JP2002256282A - Fragrance composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a fragrance composition having mild and fresh green color and floral nature, high in sense and durability, and suitable for cosmetics and foods/drinks. SOLUTION: This fragrance composition comprises a phenylacetaldehyde O-alkyloxime of the general formula (1) (wherein, R is a 1-6C alkyl) as the active ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a perfume composition capable of imparting a fresh, clean, floral and mild fragrance and having a long lasting effect. In particular, it relates to a fragrance composition useful as a fragrance for cosmetics and a fragrance for food and drink.

[0002]

2. Description of the Related Art In recent years, there has been a need for fragrances for cosmetics and fragrances for foods and beverages, which have diversified consumer preferences and have a new type of fragrance and flavor that have not existed before. There is a demand for the development of a unique fragrance material that is growing, has a mild and fresh flavor, and is excellent in sustainability. Against this background, research has been carried out to combine perfume materials as appropriate and by changing the amount of blending, and to mix them so as to have a naturalness as much as possible. However, the development of a fragrance composition which is excellent in respect of the above is not yet sufficient.

On the other hand, in recent years, Michelia cham
mpaca (Magnoliaceae), Ginger Lily
(Ginger family) and Citrus unshiuMar
It is known that a small amount of phenylacetaldehyde O-alkyl oxime is present as an aroma component of the flower of Coritch (Satsuma mandarin) (Agricultural Biological Chemistry (Agric. Biol.)).
Chem. Vol. 43, No. 1, 195 pages, 1979
Year).

[0004]

Under such circumstances, the present inventors have focused on aromatic aldehyde derivatives, particularly oxime bodies, contained in the fragrance of natural flowers.
They were synthesized and the odor characteristics of each compound were studied.

As a result, the general formula (1)

Embedded image (Wherein, R represents a C ₁ -C ₆ alkyl group) containing a phenylacetaldehyde O-alkyl oxime represented by the formula: Gives a mild, natural-like fragrance, and has excellent sustainability.
The present invention has been completed.

[0006] That is, an object of the present invention is to provide a perfume composition containing the compound of the above general formula (1), which imparts a fresh, green, floral fragrance, a mild natural fragrance, and is excellent in persistence. It is in.

In the present invention, the oxime of the above general formula (1) includes stereoisomers of syn or oxime, and any of them and mixtures thereof can be used.

[0008] These oximes can be easily synthesized by known methods. For example, an aqueous solution of phenylacetaldehyde and an O-alkylhydroxylamine mineral acid salt is dropped and reacted with an aqueous alkali solution while stirring under cooling, whereby phenylacetaldehyde O
-Alkyl oximes can be synthesized.

The amount of the compound represented by the general formula (1) in the fragrance composition of the present invention can be arbitrarily selected according to the fragrance characteristics to be expressed by the composition. 0.001 to 30% by weight, preferably 0.05 to 1% by weight of one or more compounds of (1)
A blending amount in the range of about 5% can be mentioned.

The oxime of the present invention comprises a natural essential oil, a natural flavor,
Also, it is in harmony with many known perfume substance components derived from synthesis, and by containing the same, a novel perfume composition can be prepared. For example, citrus essential oils such as orange, lemon, lime and grapefruit, lavender oil,
It blends well with natural essential oils such as coriander oil, jasmine oil, geranium oil, and bergamot oil, and is mild, fresh and emphasizes the characteristics of the essential oil.

Thus, according to the present invention, the above formula (1)
By blending the compound of formula (1) in a specific amount, a fragrance composition that imparts a mild, fresh green, floral and highly palatable fragrance can be provided. The present invention can provide cosmetics, foods and drinks, health, hygiene, pharmaceuticals, and the like, which are characterized by containing the compound as an aroma component. For example, perfumes, soaps, body shampoos, shampoos and rinses, detergents, hair creams, pomades, and other hair cosmetic bases;
It is possible to provide cosmetics in which an appropriate amount capable of imparting a unique aroma is added to oscilloscope, lipstick, other cosmetic bases, cosmetic detergent bases, and the like. Also, for example, juice drinks,
Beverages such as fruit liquors, milk drinks, carbonated drinks; ice creams, sorbets, frozen desserts such as popsicles; Japanese and Western sweets, jams, chewing gums, breads, coffee, cocoa, tea, tea Soups such as Japanese soups and Western soups; flavor seasonings, various instant beverages and foods;
It is possible to provide foods and drinks to which various snack foods and the like are added in an appropriate amount capable of imparting the unique aroma and flavor. Furthermore, laundry, disinfecting detergents, room air fresheners and other various health and hygiene materials; health, hygiene and medicines such as flavoring and fragrance for facilitating taking of medicines can be provided. .

Hereinafter, the synthesis examples of the alkyl oxime and the present invention will be described in more detail with reference to examples.

[0013]

Reference Example 1 Synthesis method of phenylacetaldehyde O-methyl oxime 9.7 g of phenylacetaldehyde, 7.5 g of O-methylhydroxyamine hydrochloride and 15 g of water were charged into a flask, and cooled with ice water to obtain a 15% aqueous solution of sodium carbonate. 6
3.5 g was dripped at an internal temperature of 9 to 12 ° C. over 80 minutes and stirred. Thereafter, the reaction is stirred at room temperature for 3 hours. Water was added to the reaction solution, and the mixture was extracted with ether, washed with brine, dehydrated, and the ether was distilled off to obtain 12 g of crude phenylacetaldehyde O-methyl oxime. This was purified by distillation under reduced pressure, and 11.1 g of a mixture of phenylacetaldehyde O-methyloxime syn and anti (boiling point: 74 ° C./3 mmH
g, GLC purity 97.8%, yield 92.5%).
According to the above synthesis method, various O-alkylhydroxyamine hydrochlorides were used instead of O-methylhydroxyhydrochloride to obtain the corresponding compounds of formula (1). Table 1 shows their aromas.

[0014]

[Table 1]

[0015]

3 g of phenylacetaldehyde O-methyl oxime was mixed with 97 g of the above composition to prepare a novel compounded fragrance composition. This new prepared perfume composition and the lira-type prepared perfume composition to which the compound was not added were compared by 10 expert panelists. As a result, all of the 10 expert panelists added the compound to the new compounded fragrance composition, which emphasized the citrus-like aroma with a fresh, fresh green sensation. Excellent.

Example 2 In Example 1, O-ethyl oxime, On-butyl oxime, and On-hexyl oxime were used in place of phenylacetaldehyde O-methyl oxime according to the method for synthesizing phenylacetaldehyde O-methyl oxime. 3 g each of which is a lira-type blended perfume composition 97
g of each of the new perfume compositions. This new formulation was compared by 10 expert panelists. As a result, all of the 10 expert panelists found that O-ethyl oxime was fresh, citrus-like with a soft green sensation, On-butyl oxime was flower-like with a mild green sensation, and On-hexyl oxime was Has a fresh but bluish herbaceous texture, each with an enhanced aroma, all of which have the characteristics of a natural lira, and are considered to be excellent in sustainability.

[0018]

4 g of phenylacetaldehyde O-isopropyl oxime synthesized according to the synthesis method of phenylacetaldehyde O-methyl oxime was added to 96 g of the above composition.
The mixture was mixed to prepare a new pineapple-like compounded flavoring composition. This new compounded perfume composition and the pineapple-like compounded perfume composition to which the compound was not added were compared by 10 expert panelists. As a result, the novel compounded fragrance composition to which all the 10 expert panelers have added the compound has the characteristic of a natural pineapple with a fresh, soft, sweet, flowery fragrance emphasized, and is much more persistent. It was excellent.

Example 4 In Example 3, instead of phenylacetaldehyde O-isopropyl oxime, O-methyl oxime, 0-ethyl oxime, On-butyl oxime and phenylacetaldehyde O-methyl oxime were synthesized according to the synthesis method. Four kinds of 4 g each of Ot-butyl oxime and O-isopentyl oxime were mixed with 96 g of a pineapple-like compounded flavor composition to prepare respective new compounded flavor compositions. This newly prepared perfume composition was compared by 10 expert panelists. As a result, specialized panel 1
O-methyl oxime is a green citrus-like with a strong feeling of freshness, 0-ethyl oxime is a flower with a fresh and soft greenness, and On-butyl oxime is a mild green and herbal flower-like plant. O
-T-Butyl oxime is a flower with a mild sweetness in freshness, and O-Isopentyl oxime is a natural pineapple with a fresh bluish herbaceousness and natural pineapple with each fragrance emphasized. It was also excellent in point.

[0021]

It is evident that the present invention provides a mild, fresh green and floral fragrance composition having high palatability and durability.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Minoru Masuda Kariya Hasegawa 335, Nakahara-ku, Kawasaki-shi, Kanagawa Prefecture Inside the Technical Research Institute (72) Inventor Tohru Tatehara 335 Karijuku Hasegawa, Nakahara-ku, Kawasaki-shi, Kanagawa F-term in Technical Research Institute, Inc. (reference) 4H059 BA52 BB14 DA09

Claims (2)

[Claims] 1. A compound of the general formula (1) (Wherein, R represents a C ₁ -C ₆ alkyl group) phenylacetaldehyde O-alkyl oxime (excluding phenylacetaldehyde-O-methyl oxime) represented as the active ingredient. Perfume composition. 2. The phenylacetaldehyde O-alkyl oxime according to claim 1 (excluding phenylacetaldehyde-O-methyl oxime) in an amount of 0.001 to 30.
A fragrance composition characterized by containing by weight. [Detailed description of the invention]