JP2000303090A - Perfume composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a perfume composition which itself is stable, forms 1- pyrroline under acidic conditions or thermal cooking, and imparts favorable fragrance and flavor to food and beverage by using a 4,4-dialkoxybutylamine as the effective ingredient. SOLUTION: A 4,4-dialkoxybutylamine in an amount of 0.1-99 wt.%, preferably 0.1-50 wt.%, is added to a synthetic perfume compound (such as an aldehyde, an alcohol or an ester) or a perfume material (such as a natural essential oil). The amount of the amine added to food or beverage is 0.005-5 wt.%, preferably 0.01-0.5 wt.%. When heated or treated with an acid, the amine is decomposed into a corresponding alcohol and 4-aminobutanal and then undergoes cyclodehydration to form 1-pyrroline. Thus is obtained a food or beverage having a unique fragrance and flavor. In the formula, R is a 1-9C lower alkyl.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to 1,4-pyrroline having a flavor expression characteristic of rice cooked rice, roast chicken, corn, sesame, nuts, butter, etc. The present invention relates to a fragrance composition containing dialkoxybutylamine as an active ingredient.

[0002]

2. Description of the Related Art 1-Pyrroline is a compound having aroma characteristics such as cooked rice, roast chicken, corn, sesame, nuts and butter, and is useful as a fragrance substance. It is also known to add the compound to mashed potatoes to impart a butter-like odor (US Pat.
336138). On the other hand, 4,4-dialkoxybutylamine is a known compound, and for example, its use as a raw material for synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine is known (J. Agric.
Food Chem. VOL. 42, NO. 8,17
39, (1994)). However, there is no description or suggestion that the compound can be used as a precursor for expressing an aroma of 1-pyrroline, and that the same effect can be obtained by blending the compound in a perfume composition.

[0003]

As described above, 1-pyrroline imparts to various foods and beverages the flavor characteristics of cooked rice, roast chicken, corn, sesame, nuts, butter, and the like. Although it is a useful fragrance substance that can be used, it is unstable and easy to polymerize in its free state, and is very unstable to heat. , 1-pyrroline volatilized or polymerized, and the effect was not sufficiently exhibited.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, the above 4,4-
It has been found that dialkoxybutylamines are stable compounds themselves and are stable even when blended in a fragrance composition, but easily produce 1-pyrroline by acidic conditions or by heat treatment. Was. That is, a fragrance composition containing 4,4-dialkoxybutylamine as a flavor-expressing precursor is blended into food or drink, and 1-pyrroline is formed when the food or drink is heated and cooked, whereby a preferable fragrance flavor for the food or drink is obtained. It has been found that the present invention can be applied, and the present invention has been completed. Accordingly, an object of the present invention is to provide a fragrance composition containing 4,4-dialkoxybutylamine as an active ingredient.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Formula (1) which is an active ingredient of the present invention
Specific examples of the compound include, for example, 4,4-dimethoxybutylamine; 4,4-diethoxybutylamine;
4-dipropyloxybutylamine; 4,4-diisopropyloxybutylamine, 4,4-diisobutyloxybutylamine, and the like. Among them, 4,4-diethoxybutylamine is preferably used mainly for food and drink applications. it can. These equations (1)
Compounds are readily available on the market.

The compound of formula (1) of the present invention can be used alone as a precursor of 1-pyrroline as a flavor imparting agent for foods and drinks. Generally, however, aldehydes, alcohols and esters are used. It is desirable to use as a fragrance composition used in combination with a conventionally known fragrance material such as a synthetic fragrance compound such as a natural essential oil. Further, the compound of formula (1) or a fragrance composition containing the compound is spray-dried using, for example, dextrin, starch, modified starch or other excipients.
Powdering or granulation by vacuum drying or other known means can further facilitate use.

The compounding ratio of the compound of the formula (1) to the fragrance composition can be arbitrarily selected. For example, 0.1 to 99% by weight, preferably 0.1 to 99% by weight, based on the total amount of the composition. For example, a range of from 50 to 50% by weight, most preferably from 0.5 to 10% by weight can be exemplified.

Further, the amount of the flavor composition of the present invention to be added to the food or drink depends on the amount of the compound of the formula (1) to be added to the flavor composition.
To 5% by weight, preferably about 0.01 to 0.5% by weight.

The mechanism by which the compound of the formula (1) of the present invention is decomposed into the corresponding alcohol and 4-aminobutanal by acid treatment or heat treatment, and further subjected to dehydration cyclization to form 1-pyrroline is as follows. It is thought that it will proceed as follows.

[0010]

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Thus, according to the present invention, it is possible to provide a fragrance composition containing the compound of the above formula (1) as an active ingredient. Foods and beverages characterized by containing as

[0012] Foods and drinks which can impart or improve the flavor by using the flavor composition of the present invention include, for example, cooked rice, breads, various snacks, baked confectioneries, soups, sauces, Flavor seasonings, favorite beverages, various instant beverages and the like can be mentioned.

According to the present invention, by adding an appropriate amount of the compound of the formula (1) or a perfume composition containing the compound to these foods and drinks, foods and drinks imparted with the unique aroma and flavor can be obtained. Can be provided. Less than,
The present invention will be described more specifically with reference to Examples and Reference Examples.

[0014]

EXAMPLES Example 1 The following components (parts by weight) were mixed as a basic blended fragrance composition 1.

4 g is added to 10 g of the above-mentioned basic blended fragrance composition 1.
4-diethoxybutylamine (product 1 of the present invention) or 1-
Pyroline (Comparative product 1) was separately mixed with 1 g each to prepare a compounded flavor composition. 0.01% by weight of each of these compounded flavor compositions was added to the rice sauce and oyster "soba", and the mixture was boiled and cooled to prepare the sauce. This “sore” was applied to a oyster obtained by drying and roasting dough separately prepared by a conventional method, and dried to prepare a sample of the oyster. Further, for comparison, the above basic blended fragrance composition 1
Was added as it was in the same ratio as the two products described above (comparative product 2), and a sample sample was obtained in the same manner. The aroma of these three types of oysters was comparatively evaluated by 10 expert panelists. As a result, all of the 10 specialized panelists were able to add 4,4-diethoxybutylamine to the product 1 of the present invention.
The oyster added with was emphasized with a preferable corn odor, sesame odor, or unique fragrant odor, and was judged to be significantly superior to the other two products. On the other hand, the comparative product 1 to which 1-pyrroline was added was judged to be unsatisfactory in comparison with the comparative product 2 to which the basic blended fragrance composition 1 was added, although the fragrance was felt.

Example 2 The following components (parts by weight) were mixed as a basic blended fragrance composition 2.

4 g is added to 10 g of the above-mentioned basic preparation flavor composition 2.
1 g of each of 4-dipropyloxybutylamine (product 2 of the present invention) and 1-proline (comparative product 3) was mixed to prepare a compounded fragrance composition. After adding 0.01% by weight of each of the product of the present invention 2, the comparative product 3, and the above-mentioned basic blended fragrance composition 2 (comparative product 4) to corn cream soup prepared by an ordinary method, and boiling each for 5 minutes, The aroma was comparatively evaluated by 10 expert panelists. As a result, the corn cream soup to which all of the 10 specialized panelists added the product 2 of the present invention to which 4,4-dipropyloxybutylamine was added had a favorable odor of corn or a unique savory umami taste, and the palatability was enhanced. Had been significantly improved. On the other hand, the comparative product 3 exhibited a favorable effect of 1-proline, but was reduced by half compared with the product 2 of the present invention. Furthermore, the comparative product 4 is much more corn-like in flavor than the one without the fragrance composition.
And it was evaluated that the comparative product 3 was not strong.

Example 3: Improving the flavor of cooked rice 600 g of commercially available polished rice is sharpened and washed, divided into three parts, and 0.001 g of 4,4-diethoxybutylamine (product 3 of the present invention) is added to the other one. Are 1-pyrroline 0.001 g (comparative product 5), respectively, cooked under the same conditions as those without additive (comparative product 6), and 10 panelists who were fully trained on these three types of cooked rice The sensory evaluation was performed. As a result, the order of preference for the flavor of the rice was determined to be Product 3 of the present invention> Comparative product 5> Comparative product 6. In particular, the product 3 of the present invention was judged to be remarkably excellent in comparison with cold rice.

[0019]

According to the present invention, when a 4,4-dialkoxybutylamine is used as an aroma-expressing precursor as it is or a fragrance composition containing the compound is added to a food or drink, and the food or drink is cooked. 1-pyrroline is formed in the food and drink, and the food or drink can be imparted with a preferable flavor such as cooked rice, roast chicken, corn, sesame, nut, and butter.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4B047 LB08 LG14 LP05 4H059 BA42 BA43 BB02 BB15 BB19 BB24 BB44 CA33 CA72 DA09

Claims (1)

[Claims] [Claim 1] The following formula (1) In the formula, R represents a C1 to C9 lower alkyl group, and a perfume composition containing 4,4-dialkoxybutylamine represented by the following formula as an active ingredient: