Use of tertiary alcohols or esters as perfuming ingredients

Details Use of tertiary alcohols or esters as perfuming ingredients Use of tertiary alcohols or esters as perfuming ingredients

2002-08-19

2004-04-13

Hardee, John (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

With oxygen, halogen, sulfur, or nitrogen containing or...

C568S838000, C568S579000, C568S667000

Reexamination Certificate

active

06720295

ABSTRACT:

TECHNICAL FIELD
The present invention relates to certain alcohol and ester compounds that are useful in perfumery as perfuming ingredients, in perfumed articles or in perfuming compositions. Specifically, the invention relates to uses of compounds of formula (I)
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH
2
group. The perfuming compositions, perfuming compositions and perfumed products contain one of the compounds of formula (I) as an active ingredient, usually together with perfume co-ingredients, solvents or adjuvants of current use in perfumery.
BACKGROUND OF THE INVENTION
Among the compounds encompassed by formula (I), only 4-cyclopentyl-2-methyl-2-butanol possesses a previously known structure. That compound has been described by Okazawa et al. in Can. J. Chem., (1982), 60, 2180. However, this prior art document mentions only the synthesis of 4-cyclopentyl-2-methyl-2-butanol and does not report or suggest any utility or use of the compound in the field of perfumery.
The odor properties of the compounds of formula (I) appear as totally unexpected also in view of the fact that compounds having an unsubstituted cyclopentyl or cyclopentenyl moiety and which are useful for perfumery are rare.
SUMMARY OF THE INVENTION
The invention relates to a perfuming composition or a perfumed product comprising as active ingredient a compound of formula (I)
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH
2
group, together with at least one perfuming co-ingredient, solvent or adjuvant of current use in perfumery.
Preferably, the perfuming ingredient is a compound of formula (II)
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group and R′ represents a hydrogen atom or an acetyl group. More preferred compounds include 4-cyclopentyl-2-methyl-2-butanol, 3-cyclopentyl-1,1-dimethylpropyl acetate or 5-cyclopentyl-3-ethyl-3-pentanol.
The perfuming composition or a perfumed product is generally in the form of a perfume or a cologne, a perfumed soap, a shower or bath gel, a shampoo, a body deodorant or antiperspirant, an ambient air deodorant, a liquid or solid detergent for textile treatment, a detergent composition or a cleaning product for dishes or various surfaces, a fabric softener or a cosmetic preparation.
The invention also relates to a method to impart, enhance, improve or modify the odor properties of a perfuming composition or a perfumed product which method comprises adding to said composition or product as a perfuming ingredient a compound of formula (I)
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH
2
group, in an amount sufficient to impart, enhance, improve or modify the odor thereof with floral notes.
The invention also discloses new compounds, such as those of formula (I)
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH
2
group, provided that 4-cyclopentyl-2-methyl-2-butanol is excluded. The most preferred of these are include 4-cyclopentyl-2-methyl-2-butanol, 3-cyclopentyl-1,1-dimethylpropyl acetate or 5-cyclopentyl-3-ethyl-3-pentanol.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Surprisingly, we have now established that the compounds of formula
wherein the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group, R′ represents a hydrogen atom or an acetyl group, G represents a cyclopentyl or a cyclopentenyl radical, and X represents a oxygen atom or a CH
2
group; possess very useful and appreciated odorant properties, of the floral type, which render them very convenient for the preparation of perfumes, perfuming compositions and perfumed articles.
As examples of preferred compounds of formula (I) one can cite 4-(2-cyclopenten-1-yl)-2-methyl-2-butanol and 1-(cyclopentyloxy)-2-methyl-2-propanol. Although the typical floral note of the invention compounds characterizes both compounds, each of them has additional and specific odor notes. For instance, 4-(2-cyclopenten-1-yl)-2-methyl-2-butanol also possesses fruity and vegetable, tomato leaves type notes which render its scent fruitier and stronger than the odor of 4-cyclopentyl-2-methyl-2-butanol described below, while 1-(cyclopentyloxy)-2-methyl-2-propanol scent also possesses a woody-terpineol note.
The most preferred compounds of formula (I) are those of formula
in which the R groups represent, simultaneously or independently, a hydrogen atom or a methyl group and R′ represent a hydrogen atom or an acetyl group. Most preferably, the R groups represent a hydrogen atom.
Amongst the compounds of formula (II), 4-cyclopentyl-2-methyl-2-butanol, 3-cyclopentyl-1,1-dimethylpropyl acetate and 5-cyclopentyl-3-ethyl-3-pentanol are very much appreciated for the their excellent floral note.
4-Cyclopentyl-2-methyl-2-butanol, which is a preferred compound between those of formula (II), is highly appreciated for its ethereal, floral notes and more specifically for its powerful and fusing white flower, i.e. lily of the valley, note. When the odor of 4-cyclopentyl-2-methyl-2-butanol is compared with the one of 4-cyclohexyl-2-methyl-2-butanol (Firmenich SA ; U.S. Pat. No. 4,701,278) it appears that the former possesses a stronger top-note and impact and is closest to the odor of the lily of the valley flowers than the latter. Moreover, the 4-cyclopentyl-2-methyl-2-butanol odor is devoid of the coriander note present in the 4-cyclohexyl-2-methyl-2-butanol scent.
On the whole, the 4-cyclopentyl-2-methyl-2-butanol fragrance is similar to that of linalool but with a fresher and more pronounced lily of the valley connotation. Furthermore, the odor of 4-cyclopentyl-2-methyl-2-butanol has also a persistence in compositions, or on skin or hair, which is far superior to that of linalool.
A second preferred compounds of formula (II) is 3-cyclopentyl-1,1-dimethylpropyl acetate which possesses a lily of the valley, linalool-like fragrance with a character in between that of dihydroterpinyl acetate (origin: IFF, USA) and linalyl acetate, i.e. a floral-linalool scent with a nice fruity and citrus character.
Another compounds of formula (II) is 5-cyclopentyl-3-ethyl-3-pentanol which in addition to the floral, linalool-like notes, develops a fragrance with tea, and fruity-type notes, in particular grapefruit and strawberry-type bottom note, as well as basilic and parsley notes.
The compounds of the invention are suitable for use in fine perfumery, in perfumes, colognes or after-shave lotions, as well as in other current uses in perfumery such as to perfume soaps, preparations for the shower or the bath, such as bath salts, mousses, oils, gels or other preparations, products such as body oils, body-care products, body deodorants and antiperspirants, hair care products such as shampoos, ambient air deodorants, or cosmetic preparations.
The compounds of formula (I) can also be used in applications such as liquid or solid detergents for textile treatment, fabric softeners, or also in detergent compositions or cleaning products for cleaning dishes or varied surfaces, for industrial or household use.
In these applications, which are also an object of the invention, the compounds of formula (I) can be used alone, as well as mixed with other perfuming ingredients, solvents or additives commonly used in perfumery. The nature and variety of these co-ingredients do not

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