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WO2016037987A1 - Composés organiques ayant une odeur boisée-poivrée - Google Patents

Composés organiques ayant une odeur boisée-poivrée Download PDF

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Publication number
WO2016037987A1
WO2016037987A1 PCT/EP2015/070406 EP2015070406W WO2016037987A1 WO 2016037987 A1 WO2016037987 A1 WO 2016037987A1 EP 2015070406 W EP2015070406 W EP 2015070406W WO 2016037987 A1 WO2016037987 A1 WO 2016037987A1
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Prior art keywords
mmol
dien
formula
solution
dimethylhepta
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Ceased
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English (en)
Inventor
Philip Kraft
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Givaudan SA
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Givaudan SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/21—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • 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
    • 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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

  • the present invention relates to novel compounds possessing very characteristic dry woody-peppery odour notes of high intensity and originality.
  • the invention furthermore refers to a method for their production, and to flavour and fragrance compositions containing these.
  • Agarwood also known as oud, oodh, aloeswood, lignatoes, aioes or simply agar, is a dark resinous heartwood that forms when Aquilaria and Gyrinops trees, mainly Aquilaria agallochoa, Aquilaria malaccensis or Aquilaria sinensis, become infected with Ascomycota fungi such as Philalophora parasitica and related species. As an immune response to this attack, the trees produce a dark resin of typical dry woody-animalic, incense-like odour with a characteristic peppery spiciness and shades of amber as well as of musk.
  • Y is selected from phenyl, bicyclo[2.2.1]heptan-2-yl, and -CHR 1 R 2 , wherein R 1 and R 2 are independently selected from methyl and ethyl, or R 1 and R 2 form together with the carbon atom to which they are attached cyclo-C 5 -C 7 -alkyl (cylcopentyl, cyclohexyl, and cyctoheptyl).
  • the compounds of formula (I) possess at least one stereocenter at C-5 of the 5,6- dimethylhepta-3,6-dien-2-one skeleton, and optionally also further stereocenters in the substituent Y, and can be resolved into individual enantiomerically enriched or pure stereoisomers.
  • Resolving stereoisomers however adds to the complexity of manufacture and purification of these compounds, as does a stereoselective synthetic approach, and thus it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons.
  • this may be achieved according to methodology known in the art, e.g. by preparative HPLC and GC or by stereoselective synthesis.
  • the compounds of formula (I) may be used alone, as mixtures thereof, or in combination with a base material.
  • the 'base material' includes all known odorant molecules selected from the extensive range of natural products, and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odorants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
  • the compounds of formula (I) are unstable over prolonged time, which may result in the formation of undesired off-odours. Surprisingly, it was found that the formation of undesired off-odours can be reduced or completely eliminated by admixing the compounds of formula (I) with an essentially odourless base, such as triethanol amine (TEOA).
  • TEOA triethanol amine
  • the compounds of formula (I) may optionally be admixed with, for example, triethanol amime in a ratio of 15:1 to 3:1 (compound of formula (I) : TEOA).
  • 'fragrance composition means any composition comprising at least one compound of formula (I) and a base material, e.g. a diluent conventionally used in conjunction with odorants, such as dipropylene glycol (DPG), isopropyl myristate (IPM), triethyl citrate (TEC) and alcohol (e.g. ethanol).
  • the composition may comprise an anti-oxidant adjuvant.
  • Said anti-oxidant may be selected from Tinogard ® TT (BASF), Tinogard ® Q (BASF), Tocopherol (including its isomers, CAS 59- 02-9; 364-49-8; 18920-62-2; 121854-78-2). 2,6-bis(1 ,1-dimethylethyl)-4-methylphenol (BHT, CAS 128-37-0) and related phenols, such as hydroquinone (CAS 121-31-9).
  • BHT 2,6-bis(1 ,1-dimethylethyl)-4
  • - essential oils and extracts e.g. agarwood oil (white and/or authentic), castoreum, costus root oil, oak moss absolute, geranium oil, tree moss absolute, basil oil, fruit oils, such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;
  • alcohols e.g. cinnamic alcohol, cis-3-hexenol, citronelloi, EbanolTM, eugenol, farnesol, geraniol, Super MuguetTM, linalool, menthol, nerol, phenylethyl alcohol, rhodinol, SandaloreTM. terpineol or TimberolTM;
  • aldehydes and ketones e.g. Azurone ® [7-(3-methylbutyl)-1 ,5-benzodioxepin-3-one], anisaldehyde, a-amylcinnamaldehyde, Casbmeran ® , GeorgywoodTM, Hedione ® , hydroxycitronellal, Iso E Super ® , Isoraldeine ® KephalisTM, Lilial ® , maltol, methyl cedryl ketone, methylionone, verbenone, or vanillin;
  • Azurone ® [7-(3-methylbutyl)-1 ,5-benzodioxepin-3-one]
  • esters and lactones e.g. benzyl acetate, cedryl acetate, ⁇ -decalactone, Helvetolide ® , ⁇ -undecalactone or vetivenyl acetate;
  • heterocycles e.g. isobutylchinoline.
  • the compounds according to formula (I) may be used in a broad range of perfumed products, e.g. in any field of fine and functional perfumery, such as perfumes, air care products, household products, laundry products, body care products and cosmetics.
  • the compounds can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other odorant ingredients.
  • the proportion is typically from 0.1 to 10 weight percent of the application.
  • compounds of the present invention may be employed in a fabric softener in an amount of from 0.001 to 0.1 weight percent.
  • compounds of the present invention may be used in fine perfumery in amounts from 0.01 to 20 weight percent (e.g. up to about 10 weight percent), more preferably between 0.01 and 5 weight percent.
  • these values are given only by way of example, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.
  • the compounds as described hereinabove may be employed in a consumer product base simply by directly mixing at least one compound of formula (I), or a fragrance composition with the consumer product base, or they may. in an earlier step, be entrapped with an entrapment material, for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzyme, or the like, and then mixed with the consumer product base.
  • an entrapment material for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an
  • a method of manufacturing a perfumed product comprising the incorporation of a compound of formula ()), as a fragrance ingredient, either by directly admixing the compound to the consumer product base or by admixing a fragrance composition comprising a compound of formula (I), which may then be mixed with a consumer product base, using conventional techniques and methods.
  • the invention also provides a perfumed product comprising:
  • 'consumer product base' means a composition for use as a consumer product to fulfil specific actions, such as cleaning, softening, and caring or the like.
  • examples of such products include fine perfumery, e.g. perfume and eau de toilette; fabric care, household products and personal care products such as laundry care detergents, rinse conditioner, personal cleansing composition, detergent for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body- care products, e.g. shampoo, shower gei; air care products and cosmetics, e.g. deodorant, vanishing creme.
  • This list of products is given by way of illustration, and is not to be regarded as being in any way limiting.
  • the compounds of formula (I) may be prepared from the respective tert-butyl ketones such as 5-( tert-butyl)-6-ethyl-5-hydroxyoct-3-yn-2-one (C), which are accessible according to P. Kraft, J. S. E. Ahlin, M. Buchel, P. Sutter, Synthesis 2012, 2985-2988, for instance by by copper(l)-catalyzed Grignard reaction of the acid chlorides with tert- butyl magnesium chloride.
  • C tert-butyl ketones
  • reaction mixture was poured into ice/water (500 mL), acidified with 2 M aqueous hydrochloric acid (200 mL) to pH 1 , and extracted with ether (2 ⁇ 400 mL). The combined organic extracts were washed with water (1 x 400 mL) and brine (1 x 200 mL), dried (Na 2 SO Jardin), and concentrated under reduced pressure.
  • Odour description dark woody odour with spicy peppery facets, and aspects of Kephalis (A) and Cashmeran (B), as well as some fruity facets in the direction of apple.
  • Example 1 for the synthesis of 5-cyclopentyl-6,6-dimethylhept-3- yne-2,5-diol, from a solution of lanthanum(lll)chloride bis(lithiumchtoride) complex (49.5 mL, 29.7 mmol, 0.6 M in THF), a solution of the previously prepared 1-cyclohexyl-2,2- dimethylpropan-1-one (97%, 5.0 g, 29.7 mmol) in tetrahydrofuran (15 mL), a solution of but-3-yn-2-ol (2.35 g, 32.7 mmol) in tetrahydrofuran (50 mL), and an ethyl magnesium chloride solution in tetrahydrofuran (2 M, 35.7 mL, 71.3 mmol).
  • Odour description peppery, dark woody, pronounced of agarwood and Kephalis (A) with slightly green facets.
  • Example 1 for the synthesis of 5-cyclopentyl-6,6-dimethylhept-3- yne-2,5-diol from a solution of the lanthanum(lll)chloride bis(lithiumchloride) complex (200 mL, 120 mmol, 0.6 M in tetrahydrofuran), a solution of the previously prepared 2,2- dimethyl-1-phenylpropan-1-one (97%, 20.1 g, 120 mmol) in tetrahydrofuran (80 mL), a solution of but-3-yn-2-ol (10.4 g, 144 mmol) in tetrahydrofuran (220 mL), and an ethyl magnesium chloride solution in tetrahydrofuran (2 M, 144 mL, 288 mmol).
  • the lanthanum(lll)chloride bis(lithiumchloride) complex 200 mL, 120 mmol, 0.6 M in tetrahydrofuran
  • Example 1 for the synthesis of 5-cyclopentyl-5-hydroxy-6,6- dimethylhept-3-yn-2-one, from 6,6-dimethyl-5-phenylhept-3-yne-2,5-diol (24.3 g, 105 mmol) and a suspension of manganese dioxide (90%, 101 g, 1.05 mol) in dichloromethane (420 mL).
  • Example 1 for the synthesis of 5-cyclopentyl-6,6-dimethylhept-3- yne-2,5-diol, from a solution of the lanthanum(lll)chloride bis(lithiumchloride) complex (135 mL, 81 mmol, 0.6 M in tetrahydrofuran), a solution of the previously prepared 1- (bicyclo[2.2.1]heptan-2-yl)-2,2-dimethylpropan-1-one (96%, 15.2 g, 81 mmol) in tetrahydrofuran (65 mL), a solution of but-3-yn-2-ol (7.05 g, 98 mmol) in tetrahydrofuran (165 mL), and an ethyl magnesium chloride solution in tetrahydrofuran (2 M, 98 mL, 195 mmol).
  • Odour description dark woody, peppery, with metallic, fruity aspects.
  • Example 1 for the synthesis of 5-cyclopentyl-6,6-dimethylhept-3- yne-2,5-diol, from a solution of the lanthanum(lll)chloride bis(lithiumchtoride) complex (400 mL, 240 mmo), 0.6 M in tetrahydrofuran), a solution of the previously prepared 4- ethyl-2,2-dimethylhexan-3-one (97%, 37.5 g, 240 mmo! in tetrahydrofuran (100 mL), a solution of but-3-yn-2-ol (18.5 g, 264 mmol) in tetrahydrofuran (580 mL), and an ethyl magnesium chloride solution in tetrahydrofuran (2 M, 288 mL, 576 mmol).
  • Odour description dark woody, spicy, peppery, pronounced of Kephalis (A) and Cashmeran (B).
  • Odour description dark woody, spicy, peppery, pronounced of Kephalis (A) and Cashmeran (B).
  • (Z)-5-cyclopentyl-5,6-dimethylhepta-3,6-dien-2-one impart this modern musk cologne-type fragrance with a warm peppery signature, and a special dark woody-musky contrast recalling agarwood, albeit this is not the main character of the perfume.
  • (Z)-5-cyclopentyl-5,6-dimethylhepta-3,6-dien-2-one pushes the floral elements of the composition, wraps the hesperidic citrusy notes, and thereby provides more juiciness.
  • Example 8 Fruitv-F I oral-Wood v Floriental Feminine Fragrance
  • (Z)-5-cyclopentyl-5.6-dimethylhepta-3,6-dien-2-one provides this fruity- floral-woody floriental feminine fragrance with a strong woody-peppery signature, recalling agarwood facets.
  • (Z)-5-cyclopentyl-5,6-dimethylhepta-3,6- dien-2-one blends particularly well with vanillin, Florymoss and Evernyl, thereby much increasing the sensual part of the central base-note accord.
  • (Z)-5-Cyclopentyl-5,6- dimethylhepta-3,6-dien-2-one also actively contributes to the technical performance of the fragrance, especially its diffusion and trail (sillage).

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

Abstract

Cette invention concerne une 5,6-diméthylhepta-3,6-dién-2-one 5-substituée possédant une odeur boisée profonde très caractéristique avec une connotation poivrée épicée de type bois d'agar typique.
PCT/EP2015/070406 2014-09-08 2015-09-07 Composés organiques ayant une odeur boisée-poivrée Ceased WO2016037987A1 (fr)

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Application Number Priority Date Filing Date Title
GB1415845.5 2014-09-08
GBGB1415845.5A GB201415845D0 (en) 2014-09-08 2014-09-08 Organic compounds

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WO2016037987A1 true WO2016037987A1 (fr) 2016-03-17

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3942761A (en) * 1971-01-04 1976-03-09 Monsanto Company 4-(2'-Norbornyl)-2-butanones
EP0231896A1 (fr) * 1986-01-31 1987-08-12 Kuraray Co., Ltd. Cétones alpha- bêta non saturées et leur utilisation comme corps odorants

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3942761A (en) * 1971-01-04 1976-03-09 Monsanto Company 4-(2'-Norbornyl)-2-butanones
EP0231896A1 (fr) * 1986-01-31 1987-08-12 Kuraray Co., Ltd. Cétones alpha- bêta non saturées et leur utilisation comme corps odorants

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