Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
2001-12-07
2003-05-06
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S008000, C568S700000, C568S822000, C568S823000, C568S825000
Reexamination Certificate
active
06559118
ABSTRACT:
FIELD OF THE INVENTION
This invention concerns novel fragrance compounds, and perfumes and perfumed products comprising the novel compounds.
SUMMARY OF THE INVENTION
In one aspect, the present invention provides a compound having the structure
where R
1
is a lower alkyl group, R
2
, R
3
, R
4
and R
5
is each independently hydrogen or a lower alkyl group, R
6
is hydrogen, a lower alkyl group, an alkylidene group or a lower alkenyl group and R
7
is hydrogen or a lower alkyl group.
For brevity and simplicity, such materials will be referred to as “the compound”, “the novel compound” or “the compound of the invention”.
The compounds of the invention may exist in a number of isomeric forms, and the invention includes within its scope each individual isomer and also mixtures of isomers.
The term “lower alkyl” is used in this specification to mean an alkyl group having from 1 to 4 carbon atoms.
The term “lower alkenyl” is used in this specification to mean an alkenyl group having from 1 to 4 carbon atoms.
The compounds of the invention can possess fragrance or odour properties which are generally regarded as interesting, pleasant or attractive.
The currently preferred compound in accordance with the invention has R
1
, R
2
, R
5
, R
6
and R
7
=CH
3
; R
3
and R
4
=H, with a double bond in the ring at the 34 position. This compound thus has the structure
and is 2-methyl-1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-1-propanol. For brevity this compound is referred to herein as compound 1. Compound 1 has desirable odour properties, generally of a blackcurrant, green, buchu, cassis nature, and appears to have good substantivity. The compound also has good performance against kitchen malodour. Materials having cassis odour are of great interest to the fragrance industry, with such materials, eg Neocaspirene (described in U.S. Pat. No. 4537702), generally being of high value. Naturally occurring materials with cassis odour contain sulphur and the commonest synthetic materials with cassis odour contain sulphur or oximes. Compounds of the invention thus have the advantage of lacking sulphur or oximes. Compounds of the invention also constitute the first known alcohols having cassis odour.
Further compounds of the invention include the following:
Odour (Dry)
Odour (Fresh)
Strong Celery
Strong Earthy Medium Potato Medium Green
1-(1,2-dimethyl-3-cyclohexen-1-yl)-2-methyl-1-propanol
Medium Fruity Medium Floral Weak Earthy
Strong Metallic Medium Floral Medium Herbal
1-(1,3-dimethyl-3-cyclohexen-1-yl)-2-methyl-1-propanol
Medium Minty Medium Fruity Weak Floral
Medium Fruity Medium Fatty
2-methyl-1-(1,3,4-trimethyl-3-cyclohexen-1-yl)-1-propanol
Weak Woody Weak Patchouli Weak Grapefruit/ Rhubarb
Weak Earthy Weak Minty Weak Cam- phoraceous
2-methyl-1-(1,2,4-trimethylcyclohexyl)-1-propanol
Fruity Cassis
Fruity Cassis
2-methyl-1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-3-buten-1-ol
Fruity Green Cassis
Fruity Green Cassis
2-methyl-1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-1-butanol
Woody Patchouli
Earthy Woody Patchouli
2-methyl-1-(1,2,4,6-tetramethyl-3-cyctohexen-1-yl)-2-propen-1-ol
Woody Herbal Cassis
Woody Herbal Cassis
2-methyl-1-(1,2,4,6-tetramethyl-3-cyclohexen-1-yl)-1-propanol
Strong Herbal Strong Sweet Strong Minty Cassis
Strong Herbal Strong Earthy Strong Minty
2-methyl-1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-2-propen-1-ol
Medium Fruity Medium Buchu Medium Cassis
Medium Green Medium Herbal
2-methyl-1-(1,2,4,trimethyl-3-cyclohexen-1-yl)-2-buten-1-ol
Medium Fruity Medium Cassis
Medium Fruity Medium Minty
1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-3-penten-1-ol
Medium floral Medium Salicylate
Medium Fruity Medium Green Medium Floral
3-methyl-1-(1,2,4-trimethyl-3-cyclohexen-1-yl)-2-buten-1-ol
Fruity Green
Green Fruity
2-methyl-1-(1,3,4-trimethyl-3-cyclohexen-1-yl)-2-propen-1-ol
Aniseed Herbal Orris
Fruity Aniseed Orris
1-(1,3,4-trimethyl-3-cyclohexen-1-yl)-1-propanol
The odour properties of the compounds of the invention mean that a compound or mixture of compounds in accordance with the invention may be used as such to impart, strengthen or improve the odour of a wide variety of products, or may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume. The compounds are stable and substantive. For the purposes of this invention a perfume 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, hair and/or product for which an agreeable odour is indispensable or desirable. Example 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, body, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc.
Other fragrance materials which can be advantageously combined with one or more compounds 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, nitrites, 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, NJ., 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, Ill. USA.
Examples of fragrance materials which can be used in combination with one or more compounds according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenyl-ethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzylcarbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, &agr;-hexylcinnamaldehyde, 2-methyl-3p-tert-butylphenyl)propanal, 2-methyl-3-(p-isopropylphenyl)propanal, 2-(p-tert-butylphenyl)-propanal, 2,4-dimethyl-cyclohex-3-enyl-carboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxyaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, n-decanal, n-dodecanal, 9decen-1-ol, phenoxyethyl isobutyrate, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, geranyl nitrile, citronellyl nitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropin, coumarin, 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 a 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 one or more compounds 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
Cole Monique T.
Morgan & Lewis & Bockius, LLP
Quest International B.V.
Warden Jill
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