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WO1999021813A1 - Novel fragrance compound - Google Patents

Novel fragrance compound Download PDF

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Publication number
WO1999021813A1
WO1999021813A1 PCT/GB1998/003128 GB9803128W WO9921813A1 WO 1999021813 A1 WO1999021813 A1 WO 1999021813A1 GB 9803128 W GB9803128 W GB 9803128W WO 9921813 A1 WO9921813 A1 WO 9921813A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
propan
cyclododecadienyl
perfume
acetate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB1998/003128
Other languages
French (fr)
Inventor
David Munro
Charles Stanley Sell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan Nederland Services BV
Original Assignee
Quest International BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Quest International BV filed Critical Quest International BV
Priority to AU95482/98A priority Critical patent/AU9548298A/en
Publication of WO1999021813A1 publication Critical patent/WO1999021813A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/16—Alcohols containing rings other than six-membered aromatic rings containing rings with more than six ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Definitions

  • This invention concerns a novel fragrance compound, its method of production and its use in perfumes and perfumed products.
  • the invention provides 2-(cyclododecadienyl)-1-propan-1-ol.
  • the novel compound has the structure shown in Figure 1 , in which one double bond may have E- or Z-geometry, the remaining double bond being E-.
  • the compound can be produced by reaction of 2-(cyclododecadienyl)propan-1-al, which is one of the products of Lewis acid-catalysed reaction of 1 ,5,9-cyclododecatriene with propylene oxide, e.g. using AICI 3 as catalyst.
  • the principal product of this reaction is 2-(4,8-cyclododecadienyl)propan-1-al.
  • Reduction is conveniently effected using sodium borohydride, with the principal product being 2-(4,8-cyclododecadienyl)-1-propan-1-ol.
  • the Meerwein-Ponndorf reaction may alternatively be used.
  • the invention provides a method of making the compound of the invention, comprising reducing 2-(cyclododecadienyl) propan-1-al.
  • the compound of the invention exhibits an odour of amber, and so may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume.
  • a per ume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensable or desirable.
  • Such products are: fabric washing powders, washing liquids, fabric softeners and other fabric care products, detergents and household cleaning, scouring and disinfection products; air fresheners, room sprays and pomanders, soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products, cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc
  • fragrance materials which can be advantageously combined with the compound according to the invention in a perfume are, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc , but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nit ⁇ les, etc , including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds
  • fragrance materials are mentioned, for example, in S Arctander, “Perfume and Flavor Chemicals” (Montclair, N J , 1969), in S Arctander, “Perfume and Flavor Materials of Natural Origin” (Elizabeth, N J , 1960) and in “Flavor and Fragrance Materials - 1991", Allured Publishing Co Wheaton, III USA
  • fragrance materials which can be used in combination with the compound according to the invention are geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpmeol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, t ⁇ chloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate
  • Solvents which can be used for perfumes which contain the compound according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • the quantities in which the compound according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the compound is used and on the olfactive effect desired. It is therefore only possible to specify wide limits, which, however, provide sufficient information for the specialist in the art to be able to use the compound according to the invention for his specific purpose.
  • an amount of 0.01% by weight or more of the compound according to the invention will generally have a clearly perceptible olfactive effect.
  • the amount is 0.1 to 80% by weight, more preferably at least 1 %.
  • the amount of the compound according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm. However, levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed.
  • the invention thus provides a perfume comprising the compound of the invention in an olfactively effective amount.
  • the invention also covers a perfumed product comprising the compound of the invention.
  • Figure 1 shows the structure of 2-(cyclododecadienyl)propan-1-ol
  • Figure 2 shows the major products of Lewis acid-catalysed reaction of

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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

The novel compound 2-(cyclododecadienyl)propan-1-ol exhibits an odor of amber and so finds use in perfumes and in perfumed products.

Description

Novel Fragrance Compound
Field of the invention
This invention concerns a novel fragrance compound, its method of production and its use in perfumes and perfumed products.
Summary of the Invention
In one aspect the invention provides 2-(cyclododecadienyl)-1-propan-1-ol.
For brevity and simplicity, this material will be referred to herein as "the compound", "the novel compound" or "the compound of the invention".
The novel compound has the structure shown in Figure 1 , in which one double bond may have E- or Z-geometry, the remaining double bond being E-.
The compound can be produced by reaction of 2-(cyclododecadienyl)propan-1-al, which is one of the products of Lewis acid-catalysed reaction of 1 ,5,9-cyclododecatriene with propylene oxide, e.g. using AICI3 as catalyst. The principal product of this reaction is 2-(4,8-cyclododecadienyl)propan-1-al. Reduction is conveniently effected using sodium borohydride, with the principal product being 2-(4,8-cyclododecadienyl)-1-propan-1-ol. The Meerwein-Ponndorf reaction may alternatively be used.
In a further aspect the invention provides a method of making the compound of the invention, comprising reducing 2-(cyclododecadienyl) propan-1-al.
The compound of the invention exhibits an odour of amber, and so may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume. For the purposes of this invention a per ume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensable or desirable. Examples of such products are: fabric washing powders, washing liquids, fabric softeners and other fabric care products, detergents and household cleaning, scouring and disinfection products; air fresheners, room sprays and pomanders, soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products, cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc
Other fragrance materials which can be advantageously combined with the compound according to the invention in a perfume are, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc , but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitπles, etc , including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds
Such fragrance materials are mentioned, for example, in S Arctander, "Perfume and Flavor Chemicals" (Montclair, N J , 1969), in S Arctander, "Perfume and Flavor Materials of Natural Origin" (Elizabeth, N J , 1960) and in "Flavor and Fragrance Materials - 1991", Allured Publishing Co Wheaton, III USA
Examples of fragrance materials which can be used in combination with the compound according to the invention are geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpmeol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, tπchloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, α-hexylcinnamaldehyde, 2-methyl-3-(p-tert-butylphenyl)propanal, 2-methyl-3- (p-ιsopropylphenyl)propanal, 3-(p-tert-butylphenyl)-propanal, 2,4-dιmethylcyclohex-3-enyl- carboxaldehyde, tπcyclodecenyl acetate, tπcyclodecenyl propionate,
4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaidehyde, 4-(4-methyl-3-pentenyl)-3- cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran , 3-carboxymethyl-2-pentylcyclopentane , 2-n-heptyicyclopentanone, 3-methyl-2-pentyl-2- cyclopentenone, n-decanal, n-dodecanal, 9-decenol-1 , phenoxyethyl isobutyrate, phenylacetaldehyde dimethylacetal, phenylacetaldehyde diethylacetal, geranyl nitπle, citronellyl nitπle, cedryl acetate, 3-ιsocamphylcyclohexanol, cedryl methyl ether, isolongifoianone, aubepine nitπle, aubepine, heliotropin, coumaπn, eugenol, vanillin, diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylionones, irones, cis-3-hexenol and esters thereof, indan musks, tetralin musks, isochroman musks, macrocyclic ketones, macrolactone musks, ethylene brassylate.
Solvents which can be used for perfumes which contain the compound according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
The quantities in which the compound according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the compound is used and on the olfactive effect desired. It is therefore only possible to specify wide limits, which, however, provide sufficient information for the specialist in the art to be able to use the compound according to the invention for his specific purpose. In perfumes an amount of 0.01% by weight or more of the compound according to the invention will generally have a clearly perceptible olfactive effect. Preferably the amount is 0.1 to 80% by weight, more preferably at least 1 %. The amount of the compound according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm. However, levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed.
In a further aspect the invention thus provides a perfume comprising the compound of the invention in an olfactively effective amount.
The invention also covers a perfumed product comprising the compound of the invention.
The invention will be further described, by way of illustration, in the following Example and with reference to the accompanying figures, in which:
Figure 1 shows the structure of 2-(cyclododecadienyl)propan-1-ol; and
Figure 2 shows the major products of Lewis acid-catalysed reaction of
1 ,5,9-cyclododecatriene with propylene oxide, and subsequent conversion of
2-(cyclododecadienyl)propan-1-al to the compound of the invention. Example
(a) Lewis Acid-Catalysed Reaction of 1 ,5,9-Cyclododecatriene with Propylene Oxide
1 ,5,9-cyclododecatriene (150 g; 0.924 mol) and propylene oxide (69 g; 1.2 mol) were mixed together, and added, with stirring, to a suspension of AICI3 (129 g; 0.96 mol) in CH2CI2 (750 ml) at -50° C. The reaction mixture was allowed to reach ambient temperature, then was added to a mixture of ice (4000 ml) and diethyl ether (2000 ml). The ether layer was separated and dried over MgS04. Chromatography (silica; hexane) gave recovered 1 ,5,9-cyclododecatriene (51.2 g). Further elution, using a mixture of hexane (90%) and diethyl ether (10%) as eluent gave a pale yellow oil (27.2 g), which was identified as 2-(cyclododecadienyl)propan-1-al. M+220. Kovats 1755, 1773, 1775, 1781.
H NMR (CDCI3) Signal Multiplicity Area Assignment
9.78 d 1 CHO
9.71 d
5.60 - 5.12 m 4 CH=CH
2.53 - 1.12 m 16 CH2 and CH
1.10 d 3 CH3
0.94 d
The main products of the reaction of 1 ,5,9-cyclododecatriene (1) are shown in Figure 2. These are 2-(cyclododecadienyl)propan-1-al (2) (15 - 22% conversion, based on recovered cyclododecatriene), 2-methyl-2,3,3a,4,5,8,9, 12,13,13a-decahydrocyclododeca[b]furan (3) (5% conversion), and a complex mixture of isomeric (M+220) and higher molecular weight alcohols (40 - 55% conversion), from which the tricyclic propan-2-ol (4) was isolated.
(b) Reduction of 2-(Cyclododecadienyl)propan-1-al to 2-(Cyclododecadienyl)propan-1-ol
2-(Cyclododecadienyl)propan-1-al (4 g; 0.018 mol), obtained as above, dissolved in ethanol (10 ml), was added dropwise to a suspension of NaBH4 (1.0 g; 0.026 mol) in ethanol (80 ml). After complete addition, the reaction mixture was allowed to stir for 1 hour, then most ethanol was removed in vacuo. CH2CI2 (150 ml) was then added, and the reaction mixture stirred while adding 2N HCI (aq) dropwise, until effervescence ceased. The organic layer was separated, washed, and dried over MgSO„. Chromatography (silica; hexane 50%, diethyl ether 50%) gave a colourless oil (3.3 g, 81%), identified as
2-(cyclododecadienyl)propan-1-ol ((5) in Figure 2). A sample (2 g) was short-path distilled, b.p. 115° C at 1 mbar. M+222. The material consists of five isomers.
Kovats Area
1822 21.2%
1836 14.0%
1839 9.4%
1845 22.5%
1854 29.1% Total: 96.2%
H NMR (CDCI3) Signal Multiplicity Area Assignment
5.50 - 5.08 m 4 CH=CH
3.71 - 3.29 AB complex 2 CH2OH
2.20 s 1 OH
2.38 - 1.02 m 16 ring CH2 + CHCH(CH3)OH
1.00 - 0.79 t overlapping 3 CH3
3C NMR (CDCI3) 132.603, 132.567, 132.384, 132.311 , 132.238, 132.064, 131.972, 131.680, 131.657, 131.570, 131.524, 131.360, 131.214, 129.650,
129.558, 129.357, 129.101 , 128.955, 128.726, 128.397 (all
CH=CH)
67.407, 65.803, 65.201 , 64.003, 63.900 (all CH2OH)
37.268, 36.317, 36.107, 35.220, 34.781 (all CH) 32.504, 31.608, 31.297, 30.858, 30.739, 29.313, 28.581 , 27.914, 27.146,
26.213, 25.317, 24.594, 23.781 , 22.638 (all CH2)
15.990, 15.505, 14.966 (CH)
10.952, 10.549 (CH3) Catalytic hydrogenation of the compound of the invention produces 2-cyclododecylpropan-1-ol, which is a known substance exhibiting an intense and tenacious amber character.

Claims

1. The compound 2-(cyclododecadienyl)propan-1 -ol.
2. The compound 2-(4,8-cyclododecadienyl)propan-1-ol.
3. The compound of claim 1 or 2, prepared by reduction of 2-(cyclododecadienyl)- propan-1-al.
4. The compound of claim 3, wherein the 2-(cyclododecadienyl)propan-1-al is made by Lewis acid-catalysed reaction of 1 ,5,9-cyclododecatriene with propylene oxide.
5. A method of making the compound of claim 1 , comprising reducing 2-(cyclododecadienyl)propan-1-al.
6. A method according to claim 5, wherein the 2-(cyclododecadienyl)propan-1-al is made by Lewis acid-catalysed reaction of 1 ,5,9-cyclododecatriene with propylene oxide.
7. A method according to claim 6, wherein the Lewis acid is AICI3.
8. A perfume comprising the compound of claim 1 , 2, 3 or 4 in an olfactively effective amount.
9. A perfume according to claim 8, wherein the compound is present in an amount of at least 0.01% by weight.
10. A perfume according to claim 9, wherein the compound is present in an amount in the range 0.1 to 80% by weight.
11. A perfumed product comprising a compound according to claim 1 , 2, 3 or 4 or a perfume according to claim 8, or 10.
PCT/GB1998/003128 1997-10-28 1998-10-21 Novel fragrance compound Ceased WO1999021813A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU95482/98A AU9548298A (en) 1997-10-28 1998-10-21 Novel fragrance compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97308580.6 1997-10-28
EP97308580 1997-10-28

Publications (1)

Publication Number Publication Date
WO1999021813A1 true WO1999021813A1 (en) 1999-05-06

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Application Number Title Priority Date Filing Date
PCT/GB1998/003128 Ceased WO1999021813A1 (en) 1997-10-28 1998-10-21 Novel fragrance compound

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AU (1) AU9548298A (en)
WO (1) WO1999021813A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4948780A (en) * 1987-02-06 1990-08-14 Consortium Fur Elektrochemische Industrie Gmbh Alcohols and ethers having cyclododecyl and cyclododecenyl groups, process for their preparation and scents containing same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4948780A (en) * 1987-02-06 1990-08-14 Consortium Fur Elektrochemische Industrie Gmbh Alcohols and ethers having cyclododecyl and cyclododecenyl groups, process for their preparation and scents containing same

Also Published As

Publication number Publication date
AU9548298A (en) 1999-05-17

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