Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2003-02-14
2004-05-11
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S008000, C512S009000, C512S011000, C512S013000, C512S025000, C426S650000
Reexamination Certificate
active
06734158
ABSTRACT:
BACKGROUND ART
The present invention relates to the perfume and flavor industry. It concerns more particularly the use as perfuming or flavoring ingredient of 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane
The 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane has been cited twice in the prior art (T. Shibamoto et al. in
J. Agric. Food. Chem
., 1995, 43, 2664 or in
J. Agric. Food. Chem
., 1998, 46, 2212)
In its first paper, the author discloses only that 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane is one of the many volatile products present in a mixture obtained by the Maillard reaction between pure D-glucose and pure L-cysteine.
In the second reference, the author reports a synthesis and the mass spectras of a series of thiazolidine derivatives, including 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, with the aim of building a mass spectra library of said compounds.
However in said documents there is no mention or suggestion of any organoleptic properties of the specific compounds of formula (I), or of any potential use of said compounds as perfuming or flavoring ingredients. Perfuming compositions containing said products are not disclosed either.
SUMMARY OF THE INVENTION
The present invention is directed towards a method to confer, enhance, improve or modify the odor or flavor properties of a perfuming or flavoring composition or of a perfumed or flavored article, which method comprises adding to the composition or article an effective amount of 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane.
Another aspect of the invention provides perfumed or flavored consumer product or perfuming or flavoring compositions comprising as active ingredient 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
Surprisingly, we have now established that 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, of formula
possesses surprising organoleptic properties which have been found to be particularly useful and appreciated for the preparation of perfumes, perfuming compositions and perfumed consumer product, as well as for the preparation of flavors, flavoring compositions and flavored consumer product.
The 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane is much appreciated by perfumers for its odor which is cereal-like and remarkably natural, having cracker and pop-corn notes, together with an excellent roasted coffee character and basmati rice type bottom note. Said odor, which is quite unusual for a perfumery ingredient, brings an interesting and original cereal-like connotation to the modern perfumery.
Furthermore, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and its isomers have also the advantage to be surprisingly stable in all the types of perfumery media.
As anticipated above, the compounds of formula (I) are also useful as flavoring ingredients, i.e. to impart taste to flavoring compositions and foods or beverages. For instance 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane is able to impart nutty, praline and hazelnut flavor notes.
The invention concerns the use of 6-methyl-7-oxa-1-thia-4azaspiro[4.4]nonane as perfuming or flavoring ingredients, in other words it concerns a method to confer, enhance, improve or modify the odor or flavor properties of a perfuming or flavoring composition or of a perfumed or flavored consumer article, which method comprises adding to said composition or article an effective amount of 6-methyl-7-oxa-1-thia-4-azaspiro [4.4]nonane. By “use of 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane” it has to be understood here the use of the compound in any of its forms which can be advantageously employed in perfumery or in flavors. Such forms include the compound itself or a composition of matter consisting of a compound of formula (I) and a solvent commonly used in perfumery or in flavors. As examples of said solvents used in perfumery, one can cite compounds such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used. As examples of solvents commonly used in flavors, one can cite compounds such as propylene glycol, triacetine, triethyl citrate, benzylic alcohol, benzyl benzoate, ethanol, vegetal oils or terpenes.
Additionally, the present invention concerns a perfuming composition comprising the compound of formula (I). Generally speaking, by “perfuming composition” we mean here a mixture or composition comprising at least two perfuming ingredients, in any of their forms, and possibly one or more solvents commonly used in perfuming compositions. Therefore, a perfuming composition according to the invention is a composition comprising an olfactive effective amount of the invention's compound, together with one or more perfuming co-ingredients and possibly one or more solvents commonly used in perfumery.
The nature and type of these perfuming co-ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to the nature of the product to be perfumed and the desired olfactory effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils of natural or synthetic origin. Many of these ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., U.S.A., or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.
Similarly, a detailed description of the nature and type of solvents commonly used in perfuming compositions cannot be exhaustive. A skilled person in the art is able to select them on the basis of the nature of the product to be perfumed. However, as non-limiting examples of such solvents, one can cite, in addition to the solvents mentioned above, also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark ISOPAR® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark DOWANOL® (origin: Dow Chemical Company).
It is also understood that any composition resulting from a chemical synthesis in which the compound of the invention is involved as a starting intermediate or as an end-product is not a perfuming composition according to the invention.
The perfuming compositions according to the invention may be in the form of a simple mixture of the various co-ingredients and solvents, or also in the form of a bi-phasic system such as an emulsion or microemulsion. Such systems are well known to a person skilled in the art.
As previously mentioned, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, in any of its forms, or a perfuming composition comprising said compound, is a useful perfuming ingredient which can be advantageously used in all the fields of modern perfumery such as fine perfumery or functional perfumery to obtain perfumed consumer products. Such perfumed consumer products, which include a consumer article comprising an olfactive effective amount of the invention's compound, in any of its forms, are also an object of the present invention.
Suitable consumer articles comprise solid or liquid detergents and fabric softeners as well as all the other articles common in perfumery, namely perfumes, colognes or after-shave lotions, perfumed soaps, shower or bath salts, mousses, oils or gels, hygiene products or hair care products such as shampoos, body-care products, deodorants or antiperspirants, air fresheners and also cosmetic preparations. As detergents are intended applications such as detergent compositions or cleaning products for washing up or for cleaning various surfaces, e.g. intended for textile, dish or har
Firmenich SA
Winston & Strawn LLP
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