HK1211437B - Agent for imparting hardened oil flavor - Google Patents

Description

Hardened oil flavor imparting agent

Technical Field

The present invention relates to a hardened oil flavor imparting agent. More specifically, the present invention relates to a hardened oil flavor-imparting agent containing (E) -6-octenal, a hardened oil flavor-imparting agent composition characterized by containing (E) -6-octenal as an active ingredient, and a hardened oil flavor-imparted fat product containing the hardened oil flavor-imparting agent or the hardened oil flavor-imparting agent composition.

Background

Hardened oils are widely used in fatty foods such as margarine, shortening, cream butter (butter cream) and the like; snacks such as doughnuts, cakes, chocolates, etc.; oil for frying other foods, etc. In addition, recently, the high melting point, heat resistance, oxidation stability, and the like of the microwave food are effectively utilized, and the crispy feeling and the deep-fried just-fried state of the food such as fried food contribute to the improvement of the quality of the microwave food.

The hardened oil is an edible processed oil which is solid at ordinary temperature, and is produced by a method of hydrogenating vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, palm kernel oil, and the like, or animal oils and fats such as whale oil, fish oil, beef tallow, lard, and the like at a temperature of about 160 to about 180 ℃ in the presence of a nickel catalyst and the like. Hardened oils are produced from inexpensive oil-and-fat raw materials and have stable quality, and therefore, they are used in a large number of applications.

In most cases, fats and oils have retained flavors inherent in raw materials such as sesame oil, soybean oil, rapeseed oil, and lard as raw materials, and in such cases, the flavors are utilized effectively for food production. However, depending on the food, the unique flavor of the material may be an obstacle. The hardened oil is produced into hardened oil which removes the peculiar smell and peculiar smell of vegetable oil or animal oil as raw materials, has mild fragrance and flavor, and is easy to be used in a wide range of foods.

The hardened oil has odors called "hydrogenated odor (water-added odor)", "hydrogenated off-flavor", "off-flavor ( り odor)", "hardened odor", "hardened oily odor", and the like. The cause of the odor is aldehydes and ketones typified by 6-nonenal, and fatty acids present in oils and fats are generated under the influence of light, heat, and the like (non-patent documents 1 and 2).

These odors have been regarded as offensive odors and are generally rejected. However, recently, it is considered that a thick and elegant taste is imparted to a food containing a hardened oil after food processing such as heating (Rang, されるねっとりとした top な, gan12373). For example, in the case of using hardened oil-and-fat as frying oil for doughnuts, it is considered that the resultant doughnuts are endowed with an elegant and delicious cooking feeling which cannot be expressed, and the fried doughnuts are expected to be purchased by consumers and provide a sufficient feeling of satisfaction when tasted. In addition, although products using hardened oils such as margarine and fat spread (fat spread) have been developed as alternatives to butter, their unique body taste (コク) and good taste increase the milk flavor, and they are accepted by ordinary consumers over a long period of several decades and gradually permeate into them, resulting in a favorable flavor.

On the other hand, it is known that the trans fatty acid content in oils and fats increases by hydrotreating. Recently, the federal government of the united states has issued indications that trans fatty acids may be a cause of causing, for example, pulse and flow sclerosis, and as a result, the use of a hardened oil containing a large amount of trans fatty acids is increasingly being abandoned, and there is a strong desire for effective solutions such as the development of alternative fats and oils.

Therefore, fat and oil products having reduced trans-fatty acids and having physical properties (melting point and the like) close to those of hardened oils, that is, hardened oil substitutes prepared by combining liquid fats and oils with palm oil, lard, lightly hydrogenated fats and oils, fully hydrogenated fats and oils, and the like, and further performing transesterification or the like have been developed. However, this method has a problem that the unique flavor of hydrogenated taste is lost if the degree of hydrogenation is decreased. Therefore, there is a strong need to develop a method for reducing the trans fatty acid content and imparting a flavor to a hardened oil.

In view of the above problems, for example, the following methods are disclosed: a method of using fractionated hard oils of palm oil in an amount of 50 mass% or more (i.e., separating hard-sub oils) to reduce the trans-fatty acid content and release the flavor derived from hydrogenated fats and oils (patent document 1); provided is a method for cooking a fat or oil by heating, which can reduce the trans fatty acid content and impart the same "hardened oil flavor" as that in the conventional cooking using a hardened oil by using palm oil and lard or a fat or oil which is only slightly hydrogenated in place of a conventional hardened oil (patent document 2); a method of reducing the trans-fatty acid content and releasing the flavor of hydrogenated oils and fats by using palm oil purified by distillation (patent document 3); a method of reducing the trans-fatty acid content and releasing the flavor derived from hydrogenated fats and oils by fractionating hard oils with less than 50% palm oil and fractionating soft oils with 65% or less palm oil (patent document 4). However, the proposals of patent documents 1 to 4 contain a large amount of palm-derived oils and fats, and the liquid oil flavor due to linoleic acid may cause a decrease in flavor, and a large amount of fractionated hard parts are incorporated, which results in insufficient flavor quality and strength.

For these hardened oils to replace fats and oils, methods for supplementing the flavor of hardened oils have also been developed. For example, a hardened oil flavor imparting agent characterized by containing vanillin and/or ethyl vanillin as an active ingredient is disclosed (patent document 5), but the volatility is slightly improved as compared with the flavor when hydrogenated oil and fat is used, and the flavor quality and strength are insufficient. Further, the flavor of a hydrogenated oil and fat of a low trans fatty acid oil and fat can be enhanced by using a partially hydrogenated oil and fat having a peroxide value (POV) within a specific range (patent document 6), but in order to obtain an oil and fat having a high POV, a special treatment for increasing the peroxide value is required, which takes time and labor. Further, it is disclosed that the fat or oil obtained by hydrogenating the deodorized fat or oil has a creamy flavor (patent document 7), but the fat or oil is deteriorated at a temperature during the hydrogenation treatment, and further has an unpleasant odor component having a high volatility, and is insufficient in flavor quality.

Documents of the prior art

Patent document

Patent document 1: japanese laid-open patent publication No. 2008-271818

Patent document 2: japanese laid-open patent publication No. 2009-5681

Patent document 3: japanese laid-open patent publication No. 2009-240220

Patent document 4: japanese patent laid-open publication No. 2010-99037

Patent document 5: international publication No. 2008/032852

Patent document 6: japanese laid-open patent publication No. 2009-89684

Patent document 7: japanese Kokai publication No. 2010-504753

Non-patent document

Non-patent document 1: "flavor component of food fat or oil (component of the bone of food fat or oil におい)", oil chemistry 17(1), 2 to 18(1968)

Non-patent document 2: "search for the odor component of fat and oil (2 nd report) hydrogenation (component について (2 nd 2 ) of fat and oil におい, Zhikensuo for water intake)", oil chemistry 19(9), 883 to 887 (1970).

Disclosure of Invention

Problems to be solved by the invention

The present invention aims to provide a hardened oil flavor-imparting agent capable of imparting the same "hardened oil flavor" as that of conventional hardened oils to a so-called substitute for conventional hardened oils, i.e., a hardened oil substitute made by combining non-hardened oil, palm oil, lard, slightly hydrogenated oils, fully hydrogenated oils, or the like, i.e., an oil product having reduced trans-fatty acids and having physical properties (melting point or the like) close to those of hardened oils.

Means for solving the problems

The present inventors have conducted extensive studies to achieve the above object, and as a result, have surprisingly found that addition of (E) -6-octenal to a liquid fat at a predetermined concentration can impart a "hardened oil flavor" to the fat and oil, and can also impart a high-quality aroma and flavor called "hardened oil flavor" to a food cooked with the fat and oil, thereby completing the present invention.

Thus, the present invention provides the following,

(1) a hardened oil flavor imparting agent comprising (E) -6-octenal;

(2) a hardened oil flavor imparting agent composition characterized by containing (E) -6-octenal as an active ingredient;

(3) a hardened oil flavor imparting agent composition characterized by containing (E) -6-octenal and the following component A,

component A: at least one selected from the group consisting of 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal and (E) -2-nonenal;

(4) the hardened oil flavor imparting agent composition described in (2), wherein (E) -6-octenal is contained at a concentration within a range of 10ppb to 10 ppm;

(5) the hardened oil flavor imparting agent composition according to any one of (2) to (4), which contains 10ppb to 10ppm of (E) -6-octenal, and which is used for adding to a fat or oil product having a hardened oil content of less than 50% of the total amount of fat or oil so that the (E) -6-octenal is in a range of 10ppt to 10ppb in the fat or oil product;

(6) the hardened oil flavor imparting agent composition described in (3) contains (E) -6-octenal and the component A, wherein the content of (E) -6-octenal is 10ppb to 10ppm, and the ratio of (E) -6-octenal to the component A is: (E) -6-octenal)/3-methyl-2, 4-nonanedione = 0.01-10, ((E) -6-octenal)/(E) -6-nonenal = 0.01-10, ((E) -6-octenal)/(Z) -6-octenal = 0.01-10, ((E) -6-octenal)/(E) -2-nonenal = 0.01-10 or ((E) -6-octenal)/trans-4, 5-epoxy-2 (E) -decenal = 0.01-100;

(7) a hardened-oil-flavored oil or fat product containing the hardened-oil-flavored agent of (1) or the hardened-oil-flavored agent composition of any one of (2) to (6), wherein the concentration of (E) -6-octenal in the oil or fat product is within the range of 10ppt to 10 ppb;

(8) (7) the grease product, wherein the hardened oil content is less than 50% of the total amount of grease;

(9) a perfume composition containing 10ppb to 10ppm of (E) -6-octenal, which is used for adding to an oil product having a hardened oil content of less than 50% of the total amount of oil and fat, and wherein the amount of (E) -6-octenal in the oil product is in the range of 10ppt to 10 ppb;

(10) (9) the perfume composition comprising (E) -6-octenal and the following component A,

component A: is selected from more than one of 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal and (E) -2-nonenal,

(E) the ratio of 6-octenal to component A is: (E) -6-octenal)/3-methyl-2, 4-nonanedione = 0.01-10, ((E) -6-octenal)/(E) -6-nonenal = 0.01-10, ((E) -6-octenal)/(Z) -6-octenal = 0.01-10, ((E) -6-octenal)/(E) -2-nonenal = 0.01-10 or ((E) -6-octenal)/trans-4, 5-epoxy-2 (E) -decenal = 0.01-100;

(11) an oil or fat product having a hardened oil content of less than 50% of the total amount of oil or fat, wherein the fragrance composition of (9) or (10) is added so that the concentration of (E) -6-octenal in the oil or fat product is within the range of 10ppt to 10 ppb.

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, a high-quality aroma or flavor called "hardened oil flavor" can be imparted to a fat or oil by adding a hardened oil flavor imparting agent to the fat or oil to prepare a margarine or a spread fat, and a high-quality aroma or flavor called "hardened oil flavor" can be imparted to a food by heating and cooking the food using the fat or oil to which the hardened oil flavor imparting agent of the present invention is added as a frying oil, or by directly adding the fat or oil to the food and performing heating processing. As used herein, the term "hardened oil flavor" means a thick and elegant taste resulting from food processing such as heating of a food containing a hardened oil, at least a vegetable-based hardened oil, and in particular, a soybean hardened oil.

Hereinafter, the flavor-imparting agent for hardened oils and the fat and oil products imparted with the flavor of hardened oils of the present invention will be described in further detail.

It is known that (E) -6-octenal, which is an active ingredient of the hardened oil flavor-imparting agent of the present invention, is a flavor compound, and it is known that 1 to 25ppm (EFSA Journal 2011; 9(11): 2397, p.22, p.27, p.44 (TableII.1.1), p.45(TableII.1.2)) can be added to various foods and beverages such as dairy products, fatty foods, fruit processed products, vegetable processed products, snacks, grains, baked goods, meat products, fish and shellfish products, egg processed products, sweeteners, soups, alcoholic beverages, nonalcoholic beverages, and the like. However, the use and properties of the hardened oil flavor imparting agent are not known at all, and the above-mentioned document does not describe or teach that the hardened oil flavor can be imparted to a fat or oil food at a concentration of 10ppt to 10ppb which is far lower than the above-mentioned use concentration (1 to 25 ppm).

On the other hand, the geometric isomer (Z) -6-octenal of the compound of the present invention is also known as a fragrance compound, and its use in, for example, perfume cosmetics or perfume cosmetics is proposed (U.S. Pat. Nos. 4192781 and 4132675). These U.S. patents show that (Z) -6-octenal has a fragrance like fat, like soap, like vegetable (グリーン sample), like fruit, and can also be used as a flavorant (flavor). Furthermore, it is described that (Z) -6-octenal has aroma characteristics similar to those of vegetables and melons (J. Am. Oil chem. Soc., 58 (6)), 680-682(1981)), and that (Z) -6-octenal can also be used as a milk flavor enhancer (Japanese patent laid-open No. 2003-189). However, these documents do not describe at all (E) -6-octenal, which is a geometric isomer of (Z) -6-octenal, and do not describe or even teach the aroma characteristics.

The active ingredient (E) -6-octenal of the present invention can be obtained by separation from a mixture of geometric isomers of 6-octenal by a gas chromatography (fraction ガスクロマトグラフィー), and can be synthesized, for example, by the method described in J.am.chem.Soc., 86, 1964, 3759-.

The present invention relates to a hardened oil flavor-imparting agent characterized by containing (E) -6-octenal as an active ingredient. The active ingredient (E) -6-octenal of the present invention can impart a hardened oil flavor to a fat or oil product such as a margarine or a spread fat by adding (E) -6-octenal to the fat or oil product such as a margarine or a spread fat in the range of usually 10ppt to 10ppb, preferably 20ppt to 5ppb, and more preferably 50ppt to 2 ppb.

When (E) -6-octenal is added to the above-mentioned fat or oil product, the amount of (E) -6-octenal added to exert the effect as a hardened oil flavor imparting agent is extremely small and in a specific range in the fat or oil product, and therefore, it is preferable to prepare a hardened oil flavor imparting agent composition.

The hardened oil flavor imparting agent composition of the present invention contains the (E) -6-octenal at a concentration of usually 10ppb to 10ppm, preferably 20ppb to 5ppm, and more preferably 50ppb to 2ppm, based on the mass of the imparting agent composition. Further, the hardened oil flavor imparting agent composition is added to the oil and fat product in an amount of about 0.01% to 1% and the addition concentration of (E) -6-octenal to the oil and fat product is in the range of 10ppt to 10ppb, preferably 20ppt to 5ppb, more preferably 50ppt to 2ppb in the oil and fat product, whereby the oil and fat product can be imparted with a thick, elegant and savory taste and body taste which are extremely similar to the "hardened oil flavor".

If the addition concentration of (E) -6-octenal to the oil or fat product is less than 10ppt, the effect of imparting a hardened oil flavor is insufficient, and if the addition concentration of (E) -6-octenal to the oil or fat product is greater than 10ppb, the aldehyde-like aroma peculiar to (E) -6-octenal is prominent, which is not preferred.

The fat or oil product to which the hardened oil flavor imparting agent of the present invention is added is preferably a fat or oil product having less than 50% by mass of hardened oil, more preferably less than 30% by mass of hardened oil, and particularly preferably less than 20% by mass of hardened oil, whereby a "hardened oil flavor" having good aroma and flavor can be imparted to the fat or oil product even if the trans fatty acid content is reduced. An oil or fat product having a hardened oil content of more than 50% by mass inherently has a hardened oil flavor, and therefore the use of the product of the present invention is not necessary, but the product has a disadvantage of containing a large amount of trans fatty acids.

The non-hardened oil used in the oil or fat product of the present invention is not particularly limited, and examples thereof include any edible oil such as soybean oil, rapeseed oil, safflower oil, corn oil, sunflower oil, cottonseed oil, rice bran oil, olive oil, palm oil, coconut oil, sesame oil, beef tallow, lard, fish oil, and medium-chain triglycerides, and processed oils and fats obtained by subjecting these to treatment such as fractionation and transesterification. These raw oils and fats themselves are preferably highly purified to such an extent that they have no or little aroma.

Examples of hardened oils used in the oil and fat products of the present invention include vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, and palm kernel oil, or animal oils and fats such as fish oil, beef tallow, and lard, which are used as raw materials and hydrogenated by a method of hydrogenating the oils and fats at a temperature of about 120 to about 200 ℃ in the presence of a nickel catalyst, and hardened oils having a melting point of 10 to 40 ℃, particularly 20 to 35 ℃ are preferred, and examples thereof include hardened oils such as rapeseed oil, soybean oil, sunflower seed oil, cottonseed oil, peanut oil, rice bran oil, corn oil, safflower oil, kapok oil (kapok oil), sesame oil, and evening primrose oil, and these hardened oils may be used alone or in combination of two or more.

In addition, the oil or fat product of the present invention preferably has a trans fatty acid content of 3% by mass or less. Trans fatty acids are contained in nature, for example, in milk fat at a content of about 5 mass%, and although it is considered that the intake of trans fatty acids to such an extent has little influence on health, according to the present invention, a hardened oil-flavored fat to which a "hardened oil flavor" is imparted can be obtained while the trans fatty acid content is reduced, which is a concern in health, as described above.

The trans-fatty acid content in the fat or oil can be determined according to AOCS Official Method Ce 1f-96(Revised 2002).

In the fat and oil product of the present invention, palm-derived fat and oil may be used as a part of the non-hardened oil, and the use of palm-derived fat and oil can improve the thermal stability of the fat and oil product, and can impart a good "hardened oil flavor" based on a pure (plain) palm oil flavor. The content of the non-hardened fats and oils derived from palm is not particularly limited, and may be changed in a wide range depending on the use of the hardened oil-flavored fats and oils, and is usually at least 50 mass%, particularly at least 60 mass%, and more particularly at least 80 mass% based on the mass of the hardened oil-flavored fats and oils. Examples of the palm-derived fat and oil include palm oil and palm olein.

The hardened oil flavor imparting agent composition of the present invention may contain, in addition to (E) -6-octenal, at least one flavor selected from the group consisting of 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal, and (E) -2-nonenal. This can impart a better hardened oil flavor to the fat or oil product.

When at least one selected from the group consisting of 3-methyl-2, 4-nonanedione, (E) -6-nonenal, (Z) -6-octenal and (E) -2-nonenal is used as the component a, the ratio of the (E) -6-octenal to the other perfumes may be in the range of ((E) -6-octenal)/a =0.001 to 100, preferably 0.01 to 10, and the ratio of ((E) -6-octenal)/trans-4, 5-epoxy-2 (E) -decenal =0.001 to 1000, preferably 0.01 to 100, on a mass basis.

The hardened oil flavor imparting agent composition of the present invention may further contain, as necessary, conventional flavor compounds used for dairy flavor and the like such as cream flavor, and examples thereof include: acids such as formic acid, propionic acid, butyric acid, valeric acid, isovaleric acid, caproic acid, trans-2-hexenoic acid, heptanoic acid, caprylic acid, pelargonic acid, 5-hydroxynonanoic acid, capric acid, 2-decenoic acid (デセン acid), 4-decenoic acid, 5-decenoic acid, 6-decenoic acid, 9-decenoic acid, 5-hydroxydecenoic acid, 5-hydroxyundecanoic acid, lauric acid, 5-hydroxydodecanoic acid, myristic acid, pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and the like; aldehydes such as acetaldehyde, propionaldehyde, butyraldehyde, 2-butenal, hexanal, octanal, 4-heptenal, 2, 4-octadienal, nonanal, 2-nonenal, 2, 4-nonadienal, 2, 6-nonadienal, decanal, 2, 4-decadienal, undecanal, 2, 4-undecadienal, laurinaldehyde, benzaldehyde, vanillin, ethyl vanillin, furfural, and the like; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, dodecyl acetate, phenylethyl acetate, ethyl lactate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl enanthate, ethyl caprylate, isoamyl caprylate, heptyl caprylate, methyl pelargonate, ethyl pelargonate, methyl caprate, ethyl undecanoate, methyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, diethyl sebacate, ethyl 5-hydroxycaproate, ethyl 5-hydroxydecanoate, ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate, ethyl hexanoate, ethyl decanoate, ethyl undecanoate, propyl 5-hydroxy, Esters such as ethyl 5-hydroxy-9-methyldecanoate; alcohols such as ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenethyl alcohol, and furfuryl alcohol; ketones such as 2-heptanone, 2-octanone, 3-octanone, 1-octen-3-one, 2-nonanone, 3-nonanone, 8-nonen-2-one, 2-undecanone, 2-tridecanone, acetoin, 5-hydroxy-4-octanone, diacetyl, 2, 3-pentanedione, 2, 3-hexanedione, 2, 3-heptanedione, acetylisovaleryl, p-methoxyacetophenone, benzophenone, and maltol; 3-hydroxy-2-methyl-4H-pyran-4-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 2, 5-dimethyl-4-hydroxy-3 (2H) -furanone, 3-methyl-1, 2-cyclopentadione, 3-ethyl-1, 2-cyclopentadione, 3, 4-methylenedioxybenzaldehyde, 3-hydroxy-4, 5-dimethyl-2 (5H) -furanone, 5-ethyl-3-hydroxy-4-methyl-2 (5H) -furanone, 2-ethyl-4-hydroxy-5-methyl-3 (2H) -furanone, and mixtures thereof, Oxygen-containing cyclic compounds such as 3, 4-dimethyl-1, 2-cyclopentadione; nitrogen-containing compounds such as phenethyl anthranilate, trimethylamine, indole, 3-methylindole, pyridine, isoquinoline, pyrazine, and methylpyrazine; methyl mercaptan, isobutyl mercaptan, 2, 4-dithiolane (2,4- ジチアペンタン), dimethyl sulfide, dimethyl disulfide, 2, 4-dithiolane, dimethyl trisulfide, dimethyl sulfoxide, dimethyl sulfone, methyl mercaptan, methylsulfonylmethane, methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, 2-methyl-3-butanethiol, bromal (methylanal), ethyl thioacetate, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, 4-methyl-5-hydroxyethylthiazole (Sulfrol), thiomethyl acetolactate (アセチル lactic acid チオメチルエステル), thiomethyl propionyl lactate, thiomethyl butyryl lactate, thiomethyl valeryl lactate, thiomethyl 2-methylbutyryl lactate, thiomethyl butyryl lactate, dimethylbutyryl lactate, Sulfur-containing compounds such as thiomethyl decanoyl lactate, thioethyl acetolactate, thioethyl propionyl lactate, thioethyl butyryl lactate, thioethyl valeryl lactate and thiopropyl isohexanoyl lactate; gamma-caprolactone, gamma-heptolactone, gamma-octalactone, gamma-nonalactone, gamma-decalactone, 7-decen-4-lactone, 3-methyl-4-decen-4-lactone, 3-methyl-5-decen-4-lactone, gamma-undecalactone, gamma-dodecalactone, gamma-tridecanolide, gamma-tetradecanolide, -caprolactone, 2-hexene-5-lactone, 2-heptene-5-lactone, -octalactone, 2-octene-5-lactone, 4-methyl-5-octalactone, -nonalactone, 2-nonene-5-lactone, 4-methyl-5-nonalactone, gamma-decalactone, gamma-nonalactone, 3-methyl-4-decen-4-lactone, 3-methyl-5-decen-4-lactone, 2-octene-5-lactone, 2-, -decalactone, 2-decen-5-olide, 4-methyl-5-decalactone, -undecalactone, 2-undecen-5-olide, 4-methyl-5-undecalactone, -dodecalactone, 2-dodecen-5-olide, 4-methyl-5-dodecalactone, -tridecanolide, 2-tridecene-5-olide, 4-methyl-5-tridecanolide, -tetradecanolide, 2-tetradecene-5-lactone, 2-pentadecen-5-olide, 2-hexadecene-5-lactone, 2-heptadecen-5-lactone, 2-octadecene-5-lactone, lactones such as 2-nonadecen-5-lactone, 2-eicosene-5-lactone, and decalactone, but the present invention is not limited thereto.

The hardened oil flavor imparting agent composition of the present invention may contain the above-mentioned perfume compound at a concentration of usually 0.001 to 50 mass%, preferably 0.1 to 15 mass%, more preferably 1 to 5 mass% based on the mass of the hardened oil flavor imparting agent composition of the present invention.

The hardened oil flavor imparting agent composition of the present invention may contain the fatty acid at a concentration of usually 0.1 to 95 mass%, preferably 1 to 60 mass%, more preferably 5 to 30 mass% based on the mass of the imparting agent composition.

Further, in the hardened oil flavor-imparting composition of the present invention, a solvent component such as MCT (medium chain triglyceride) and glycerin; antioxidants such as vitamin E; the spice and spice extract can be used as oil soluble component of food.

The hardened oil flavor-imparting agent or hardened oil flavor-imparting agent composition of the present invention described above is obtained by directly adding to, for example, doughnuts, breads or a premix thereof; these foods can be given a hardened oil flavor by heating cakes, pies, chocolates and other desserts, and hardened oil-flavored oils and fats can also be prepared by adding them to oils and fats.

Examples of the raw oils and fats that can be used for preparing the hardened oil-flavored oils and fats by adding the hardened oil-flavor imparting agent of the present invention include any edible oils and fats such as soybean oil, rapeseed oil, safflower oil (saflower oil), corn oil, sunflower oil, cottonseed oil, rice bran oil, olive oil, palm oil, coconut oil, sesame oil, beef tallow, lard, fish oil, hardened oils, and MCT, and processed oils and fats obtained by subjecting these to fractionation, hydrogenation, transesterification, and the like. These raw oils and fats themselves are preferably highly purified to such an extent that they have no or little aroma.

The raw material fat or oil used in the hardened oil-flavored fat or oil of the present invention may be a hardened oil as a part of the raw material fat or oil, and preferably 1 to 20 mass%, particularly 2 to 10 mass% of the hardened oil and 80 to 99 mass%, particularly 90 to 98 mass% of the non-hardened oil are used, whereby the fat or oil can be imparted with a hardened oil flavor having good aroma and flavor even if the trans fatty acid content is reduced. By adopting such a blending ratio, the trans fatty acid content in the hardened oil-flavored fat can be reduced to 3% by mass or less, and a good hardened oil flavor can be imparted. Trans fatty acids are contained in nature, for example, in milk fat in an amount of about 5 mass%, and it is generally considered that intake of trans fatty acids to this extent has little influence on health. If the content of the hardened oil in the hardened-oil-flavored fat is too large, an unpleasant hydrogenated taste is felt when the fat is used for cooking, and if the content is too small, a satisfactory hardened-oil flavor cannot be sufficiently imparted.

Examples of the hardened oil used in this case include hardened oils obtained by a method in which vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, and palm kernel oil, or animal oils and fats such as fish oil, beef tallow, and lard are used as raw materials, and the raw materials are hydrogenated in the presence of a nickel catalyst or the like at a temperature of about 120 to about 200 ℃.

The raw material fat or oil used in the hardened oil-flavored fat or oil of the present invention may be palm-derived fat or oil as a part of the raw material fat or oil. Examples of the oil and fat derived from palm include palm oil and palm olein. In particular, if a hardened oil-flavored fat blended with palm oil is used for a spread fat or the like, it is preferable because it has a suitable hardness when applied to bread or the like to a moderate degree.

Further, the hardened oil-flavored fat or oil of the present invention may further contain additives such as an emulsifier, an antioxidant, an antifoaming agent, and a coloring agent, as required.

The hardened oil flavor imparting agent, hardened oil flavor imparting agent composition, or hardened oil flavor fat and oil of the present invention can be used for producing spreads, margarines, and the like, and can impart a hardened oil flavor such as a thick and thick, elegant taste to spreads, margarines, and the like, and can impart creamy (creamy) milky texture. In addition, any food containing fat or oil other than spread food, margarine, and the like can be widely used, and the same effect can be obtained. Examples of the fat-and-oil-containing food and drink include: common beverages such as milk, soybean milk, milk beverage, milk-containing coffee beverage, milk-containing black tea beverage, lactic acid bacteria beverage, and cacao; desserts such as yogurt, jelly, pudding, mousse (mousse): butter-like substances such as cream and fresh cream; processed snacks such as baked snacks and steamed snacks including western snacks such as various cakes and stuffed pastries and japanese snacks; frozen desserts such as ice cream; chocolate such as milk chocolate; common snack foods such as chewing gum, hard candy, nougat, jelly bean (jelly beans); bread such as sweet bread (seed パン); seasonings such as miso, soy sauce, soup (だし), seasoning (dressing), mayonnaise, amino acid-based seasoning, nucleic acid-based seasoning, sour seasoning, fermented seasoning, pork extract, chicken extract, fish and shellfish extract, yeast extract, proteolysis product, fish sauce, bean paste, dried fish (pepari), kelp soup, soup stock, chinese seasoning (zhouzhuhuasu), barbecue seasoning juice, curry paste, instant stew soup (シチュー), instant soup (スープ), instant broth (ダシ), compound seasoning, and the like, and the topping of noodles (buckwheat noodles, linden, hand-pulled noodles, pasta, etc.); sauce for barbecue, roast chicken, roast eel slice, etc., or coating sauce such as tomato sauce, etc.; soup such as corn soup, clear soup, egg soup, thick soup, miso soup, etc.; processed livestock products such as ham, sausage, cheese, etc.; cylindrical minced aquatic products such as fish cake, crab stick (カニカマ), and fish cake; sterilizing bagged food; snacks such as potato chips, crackers, rice cakes, cookies, and the like; sweet seafood, home dishes, frozen foods, stews, fried foods, baked goods, etc., but not limited thereto.

The present invention will be described more specifically with reference to examples.

[ examples ]

Reference example 1 preparation of a margarine composition based on hardened oil

An oil phase was prepared by mixing 603g of hardened soybean oil (melting point: 34 ℃) with 200g of soybean oil, and mixing 1g of soybean lecithin and 1g of sorbitan monostearate with the oil heated to 70 ℃. In addition, 20g of skimmed milk powder and 3g of sugar ester were mixed with 180g of water, and then sufficiently dissolved at 70 ℃ to prepare an aqueous phase. Then, the oil phase and the water phase were emulsified by a high-pressure homogenizer, and cooled and solidified to prepare a margarine composition containing 75.1% of hardened oil in the fat (reference 1).

Reference example 2 preparation of a margarine composition with reduced hardened oil (less than 20% in fat and oil)

160g of hardened soybean oil (melting point: 34 ℃ C.), 393g of palm oil (melting point: 42 ℃ C.) and 250g of soybean oil were mixed, and 1g of soybean lecithin and 1g of sorbitan monostearate were mixed with the oil heated to 70 ℃ to prepare an oil phase. In addition, 20g of skimmed milk powder and 3g of sugar ester were mixed with 180g of water, and then sufficiently dissolved at 70 ℃ to prepare an aqueous phase. Then, the oil phase and the water phase were emulsified by a high-pressure homogenizer, and cooled to solidify, thereby obtaining a margarine composition containing 19.9% of a hardened oil in the fat (reference 2).

Example 1 preparation of a margarine composition to which (E) -6-octenal was added

In the preparation of the oil phase in reference example 2, (E) -6-octenal was added to the oil phase (diluted appropriately with soybean oil) to prepare a margarine composition such that the concentration of (E) -6-octenal in the margarine composition was as shown in table 1, and these were used as the present invention products 1 to 4 and the comparative products 1 to 4.

(sensory evaluation)

The flavor of the margarine compositions containing (E) -6-octenal added to the margarine compositions of the present invention nos. 1 to 4 or the comparative examples nos. 1 to 4 and the margarine compositions of the reference nos. 1 and 2 was evaluated organoleptically by 10 well-trained panelists. The evaluation was scored according to the following evaluation criteria, and the total score is shown in table 1. In addition, the results of the summary of the average sensory evaluation of the whole panelists are also shown in table 1;

evaluation criteria

The thick and elegant taste and the mellow taste were 3 minutes as strong as those of the hardened oil-based product (reference product 1)

The sticky and elegant taste and the mellow taste are slightly inferior to those of the main hardened oil (reference product 1. cndot.) 2

It did not feel sticky and elegant, and tastier.

[ Table 1]

TABLE 1 organoleptic evaluation of margarine compositions

。

As shown in Table 1, the result was that the margarine composition of reference 1 using 75.1% of a hardened oil in the fat or oil felt thick and elegant deliciousness and richness, but also felt an unpleasant hydrogenated taste. On the other hand, the margarine composition of reference 2 using 19.9% of the hardened oil in the fat and oil had no sticky and delicious taste and was fragrant with a vegetable oil. On the other hand, the margarine compositions (the amount of the hardened oil used in the fat and oil is 19.9%) of the present inventions 1 to 4, which were flavor compositions obtained by adding (E) -6-octenal to reference 2, were imparted with a thick and elegant taste and body taste like hardened oil, and no unpleasant hydrogenated taste was perceived. When the addition concentration of (E) -6-octenal is within the range of 10ppt to 10ppb in terms of the addition concentration in the margarine composition, the result is that a thick and delicious taste and a rich and mellow taste are imparted to the margarine composition, and the margarine composition has a flavor without particularly unpleasant feeling. On the other hand, if the concentration of (E) -6-octenal added is within a range of less than 10ppt based on the concentration of (E) -6-octenal added to the margarine composition, the margarine composition will not be imparted with a thick delicious taste and a rich body taste, and if the concentration of (E) -6-octenal added is within a range of more than 10ppb based on the concentration of (E) -6-octenal added to the margarine composition, the margarine composition will be imparted with a thick delicious taste and a rich body taste as a result, but will have a pungent characteristic aroma of aldehyde, and will feel slightly unpleasant.

Reference example 3 preparation of base cream (base バター) flavor composition

A base cream flavor composition (reference 3) was prepared according to the formulation shown in table 2.

[ Table 2]

TABLE 2 formulation of base cream flavor composition (reference 3)

。

Reference example 4 preparation of a margarine composition based on hardened oil

An oil phase was prepared by mixing 603g of hardened soybean oil (melting point: 34 ℃) with 200g of soybean oil, and mixing 1g of soybean lecithin and 1g of sorbitan monostearate with the oil heated to 70 ℃. In addition, 20g of skimmed milk powder and 3g of sugar ester were mixed with 180g of water, and then sufficiently dissolved at 70 ℃ to prepare an aqueous phase. Then, the oil phase, the water phase and 1g of the base cream flavor composition (reference 3) shown in Table 2 were emulsified by a high-pressure homogenizer, cooled and solidified to prepare a margarine composition (reference 4) containing 75.1% of hardened oil in the fat.

Reference example 5 preparation of a margarine composition reduced in hardened oil (20% or less in fat and oil)

160g of hardened soybean oil (melting point: 34 ℃ C.), 393g of palm oil (melting point: 42 ℃ C.) and 250g of soybean oil were mixed, and 1g of soybean lecithin and 1g of sorbitan monostearate were mixed with the oil heated to 70 ℃ to prepare an oil phase. In addition, 20g of skimmed milk powder and 3g of sugar ester were mixed with 180g of water, and then sufficiently dissolved at 70 ℃ to prepare an aqueous phase. Then, the oil phase, the water phase and 1g of the base cream flavor composition (reference 3) shown in Table 2 were emulsified by a high-pressure homogenizer, cooled and solidified to prepare a margarine composition (reference 5) containing 19.9% of a hardened oil in the fat.

Example 2 preparation of a margarine composition to which (E) -6-octenal was added

Cream flavor compositions (inventive products 5 to 8 and comparative products 5 to 8, respectively) containing (E) -6-octenal in the amounts (concentrations) shown in table 3 were prepared for the base cream flavor composition of reference example 3, and these cream flavor compositions were added in place of the base cream flavor composition of reference example 5 (reference product 3) to prepare a margarine composition.

[ Table 3]

。

(sensory evaluation)

The flavor of the margarine compositions containing the creamy flavor compositions of the present invention nos. 5 to 8 or comparative nos. 5 to 8 and the margarine compositions of reference nos. 4 and 5 were evaluated organoleptically by 10 well-trained panelists. The evaluation was scored according to the following evaluation criteria, and the total score is shown in table 4. In addition, the results of the summary of the average sensory evaluation of the whole panelists are also shown in Table 4,

evaluation criteria

The thick and elegant taste and body like the hardened oil were the same strength as those of the margarine (reference 4) made of the hardened oil main body (5 min.)

The thick and elegant taste and the mellow flavor of the hardened oil are only different from those of the margarine (reference 4) made of the hardened oil main body by 4 minutes

The hardened oil-like sticky and elegant taste and mellow flavor are slightly inferior to those of the margarine (reference 4) made of the hardened oil main body

The sticky and elegant taste and the mellow taste like the hardened oil are much inferior to those of the margarine (reference product 4) made of the hardened oil main body

Almost no sticky and elegant taste and a rich flavor like hardened oil were felt (1 part).

[ Table 4]

。

As shown in table 4, the margarine composition of reference 4, which used 75.1% of the hardened oil and the base cream flavor composition added to the fat and oil, perceived a slight creamy flavor and a thick and elegant taste and richness like the hardened oil, but also perceived an unpleasant hydrogenated flavor. On the other hand, the margarine composition of reference 5, which used 19.9% of a hardened oil and added a base creamy flavor composition to the oil and fat, had a slight creamy flavor but had no thick and delicious taste and was a flavor derived from vegetable oil. On the other hand, the margarine compositions of the present invention 5 to 8 (the amount of the hardened oil used in the fat and oil was 19.9%) in which the flavor composition obtained by adding (E) -6-octenal to the flavor composition of reference product 3 was imparted with a light flavor like cream and a thick and elegant taste and body taste like hardened oil, and no unpleasant hydrogenated flavor was perceived. When the addition concentration of (E) -6-octenal is within the range of 10ppb to 10ppm (10 ppt to 10ppb in terms of the addition concentration in the margarine composition) based on the concentration in the flavor composition, the result is that the margarine composition is imparted with not only a light aroma like cream but also a thick and elegant, delicious and mellow flavor like hardened oil and also a flavor without a particularly unpleasant feeling. On the other hand, if the concentration of (E) -6-octenal added is in the range of less than 10ppb by the concentration in the flavor composition (less than 10ppt by the concentration in the margarine composition), thick and elegant deliciousness and richness such as hardened oil are not imparted to the margarine composition, and if the concentration of (E) -6-octenal added is in the range of more than 10ppm by the concentration in the flavor composition (more than 10ppb by the concentration in the margarine composition), thick and elegant deliciousness and richness such as hardened oil are imparted to the margarine composition as a result, but the margarine composition has an irritant characteristic fragrance of aldehyde, and a slightly unpleasant feeling is felt.

(example 3)

A creamy fragrance composition was prepared by adding (E) -6-nonenal, and 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal, or (E) -2-nonenal to 1 part by mass of the base creamy fragrance composition of reference 3.

[ Table 5]

。

(sensory evaluation)

A margarine composition (composition in which the flavor part of reference 5 was replaced) was prepared by adding 1g (about 0.1%) of each of the creamy flavor compositions of the present invention products 9 to 15 to the base cream flavor composition instead of the base cream flavor composition of reference 3 (reference 3). These margarine compositions were subjected to sensory evaluation of their flavor by 10 well-trained panelists in comparison with reference 4 (75.1% hardened oil in fat). The evaluation was performed according to the same criteria as in example 2, and the total score and the average sensory evaluation summary result of the whole panelists are shown in table 6.

[ Table 6]

。

As shown in Table 6, the margarine-like composition of invention 9, to which (E) -6-nonenal was added to the creamy flavor composition of reference 3, had a slightly inferior flavor of hardened oil, but had a thick, elegant, delicious and mellow taste like hardened oil compared with reference 4 (a margarine composition mainly composed of hardened oil), whereas the margarine-like composition to which creamy flavor compositions (invention products 10 to 15) further containing 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal or (E) -2-nonenal were added, as with reference product 4, a thick and elegant taste and richness like hardened oil were perceived, and no hydrogenated taste was observed, and the taste was good.

Claims (13)

1. Use of (E) -6-octenal for producing a hardened oil flavor imparting agent.
2. 2. Use according to claim 1, for a fat or oil product in which the hardened oil content of the hardened oil-based flavor imparting agent is less than 50% by mass relative to the total amount of fat or oil.
3. 3. Use according to claim 2, wherein the hardened oil content is less than 20% by mass relative to the total amount of fat.
4. 4. The use according to claim 2, wherein (E) -6-octenal is contained in the oil or fat product at a concentration in the range of 10ppb to 10 ppm.
5. 5. A hardened oil flavor imparting agent composition characterized by containing (E) -6-octenal as an active ingredient at a concentration within the range of 10ppb to 10 ppm.
6. 6. A hardened oil flavor imparting agent composition characterized by containing (E) -6-octenal and the following component A,

   component A: is selected from more than one of 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal and (E) -2-nonenal.
7. 7. A hardened oil flavor imparting agent composition according to claim 5 or 6, characterized by containing 10ppb to 10ppm of (E) -6-octenal and being used for adding to a fat or oil product having a hardened oil content of less than 50% of the total amount of fat or oil, wherein the (E) -6-octenal is contained in the fat or oil product in a range of 10ppt to 10 ppb.
8. 8. A hardened oil flavor imparting agent composition according to claim 6, which contains (E) -6-octenal and the component A, wherein the content of (E) -6-octenal is 10ppb to 10ppm, and the ratio of (E) -6-octenal to the component A is: ((E) -6-octenal)/3-methyl-2, 4-nonanedione = 0.01-10, ((E) -6-octenal)/(E) -6-nonenal = 0.01-10, ((E) -6-octenal)/(Z) -6-octenal = 0.01-10, ((E) -6-octenal)/(E) -2-nonenal = 0.01-10 or ((E) -6-octenal)/trans-4, 5-epoxy-2 (E) -decenal = 0.01-100.
9. 9. A hardened-oil-flavored fat or oil product comprising the hardened-oil-flavoring agent according to claim 1 or the hardened-oil-flavoring agent composition according to any one of claims 5 to 8, wherein the concentration of (E) -6-octenal in the fat or oil product is within the range of 10ppt to 10 ppb.
10. 10. The fat and oil product of claim 9, wherein the hardened oil content is less than 50% of the total fat and oil content.
11. 11. A fragrance composition containing 10ppb to 10ppm of (E) -6-octenal, which is used for adding to an oil or fat product having a hardened oil content of less than 50% of the total amount of oil or fat, wherein the (E) -6-octenal is contained in the oil or fat product in a range of 10ppt to 10 ppb.
12. 12. The perfume composition according to claim 11, wherein the perfume composition comprises (E) -6-octenal and the following component A,

    component A: is selected from more than one of 3-methyl-2, 4-nonanedione, trans-4, 5-epoxy-2 (E) -decenal, (E) -6-nonenal, (Z) -6-octenal and (E) -2-nonenal,

    (E) the ratio of 6-octenal to component A is: ((E) -6-octenal)/3-methyl-2, 4-nonanedione = 0.01-10, ((E) -6-octenal)/(E) -6-nonenal = 0.01-10, ((E) -6-octenal)/(Z) -6-octenal = 0.01-10, ((E) -6-octenal)/(E) -2-nonenal = 0.01-10 or ((E) -6-octenal)/trans-4, 5-epoxy-2 (E) -decenal = 0.01-100.
13. 13. An oil or fat product having a hardened oil content of less than 50% of the total amount of oil or fat, wherein the fragrance composition according to claim 11 or 12 is added so that the concentration of (E) -6-octenal in the oil or fat product is within the range of 10ppt to 10 ppb.