WO2011029743A1 - Compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal - Google Patents

Compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal Download PDF

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Publication number
WO2011029743A1
WO2011029743A1 PCT/EP2010/062662 EP2010062662W WO2011029743A1 WO 2011029743 A1 WO2011029743 A1 WO 2011029743A1 EP 2010062662 W EP2010062662 W EP 2010062662W WO 2011029743 A1 WO2011029743 A1 WO 2011029743A1
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methyl
fragrance
fragrance composition
total amount
composition according
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PCT/EP2010/062662
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English (en)
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Wolfgang Krause
Ralf Pelzer
Jörg Botzem
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Basf Se
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • 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
    • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms

Definitions

  • the present invention relates to fragrance compositions of the lily of the valley-type comprising 2,5,7,7-tetramethyloctanal (Lyrisal®) and 2-isobutyl-4-methyl-tetrahydro- 2H-pyran-4-ol.
  • the present invention further relates to a method for producing a perfumed product or article as well as perfumed or aromatized articles comprising the fragrance compositions of the present invention.
  • Lily of the valley- or muguet-type fragrances are widely used and accepted in a large variety of consumer products such as for example detergents of all kind, washing soaps and hygiene and cosmetic products of all kinds.
  • Blends or mixtures of those lily of the valley- or muguet-type fragrances (hereinafter referred to as "fragrance compositions") often contain the synthetic compound 2-methyl-3-(4-tert.-butylphenyl)propanal of formula (I)
  • Lysmeral® also known under the tradenames Lysmeral® (BASF SE), Lilial® (Givaudan SA) and Lilestralis® (Innospec Inc.). Some of those product may also contain the meta- substituted isomer 2-methyl-3-(3-tert.-butylphenyl)propanal (CAS Registry Number 62518-65-4) of formula (II)
  • EP 0 252 378 discloses aliphatic aldehydes and their use as fragrance ingredients. Specifically, 2,5,7,7-tetramethyloctanal is described as a valuable fragrance ingredient with an intense lily-of-the-valley note. Furthermore, a method for the preparation of the abovementioned aldehydes is disclosed comprising base catalyzed condensation of the corresponding precursor aldehydes followed by catalytic hydrogenation.
  • EP 0 269 999 discloses the corresponding aliphatic alcohols and esters and their use as fragrance ingredients. Specifically, 2,5,7,7-tetramethyloctanol is described as a valuable fragrance ingredient with a flowery rose-like note. The document further discloses the preparation of 2,5,7,7-tetramethyloctanol by hydrogenation of the corresponding aldehyde 2,5,7,7-tetramethyloctanal.
  • EP 0 395 982 discloses beta, gamma-unsaturated nitriles, the preparation thereof and their use as scents. More specifically, 4,7,9,9-tetramethyl-dec-3-en-nitrile is disclosed as well as the preparation thereof by condensation of 2,5,7,7-tetramethyloctanal with cyanoacetic acid. The reaction product is described as having a waxy, floral and fresh fragrance note.
  • WO 2009/027957 discloses perfumes wherein the compound 2-methyl-3-(4-tert.- butylphenyl)propanal is replaced by other perfume raw materials in accordance with specific mass ratio replacement levels.
  • fragrances or fragrance compositions with similar, preferable exchangeable fragrance characteristics to those of known lily of the valley- or muguet-type fragrances, especially of para- or meta- substituted dihydrocinnamaldehyde derivatives such as for example the compounds of formula (I) and/or (II).
  • the fragrances or fragrance compositions should be readily accessible in technical quantities under economically favorable conditions.
  • fragrance composition comprising a) 2,5,7,7-tetramethyloctanal and
  • d) optionally one or more diluent(s).
  • fragrance compositions of the present invention comprising 2,5,7,7-tetramethyloctanal of formula (III)
  • fragrance compositions of the present invention comprise at least organoleptically active quantities of 2,5,7,7-tetramethyloctanal (CAS Registry Number 1 141 19-97-0) of formula (III)
  • the compound 2,5,7,7-tetramethyloctanal of formula (III) may, if desired, be used in optically active or diastereomerically enriched form or in another preferred embodiment in form of a racemic mixture of diastereomers.
  • 2,5,7,7-tetramethyloctanal of formula (III) may be synthesized in pure form, e.g. according to the route as described in EP 0 252 378 by base catalyzed condensation of 3,5,5- trimethylhexanal with propionic aldehyde and subsequent catalytic hydrogenation.
  • the compound 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol of formula (IV) may advantageously be used in form of a mixture of the respective diastereomers (cis/trans) both either in optically active or preferably in racemic form.
  • 2-isobutyl-4-methyl- tetrahydro-2H-pyran-4-ol of formula (IV) is commercially available, e.g. under the trade names Florol® (Firmenich S.A.) and Florosa® (Givaudan S.A.) in form of dia- stereomeric mixtures and may be used as such.
  • the fragrance compositions of the present invention comprise diastereomers of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol of formula (IV) with at least 62% of the cis form.
  • the fragrance composi- tions of the present invention comprise diastereomers of 2-isobutyl-4-methyl- tetrahydro-2H-pyran-4-ol of formula (IV) having 65-95% of the cis form and 5-35% of the trans form, very preferred 70-80% cis form and 20-30% trans form.
  • fragrance compositions of the present invention may also optionally comprise as component or components c) one or more additional fragrance substance(s).
  • the fragrance compositions of the present invention may also optionally comprise as component or components d) one or more diluent(s).
  • the fragrance compositions of the present invention may also optionally comprise further constituents known to those of skill in the art as common ingredients in fragrance compositions.
  • fragrance compositions of the present invention can be combined advantageously can be found for example in S. Arctander, Perfume and Flavor Materials, Vol. I and 1 1 , Montclair, N.J., 1969, self- published, or in K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.
  • fragrance compositions of the present invention can be combined with one or more individual fragrance substances known to those of skill in the art as additional fragrance substance c) or o as an additional component to be combined or mixed with the fin- ished fragrance composition, comprising but not limited to, for example, fragrances selected from the following groups: of hydrocarbons, such as, for example, 3-carene; alpha-pinene; beta-pinene; alpha- terpinene; gamma-terpinene; p-cymene; bisabolene; camphene; caryophyllene;
  • phenylacetaldehyde 3-phenylpropanal; hydratropaldehyde; 3-(3-lsopropyl- phenyl)butanal, 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4- ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-
  • Preferred fragrance substances c) according to the present invention are those, selected from the group of fragrance compounds consisting of 7-hydroxy-3,7- dimethyloctanal; 4-isopropyl-cyclohexylmethanol; limonene; hexanol; octanol; 3- octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 3,7-dimethyl-6-octenenitrile; 3,7-dimethyl-octanenitrile; (E)- and (Z)-3-hexenyl formate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; citronellol; gera- niol; nerol; linalool; lavandul
  • the fragrance compositions of the present invention comprise one or more, usually 1 to 20, preferably 1 to 10, more preferably 1 to 8, more preferably 1 to 6, more preferably 1 to 5, more preferably 1 to 4, even more preferably 1 to 3 and most preferably 1 or 2 additional fragrance substances selected from the group of fragrance listed above, whereas the fragrance substances 7-hydroxy-3,7- dimethyloctanal and 4-isopropyl-cyclohexylmethanol are particularly preferred fragrance substances c) comprised by the fragrance compositions of the present inven- tion.
  • fragrance compositions of the present invention are those comprising 7-hydroxy-3,7-dimethyloctanal (Hydroxycitronellal, CAS Registry Number 107- 75-5) of formula (V) as additional fragrance substance c).
  • fragrance compositions of the present invention are those comprising 4-isopropyl-cyclohexylmethanol (4-(1 -methylethyl)-cyclohexanemethanol); CAS Registry Number 13828-37-0) of formula (VI)
  • fragrance substance c The compounds 7-hydroxy-3,7-dimethyloctanal of formula (V) and 4-isopropyl-cyclohexylmethanol of formula (VI) are known and commercially widely available e.g. as Mayol® (Firmenich SA), MeijiffTM (International Flavors & Fragrances Inc.) or may be synthesized by known methods. Further particularly preferred fragrance compositions of the present invention are those comprising 2,6-dimethylheptan-2-ol (CAS Registry Number 13254-34-7) of formula (VII) as additional fragrance substance c).
  • fragrance compositions of the present invention are those comprising 3,7-dimethyl-octan-1 ,7-diol (Hydroxycitronellol; CAS Registry Number 107- 74-4) of formula (VIII) as additional fragrance substance c).
  • fragrance compositions of the present invention are those comprising 4-(Octahydro-4,7-methano-5H-inden-5-yliden)butanal; CAS Registry Number 30168-23-1 ) of formula (IX), as additional fragrance substance c).
  • the compound 4-(Octahydro-4,7-methano-5H- inden-5-yliden)butanal is commercially available as Dupical® (Givaudan).
  • fragrance compositions of the present invention are those comprising the compounds 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 - carboxaldehyde of formula (X) and/or 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 - carboxaldehyde of formula (XI) (CAS Registry Number 31906-04-4 and 51414-25-6 respectively),
  • the compounds 4-(4-Hydroxy-4-methylpentyl)- 3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 - carboxaldehyde are commercially available as a 70:30 mixture under tradenames Kovanol® (Takasago) or Lyral® (International Flavors & Fragrances Inc.).
  • fragrance compositions of the present invention comprise or (substantially) consist of the components
  • d) optionally one or more diluent(s).
  • fragrance compositions of the present invention comprise or (substantially) consist of the components
  • fragrance compositions of the present invention comprise or (substantially) consist of the components
  • d) optionally one or more diluent(s).
  • fragrance compositions of the present inven- tion comprise or (substantially) consist of the components
  • fragrance compositions of the present invention comprise or (substantially) consist of the components
  • d) optionally one or more diluent(s).
  • fragrance compositions of the present invention comprise or consist of the components a) 2,5,7,7-tetramethyloctanal of formula (III) and
  • d) optionally one or more diluent(s).
  • d) optionally one or more diluent(s).
  • d) optionally one or more diluent(s).
  • additional fragrance substances means one or more, usually 1 to 20, preferably 1 to 10, more preferably 1 to 8, more preferably 1 to 6, more preferably 1 to 5, more preferably 1 to 4, even more preferably 1 to 3 and most preferably 1 or 2 additional fragrance substances selected from the group of fragrance substances c) listed above other than 7-hydroxy- 3,7-dimethyloctanal and 4-isopropyl-cyclohexylmethanol and 4-(Octahydro-4,7- methano-5H-inden-5-yliden)butanal and 2,6-dimethylheptan-2-ol and 3,7-dimethyl- octan-1 ,7-diol and 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 2-isobutyl-4- methyl-tetrahydro-2H-pyran-4-ol may generally be varied within a broad range.
  • the weight-based ratio of the total amount 2,5,7,7-tetramethyloctanal to the total amount of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol in the finished fragrance com- position ranges from about 100:1 to about 1 :100, more preferably from 50:1 to 1 :50, more preferably from 30:1 to 1 :30, more preferably from 20:1 to 1 :20, more preferably from 10:1 to 1 :10 and most preferably from 5:1 to 1 :5.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 2,6-dimethylheptan-2- ol may also generally be varied within a broad range.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 2,6- dimethylheptan-2-ol in the finished fragrance composition ranges from about 50:1 to about 1 :50, more preferably from 20:1 to 1 :10, more preferably from 20:1 to 1 :1 , and most preferably from 10:1 to 1 :1.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 3,7-dimethyl-octan- 1 ,7-diol may also generally be varied within a broad range.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 3,7- dimethyl-octan-1 ,7-diol in the finished fragrance composition ranges from about 1 :30 to about 30:1 , more preferably from 10:1 to 1 :10, more preferably from 5:1 to 1 :5, and most preferably from 3:1 to 1 :3.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 7-hydroxy- 3,7-dimethyloctanal may also generally be varied within a broad range.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 7-hydroxy-3,7-dimethyloctanal in the finished fragrance composition ranges from about 30:1 to about 1 :30, more preferably from 10:1 to 1 :10, more preferably from 5:1 to 1 :5 and most preferably from 3:1 to 1 :3.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 4-isopropyl- cyclohexylmethanol may also generally be varied within a broad range.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 4-isopropyl-cyclohexylmethanol in the finished fragrance composition ranges from about 30:1 to about 1 :30, more preferably from 20:1 to 1 :10, more preferably from 15:1 to 1 :1 , more preferably from 10:1 to 1 :1 and most preferably from 5:1 to 1 :1.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 4-(Octahydro- 4,7-methano-5H-inden-5-yliden)butanal may generally be varied within a broad range.
  • the weight-based ratio of the total amount 2,5,7,7-tetramethyloctanal to the total amount of 4-(Octahydro-4,7-methano-5H-inden-5-yliden)butanal in the finished fragrance composition ranges from about 100:1 to about 1 :100, more preferably from 50:1 to 1 :50, more preferably from 30:1 to 1 :30, more preferably from 20:1 to 1 :20, more preferably from 10:1 to 1 :10 and most preferably from 5:1 to 1 :5.
  • the weight-based ratio of the total amount of 2,5,7,7-tetramethyloctanal to the total amount of 4-(4-Hydroxy-4- methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3- cyclohexen-1 -carboxaldehyde may generally be varied within a broad range.
  • the weight-based ratio of the total amount 2,5,7,7-tetramethyloctanal to the total amount of 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4- Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde in the finished fragrance composition ranges from about 100:1 to about 1 :100, more preferably from 50:1 to 1 :50, more preferably from 30:1 to 1 :30, more preferably from 20:1 to 1 :20, more preferably from 10:1 to 1 :10 and most preferably from 5:1 to 1 :5.
  • the fragrance compositions according to the present invention comprise at least or- ganoleptically active quantities of the named ingredients 2,5,7,7-tetramethyloctanal and 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol and, if present, of the optional further fragrance substances 7-hydroxy-3,7-dimethyloctanal and/or 4-isopropyl- cyclohexylmethanol and, if present of the optional further fragrance substances, preferably 2,6-dimethylheptan-2-ol and/or 3,7-dimethyl-octan-1 ,7-diol.
  • or- ganoleptically active amount means an amount sufficient to stimulate an olfactorial impression in a human being, especially the olfactorial impression of a typical lily of the valley- or muguet-type scent.
  • fragrance substances of the present invention especially in the case of those comprising 2,5,7,7-tetramethyloctanal and 2-isobutyl-4-methyl-tetrahydro-2H- pyran-4-ol and 7-hydroxy-3,7-dimethyloctanal and 4-isopropyl-cyclohexylmethanol generally only minor amounts or concentrations are necessary to generate the desired lily of the valley- or muguet-type fragrance.
  • fragrance substances of the present invention especially in the case of those comprising 2, 5, 7, 7-tetramethyloctanal and 2-isobutyl-4-methyl- tetrahydro-2H-pyran-4-ol and 7-hydroxy-3,7-dimethyloctanal and 4-isopropyl- cyclohexylmethanol and 4-(Octahydro-4,7-methano-5H-inden-5-yliden)butanal and 4- (4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4- methylpentyl)-3-cyclohexen-1 -carboxaldehyde also generally only minor amounts or concentrations are necessary to generate the desired substantive lily of the valley- or muguet-type fragrance.
  • fragrance substances of the present invention especially in the case of those comprising 2, 5, 7, 7-tetramethyloctanal and 2-isobutyl-4- methyl-tetrahydro-2H-pyran-4-ol and 4-(Octahydro-4,7-methano-5H-inden-5- yliden)butanal and optionally 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 - carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde also generally only minor amounts or concentrations are necessary to generate the desired substantive lily of the valley- or muguet-type fragrance.
  • compositions of the present invention comprise or consist of, based on the total amount of the finished composition, a total amount of 2, 5, 7, 7-tetramethyloctanal in the range from about 0,1 to 95 wt.%, preferably from about 0,1 to 90 wt.%, more preferably from 0,1 to 50 wt.%, more preferably from 0,1 to 30 wt.%, more preferably from 0,1 to 20 wt.%, more preferably from 0,1 to 15 wt.%, more preferably from 0,2 to 10 wt.%, even more preferably from 0,5 to 10 wt.% and most preferably in the range from 1 to 5 wt.%.
  • compositions of the present invention comprise or consist of, based on the total amount of the finished composition, a total amount of 2,5,7,7- tetramethyloctanal in the range from about 15 to 90 wt.%, preferably from about 30 to 80 wt.%, more preferably from 50 to 70 wt.%.
  • compositions of the present invention comprise or consist of, based on the total amount of the finished composition, a total amount of 2-isobutyl-4-methyl- tetrahydro-2H-pyran-4-ol in the range from about 0,1 to 95 wt.%, preferably from about 0,1 to 90 wt.%, more preferably from 1 to 90 wt.%, more preferably from 1 to 70 wt.%, more preferably from 5 to 50 wt.%, more preferably from 10 to 50 wt.%, even more preferably from 10 to 40 wt.% and most preferably in the range from 20 to 30 wt.%.
  • compositions of the present invention comprise or consist of, based on the total amount of the finished composition, a total amount of 2-isobutyl-4- methyl-tetrahydro-2H-pyran-4-ol in the range from about 5 to 80 wt.%, preferably from about 10 to 60 wt.%, more preferably from 15 to 45 wt.%.
  • compositions of the present invention comprising 7-hydroxy-3,7- dimethyloctanal comprise or consist of, based on the total amount of the finished com- position, a total amount of 7-hydroxy-3,7-dimethyloctanal in the range of up to 30 wt.%, preferably from 0,1 to 30 wt.%, more preferably from 0,5 to 25 wt.%, more preferably from 1 to 20 wt.%, even more preferably from 1 to 10 wt.% and most preferably in the range from 2 to 4 wt.%.
  • compositions of the present invention comprising 4-isopropyl- cyclohexylmethanol comprise or consist of, based on the total amount of the finished composition, a total amount of 4-isopropyl-cyclohexylmethanol in the range of up to 30 wt.%, preferably from 0,01 to 30 wt.%, more preferably from 0,1 to 20 wt.%, more preferably from 0,1 to 10 wt.%, even more preferably from 0,1 to 5 wt.% and most preferably in the range from 0,1 to 2,5 or even to 1 wt.%.
  • compositions of the present invention comprising 4-(4-Hydroxy-4- methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3- cyclohexen-1 -carboxaldehyde comprise or consist of, based on the total amount of the finished composition, a total amount of 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 - carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde in the range of up to 30 wt.%, preferably from 0,01 to 30 wt.%, more preferably from 0,1 to 20 wt.%, more preferably from 0,1 to 10 wt.%, even more preferably from 0,1 to 5 wt.% and most preferably in the range from 0,1 to
  • compositions of the present invention comprising 4-(4- Hydroxy-4-methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4- methylpentyl)-3-cyclohexen-1 -carboxaldehyde comprise or consist of, based on the total amount of the finished composition, a total amount of 4-(4-Hydroxy-4- methylpentyl)-3-cyclohexen-1 -carboxaldehyde and/or 3-(4-Hydroxy-4-methylpentyl)-3- cyclohexen-1 -carboxaldehyde in the range of up to 10 wt.%, preferably from 0,01 to 8 wt.%, more preferably from 0,1 to 5 wt.%, more preferably from 0,1 to 2.5 wt.%.
  • the perfume compositions of the present invention do preferably not contain significant amounts of 2-methyl-3-(4-tert.-butylphenyl)propanal (the para-substituted compound of formula (I)).
  • the weight-based ratio of 2-methyl-3-(3-tert.- butylphenyl)propanal to 2-methyl-3-(4-tert.-butylphenyl)propanal, if present at all, in the finished perfume composition ranges from over 10000:1 or higher to 50:1 , preferably from 10000:1 to 100:1 .
  • the fragrance compositions of the present invention comprise, based on the total amount of the finished composition, a total amount of 2-methyl-3-(4-tert.-butylphenyl)propanal of 1 wt.% or less, preferably of 0,5 wt.% or less, more preferably of 0,1 wt.% or less, more preferably of 0,05 wt.% or less and most preferably of 0,01 wt.% or less.
  • the fragrance compositions of the present invention are substantially free of 2-methyl-3-(4- tert.-butylphenyl)propanal of formula (I), meaning that it comprises based on the total amount of the finished composition, a total amount of 2-methyl-3-(4-tert.-butylphenyl) propanal of 0,005 wt.% or less, preferably of 0,001 wt.% or less.
  • the fragrance compositions of the present invention may optionally comprise as component d) one or more diluent(s).
  • the expression "one or more diluent(s)" means that one diluent or a mixture of two or more diluents may be present in fragrance compositions.
  • fragrance means a substance known to those of skill in the art as a suiable solvent for perfume or fragrance compositions such as, e.g. an alcohol such as ethanol or isopropanol and/or a polyol or an ether derived thereof such as diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, dialkyl esters of 1 ,2- cyclohexanedicarboxylic acid, especially 1 ,2-cyclohexanedicarboxylic acid diisononyl ester (Hexamoll® DINCH, BASF SE) or and the like.
  • an alcohol such as ethanol or isopropanol
  • a polyol or an ether derived thereof such as diethylene glycol monoethyl ether, glycerol, propylene glycol,
  • particularly preferred fragrance compositions according to the present invention comprise one or more diluents) d) selected from the group consisting of diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and dialkyl esters of 1 ,2-cyclohexanedicarboxylic acid, especially 1 ,2-cyclohexanedicarboxylic acid diisononyl ester.
  • diluents selected from the group consisting of diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and dialkyl esters of 1 ,2-cyclohexanedicarboxylic acid, especially 1
  • the components of the fragrance compositions according to the present invention namely 2,5,7,7-tetramethyloctanal and 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol and, if present, of the optional further fragrance substances 7-hydroxy-3,7- dimethyloctanal and/or 4-isopropyl-cyclohexylmethanol and, if present other optional further fragrance substances, preferably 2,6-dimethylheptan-2-ol and/or 3,7-dimethyl- octan-1 ,7-diol and/or 4-(Octahydro-4,7-methano-5H-inden-5-yliden)butanal as well as the diluent(s), if present, may be blended or mixed by conventional techniques known to those of skill in the art.
  • Exemplary fragrance compositions according to the present invention may comprise, based on the total amount of the composition, e.g.:
  • Particularly preferred fragrance compositions according to the present invention may comprise, based on the total amount of the composition, e.g.
  • fragrance compositions of the present invention can also be combined with extracts of natural raw materials such as essential oils, concretes, absolutes, resins, resi- noids, balsams, tinctures and the like known to those of skill in the art, comprising but not limited to, for example:
  • Ambergris tincture amyris oil; angelica seed oil; angelica root oil; aniseed oil; valerian oil; basil oil; treemoss absolute; bay oil; mugwort oil; benzoin resin; bergamot oil;
  • the fragrance compositions of the present invention can also be combined with antioxidants (stabilizers) known to those of skill in the art, comprising but not limited to, for example: phenolic antioxidants such as sodium salicylate, 2,4-dihydroxybenzophenone, 2,6-di-t- butyl-p-cresol, butylated hydroxyanisole (BHA), 2,6-di-t-butyl-4-methylphenol (BHT), 2,6-di-t-butyl-4-ethylphenol, stearyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, propyl 3,4,5-trihydroxybenzoate, hydroquinone, and catechol; bisphenolic antioxidants such as 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'- methylenebis(4-ethyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 4,4'-
  • the fragrance compositions of the present invention may contain the usual amounts of fixatives known to those of skill in the art.
  • Preferred fixative for the use in the fragrance compositions of the present invention include but are not limited to sandalwood, ambra products, polycyclic, macrocyclic and alicyclic substances like Am- brox® (Firmenich SA), Galaxolide® (Int. Flavors & Fragrances Inc.), Tonalide, Exalto- lide® (Firmenich SA), Habanolide® (Firmenich SA) und Helvetolide® (Firmenich SA).
  • the fragrance compositions of the present invention can also comprise encapsulating substances like cyclodextrines; chelating and complexing agents like EDTA or citric acid.
  • the fragrance compositions of the present invention may advantageously used for em- parting and/or enhancing an odor or flavor of a product or article of all kind with a lily of the valley- or muguet-type note or with a syringa-type note, a magnolia-type note, a cyclamen-type note or a hyacinth-type note, preferably with a lily of the valley- or muguet-type note.
  • a further embodiment of the present invention therefore relates to a method for emparting and/or enhancing an odor or flavor of a product or article with a lily of the valley- or muguet-type note or with a syringa-type note, a magnolia-type note, a cyclamen-type note, a hyacinth-type note or a lilac-type note, preferably with a lily of the valley- or muguet-type note, comprising bringing into contact or mixing with or add- ing to said product or article an organoleptically active quantity of a fragrance composition according to the present invention whereas the term "organoleptically active quantity" has the meaning as defined above.
  • the fragrance compositions of the present invention may be used or applied in every suited form e.g. in pure form or in form of dilutions or mixtures as well as in microencapsulated form.
  • a further embodiment of the present invention relates to a method for producing a perfumed product or article comprising bringing into contact or mixing with or adding to said product or article an organoleptically active quantity of the fragrance composition according to the present invention.
  • the present invention relates to a perfumed or aromatized product or article comprising an organoleptically active quantity of the fragrance composition according to the present invention as hereinbefore described.
  • the perfumed or aromatized articles or products accessible by the present invention may be a perfumed or aromatized article of manufacture of all kind.
  • Preferred aromatized or perfumed articles or products comprise, but are not limited to, e.g. perfumes, detergents and washing soaps, both liquid and solid and toilet articles of all kinds.
  • Preferred perfumed or aromatized articles according to the present invention are selected from the group consisting of extracts, eaux de perfume, eaux de toilette, after-shave lotions, eaux de Co- logne, pre-shave products, splash colognes, perfumed refreshing tissues, acidic, alkaline and neutral cleaning products, textile fresheners, ironing aids, liquid detergents, powder detergents, fabric preconditioners, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air purifiers, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depila- tory creams and lotions, after-shave creams and lotions, tanning creams and lotions, treatment cosmetic products, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and propellants.
  • Fragrance composition 1 has an intense and harmonious lily of the valley note with slightly less power than fragrance characteristics of pure 2-methyl-3-(4-tert.- butylphenyl) propanal (Lysmeral®, BASF SE).
  • Fragrance composition 2 has an intense and harmonious lily of the valley note indistinguishable from the fragrance characteristics of pure 2-methyl-3-(4-tert.-butylphenyl) propanal (Lysmeral®, BASF SE).
  • Example 3 Fragrance Composition 3:
  • Fragrance composition 3 has an intense and harmonious lily of the valley note indistin- guishable from the fragrance characteristics of pure 2-methyl-3-(4-tert.-butylphenyl) propanal (Lysmeral®, BASF SE).
  • Fragrance composition 4 has an intense and harmonious lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Total 100 Fragrance composition 5 has an intense and harmonious lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 6 has an intense and harmonious lily of the valley note very similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 7 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Example 8 Fragrance Composition 8:
  • Fragrance composition 8 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 9 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Example 10 Fragrance Composition 10:
  • Fragrance composition 10 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Fragrance composition 1 1 has an intense and harmonious lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 12 has an intense and harmonious lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 13 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Example 14 Fragrance Composition 14:
  • Fragrance composition 14 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 15 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 16 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with stronger impact.
  • Fragrance composition 17 has an intense and powerful lily of the valley note very similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE)
  • Total 100 Fragrance composition 18 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Fragrance composition 19 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Fragrance composition 20 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Example 21 Fragrance Composition 21 :
  • Fragrance composition 21 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Fragrance composition 22 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Total 100 Fragrance composition 23 has an intense and powerful lily of the valley note similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE) with slightly stronger impact.
  • Fragrance composition 24 has an intense and powerful lily of the valley note very simi- lar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE)
  • Fragrance composition 25 has an intense and powerful lily of the valley note very similar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE)
  • Example 26 Fragrance Composition 26:
  • Fragrance composition 26 has an intense and powerful lily of the valley note very simi- lar to that of pure 2-methyl-3-(4-tert.-butylphenyl)propanal (Lysmeral®, BASF SE)

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Abstract

La présente invention concerne des compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal et du 2-isobutyl-4-méthyl-tétrahydro-2H-pyran-4-ol. La présente invention concerne, en outre, un procédé de production d'un produit ou d'un article parfumé, ainsi que des articles parfumés ou aromatisés comprenant les compositions de parfum de la présente invention.
PCT/EP2010/062662 2009-09-09 2010-08-31 Compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal WO2011029743A1 (fr)

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EP09169877 2009-09-09
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EP09179384.4 2009-12-16

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CN103030538A (zh) * 2011-10-07 2013-04-10 西姆莱斯有限公司 具有铃兰香调的香料
US20130230476A1 (en) * 2010-11-10 2013-09-05 Basf Se Fragrance Compositions Comprising Special Mixtures of Diastereomers of 2-Isobutyl-4-Methyl-Tetrahydro-2H-Pyran-4-OL
JP2016518460A (ja) * 2012-10-15 2016-06-23 ジボダン エス エー 有機化合物
WO2019122236A1 (fr) 2017-12-21 2019-06-27 Firmenich Sa Procédé d'identification de modulateurs allostériques positifs pour des récepteurs odorants
CN110809622A (zh) * 2017-06-19 2020-02-18 西姆莱斯有限公司 新型的龙涎香类和/或吲哚类的芳香剂组合物
WO2020127325A2 (fr) 2018-12-19 2020-06-25 Firmenich Sa Utilisation de composés volatils pour moduler la perception du muguet floral
WO2021069331A1 (fr) * 2019-10-10 2021-04-15 Firmenich Sa Substance odorante au parfum de muguet

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130230476A1 (en) * 2010-11-10 2013-09-05 Basf Se Fragrance Compositions Comprising Special Mixtures of Diastereomers of 2-Isobutyl-4-Methyl-Tetrahydro-2H-Pyran-4-OL
CN103030538A (zh) * 2011-10-07 2013-04-10 西姆莱斯有限公司 具有铃兰香调的香料
US20130090390A1 (en) * 2011-10-07 2013-04-11 Symrise Ag Fragrances with note of lily of the valley
JP2016518460A (ja) * 2012-10-15 2016-06-23 ジボダン エス エー 有機化合物
CN110809622A (zh) * 2017-06-19 2020-02-18 西姆莱斯有限公司 新型的龙涎香类和/或吲哚类的芳香剂组合物
CN110809622B (zh) * 2017-06-19 2024-05-24 西姆莱斯有限公司 新型的龙涎香类和/或吲哚类的芳香剂组合物
WO2019122236A1 (fr) 2017-12-21 2019-06-27 Firmenich Sa Procédé d'identification de modulateurs allostériques positifs pour des récepteurs odorants
WO2020127325A2 (fr) 2018-12-19 2020-06-25 Firmenich Sa Utilisation de composés volatils pour moduler la perception du muguet floral
WO2021069331A1 (fr) * 2019-10-10 2021-04-15 Firmenich Sa Substance odorante au parfum de muguet

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