JPS59148714A - Fragrance-promoting agent - Google Patents

Abstract

PURPOSE:To provide a fragrance-promoting agent composed of dibenzothiophene or its derivative, effective to strengthen the after-fragrance, and give the thickness, density and deepness of natural fragrance to a compound perfumery having rose-based floral note. CONSTITUTION:The objective fragrnace-promoting agent is composed of one or more compounds selected from dibenzothiophene of formula (X is H, methyl or ethyl) and its derivative. It cannot be anticipated that dibenzothiophene or its alkyl derivative can give natural fragrance by itself, however, it gives a compound perfumery having the thickness, density and deepness of natural fragrance when compounded to a compound perfumery. The dibenzothiophene and its derivative exist in marine sediment, high-boiling fraction of petroleum, etc. as well as rose oil, and can be obtained also as a synthetic product. Dibenzothiophene and its derivative may be used singly or in combination.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an aroma reinforcing agent which, when added to a floral-like blended fragrance based on sip and sip, strengthens the aftertaste of the fragrance and gives it a natural feel.

Rose oil, along with jasmine oil, is one of the most valuable natural fragrances that has been used since ancient times.

However, the quality of rose oil varies greatly depending on the rose species, production area, extraction method, etc. Now commonly used. Among the rose oils, rose oil from Bulgaria is the best, followed by Morocco and Turkey, and these three types are mainly used as natural fragrances, but even rose oils from the same production area vary greatly depending on the lot. At present, it is difficult to obtain rose oil of consistent quality.

On the other hand, studies are being conducted on mixed fragrances (synthetic fragrances, or mixtures of synthetic fragrances and natural oils) that are easy to obtain with a certain quality and may be cheap. The reality is that it is still far behind in terms of width, depth, etc.

- In view of the above circumstances, the inventors of the present invention have conducted extensive research to obtain a blended fragrance that is of constant quality, inexpensive, and has the richness, breadth, and depth of a more natural fragrance. It was discovered for the first time that dibenzothiophene and its alkyl derivatives are among the sulfur-containing compounds contained as trace components in oil, and that dibenzothiophene and its alkyl derivatives greatly contribute to the naturalness of rose oil. Ta. In other words, dibenzothiophene and its alkyl derivatives have a ``spicy, powdery, chemical-like odor'' when used alone, and it is difficult to imagine that they can impart a natural-like aroma, but when added to a blended fragrance, This significantly improves the richness, breadth, and depth of the fragrance. The present inventors have completed the present invention based on these findings.

That is, the present invention is an aroma reinforcing agent consisting of one or more selected from the group consisting of dibenzothiophene and derivatives thereof represented by the following general formula. Next, the structure of the present invention will be described.

(Left below) Dibenzothiophene and its derivatives used in the present invention are:
It is represented by the above general formula, and each of the two benzene rings has 0, 1, or 2 substituents. Either one of the two may be substituted on one benzene ring. In other words, the combination of the number of substituents on one benzene ring and the number of substituents on the other benzene ring is completely arbitrary, up to two for each. Moreover, the position of the substituent is also completely arbitrary. Furthermore, the substituent is CI (3 or 02H
.

However, when there are two or more substituents in total on both benzene rings, all of them may be OH3, 02H, or both OH3 and 02H. Specific examples of compounds of the above general formula include dibenzothiophene when all X's are H; monomethyldibenzothio when 3 of X's are H and 1 is OH; 7 dibenzothiophene and sono derivatives used in the present invention; It is known that it exists not only in rose oil, which was first discovered by the present inventors, but also in marine sediments and high-boiling fractions of petroleum. On the other hand, as a synthetic product, dibenzothiophene is already commercially available as a reagent, and examples of synthesis of methyl derivatives of dibenzothiophene are also known. (Bull, Ohem, Soc.
.

Jpn, ) Volume M-Pages 2374-2378, 1981
Year: Soc, Ohim, Fr, Vol. 9, pp. 3299-3306, 197.1; Synthesis, Vol. 8, pp. 532-533; (1975) The dibenzothiophene alkyl derivatives used in the present invention can be produced by applying these known methods mutatis mutandis. The dibenzothiophene and its derivatives used in the present invention may be either the above-mentioned natural extracts or synthetic products, or a combination of both.

In the present invention, one or more of the above-mentioned dibenzothiophenes and derivatives thereof are selected and blended into the perfume composition. The blended amount is 000 in the total amount of blended fragrance.
If it is less than 3 to 3% by weight oO,003% by weight, the effect of improving the richness, breadth, depth, etc. of the fragrance will be poor, and if it exceeds 3% by weight, the balance of the fragrance will be lost, which is not preferable.

The aroma enhancer of the present invention was developed by the present inventors from the viewpoint of what causes the differences between rose oil production areas, species, and lots, and what should be done to always obtain high-quality rose oil. As a result of research on natural rose oil, it was discovered for the first time as a trace component in rose oil. Moreover, it has a spicy, powdery, chemical-like odor that is far different from the scent of rose on its own, but it is used in mixed fragrances. This is the first time that we have discovered that when blended with a natural fragrance, it can imitate the richness, breadth, and depth of the fragrance.

Next, the present invention will be explained in more detail by giving extraction examples, synthesis examples, and examples of the present invention. The present invention is not limited thereby. The blending amount is in weight%.

(0 development from low) Kaigen, Nbonito (6M4<k to tafi (X9)) Extract 90g of Bulgarian essential rose oil with n-pentane and propylene glycol, and use Kieselgel. ) 6
0 (manufactured by Merck & Co., West Germany) 30 fif filled with 40 o-
The mixture was applied to an iφX 500 column and developed with 3J of n-hexane to obtain 8 fractions, of which the 5th fraction was removed from the solvent to obtain 0.05% of a colorless and transparent viscous liquid. .

When this product was analyzed by gas chromatography under the following conditions, the retention time (TR) was 9.2 to 13.5 minutes, including dibenzothiophene and 1,! ,
-, 2-, 3-, and 4-methyldibenzothiophene peaks were observed, and these were collected together. The yield is 14.
It was 4q.

Gas chromatography conditions column; 5% P'EG 20M/Ohromosor
b W 80-100 mesh 3 φ - 0.08 mol (9.9 g) of methylthiophenol was reacted in a 10% caustic soda aqueous solution to obtain 1-0-methylphenyl-1-〇nitrophenyl sulfuride, and then in 50% ethanol under hydrochloric acid acidity. Reduces nitro groups using iron as a catalyst. Next, this was placed in an argon stream.
S4-methyldibenzothiophene was obtained by ring closure by reaction with t-butylthionitrate at 160°C. After crudely distilling this, it is separated by silica gel column chromatography.
Purified 4-methyldibenzothiophene was obtained.

This product was a pale yellowish white powder, and the yield was 0.79 (yield 5%).

In a similar manner, 1-12-1 and 3-methyldibenzothiophene, 4,6-dimethyldibenzothiophene, and 4-ethyldibenzothiophene were obtained.

Examples 1 to 6 (Perfume preparation examples) Compound fragrances were prepared in the amounts shown in Table 1. Table 1 also shows the evaluation results for each fragrance. The evaluation method and display of evaluation points are as follows.

A panel of 10 experts conducted a sensory evaluation on the richness, breadth, depth, naturalness, and overall balance of the fragrance.

◎: 9 or more out of 10 seniors and junior high school students.

○：〃〃　7 people △：〃〃〃〃5 people X: // 2 people (Margin below)

Claims (1)

[Scope of Claims] A fragrance reinforcing agent consisting of one or more selected from the group consisting of the following general formula.