JPH0785703B2 - Flavor composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Field of the Invention The present invention relates to 4-hydroxy-2 (5) -ethyl-5 (2).
-Methyl-3 (2H) -furanone and a furfuryl alcohol are used as a flavor composition.

(Prior art) The aroma components of soy sauce were separated and concentrated by headspace gas concentration method, continuous distillation extraction method, and direct column concentration method, and these were analyzed by gas chromatography. It is known that the components consist of various substances (Journal of Japan Food Industry Society,
Vol. 36, No. 7, 609-614 (1989)), further proceeding to separate and identify these substances from each other, there is no report on the interaction between the substances.

(Problems to be Solved by the Invention) The present invention can be separated from the aroma component of soy sauce.
-Hydroxy-2 (5) -ethyl-5 (2) -methyl-
An object is to provide a flavor composition containing 3 (2H) -furanone and furfuryl alcohol as active ingredients.

(Means for Solving the Problems) The present inventor has found that when the soy sauce aroma component is concentrated by a vacuum distillation method or a vacuum continuous distillation extraction method (vacuum SDE method), the salty odor peculiar to soy sauce completely disappears. It was On the other hand, a salty odor was strongly felt from the aroma concentrate obtained by the direct column concentration method (Journal of the Japanese Food Industry Society). Therefore, we compared the aroma concentration methods and tried to elucidate the causative agent of this salty odor.

The aroma components were identified by the GC-MS (EI, CI) method and the retention index. The salty fraction was separated and purified by scraping off the fraction with the strongest odor by normal phase and reverse phase TLC method and extracting with ether or alcohol to obtain a crudely purified product. Sensory tests were conducted by 10 panelists, using rank method for odor quality and limit method for odor intensity.

As a result, 53 aroma components were identified or estimated.
Crude products obtained by normal phase and reverse phase TLC methods gave two distinct bands when normal phase TLC was performed again. One has a sweet caramel-like odor, and is 4-Hdroxv- by the GC-MS method.
2 (5) -ethyl-5 (2) -methyl-3 (2H) -furan
Identified as one (HEMF). The other fraction is Ethylllact
ate, Furfurylalcohol (FA), 2-Acetylpyrrol, which had a fermentation odor. From these fractions, the salty smell of the original soy sauce was hardly recognized,
It was speculated that the salty odor was due to a synergistic effect between the two bands. That is, as a result of a sensory test, a strong synergistic effect was observed between HEMF and FA in terms of odor quality, and it was found that salty and soy sauce-like odors were significantly enhanced when both substances were mixed in equal amounts. FA was recovered by either method, but HEMF was not recovered by distillation method or SDE method at all, and could be recovered only by column method, and the concentration in the sample was 20.5 ppm.

In other words, HEMF (sweet caramel odor) and FA (volatile odor) are both known substances, but it is new to the present inventor that the mixture of both substances changes to a completely different salty odor due to interaction. The present invention has been completed based on such knowledge.

Hereinafter, the present invention will be described in detail.

In the present invention, as described above, 4-hydroxy-2 (5)-
Ethyl-5 (2) -methyl-3 (2H) -furanone (HEM
F) and a furfuryl alcohol (FA) -containing flavor composition.

Since both substances that are active ingredients are known substances,
In preparing the composition of the present invention, both commercially available substances may be used after purification if necessary, but from the viewpoint of food safety, it is desirable to use the one separated from soy sauce.

There is no particular limitation on the mixing ratio of both substances, as long as a salty odor and a soy sauce-like odor are exhibited as a synergistic action of both substances. With regard to this ratio, since neither of the substances has a salty odor of soy sauce, a person skilled in the art considers the use of the flavor composition of the present invention as a product, etc. Can be easily determined, but as will be understood from Experiment 1 below,
HEMF: FA is in the range of 80:20 to 20:80.

Experimental Example 1 Dozens of peaks obtained by elution of the column adsorption fraction obtained by treating soy sauce with porous polymer beads “Polapack Q” (trade name: manufactured by Waters) using ether were subjected to thin-layer chromatography. The HEMF was attached and purified.

Table 1 shows this HEMF and commercially available furfuryl alcohol (FA).
The mixture was mixed at the ratio (weight ratio) shown in, and diluted with water so that the concentration became 10 ppm.

The above-mentioned samples were evaluated by 10 panelists using the following evaluation items and scales.

The results are shown in Table 2. From this result, HEMF: FA is 80: 20-2
At 0:80, the interaction of the two made the flavor stronger (especially salty flavor), and it was the highest at 50:50.

The flavor composition of the present invention can be used for miso soup and the like, but HE is an active ingredient for such applications.
The flavor composition of the present invention consisting only of MF and FA is too thick and inconvenient to use and handle. In such a case, the flavor composition of the present invention may be composed of both substances as active ingredients and a suitable diluent used in foods.

Examples of the diluent include water, propylene glycol and glycerol when the flavor composition of the present invention is in a liquid state, and lactose and sorbitol when it is in a powder form.

In addition to the diluent, cyclodextrin or the like may be added to the flavor composition of the present invention for the purpose of maintaining quality. In addition, it goes without saying that appropriate substances may be added as long as they do not impair the purpose of the flavor composition of the present invention.

HEMF and FA as active ingredients of the flavor composition of the present invention,
As described above, from the viewpoint of food safety, it is desirable to separate it from soy sauce.

In order to separate both substances from soy sauce, it is advisable to first separate the aroma components containing both substances from soy sauce, and then separate the separated aroma components to isolate these two substances.

As a method for collectively separating the aroma components from soy sauce, vacuum distillation method, vacuum SDE method, direct column concentration method, etc. can be considered. Since the salty odor of the soybean has completely disappeared, it is unlikely that HEMF and FA, which exhibit the salty odor of soy sauce as a synergistic effect, coexist when these two are used, and it is the last to obtain both substances. It is recommended to use the direct color enrichment method of.

Therefore, the direct column concentration method will be described. In this method, soy sauce, which is a raw material, is passed through a column filled with an aroma collecting agent to adsorb the aroma to the aroma collecting agent, thereby separating the aroma.

As a scavenger, a copolymer of styrenedivinylbenzene,
Porous polymer fillers such as Porapak Q, QS, R
And S (manufactured by Waters) and inorganic kieselso-based fillers such as Chromosorb 105 and 106 (manufactured by Manville) are preferable from the viewpoint of operability.

The aroma components thus separated are separated to obtain HEMF and FA.
For the isolation, the adsorbed aroma component may be fractionally desorbed by using an appropriate desorbent. Suitable desorbents include ethers and alcohols, with alcohols being preferred from the viewpoint of food safety.

The fact that HEMF and FA are separately separated in the separated fraction can be confirmed by silica gel thin layer chromatography or the like.

In order to remove the desorbing agent from each fraction containing HEMF and FA to isolate the respective substances, for example, reverse phase thin layer chromatography is performed. When the desorbent is harmless in terms of food safety such as alcohol, the flavor composition of the present invention can be obtained in a liquid form by simply combining the desorbed fractions of both substances.

By the way, the method of separating the aroma components from soy sauce, which is a raw material, by adsorbing and separating the aroma components from the raw material soy sauce through a column filled with porous polymer beads as a scent capturing agent, and then separating and desorbing the aroma components is Separation of HEMF and FA by polymer bead chromatography.

In the direct column concentration, the non-adsorbed fraction obtained after adsorbing and separating the aroma components including HEMF and FA is a seasoning liquid having a strong and mellow taste. This seasoning liquid can be used as a soy sauce substitute as it is, and is also useful as a raw material for noodle sauce and various sauces.

(Example) The present invention will be further described with reference to the following examples.

Example 1 HEMF prepared by the preparation method shown in Experimental Example 1 and commercially available HEMF
Water was added to a mixture of FA at a ratio of 1: 1 (weight ratio) so that the concentration was adjusted to 20 ppm.

A sensory evaluation of this product by 10 panelists revealed a salty aroma with a strong browning odor.

Furthermore, 30% (weight ratio) of lactose in this aqueous solution as lactose
After adding and mixing, add water to freeze-dried powder and add HEMF +
An aqueous solution prepared by adjusting FA to 20 ppm by weight also exhibited a similar salty aroma.

Example 2 1000 ml of soy sauce was passed through Polapack Q (manufactured by Waters Co.) which had been sufficiently swollen with water, and the adsorbed flavor component was eluted with ethanol and then desolvated at 80 ° C. for a short time to obtain about 0.6 ml of an extract. This was diluted with 1000 ml of water.

As a result of sensory evaluation of this aqueous solution by seven panelists, a strong salty aroma like soy sauce was exhibited.

(Effects of the Invention) According to the present invention, 4-hydroxy-2 (5) -ethyl-5 (2) -methyl-3 (2H) -furanone and almost no salty odor of soy sauce alone and Furfuryl alcohol provides a flavor composition that exhibits the salty and soy sauce-like odor of soy sauce.

Claims (3)

[Claims] 1. 4-Hydroxy-2 (5) -ethyl-5
A flavor composition comprising (2) -methyl-3 (2H) -furanone and furfuryl alcohol as active ingredients. 2. The 4-hydroxy-2 (5) -ethyl-5.
The flavor composition according to claim 1, wherein (2) -methyl-3 (2H) -furanone and the furfuryl alcohol are separated from soy sauce. 3. The flavor composition according to claim 2, wherein the separation from the soy sauce is performed by porous polymer bead column chromatography.