PERFUME COMPOSITIONS AND PERFUMED PRODUCTS WHICH CONTAIN AN ALKYL 2-MERCAPTOBENZOATE AS BASIC COMPONENT

Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances having a long-lasting flowery and somewhat spicy odour with a not very pronounced sulphurous note and corresponding to the formula wherein R represents a methyl or ethyl group.

Description: The invention relates to perfume compositions which contain an alkyl 2-mercaptobenzoate and to products perfumed with these compounds or with said compositions. There is a continuing interest in the preparation and use of synthetic fragrance materials and the use thereof in products to be perfumed. Said interest is stimulated by the inadequate quantity and often changing quality of natural fragrance materials. Although sulphur compounds usually do not have a pleasant odour it has nevertheless emerged that they play an essential role in many natural odour complexes. Therefore there is a need for compounds with a "sulphurous" odour note which is clearly present but is not too prominent, preferably combined with other, pleasant odour notes so that the compounds can readily be combined with known fragrance materials. Surprisingly, it has now been found that alkyl 2-mercapto­ benzoates having the following general formula: wherein R represents a methyl or ethyl group, are valuable and powerful fragrances. The compounds have a very long-lasting flowery and, to some extent, spicy odour with a not very pronounced sulphorous note. In relation to the compounds according to the invention US Patent No. 3,984,573 states that they are suitable for improving concord grape aroma by intensifying the meaty and breadlike character therein. It was not possible, however, to conclude from this that the compounds would be suitable as fragrance materials or that they would have a flowery-spicey odour character. The compounds according to the invention can be prepared by methods known in the literature, for example, as described in the above-mentioned US Patent, in particular in Examples I and II. The compounds can be used as such as fragrances, or they can first be mixed with suitable carriers or diluants. However, they will preferably be combined with other individual compounds or with mixtures such as essential oils to form perfume compositions in the manner usual for the forming of such compositions. In this connection the term "perfume preparation" is under­ stood to mean a mixture of fragrance materials and optionally auxiliary substances, that may be dissolved in a suitable solvent or mixed with a powdery substrate and used to impart a desired odour to the skin and/or to various products. Examples of such products are: soaps, detergents, air fresheners, room sprays, pomanders, candles, cosmetics such as creams, ointments, toilet waters, pre- and aftershave lotions, talcum powders, hair-care products, body deodorants and anti-perspirants. Fragrance materials and mixtures thereof which can be used in combination with the compounds according to the invention for the preparation of perfume compositions are e.g. natural products such as essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic fragrance materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetyls, ketyls, nitriles etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds. Examples of fragrance materials which can be used in combination with the compounds according to the invention are: geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalool, citronellol, citronellyl acetate, dihydro myrcenol, dihydro myrcenyl acetate, tetrahydro myrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzylcarbinol, trichloromethyl-phenyl-carbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, α-hexyl­ cinnamaldehyde, 2-methyl-3-(p-tert-butylphenyl)propanal, 2-methyl­ -3-(p-isopropylphenyl)-propanal, 3-(p-tert-butylphenyl)propanal, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy­ -4-methylpentyl)-3-cyclohexene carbaldehyde, 4-(4-methyl-3-pen­ tenyl)-3-cyclohexene carbaldehyde, 4-acetoxy-3-pentyl-tetrahydro­ pyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopenta­ none, 3-methyl-2-pentyl-2-cyclopentanone, n-decanal, n-dodecanal, 9-decenol-1, phenoxyethyl isobutyrate, phenylacetaldehyde dimethyl­ acetyl, phenylacetaldehyde diethylacetyl, geranyl nitrile, citronellyl nitrile, cedryl acetate, 3-isocamfyl-cyclohexanol, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropine, coumarin, eugenol, vanillin, diphenyl oxide, hydroxy­ citronellal, ionones, methylionones, isomethylionones irones, cis-3-hexenol and esters thereof, indan-musks, tetralin-musks, isochroman-musks, macrocyclic ketones, macrolactone musks, ethylene brassylate, aromatic nitromusks. Auxiliary substances and solvents which can be used in perfume compositions which contain compounds according to the invention are e.g.: ethanol, isopropanol, diethylene glycol mono­ ethyl ether, diethyl phthalate, etc. The quantities in which the compounds according to the invention can be used in perfume compositions or products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product in which the fragrance is used, on the nature and the quantity of the other compounds in the perfume composition and on the intended odour effect. For this reason it is only possible to qive rough limits, but this provides sufficient information for those skilled in the art to be able to use the compounds according to the invention independently. In most cases a quantity of only 0.01% by weight in a perfume composition will already be sufficient to obtain a clearly perceptible odour effect. On the other hand, in order to achieve special odour effects, it is possible to use quantities of 10% by weight or even more in a composition. In products perfumed by means of perfume compositions said concentrations are proportionately lower, depending on the quantity of composition used in the product. The following examples serve solely to illustrate the preparation and use of the compounds according to the invention. The invention is not, however, limited thereto. Example 1 A perfume composition of the flowery type was prepared according to the recipe below:

Claims: 1. Perfume composition and perfumed product, characterized by a content of one or both compounds having the formula wherein R represents a methyl or ethyl group. 2. Perfume composition according to Claim 1, characterized by a content of at least 0.01% by weight of one or both compounds having the formula (1), wherein R has the meanings stated in Claim 1. 3. Use of a perfume composition according to Claim 1 or 2 or of one or both compounds having the formula 1, wherein R has the meanings stated in Claim 1, for perfuming products.

Inventors: DE VALOIS, PIETER JOHANNIS, HEIDEMAN, THEO, VAN DEN HEUVEL, HENRY LODEWIJK ALEXANDER, WILLE, HANS JULIUS
Applicants: NAARDEN INTERNATIONAL N.V.
Application year: 1986
Main classification: C11B9
IPC codes: A61K8, C11B9, A61Q13