JPS61199759A - Prepartion of flavoring additive - Google Patents

Abstract

PURPOSE:To obtian a flavoring additive having the roast flavor such as roast feeling and roast sweet smell, with simple operation, by heating and reacting an amino acid (derivative) with a sugar in the presence of a specific powdery material in the absence of solvent. CONSTITUTION:The objective flavoring additive is produced by reacting an amino acid (derivative) such as alanine, glutamic acid, etc. with a sugar such as glyceraldehyde, etc. under heating, in the presence of a powdery material incompatible with either of the reaction raw materials and infusible at the reaction temperature, and in a non-solution state, i.e. in the absence of a solvent. The powdery material is preferably a porous inorganic powder. Preferably, the reaction system is treated with water, organic solvent and/or animal or vegetable oil or fat to extract the reaction product attached or adsorbed to the powdery material, and the powdery material is separated by filtration to obtain the reaction product.

Description

DETAILED DESCRIPTION OF THE INVENTION (A. Field of Industrial Application) The present invention relates to a method for producing flavor additives, and particularly to a novel method for producing flavor additives having roasted aroma.

(Conventional Art) Many foods are eaten by being heat-treated. When food is heated, volatile metals that did not exist before heating appear due to the decomposition of the components contained in the food and reactions between the components. Although the production mechanism of these compounds has not yet been elucidated except for a very small portion, it is believed that the Maillard reaction, an amino-carbonyl reaction between amino acids and sugars, plays an important role.

Many proposals have been made to utilize products obtained by amino-carbonyl reactions using amino acids and sugars as main raw materials as flavor additives. Among these, a particularly commonly used production method is a method in which a mixture containing an amino eIR and a saccharide is subjected to a heating reaction in the presence of a solvent such as water, an organic solvent, an animal or vegetable oil or fat, particularly water. However, the flavor obtained by this method is limited to foods that are eaten or eaten by roasting, such as grilled meat,
As a flavor additive for use in grilled fish, baked confectionery, bread, nuts, coffee, cocoa, etc., it lacks a roasted feel and a desirable burnt odor, and is therefore unsatisfactory.

(C1 Problems to be Solved by the Invention) The present inventors have been conducting research on the production of flavor additives with such a roasted taste, but the heating reaction of amino acids and S species in the absence of a solvent has not been achieved. We have found that it is possible to obtain a flavor additive that satisfies the above-mentioned drawbacks. However, the reaction product in the absence of a solvent is highly viscous and tar-like, making it difficult to maintain uniformity within the reaction system, resulting in a lack of reproducibility and difficulty in providing diversity in aroma characteristics. Furthermore, it has the disadvantage that it is difficult to process it after the reaction to convert it into a form that is easy to use as a flavor additive.

It is an object of the present invention to provide an improved method for producing flavor additives by the Maillard reaction.

A further object of the present invention is to provide a method for producing flavor additives having an excellent roasted feel and roasted aroma such as a burnt smell with good reproducibility and simple operations.

(Means for Solving Twenty Problems) The object of the present invention is to produce a flavor additive by heating and reacting an amino acid or its derivative with sugar.
The reaction is achieved by carrying out the reaction in a non-solution system in the presence of powder or granules that are incompatible with the reaction raw materials used and do not melt under the reaction temperature conditions.

The amino acids and sugars used as reaction raw materials in the method of the present invention may essentially be any of those capable of causing the conventionally known Maillard reaction.

Specific examples of amino acids include alanine, glycine, lysine, hydroxylysine, valine, arginine, glutamic acid, aspartic acid, cystine, cysteine, serine, proline, hydroxyproline, histidine, methionine, tryptophan, threonine, tyrosine, phenylalanine, and leucine. , inleucine, aminobutyric acid, etc., or one or a mixture of two or more of their salts, but of course the present invention is not limited to these.

Specific examples of sugars include glyceraldehyde, erythrose, arabinose such as Lz, t-sualahinose, xylose, lipose, glucose, mannose, and galactose, and ketoses such as dihydroxyacetone, xylulose, ribulose, fructose, and nrubose. Furthermore, examples include deoxy sugars such as 2-deoxyribose, rhamnose, and fucose, and oligosaccharides such as maltose, cellobiose, inmaltose, lactose, and sucrose, or a mixture of two or more of them. It is not limited.

The essence of the present invention is to react both of these reaction materials in a non-solution system, that is, in a system substantially free of solvent, and to have powder and granules present in the reaction system.

The powder and granules are required to be incompatible with the reaction raw materials used and non-meltable under the reaction temperature conditions. In the present invention, granular material means powder, granular material, or a mixture thereof. The particle size and shape are not particularly limited, but the particle size is usually 0.
It is preferably 0.001 to 5, particularly 0.001 to 1, and preferably spherical in shape.

Although essentially any powder may be used as long as it has the above characteristics, porous inorganic powder is particularly preferred. This is presumed to be because a more favorable effect is exhibited when the reaction raw materials adsorbed not only on the surface of the powdery material but also inside the porous material participate in the reaction. The chemical composition of such powder or granules is not particularly limited, but alkaline earth metals or their salts or oxides, non-metals belonging to Group Ⅰ or their oxides, etc. are preferably used because of their ease of availability. It will be done. Preferred examples of granular materials include alumina, silica gel, cane earth, and activated carbon.

The mixing ratio of amino acids and sugars is 100:1-0.
01:1, especially in the range from 10:1 to 0.01:1.

It is desirable that the amount of powder used is sufficient so that at least one part, preferably the main part, of the reaction occurs on the powder or granule (including in the pores) or in its vicinity, and the reaction raw material and the powder should be Expressed as a weight ratio of 100:1 to 0.001:1, preferably 20:1 to 0.01:1. Preferably 5 for the hook:
A range of 1 to 0.1:1 is used.

There is a mutual relationship between the heating temperature and time in a heating reaction; in a reaction with high catalysis, it is better to carry out the reaction in a short time, and conversely, in a reaction at a relatively low temperature, it is better to carry out the reaction for a long time. Usually, the heating temperature is about 50-250℃, preferably about 80-250℃
A range of 0.000C is used. The heating time is usually about 15
A range of seconds to 150 hours, preferably about 30 seconds to 10 hours is used.

Optimal conditions can be freely selected depending on the type of reaction raw material used, the amount of powder and granules, and the flavor and characteristics of the flavor composition expected.

Reactions can be conducted in open or closed systems, as well as in batch and continuous sweat systems.
This can be done in any existing device form.

The pressure can be carried out under reduced pressure conditions, atmospheric pressure, naturally occurring pressure, or pressurized conditions, but it is possible to do it under 150 Kf.
/css" or less is convenient. In addition to normal air, it can also be carried out in an atmosphere of helium gas, argon gas, nitrogen gas, carbon dioxide gas, etc.

The heated reaction product is separated from the powder by an appropriate means.

Preferred separation operations include a combination of solvent extraction and filtration.

The solvent can be appropriately selected from water, organic solvents, animal and vegetable oils and fats, and specifically, water, methanol, ethanol, hexane, ethyl acetate, impropatol, acetone, cyclohexane, pentane, and polyhydric solvents such as propylene glycol and glycerin. Alcohol, triglycerides containing short-chain and medium-chain fatty acid esters, animal fats such as beef tallow, pork tallow, and mutton tallow, soybean oil, safflower oil, sesame oil, rapeseed oil, cottonseed oil, olive oil, peanut oil, cocoa butter, and coconut oil. ,
Preferred examples include one or a mixture of two or more vegetable oils such as palm oil. More preferable examples include water, ethanol, and one or a mixture of two or more of polyhydric alcohols such as propylene glycol and glycerin, triglycerides containing medium-chain fatty acid esters, and vegetable oils and fats such as rapeseed oil, cottonseed oil, and olive oil. I can do it.

The extraction method may be batchwise or continuous. Further, filtration can also be performed by existing solid-liquid separation methods such as pressurization, reduced pressure, natural filtration, etc. Further, the obtained solution can be used in any form such as solution, paste, powder, etc. by operations such as concentration, solvent recovery, and drying.

The product thus obtained has a strong roasted odor, a roasted aroma based on a burnt odor, and can be used as a flavor additive in floor desks and in the food industry.

In particular, its excellent properties are exhibited when used as a yakiniku-like flavor, a grilled fish-like flavor, a baked confectionery-like flavor T4+, a han-like flavor, a nutty-like flavor, a coffee-like flavor, a cocoa-like flavor, etc.

The method of the present invention is simple and has excellent reproducibility, and the selection range of extraction solvents is extremely wide, so it can be used for a wide range of purposes regardless of water solubility or oil solubility. Furthermore, since the aroma characteristics of the resulting product can be subtly changed by selecting the powder or granules used, it is possible to obtain flavor additives with appropriate quality characteristics depending on the characteristics of the object to be flavored.

Next, the present invention will be specifically explained with reference to Examples.

Example 1 7 lactose 10? , arginine 5t, glutamic acid 1
? , alanine 12, cystine 14. 10f of silica gel was placed in a three-electrode flask, stirred at 100°C for 2 hours, and then cooled. Furthermore, the reactants are 302 water: glycerin = 1
: Add the mixture of 1 and stir at 50℃ for 1 hour,
Solid matter was removed by door to door to obtain a coffee flavor substance having a roasted aroma with a light roast feeling.

Comparative Example 1 In Example 1, silica gel was not added and instead 30
Add the 1:1 mixture of water and glycerin from Step 2 and heat to 100°C.
After stirring at 50° C. for 2 hours, the mixture was cooled, further stirred at 50° C. for 1 hour, and then cooled to obtain a coffee flavor substance.

The flavor substances obtained in Example 1 and Comparative Example 1 were each diluted 50 times with water, and a panel of 20 well-trained inspectors conducted a sensory test for flavor and palatability. As shown in Table 1, it was determined that the coffee flavor material of Example 1 was preferable.

Table 1 Example 2 Glucose 60t1 Aspartic acid 8t, Leucine 6
? , phenylalanine 3t, lysine hydrochloride 5t1 glutamine salt 52, proline 3? , activated carbon 90? After putting the mixture in an autoclave and stirring it at 120℃ for 1 hour,
Cooled.

After cooling, add 100t of propylene glycol to 40°C again.
After heating and stirring for 30 minutes, the solids were removed under reduced pressure using a Buchner funnel to obtain a cocoa flavor substance with a sweet roasted taste.

Comparative Example 2 In Example 1, activated carbon was not added, instead 100 f of propylene glycol was added, stirred at 120°C for 1 hour, cooled, further stirred at 40°C for 30 minutes, and then filtered under reduced pressure using a Buchner funnel. A cocoa flavor substance was obtained.

The cocoa flavor substances obtained in Example 2 and Comparative Example 2 were each diluted 50 times with water, and a panel of 20 well-trained inspectors conducted a sensory test for flavor and palatability. As shown in Table 2, it was determined that the cocoa flavor material of Example 2 was preferable.

Table 2 Example 3 Glucose 10? , alanine 49. Leucine 32, Threonine 29. Tyrosine 2t, lysine hydrochloride 49. Keystone earth 302 was placed in a three-electrode flask, stirred at 130° C. for 2 hours under a stream of nitrogen gas, and then cooled. Further, 20 f of refined coconut oil was added to the reaction mixture, stirred at 60° C. for 30 minutes, and then cooled. The solid matter was filtered under reduced pressure using a Buchner funnel to obtain a nutty flavor substance having a roasty aroma.

Comparative Example 3 In Example 3, cinnabar earth was not added and instead 20
The refined coconut oil from step 2 was added, stirred at 130° C. for 2 hours, cooled, further stirred at 60° C. for 30 minutes, cooled, and filtered under reduced pressure using a Buchner funnel to obtain a nut flavor substance.

The nut flavor substances obtained in Example 3 and Comparative Example 3 were each dispersed in 500 times the amount of warm water, and a sensory test was conducted on flavor and palatability by a panel of 20 well-trained inspectors. . As shown in Table 3, the nut flavor material of Example 3 was determined to be preferable.

Table 3 Example 4 Fructose 5? , Glucose 5? , glutamic acid 32
, aspartic acid 21. cystine 4y1 arginine 1y
, methionine 1? , Alumina 20F was placed in a three-electrode flask, stirred at 130°C for 30 minutes, and then cooled. Further, safflower oil 21 was added to the reaction mixture, stirred at 50°C for 1 hour, cooled, and solid matter was filtered off to obtain a roasted chicken flavor substance.

Comparative Example 4 Safflower oil 202 was added instead of alumina in Example 4, stirred at 130°C for 30 minutes, cooled, further stirred at 50°C for 1 hour, cooled, and solids were filtered out. , yielded a roasted chicken flavor substance.

The roasted chicken flavor substances obtained in Example 4 and Comparative Example 4 were each dispersed in 500 times the volume of warm water, and a panel of 20 well-trained inspectors conducted a sensory test for flavor and palatability. As shown in Table 4, the roasted chicken flavor material of Example 4 was determined to be preferable.

Table 4

Claims (3)

[Claims] (1) When producing flavor additives by heating and reacting amino acids or derivatives thereof with sugar, in the presence of powder or granules that are incompatible with the reaction raw materials used for the reaction and do not melt under the reaction temperature conditions. A method for producing a flavor additive, characterized in that the process is carried out in a non-solution system. (2) The method according to claim 1, wherein the powder or granule is a porous inorganic powder or granule. (3) After the reaction, the system is treated with water, an organic solvent, and/or animal and vegetable oils to extract the reaction products attached to or adsorbed on the powder, and then the powder is filtered to obtain the reaction products. A method according to claim 1, comprising: