TW202320647A - Hydrogenated odor imparting agent, method for producing same, method for imparting hydrogenated odor to foodstuffs, use of oxidized products for imparting hydrogenated odor to foodstuffs, and foodstuffs containing hydrogenated odor imparting agent - Google Patents

Abstract

Provided are a hydrogenated odor imparting agent containing as an active ingredient a compound other than (E)-6-octenal that can impart a hydrogenated odor to foodstuffs; a method for producing the aforesaid hydrogenated odor imparting agent; a method for imparting a hydrogenated odor to foodstuffs, including the step of adding a hydrogenated odor imparting agent to the foodstuffs; use of the above compound for imparting a hydrogenated odor to foodstuffs; and foodstuffs containing the aforesaid compound. The hydrogenated odor imparting agent contains as an active ingredient an oxidized product of fatty acids with 18 carbon atoms that have a hydroxyl group or an oxo group at the 10<SP>th</SP> position, derivatives of the fatty acids or salts thereof. The method for producing the hydrogenated odor imparting agent includes the step of oxidizing the compound. The method for imparting a hydrogenated odor to foodstuffs includes the step of adding an oxidized product of the compound to the foodstuffs. The oxidized product of the compound is used to impart a hydrogenated odor to the foodstuffs, and the foodstuffs contain the oxidized product of the compound.

Description

Hydrogenated flavor-imparting agent, method for producing same, method for imparting hydrogenated flavor to food, use of oxidized product for imparting hydrogenated flavor to food, and food containing hydrogenated flavor-imparting agent

The present invention relates to a hydrogenated flavor-imparting agent, a method for producing the same, a method for imparting a hydrogenated flavor to food, use of an oxidized product for imparting a hydrogenated flavor to food, and a food containing the hydrogenated flavor-imparting agent.

Hydrogenated oil has been widely used in oily foods such as margarine, shortening, butter, pastries such as donuts, cakes, chocolates, and frying oil for other foods.

Hydrogenated oil is prepared by adding about 160 to Manufactured at a temperature of about 180°C, hydrogenation in the presence of a nickel catalyst, etc. Hydrogenated oil is a solid edible processed oil at room temperature. Because it can be produced from cheap oil raw materials and has stable quality, it can be used in large quantities and in a wide range of applications.

Hydrogenated oils have an odor called "hydrogenated smell". As a result of food processing such as heating food containing hydrogenated oil, it is considered that there is a tendency to impart a viscous and elegant sweetness to brewing. For example, when oil containing hydrogenated oil is used as the frying oil for donuts, it can impart a sweet cooking feeling to the finished donuts, thereby stimulating consumers' willingness to purchase and providing sufficient satisfaction when eating . In addition, the unique richness and sweetness of products using hydrogenated oils such as margarine and fat spread can enhance the flavor of these products.

On the other hand, hydrotreatment is known to increase the trans fatty acid content of oils and fats. Recently, as a result of the U.S. federal government's announcement of labeling guidelines that trans fatty acids may be the cause of arteriosclerosis, etc., the use of hydrogenated oils containing a large amount of trans fatty acids has become more and more disliked, and effective measures such as the development of alternative oils and fats are strongly expected. solution.

Cited Document 1 describes a hydrogenated oil flavoring agent composed of (E)-6-octenal.

[Prior Art Literature]

[Patent Document]

[Patent Document 1] International Publication No. 2014/167957

However, in Cited Document 1, there is only a description that hydrogenated oil flavor can be imparted to oil and fat products with reduced hydrogenated oil, but there is no sufficient description on the aspect of imparting hydrogenated oil flavor to oil and fat products without hydrogenated oil.

Therefore, in addition to (E)-6-octenal, there is also a demand for a hydrogenated odor imparting agent that can impart a hydrogenated odor to fats and oils as an active ingredient.

The problem to be solved by the present invention is to provide a hydrogenated flavor imparting agent which can impart a hydrogenated flavor to food as an active ingredient other than (E)-6-octenal. In addition, another problem to be solved by the present invention is to provide a method for producing the hydrogenated flavor imparting agent, a method for imparting a hydrogenated flavor to food including the step of adding the hydrogenated flavor imparting agent to food, and a method for imparting hydrogenated flavor to food. Use of the above compound for taste, and food containing the above hydrogenated taste imparting agent.

As a result of intensive research, the inventors of the present invention found that the oxidized product of a C18 fatty acid having a hydroxyl group or a pendant oxygen group at the 10-position, its derivatives, or a salt thereof can impart a hydrogenated taste to foods. The present invention has been accomplished based on these findings.

The above-mentioned problems of the present invention are solved by the following means.

The present invention is a hydrogenated odor-imparting agent, which contains, as an active ingredient, a C18 fatty acid having a hydroxyl group or a pendant oxygen group at the 10-position or its derivatives or their salts after oxidation treatment.

The aforementioned fatty acid preferably contains 10-hydroxy-12-octadecenoic acid.

The above oxidation treatment is preferably heat oxidation treatment.

The peroxide value of the oxidized product is preferably not less than 0.5 and not more than 200.

The hydrogenated flavor-imparting agent preferably imparts at least one flavor selected from the group consisting of sweetness and milky taste.

The present invention relates to a method for producing a hydrogenated flavor imparting agent, comprising the step of oxidizing a fatty acid having 18 carbon atoms having a hydroxyl group or a pendant oxygen group at the 10-position, or a derivative thereof, or a salt thereof.

The present invention is a method for imparting a hydrogenated flavor to food, comprising the step of adding the aforementioned hydrogenated flavor imparting agent to the food.

The present invention relates to the use of oxidation-treated fatty acid with 18 carbon atoms having a hydroxyl group or a pendant oxygen group at the 10-position or its derivatives or salts thereof for imparting a hydrogenated taste to foods.

The present invention is a food comprising the aforementioned hydrogenated taste-imparting agent.

The present invention provides a hydrogenated flavor-imparting agent which contains, as an active ingredient, a compound capable of imparting a hydrogenated flavor to food other than (E)-6-octenal. In addition, the present invention relates to a method for producing the hydrogenated flavor imparting agent, a method for imparting a hydrogenated flavor to food including the step of adding the hydrogenated flavor imparting agent to food, and a use of the above-mentioned compound for imparting a hydrogenated flavor to food, and Foods containing the hydrogenated taste-imparting agent.

FIG. 1 presents the structural diagram of various fatty acids in the metabolic pathway of α-linolenic acid through intestinal flora.

FIG. 2 shows the structural diagram of various fatty acids in the metabolic pathway of linoleic acid through intestinal flora.

FIG. 3 presents the structural diagram of various fatty acids in the metabolic pathway of γ-linolenic acid through intestinal flora.

4 is a graph showing the relationship between the heating and oxidation treatment time of the oxidized product of HYA-50 contained in the frying oil of Test Example 4 and the flavor of donuts fried in the frying oil.

5 is a graph showing the relationship between the heating and oxidation treatment time of the oxidized product of HYA-82 contained in the frying oil of Test Example 5 and the flavor of donuts fried in the frying oil.

6 is a graph showing the relationship between the heating and oxidation treatment time of the oxidized product of HYA-82 contained in the frying oil of Test Example 5 and the flavor of donuts fried in the frying oil.

Fig. 7 is a graph showing the relationship between the heat oxidation treatment time of the oxidized product of HYA-50 contained in the biscuit of Test Example 7 and the flavor of the biscuit.

The present invention will be described in further detail.

Moreover, when an upper limit and a lower limit of a numerical range are shown in this specification, the upper limit and the lower limit can be combined suitably, and the numerical range obtained by this is also disclosed.

[Hydrogenated odor imparting agent]

The hydrogenated flavor-imparting agent of the present invention is a fatty acid with 18 carbon atoms (hereinafter also referred to as "C18 fatty acid") having a hydroxyl group or a pendant oxygen group at the 10-position, or a derivative thereof, or a salt thereof (hereinafter also referred to as "C18 fatty acid"). "C18 fatty acid, etc.") oxidation-treated product as an active ingredient.

In the present invention, imparting a hydrogenated taste refers to imparting a special sweetness, milky taste (fragrance) or a flavor feeling of a special sweetness or milky taste when food is eaten. The hydrogenated flavor-imparting agent of the present invention is preferably for imparting at least one flavor selected from the group consisting of sweetness and milky taste to food.

The C18 fatty acid and the like are not limited to specific fatty acids and the like. Examples of C18 fatty acids include various fatty acids in the metabolic pathway of α-linolenic acid via intestinal flora (see FIG. 1 ), Various fatty acids in the metabolic pathway of linolenic acid through intestinal flora (see Figure 2), various fatty acids in the metabolic pathway of γ-linolenic acid through intestinal flora (see Figure 3), etc.

C18 fatty acids and the like preferably include 10-hydroxy-12-octadecenoic acid or its derivatives or their salts (hereinafter also referred to as "octadecenoic acid and the like").

There are cis-form and trans-form in octadecenoic acid and the like. 10-Hydroxy-cis-12-octadecenoic acid (HYA) exhibits the formula as depicted in FIG. 2 . HYA can be produced by the method for producing pendant fatty acid disclosed in International Publication No. 2013/168310. In addition, HYA is already commercially available, and examples of such commercially available products include HYA-50 manufactured by Nitto Pharmaceutical Co., Ltd., and the like.

The derivatives of 10-hydroxy-12-octadecenoic acid have 1 or 2 independent substituents at positions 2 to 9 and 11 to 17 of 10-hydroxy-12-octadecenoic acid. Derivatives of C18 fatty acids other than 10-hydroxy-12-octadecenoic acid also have 1 or 2 independent substituents at the position where no hydroxyl group or pendant oxygen group is bonded. The two substituents may be mutually the same or different. Two substituents may be linked together to form a ring. In addition, rings such as alicyclic rings, aromatic rings, and heterocyclic rings can be further condensed to form condensed rings. In addition, as a derivative of C18 fatty acid including 10-hydroxy-12-octadecenoic acid, the carboxyl group at the 1-position can be esterified with a compound represented by R-OH. Also, derivatives of C18 fatty acids including 10-hydroxy-12-octadecenoic acid may be compounds having the above-mentioned substituents and esterification of the above-mentioned carboxyl groups.

The hydrogenated odor-imparting agent of the present invention contains one or two or more oxidation-treated products such as the above-mentioned C18 fatty acids as active ingredients.

The above substituents are not particularly limited, but are preferably alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl (aromatic heterocyclic) or aliphatic heterocyclic.

The alkyl group is preferably an alkyl group with a carbon number of 1 to 36, more preferably an alkyl group with a carbon number of 1 to 18, more preferably an alkyl group with a carbon number of 1 to 6, and an alkyl group with a carbon number of 1 to 3. . As an alkyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group etc. are mentioned, for example.

The cycloalkyl group is preferably a cycloalkyl group having 3 to 10 carbon atoms, more preferably a cycloalkyl group having 3 to 8 carbon atoms. As a cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group etc. are mentioned, for example.

The alkenyl group is preferably an alkenyl group having 2 to 36 carbon atoms, more preferably an alkenyl group having 2 to 18 carbon atoms, and more preferably an alkenyl group having 2 to 6 carbon atoms. As an alkenyl group, a vinyl group, an allyl group, a butenyl group, a hexenyl group etc. are mentioned, for example.

The alkynyl group is preferably an alkynyl group with a carbon number of 2 to 36, more preferably an alkynyl group with a carbon number of 2 to 18, and more preferably an alkynyl group with a carbon number of 2 to 4. As an alkynyl group, an ethynyl group, a butynyl group, a hexynyl group etc. are mentioned, for example.

The aryl group is preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. As an aryl group, a phenyl group is mentioned, for example.

唑環、噻唑環、三唑環、呋喃環、噻吩環、苯并咪唑環、苯并

唑環、苯并噻唑環、二氫吲哚(或吲哚啉)環、吲唑環的各環基。此外，6員環的芳香族雜環及含有6員環的芳香族雜環之縮合雜環，可列舉例如：吡啶環、嘧啶環、吡嗪環、三嗪環、喹啉環、喹唑啉環的各環基。 When the aromatic heterocyclic ring is a condensed ring, in addition to the group formed only by the monocyclic aromatic heterocyclic ring, it also includes other rings condensed in the monocyclic aromatic heterocyclic ring, such as aromatic hydrocarbon rings, aliphatic hydrocarbon rings Or a group formed by condensing a heterocyclic ring. The number of ring-constituting heteroatoms constituting the aromatic heterocycle may be at least one, and the heteroatoms are preferably nitrogen atoms, oxygen atoms, and sulfur atoms. In addition, the number of ring members of the aromatic heterocycle is preferably 3 to 8 membered rings, more preferably 5 membered rings or 6 membered rings. The carbon number of the aromatic heterocycle is preferably from 5 to 24, more preferably from 5 to 18, and more preferably from 5 to 10. The carbon number of the aromatic heterocycle is preferably from 5 to 24, more preferably from 5 to 18, and more preferably from 5 to 10. 5-membered aromatic heterocycles and condensed heterocycles containing 5-membered aromatic heterocycles include, for example, pyrrole rings, imidazole rings, pyrazole rings,

Azole ring, thiazole ring, triazole ring, furan ring, thiophene ring, benzimidazole ring, benzo

Each ring group of an azole ring, a benzothiazole ring, an indoline (or indoline) ring, and an indazole ring. In addition, 6-membered aromatic heterocycles and condensed heterocycles containing 6-membered aromatic heterocycles include, for example, pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, quinoline rings, and quinazoline rings. Each ring group of the ring.

烷環、硫雜環己烷環，γ-丁內酯等。 The aliphatic heterocyclic group includes a monocyclic group composed only of an aliphatic heterocyclic ring and a group formed by condensing an aliphatic heterocyclic ring with another ring (for example, an aliphatic ring) condensed. The number of heteroatoms constituting the aliphatic heterocyclic ring may be at least one, and the heteroatoms are preferably nitrogen atoms, oxygen atoms, and sulfur atoms. In addition, the number of ring members of the aliphatic heterocyclic ring is preferably 3 to 8 membered rings, more preferably 5 membered rings or 6 membered rings. The carbon number of the aliphatic heterocycle is preferably from 0 to 24, more preferably from 1 to 18, more preferably from 2 to 10, and particularly preferably from 3 to 5. Preferred specific examples of aliphatic heterocyclic rings include pyrrolidine rings, oxolane rings, thiolane (thiolane) rings, piperidine rings, tetrahydrofuran rings, and oxane rings (tetrahydrofuran rings). Hydropyran ring), thiane (thiane) ring, piperazine ring, morpheline ring, quinuclidine, pyrrolidine ring, azetidine ring, oxetane ring, aziridine ring two

Alkane ring, thiacyclohexane ring, γ-butyrolactone, etc.

Examples of the above-mentioned substituents include the following groups.

Alkoxy (preferably an alkoxy group with a carbon number of 1 to 20, such as methoxy, ethoxy, isopropoxy, benzyloxy, etc.),

Aryloxy group (preferably an aryloxy group with a carbon number of 6 to 26, such as phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, etc.),

Heterocyclic oxy group (a group in which the above-mentioned heterocyclic group is bonded to the -O- group),

Alkoxycarbonyl (preferably an alkoxycarbonyl group with a carbonyl number of 2 to 20, such as ethoxycarbonyl, 2-ethylhexyloxycarbonyl, etc.),

Aryloxycarbonyl (preferably aryloxycarbonyl with 6 to 26 carbons, such as phenoxycarbonyl, 1-naphthyloxycarbonyl, 3-methylphenoxycarbonyl, 4-methoxyphenoxy carbonyl, etc.),

Amino groups (preferably those with carbon numbers ranging from 0 to 20 include amine groups, alkylamine groups, arylamine groups, such as amine groups (-NH ₂ ), N,N-dimethylamino groups, N,N- Diethylamino, N-ethylamino, anilino, etc.),

Sulfamoyl (sulfamoyl) (preferably sulfamoyl with a carbon number of 0 to 20, such as N,N-dimethylsulfamoyl, N-phenylsulfamoyl, etc.),

Acyl (including alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, heterocyclic carbonyl, preferably an acyl group with a carbon number of 1 to 20, such as acetyl, propionyl, butyryl, octyl, cetyl, acryl, methacryl, crotonyl, benzoyl, naphthyl, nicotyl, etc.),

Acyloxy (acyloxy) (including alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, arylcarbonyloxy, heterocyclic carbonyloxy, preferably acyloxy with a carbon number of 1 to 20 groups such as acetyloxy, propionyloxy, butyryloxy, octyloxy, hexadecyloxy, acryloxy, methacryloxy, crotonyloxy, benzoyloxy base, naphthyloxy, nicotinyloxy, etc.),

Aryloxy group (preferably an aryloxy group with a carbon number of 7 to 23, such as benzoyloxy group, etc.),

Aminoformyl group (preferably a carbamoyl group with a carbon number of 1 to 20, such as N,N-dimethylaminoformyl, N-phenylaminoformyl, etc.),

Acylamino group (preferably an acylamino group with carbon number of 1 to 20, such as acetylamino group, benzoylamino group, etc.),

Alkylthio (preferably alkylthio with 1 to 20 carbons, such as methylthio, ethylthio, isopropylthio, benzylthio, etc.),

Arylthio (preferably arylthio with 6 to 26 carbons, such as phenylthio, 1-naphthylthio, 3-methylphenylthio, 4-methoxyphenylthio, etc.),

Heterocyclic thio group (a group in which the above-mentioned heterocyclic group is bonded to the -S- group),

Alkylsulfonyl (preferably an alkylsulfonyl group with a carbon number of 1 to 20, such as methylsulfonyl, ethylsulfonyl, etc.),

Arylsulfonyl (preferably an arylsulfonyl group with a carbon number of 6 to 22, such as benzenesulfonyl, etc.),

Alkylsilyl (preferably an alkylsilyl with a carbon number of 1 to 20, such as monomethylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, etc.),

Arylsilyl group (preferably an arylsilyl group with a carbon number of 6 to 42, such as triphenylsilyl, etc.),

Phosphoryl (preferably a phosphate group with a carbon number of 0 to 20, such as -OP(=O)(R ^P ) ₂ ),

Phosphonyl (phosphonyl) (preferably a phosphoryl group with a carbon number of 0 to 20, such as -P(=O)(R ^P ) ₂ ),

Phosphinyl (preferably a phosphinyl group with a carbon number of 0 to 20, such as -P(R ^P ) ₂ ), sulfo group (sulfonic acid group), carboxyl group, hydroxyl group, mercapto group, cyano group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom, etc.). R ^P is a hydrogen atom or a substituent (preferably a group selected from the above substituents).

In addition, each of the groups listed as these substituents may be further substituted with the above-mentioned substituents.

R of the compound represented by the above-mentioned R-OH is not particularly limited, but the above-mentioned alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl (aromatic heterocyclic group) or aliphatic heterocyclic group is good. In addition, the compound represented by the above-mentioned R—OH may be a polyhydric alcohol having two or more hydroxyl groups. Examples of the polyhydric alcohol include dihydric alcohols such as ethylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, diethylene glycol, dipropylene glycol, and benzene glycol, glycerin, Trihydric alcohols such as trimethylolethane, trimethylolpropane, and 3-methylpentane-1,3,5-triol, tetrahydric alcohols such as neopentylthritol and diglycerin, and adonitol , arabitol (arabitol), xylitol, triglycerin and other 5-hydric alcohols, diperythritol, mannitol, D-sorbitol, iditol, inositol, galactitol, talose, arabitol 6-hydric alcohols such as sugar, etc.

When the derivative of C18 fatty acid is a compound obtained by esterifying the carboxyl group of C18 fatty acid with polyhydric alcohol, the base of C18 fatty acid is esterified with at least one hydroxyl group of polyhydric alcohol. The unesterified hydroxyl groups of polyhydric alcohols can be esterified with carboxylic acids other than C18 fatty acids.

A preferred C18 fatty acid ester is an ester in which the above-mentioned carboxyl groups are esterified with 1 to 3-hydric alcohols. More preferred C18 fatty acid esters are esters in which the above-mentioned carboxyl groups have been esterified with methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, or glycerol. Still more preferable C18 fatty acid esters are C18 fatty acid methyl esters, C18 fatty acid ethyl esters, mono-C18 fatty acid glycerides, di-C18 fatty acid glycerides, and tri-C18 fatty acid glycerides.

Salts of C18 fatty acids or their derivatives include metal salts and organic alkali salts. The salts are preferably metal salts.

The said metal salt contains at least 1 sort(s) chosen from the group which consists of an alkali metal salt and an alkaline earth metal salt. The alkali metal system contains at least one selected from the group consisting of lithium, sodium and potassium. The alkaline earth metal system includes at least one selected from the group consisting of magnesium, calcium, and barium.

The above-mentioned organic base is not particularly limited. An aromatic amine, an aliphatic amine, etc. are mentioned as this organic base. Preferred organic bases include: pyridine, lutidine, collidine, triethylamine, diethylamine, N,N-diisopropylethylamine , N,N-Diisopropylamylamine, Morphine, Piperidine and Pyrrolidine, etc. More preferable organic bases include, for example, pyridine, triethylamine and piperidine.

The effect of the present invention can be considered to be derived from the oxidation treatment of the common structure of C18 fatty acid or its derivatives or their salts. Therefore, a hydrogenated flavor imparting agent containing an oxidized product of a C18 fatty acid derivative or its salt as an active ingredient has the same effect as a hydrogenated flavor imparting agent containing an oxidized product of a C18 fatty acid as an active ingredient.

The peroxide value (hereinafter also referred to as "POV") of the above-mentioned oxidized products is preferably less than 200, more preferably less than 150, more preferably less than 100, more preferably less than 80, and most preferably less than 60. . In addition, the POV is preferably 0.5 or higher, more preferably 1 or higher, more preferably 5 or higher, even more preferably 10 or higher, and particularly preferably 15 or higher. POV is measured in accordance with, for example, "Standard Oils and Fats Analysis Test Method 2.5.2 Peroxide Value" (Japan Oil Chemicals Association).

The production method of the hydrogenated flavor imparting agent of the present invention includes the step of oxidizing C18 fatty acid and the like.

The above-mentioned oxidation treatment method is not particularly limited, but heat oxidation treatment is preferred. The heating temperature of heating oxidation treatment is preferably above 70°C and below 200°C, more preferably above 70°C and below 180°C, more preferably above 80°C and below 150°C, more preferably above 80°C and below 120°C. Above 90°C and below 110°C is particularly preferred. The heating time of the heating oxidation treatment is preferably from 1 hour to 150 hours, more preferably from 5 hours to 130 hours, more preferably from 10 hours to 100 hours, and more preferably from 20 hours to 90 hours. Take 25 hours More than 80 hours is better, more than 30 hours and less than 70 hours are especially good, and more than 30 hours and less than 60 hours are the best.

In addition, the above-mentioned oxidation treatment method may be an oxidation treatment that is stored at room temperature along with C18 fatty acids and the like.

Also, the heating method can be performed using a general method. The heating method is not particularly limited, as long as it is heated by an ordinary method, such as electric heating, direct flame combustion, electromagnetic induction heating, microwave, steam, hot air and other heating means installed in a container such as a pot.

During the above-mentioned oxidation treatment, oxygen may not be supplied, or oxygen may be supplied. The supply source of oxygen may be oxygen alone or oxygen containing air or the like, preferably air. The raw material is preferably stirred.

When the POV of the above-mentioned oxidized product is observed over time, it usually rises first, reaches the peak and then gradually becomes smaller than the peak. The hydrogenated flavor-imparting agent of the present invention contains the above-mentioned oxidized substance, and its POV after peaking over time is preferably 200 or less, more preferably 150 or less, more preferably 100 or less, and even more preferably 80 or less. , preferably below 60. In addition, the POV after reaching the peak is preferably 1 or more, more preferably 5 or more, more preferably 10 or more, and particularly preferably 15 or more.

The hydrogenated odor-imparting agent of the present invention may appropriately contain any components other than the above-mentioned oxidized products. Examples of any components include emulsifiers, fragrances, sour agents, sweeteners, seasonings, antioxidants, antifoaming agents, colorants, pH regulators, thickening stabilizers, food preservatives, and physiologically active substances.

[Application of oxidation treatment]

The hydrogenated flavor-imparting agent of the present invention containing the oxidized product as an active ingredient can be added to foods to impart at least one flavor selected from the group consisting of unique sweetness and milky taste to foods. The addition method is not limited. For example, the oxidized product can be directly added to food, or the oxidized product can be dissolved in edible oil to make flavor oil and then added to food. In addition, edible fats and oils to which the hydrogenated taste-imparting agent of the present invention is added can be used for frying food, and at least one flavor selected from the group consisting of unique sweetness and milky taste can be imparted to the fried food. .

In addition, the food to which the hydrogenated flavor-imparting agent of the present invention is added is not particularly limited, and examples thereof include:

Edible oil;

Margarine, spreads, butter, mayonnaise (mayonnaise), sauces, butter and other oil-processed foods (refers to foods containing edible oils as raw materials);

Milk, soy milk (soy milk), milk drinks, lactic acid drinks, sports drinks and other beverages;

Sweets such as donuts, biscuits, pies, cakes, madeleines, jelly, pudding, mousse, chocolate and fudge;

Bread such as sweet bread;

Noodles such as buckwheat noodles, udon noodles, ramen noodles and pasta;

Fried rice and other rice;

Dairy products such as cheese, butter, yogurt;

Processed meat foods such as hamburger meat, ham, and sausage;

Chikuwa, fish cake and other aquatic processed food;

Soup categories such as corn soup, clear soup, and thick soup;

Chinese monosodium glutamate, barbecue sauce and other seasonings and sauces;

Frozen food, stew, fry, grill, health food, etc. The food to which the hydrogenated flavor-imparting agent of the present invention is added is preferably at least one kind of edible oil and fat processed food, more preferably edible oil.

<Edible oil>

The above-mentioned edible oils and fats are general edible oils and fats used in the food field. Examples of the above-mentioned edible fats and oils include:

Canola oil, soybean oil, sunflower oil, cottonseed oil, peanut oil, rice oil, corn oil, safflower oil, olive oil, kapok oil, sesame oil, perilla oil, linseed oil, evening primrose oil, palm oil, shea butter (shea butter), sal butter, cocoa butter, coconut oil, palm kernel oil and other vegetable oils,

Lard, butter, chicken fat, milk fat, fish oil and other animal fats,

Synthetic oils such as medium-chain fatty acid triglycerides. In addition, processed fats and oils obtained by subjecting the above-mentioned vegetable fats and oils, animal fats and synthetic fats to at least one of hardening, fractionation and transesterification can also be used. These oils and fats can be used alone or in combination. Wherein, the above-mentioned edible fats and oils are preferably at least one of rapeseed oil, soybean oil, palm oil, corn oil, sunflower oil, olive oil, cottonseed oil, rice oil, safflower oil, lard and tallow. At least one of rapeseed oil, soybean oil, palm oil, corn oil and rice oil is more preferred.

<Auxiliary material>

In addition to the above-mentioned oxidized products and edible oils and fats, the edible oils and fats or oil-processed foods to which the above-mentioned hydrogenated flavor imparting agents are added may contain dairy products, thickening stabilizers, salt, salt flavoring agents such as potassium chloride, acetic acid, lactic acid, Acidulants such as gluconic acid, sugars, sweeteners, coloring agents, antioxidants agent, vegetable protein, egg and various egg processed products, essence, flavoring agent, pH regulator, food preservative, fruit, fruit juice and spices, etc.

<Fried food>

The fried food fried with the hydrogenated flavor-imparting agent of the present invention or the edible oil and fat added with the hydrogenated flavor-imparting agent is not particularly limited, but for example: donuts, fried bread, curry bread, piroshki ( piroshki), American hot dogs, crispy croutons, honey twist, rice crackers, snacks, fried food, tonkatsu, chicken cutlet, fried chicken, fried fish, tempura, croquette, croquette, fried French fries, chicken nuggets, hash browns, fried tofu, instant noodles, etc.

[Example]

Hereinafter, the present invention will be described in more detail according to the examples, but the present invention is not limited to the scope of these examples.

In Examples and Comparative Examples, the flavors of various foods were evaluated according to the following criteria 1 or 2.

-Evaluation criteria for food 1-

4: Stronger aroma/taste/thickness than the control example is imparted.

3: More aroma/taste/thickness than the control example was imparted.

2: Less aroma/taste/thickness than the control example is imparted.

1: Aroma/taste/thickness equivalent to those of the control example.

-Evaluation criteria for food 2-

3: Stronger aroma/taste/thickness than the control example is imparted.

2: More aroma/taste/thickness than the control example was imparted.

1: Less aroma/taste/thickness than the control example is imparted.

0: Aroma/taste/consistency equivalent to that of the control example was imparted.

Test example 1

Tear open the soft capsule coated with HYA-50 (manufactured by Nitto Pharmaceutical Co., Ltd., the purity of HYA is about 50%), and take out the contents with a spatula. HYA-50 taken out from the capsule was put into a test tube (manufactured by Metrohm Japan Co., Ltd.) of the Rancimat method at a rate of 0.5 g. Rancimat type 743) was heated to 98 °C. The POV of the oxidized product of HYA-50 was measured over time, and 4 panelists observed the odor of the oxidized product. POV is measured in accordance with "Standard Oils and Fats Analysis Test Method 2.5.5 Peroxide Value" (Japan Oil Chemistry Association). In addition, HYA-50, which has been oxidized by heating for 0 hours, is considered to have been oxidized following storage at room temperature. The results are shown in Table 1.

[Table 1]

After 20 hours from the start of the heat oxidation treatment, the POV reached a peak value, and then the POV continued to decrease. After 35 hours from the start of the thermal oxidation treatment, the odor of the thermal oxidation-treated product was smelled, and the thermal oxidation-treated product gave off a frankincense aroma.

Test Example 2: Examples 1 to 3

The oxidized product obtained by heating and oxidizing HYA-50 in Test Example 1 for 50 hours was diluted with MCT oil (Coconard MT manufactured by Kao Co., Ltd.) to 12% by mass, and the diluted HYA-50 was added to 600 g of palm In oil (Fly Fat MS manufactured by J-Oil Mills Co., Ltd.), HYA was adjusted to the concentration shown in Table 2, and the frying oil of each Example was prepared. The frying oil of the comparative example used the aforementioned palm oil. Donut dough was prepared using the donut ball mixture manufactured by Nippon Shokken Co., Ltd., and 30 g of the dough was rolled into a ball, and fried in each frying oil at 160° C. for 5 minutes to form each donut. Six judges tasted each donut, evaluated the flavor of each donut according to the aforementioned criterion 1, and calculated an average score. The results are presented in Table 2.

[Table 2]

The higher the concentration of the oxidized product obtained by heat oxidation treatment in the frying oil, the stronger the milky aroma, milky taste and sweetness of the donuts fried in the frying oil.

Test Example 3: Examples 4 and 5

In Test Example 1, the oxidized product obtained by heating and oxidizing HYA-50 for 50 hours was diluted with MCT oil (Coconard MT manufactured by Kao Co., Ltd.) to 10% by mass, and the diluted HYA-50 was added to In 300 g of palm oil (Fly Fat MS manufactured by J-Oil Mills Co., Ltd.), HYA was adjusted to the concentration shown in Table 3, and the frying oil of each Example was prepared. The frying oil of the comparative example used the aforementioned palm oil. Donut dough was prepared using the donut ball mixture manufactured by Nippon Shokken Co., Ltd., and 20 g of the dough was rolled into a ball, and fried at 160° C. for 5 minutes with each frying oil to prepare each donut.

11 panelists tasted each donut, and evaluated the flavor of each donut by the consensus of all panelists in accordance with the aforementioned criterion 1. The results are presented in Table 3.

[table 3]

The higher the concentration of the oxidized product obtained by heat oxidation treatment in the frying oil, the stronger the milky aroma, milky taste, sweetness and sweetness of the donuts fried in the frying oil.

Test Example 4: Examples 6 to 13

Each of HYA-50 obtained in Test Example 1 without heat oxidation treatment or heat oxidation treatment was diluted to 10% by mass with MCT oil (Coconard MT manufactured by Kao Co., Ltd.), and 0.04 mass % and 1.2 g of diluted HYA-50 were added to 300 g of palm oil (Fly Fat MS manufactured by J-Oil Mills Co., Ltd.) so that the HYA concentration became 0.02 mass %, and the frying oil of each example was prepared . The frying oil of the comparative example used the aforementioned palm oil. Donut dough was prepared using the donut ball mixture manufactured by Nippon Shokken Co., Ltd., and 20 g of the dough was rolled into a ball, and fried in each frying oil at 160° C. for 5 minutes to form each donut. Four judges tasted each donut, evaluated the flavor of each donut according to the aforementioned criterion 2, and calculated an average score. The results are shown in Table 4 and FIG. 4 .

[Table 4]

In Fig. 4, the 4 strips of each embodiment respectively present sweetness, sweetness, milky fragrance and milky taste from the left. The sweetness and milky taste of the donuts fried in the frying oil containing the oxidized product subjected to the heat-oxidized treatment for 50 to 70 hours are particularly strong.

Test Example 5: Examples 14 to 19

A 9:1 (mass ratio) mixed solvent of hexane and diethyl ether was passed through a Sep-Pack (registered trademark) Vac 35cc silica gel column (manufactured by Waters). Next, dissolve about 1.5 g of the same HYA-50 taken out of the soft capsule as above in 1 mL of a mixed solvent with the same composition as the aforementioned mixed solvent, and apply the resulting solution to the aforementioned silica gel column to obtain the same composition as the aforementioned mixed solvent. composition 200mL of mixed solvent was used to dissolve fatty acids other than HYA, and 200mL of diethyl ether was used to dissolve HYA to obtain HYA (HYA-82) with a purity of 82%.

The aforementioned HYA-82 was put into a test tube for the Rancimat method (manufactured by Metrohm Japan Co., Ltd.) at every 0.5 g. ) were heated to 98°C respectively. The POV of HYA-82 without heat oxidation treatment, HYA-82 with heat oxidation treatment for 10 hours, and HYA-82 with heat oxidation treatment for 50 hours was measured. POV is measured in accordance with "Basic Oils and Fats Analysis Test Method 2.5.5 Peroxide Value" (Japan Oil Chemicals Association). Also, it is considered that HYA-82 subjected to heat oxidation treatment for 0 hours is an oxidation treatment followed by storage at room temperature. The results are presented in Table 5.

[table 5]

Use 0.9 g of MCT oil (Coconard MT manufactured by Kao Co., Ltd.) to dilute the aforementioned 0.1 g of HYA-82 without heat oxidation treatment or heat oxidation treatment, and add the diluted HYA-82 to 300 g of palm oil (J - In Fly Fat MS manufactured by Oil Mills Co., Ltd., the HYA concentration was adjusted to 0.0016% by mass or 0.0164% by mass to prepare the frying oil of each Example. The frying oil of the comparative example used the aforementioned palm oil. Donut dough was prepared using the donut ball mixture manufactured by Nippon Shokken Co., Ltd., and 30 g of the dough was rolled into a ball, and fried in each frying oil at 160° C. for 5 minutes to prepare each donut. 4 judges tasted each donut, and according to the previous The flavor of each donut was evaluated according to the above-mentioned benchmark 2, and the average score was calculated. The results are shown in Table 6, Table 7, Fig. 5 and Fig. 6 . The results when the HYA concentration in the frying oil was 0.0016% by mass are shown in Table 6 and FIG. 5 , and the results when the concentration was 0.0164% by mass are shown in Table 7 and FIG. 6 .

[Table 6]

[Table 7]

In Figures 5 and 6, the 4 strips of each embodiment respectively present sweetness, sweetness, milky fragrance and milky taste from the left. It can be confirmed that the longer the heating and oxidation treatment time of HYA-82, and the The higher the concentration of the heat-oxidized oxidation products in the frying oil, the stronger the sweetness, sweetness, milky aroma and milky taste.

Test Example 6: Examples 20 and 21

In 220 g of shortening (using Facie, 100% vegetable oil manufactured by J-Oil Mills Co., Ltd.) dissolved in a bowl at 60° C., 0.044 g (HYA concentration in margarine: 0.01% by mass) obtained in Test Example 1 was added. ) or 0.088 g (HYA concentration in margarine: 0.02% by mass) of HYA-50 subjected to heat oxidation treatment for 50 hours and 0.108 g of flavor mixture (no raw materials derived from animals) were dissolved, added and stirred. Then, add 35.2 g of oat milk (sugar-free alpro oat milk manufactured by Danone Japan Co., Ltd.) to the bowl, stir it with a whipper to emulsify it, and soak it in the bowl filled with ice water Cool to precipitate crystals, and at the same time continue to stir with a whipper to prepare the margarine of each embodiment. The margarine of the comparative example was prepared in the same manner as the margarine of each of the aforementioned examples except that HYA-50 was not added.

Use a mixer to mix 210g of each margarine at low speed for 30 seconds, then at medium speed for 1 minute, then add 108g of refined sugar and 2g of salt, and then mix at medium speed for 1 minute, then add 12g of water at medium speed Stir for 1 minute, then add 300g of high-gluten flour and stir at low speed for 30 seconds to prepare the dough for each biscuit. Shape the aforementioned dough into a stick with a diameter of 4 cm, cool and harden in the refrigerator, and cut into a thickness of about 1 cm. Each of the cut doughs was baked for 18 to 20 minutes using a double-layer oven at 180° C. on the upper layer/180° C. on the lower layer to obtain each biscuit. 4 judges tasted each kind of biscuit, and evaluated the flavor of each kind of biscuit according to the aforementioned criterion 1 with the consensus of all judges. The results are presented in Table 8.

[Table 8]

Regardless of the concentration of HYA in the margarine, it was confirmed that the creamy aroma, milky taste, sweetness, sweetness, and richness of the biscuit made of the margarine containing the oxidized product subjected to heating and oxidation treatment were more rich than those without oxidation treatment Biscuits made of natural margarine are even stronger.

Test Example 7: Examples 22 to 27

0.05239 g (0.01% by mass of HYA in margarine) obtained in Test Example 1 was added to 220 g of shortening (using Facie manufactured by J-Oil Mills Co., Ltd.) dissolved in a bowl at 60°C. Stir after HYA-50 treated or heat oxidized for 20 to 70 hours. Then, 35.2 g of oat milk (sugar-free alpro oat milk manufactured by Danone Japan Co., Ltd.) was added to the bowl, stirred with a whisk to emulsify it, then soaked in a bowl filled with ice water and cooled to make Crystallization was carried out while stirring continuously with a whipper, and the margarine of each embodiment was prepared. The margarine of the comparative example was prepared in the same manner as the margarine of each of the above-mentioned examples except that HYA-50 was not added.

210 g of each margarine was stirred at a low speed for 30 seconds using a mixer, then stirred at a medium speed for 1 minute, then 108 g of refined sugar and 2 g of salt were added, and stirred for another 1 minute at a medium speed. Then add 12g of water and stir for 1 minute at medium speed, then add 300g of high-gluten flour and stir for 30 seconds at low speed to prepare various biscuit doughs. Shape the aforementioned dough into sticks with a diameter of 4 cm, cool and harden in the refrigerator, and cut into thicknesses of about 1 cm. The cut various doughs were baked for 18 to 20 minutes in the upper layer 180° C./lower layer 180° C. using a double-layer oven to obtain various biscuits. 4 judges tasted each kind of biscuit, and evaluated according to the above-mentioned evaluation standard 2, and calculated the average score. The results are shown in Table 9 and FIG. 7 .

[Table 9]

In Fig. 7, the four strips of each embodiment respectively present sweetness, sweetness, milky fragrance and milky taste from the left. The sweetness, sweetness, milky aroma and milky taste of biscuits containing margarine as a raw material of the oxidized product subjected to heat oxidation treatment for 35 to 70 hours are particularly strong.

Test Example 8: Examples 28 to 33

4 judges tasted the margarine of each embodiment prepared in Test Example 7 containing HYA-50 without heat oxidation treatment or heat oxidation treatment for 20 to 70 hours, and the margarine prepared in Test Example 7 The margarine of the control example, and according to the above-mentioned standard 1, evaluate the flavor of various margarines with the consensus of all judges. The results are presented in Table 10.

[Table 10]

It was confirmed that the margarine containing the oxidized product subjected to oxidative treatment has stronger sweetness, sweetness, and richness of taste than the margarine not containing the oxidized processed product.

Claims (9)

A hydrogenated flavor-imparting agent comprising, as an active ingredient, a fatty acid with 18 carbon atoms having a hydroxyl group or a pendant oxygen group at the 10-position, its derivatives, or an oxidized salt thereof. The hydrogenated flavor-imparting agent according to claim 1, wherein the fatty acid contains 10-hydroxy-12-octadecenoic acid. The hydrogenated odor imparting agent according to claim 1, wherein the oxidation treatment is heat oxidation treatment. The hydrogenated odor imparting agent according to claim 1, wherein the peroxide value of the oxidized product is 0.5 to 200. The hydrogenated flavor imparting agent according to any one of claims 1 to 4, which imparts at least one flavor selected from the group consisting of sweetness and milky taste. The method for producing a hydrogenated flavor-imparting agent according to any one of Claims 1 to 4, which comprises oxidizing a fatty acid having 18 carbon atoms having a hydroxyl group or a pendant oxygen group at the 10-position, or a derivative thereof, or a salt thereof processing steps. A method for imparting a hydrogenated flavor to food, comprising the step of adding the hydrogenated flavor imparting agent described in any one of Claims 1 to 4 in the food. A use of an oxidized product of a fatty acid having 18 carbon atoms having a hydroxyl group or a pendant oxygen group at the 10-position or its derivatives or salts thereof for imparting a hydrogenated taste to food. A food comprising the hydrogenated flavor-imparting agent described in any one of Claims 1 to 4.

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