S.R.L. Perfuming element for garments usable in dry cleaning, and a relative drycleaning process
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WO2018167200A1 (en) 2017-03-15 2018-09-20 Firmenich Sa Cyclohexene derivatives as perfuming ingredients
WO2018192923A1 (en) 2017-04-18 2018-10-25 Firmenich Sa Alpha alkylation of aldehyde with a polycyclic olefin
US10183273B2 (en) 2016-06-24 2019-01-22 The Procter & Gamble Company Absorbent article comprising cyclodextrin complexes
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WO2020127325A2 (en) 2018-12-19 2020-06-25 Firmenich Sa Use of volatile compounds to modulate the perception of floral muguet
JP2021517176A (ja) * 2018-03-27 2021-07-15 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ アルデヒド系匂い物質
WO2021148491A1 (en) 2020-01-24 2021-07-29 Firmenich Sa Green odorant
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US11319272B2 (en) 2017-04-18 2022-05-03 Firmenich Sa Alpha alkylation of aldehyde with a polycyclic olefin
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WO2022265935A1 (en) * 2021-06-14 2022-12-22 Genomatica, Inc. 1,3-butylene glycol compositions and methods of use thereof
WO2023166005A1 (en) 2022-03-01 2023-09-07 Firmenich Sa Process for preparing unsaturated aldehydes
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JP2020502083A (ja) * 2016-12-21 2020-01-23 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ スズランの匂い
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JP2020514332A (ja) * 2017-03-15 2020-05-21 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ 賦香成分としてのシクロヘキセン誘導体
WO2018167200A1 (en) 2017-03-15 2018-09-20 Firmenich Sa Cyclohexene derivatives as perfuming ingredients
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US11771793B2 (en) 2017-05-18 2023-10-03 Agilex Flavors and Fragrances, Inc. Malodor reduction in air care applications
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JP2022517485A (ja) * 2018-11-13 2022-03-09 シムライズ アーゲー スズランノートを有する賦香成分
JP7231728B2 (ja) 2018-11-13 2023-03-01 シムライズ アーゲー スズランノートを有する賦香成分
CN112969774A (zh) * 2018-11-13 2021-06-15 西姆莱斯有限公司 具有铃兰香味的加香成分
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