Complete English Translation of JP2018057310A

Milky Flavor and Enhancer (JP2018057310A)

JP 2018-57310 A
April 12, 2018

ABSTRACT

Problem: To provide a milky flavor-imparting or enhancing agent, a milk-based fragrance composition, and foods and drinks containing them, which impart or enhance the natural sweetness and richness of milk fat to milk, dairy products, or foods and drinks containing them.

Solution: A milky flavor-imparting or enhancing agent comprising 2,4,7-tridecatrienal as an active ingredient; a milk-based fragrance composition characterized by containing 1 ppb to 50 ppm of 2,4,7-tridecatrienal; foods and drinks characterized by containing 1 ppt to 50 ppb of 2,4,7-tridecatrienal; and a method for imparting or enhancing milky flavor by incorporating the milky flavor-imparting or enhancing agent or the milk-based fragrance composition into milk-related products.

Selected Figure: None

CLAIMS

[Claim 1]
A milky flavor-imparting or enhancing agent comprising 2,4,7-tridecatrienal as an active ingredient.

[Claim 2]
A milk-based fragrance composition characterized by containing the milky flavor-imparting or enhancing agent according to Claim 1 at a 2,4,7-tridecatrienal concentration of 1 ppb to 50 ppm.

[Claim 3]
A food or drink containing milk or dairy products, characterized by containing the milky flavor-imparting or enhancing agent according to Claim 1 or the milk-based fragrance composition according to Claim 2 at a 2,4,7-tridecatrienal concentration of 1 ppt to 50 ppb.

[Claim 4]
A method for imparting or enhancing milky flavor to a food or drink containing milk or dairy products by incorporating the milky flavor-imparting or enhancing agent according to Claim 1 or the milk-based fragrance composition according to Claim 2.

DETAILED DESCRIPTION OF THE INVENTION

Technical Field

[0001]
The present invention relates to a milky flavor-imparting or enhancing agent capable of imparting or enhancing the natural sweetness and richness with fullness characteristic of milk fat to milk, dairy products, or foods and drinks containing them. More specifically, it relates to the milky flavor-imparting or enhancing agent containing 2,4,7-tridecatrienal as an active ingredient, a milk-based fragrance composition containing 2,4,7-tridecatrienal, foods and drinks containing the milk flavor-imparting or enhancing agent or the milk-based fragrance composition, and a method for imparting or enhancing milky flavor in milk-related products.

Background Art

[0002]
Dairy products such as milk, powdered milk, butter, cheese, ice cream, and yogurt have become essential foods that have permeated the Japanese diet along with the Westernization of meals.

[0003]
However, high-quality dairy products such as milk and butter are limited to a small number of expensive domestic or imported products. Most general products are made primarily from inexpensive, low-quality imported raw materials, or suffer from a reduction or loss of aroma and flavor during the manufacturing process in Japan. Consequently, consumers have surprisingly few opportunities to enjoy the rich, full-bodied flavor and richness that dairy products inherently possess. In recent years, due to cost reduction efforts driven by rising domestic raw material prices, the amount of dairy ingredients (milk, powdered milk, butter, cheese, etc.) in milk-related products has been decreasing. At the same time, due to recent health consciousness, product development aimed at reducing the amount of dairy ingredients for purposes such as metabolic syndrome countermeasures is also increasing. However, the lack of milky sensation and milk fat sensation caused by reduced milk fat content cannot be sufficiently compensated even using existing general flavor compositions for imparting milk flavor, and there is a demand for the development of products that can impart or enhance the natural flavor of milk fat.

[0004]
To date, several proposals have been made regarding flavor improvement and flavor enhancement of dairy products such as milk, butter, and cheese. For example:

• A method for producing dairy flavors with excellent palatability, having aroma and flavor of butter, cheese, milk, etc., by enzymatically treating milk fat-containing food materials in the presence of lipase and/or blending the enzymatically treated product with branched cyclodextrin to remove irritating odors and oily unpleasant aftertastes (Patent Document 1).
• A persistent aroma/flavor-imparting agent having sustained aroma and flavor characteristics that evoke a sense of aging in fermented products such as cheese, soy sauce, miso, fish sauce, as well as butter and cheese, containing alkanoylamino acid amides as an active ingredient (Patent Document 2).
• A fragrance composition capable of imparting and enhancing aroma and flavor characteristics such as butter-like, fruit-like, cheese-like, and yogurt-like with a mild richness by adding 2-hydroxy-3-methylpentanoic acid and diacetyl and/or 2-phenylethyl cinnamate to foods and drinks (Patent Document 3).
• A flavoring composition containing 3-methylnonane-2,4-dione, capable of imparting and enhancing the flavor and richness of milk-related products to milk, dairy products, foods or drinks containing milk or dairy products, or dairy substitutes (Patent Document 4).
• A flavor improver for milk beverages or fermented milk, containing as an active ingredient a product obtained by lipase treatment of milk or dairy products and/or fermentation treatment with lactic acid bacteria, which reduces the powdery taste and odor found in fermented milk and enhances taste (milky sensation) (Patent Document 5).
• A flavor enhancer capable of imparting richness and body by adding a fraction with a molecular weight cutoff of 10,000 or more, obtained by fractionating an extract obtained by extracting roasted coffee with water, a polar organic solvent, or a mixture thereof, to dairy products, etc. (Patent Document 6).
• A fragrance composition for milk, dairy products, foods or drinks containing milk or dairy products, or dairy substitutes, containing one or more disulfide compounds selected from the group consisting of methyl 2-methyl-3-furyl disulfide, bis(2-methyl-3-furyl) disulfide, methylfurfuryl disulfide, and difurfuryl disulfide (Patent Document 7).
• A milk-based beverage with enhanced light and diffusive aroma by adding a lower fatty acid at a concentration of 0.01 to 0.5 times its detection threshold concentration in the final food or drink (Patent Document 8).
• A method for producing a milk-based flavor, characterized by blending S-methylmethionine sulfonium chloride (Patent Document 9).

There are proposals such as these.

[0005]
These proposals aim to impart or enhance the flavor and richness of products. However, they are insufficient for imparting the sweetness and richness with fullness of milk fat—for example, they impart an unwanted heated sensation (boiled milk sensation) at the same time as imparting milk flavor. Therefore, there has been a demand for proposals capable of imparting or enhancing the flavor or richness of higher-quality dairy products.

[0006]
Meanwhile, in recent years, as consumer preferences have diversified, the development of a wide variety of products is desired. This trend is particularly strong in the food and beverage industry, and there is a strong demand for the development of diverse foods and drinks that match consumer preferences. In response to these demands, even regarding fragrances, which are raw material ingredients for foods and drinks, the fragrance compounds proposed in the past cannot sufficiently meet the needs. The development of fragrance compounds with unprecedented unique aroma and flavor characteristics and excellent sustainability has become an urgent issue.

[0007]
2,4,7-Tridecatrienal has been found in cooked chicken flavor (Non-Patent Document 1), and has also been found in thermal decomposition products of arachidonic acid (Non-Patent Document 2), thermal decomposition products of phospholipids (Non-Patent Document 3), and is also known as a component that increases when human milk is frozen and stored for 2 months (Non-Patent Document 4). It is a naturally occurring volatile compound with aroma. As a fragrance application, methods for imparting a chicken-reminiscent flavor (Patent Documents 10, 11), and flavor improvers capable of imparting a woody and fibrous sensation reminiscent of freshly shaved fish flakes, especially bonito flakes (Patent Documents 12, 13), have been proposed.

[0008]
However, Non-Patent Documents 1-4 and Patent Documents 10-13 neither describe nor suggest that adding a trace amount of 2,4,7-tridecatrienal to foods and drinks having a milky flavor can impart and enhance the sweet and rich taste with fullness characteristic of milk fat, thereby improving the flavor of the foods and drinks.

Prior Art Documents

Patent Documents

[0009]

• Patent Document 1: Japanese Patent No. 2889428
• Patent Document 2: Japanese Unexamined Patent Publication No. 8-103243
• Patent Document 3: Japanese Patent No. 3437310
• Patent Document 4: Japanese Patent No. 4510339
• Patent Document 5: Japanese Patent No. 3706345
• Patent Document 6: Japanese Unexamined Patent Publication No. 2008-54507
• Patent Document 7: Japanese Patent No. 5173178
• Patent Document 8: Japanese Unexamined Patent Publication No. 2008-263903
• Patent Document 9: Japanese Unexamined Patent Publication No. 2014-77067
• Patent Document 10: Japanese Examined Patent Publication No. 41-7822
• Patent Document 11: Japanese Examined Patent Publication No. 54-12550
• Patent Document 12: Japanese Patent No. 4676572
• Patent Document 13: Japanese Patent No. 5688995

Non-Patent Documents

[0010]

• Non-Patent Document 1: Journal of American Oil Chemist's Society (1974), 51(8), 356-359
• Non-Patent Document 2: Journal of Agricultural and Food Chemistry (2003), 51(15), 4364-4369
• Non-Patent Document 3: Journal of Agricultural and Food Chemistry (2004), 52(3), 581-586
• Non-Patent Document 4: Food Chemistry (2010), 120, 240-246

Summary of the Invention

Problem to be Solved by the Invention

[0011]
The object of the present invention is to provide a milky flavor-imparting or enhancing agent that can impart or enhance the natural sweetness and richness with fullness characteristic of milk fat in a necessary and sufficient manner, and can improve the flavor of foods and drinks, as well as foods and drinks blended with the flavor-imparting or enhancing agent.

Means for Solving the Problem

[0012]
As a result of intensive research to solve the above problems, the present inventors have found that by incorporating a trace amount of 2,4,7-tridecatrienal into foods and drinks containing milk or dairy products, it is possible to impart or enhance the natural sweetness and richness with fullness characteristic of milk fat to the foods and drinks. Furthermore, they found that by adding 2,4,7-tridecatrienal to a milk-based fragrance composition and incorporating it into foods and drinks containing milk or dairy products, it is possible to more effectively and sufficiently impart and enhance the natural sweetness and richness with fullness characteristic of milk fat, and improve the flavor of the foods and drinks, leading to the completion of the present invention.

[0013]
Thus, the present invention provides the following:

(a) A milky flavor-imparting or enhancing agent comprising 2,4,7-tridecatrienal as an active ingredient.

(b) A milk-based fragrance composition characterized by containing the milky flavor-imparting or enhancing agent according to (a) at a 2,4,7-tridecatrienal concentration of 1 ppb to 50 ppm.

(c) A food or drink containing milk or dairy products, characterized by containing the milky flavor-imparting or enhancing agent according to (a) or the milk-based fragrance composition according to (b) at a 2,4,7-tridecatrienal concentration of 1 ppt to 50 ppb.

(d) A method for imparting or enhancing milky flavor to a food or drink containing milk or dairy products by incorporating the milky flavor-imparting or enhancing agent according to (a) or the milk-based fragrance composition according to (b).

[0014]
2,4,7-Tridecatrienal used in the present invention has been reported to be found in natural products, and its use as a chicken-like fragrance composition and fish oil fragrance composition has been proposed. However, it has not yet been reported as a milk component such as milk, and there is no description whatsoever of it being used as a milky flavor-imparting or enhancing agent or a milk-based fragrance composition.

Effects of the Invention

[0015]
By adding 2,4,7-tridecatrienal, the active ingredient of the milky flavor-imparting or enhancing agent of the present invention, to foods and drinks, particularly those containing milk, in an amount of 1 ppt to 50 ppb as 2,4,7-tridecatrienal, it is possible to impart or enhance unprecedented natural sweetness and richness with fullness characteristic of milk fat. Furthermore, by incorporating 1 ppb to 50 ppm of 2,4,7-tridecatrienal into a milk-based fragrance composition, it is possible to obtain a milk-based fragrance composition capable of imparting or enhancing unprecedented natural sweetness and richness with fullness characteristic of milk fat.

Mode for Carrying Out the Invention

[0016]
2,4,7-Tridecatrienal of the present invention has eight geometric isomers, all of which can be used in the present invention. However, (E,Z,Z)-2,4,7-tridecatrienal, which has been found in nature in Non-Patent Documents 1-4, etc., is preferred.

[0017]
The (E,Z,Z) isomer of 2,4,7-tridecatrienal used in the present invention can be synthesized by methods according to known literature. For example, it can be synthesized by bromination of 2-octyn-1-ol as a starting material, coupling with a Grignard derivative of (E)-2-penten-4-in-1-ol using a copper catalyst, partial hydrogenation using a Lindlar catalyst, and then oxidation with manganese dioxide (J. Agric. Food Chem. 2001, 49, 2959-2965). Alternatively, (Z,Z)-2,5-undecadien-1-ol is subjected to a one-pot oxidation Wittig reaction with manganese dioxide and an alkyl triphenylphosphoranylidene acetate to produce (E,Z,Z)-2,4,7-tridecatrienoic acid alkyl ester, which is then reduced in the presence of a hydride reducing agent to (E,Z,Z)-2,4,7-tridecatrienol, followed by oxidation to synthesize (E,Z,Z)-2,4,7-tridecatrienal (Japanese Patent No. 5473867).

[0018]
The present invention relates to a milky flavor-imparting or enhancing agent comprising 2,4,7-tridecatrienal as an active ingredient. In the present invention, by adding an effective amount of 2,4,7-tridecatrienal to foods and drinks having a milky flavor, such as milk, powdered milk, butter, cheese, ice cream, and yogurt, it is possible to impart or enhance the natural sweetness and richness with fullness characteristic of milk fat to the foods and drinks. The amount added to foods and drinks is, for example, as 2,4,7-tridecatrienal, relative to the total mass of the food or drink, with a lower limit typically of 1 ppt or more, preferably 10 ppt or more, more preferably 100 ppt or more, and an upper limit typically of 50 ppb or less, preferably 5 ppb or less, more preferably 1 ppb or less. The range of the amount of 2,4,7-tridecatrienal relative to the total mass of the food or drink can be any combination of these upper and lower limits. Within these ranges, it has an excellent effect of imparting or enhancing the natural sweetness and richness with fullness characteristic of milk fat to the food or drink. On the other hand, if the amount of 2,4,7-tridecatrienal relative to the total mass of the food or drink exceeds 50 ppb, aroma and flavor characteristics as metallic, soapy, or degraded oily off-odors appear, which is undesirable. Also, if the amount of 2,4,7-tridecatrienal added to the food or drink is less than 1 ppt, the aroma and flavor imparting effect unique to the present invention cannot be obtained.

[0019]
Here, the sweetness characteristic of milk fat differs from the so-called sweet taste provided by carbohydrates, which lingers on the tongue. It refers to the mellow, clean, full-bodied natural sweetness derived from lactose and milk fat. Also, the richness of milk fat means a rich flavor derived from milk fat and milk protein, without a persistent oily feel, and with a clean aftertaste.

[0020]
The milky flavor-imparting or enhancing agent of the present invention can be used to impart or enhance milky flavor by adding a trace amount of 2,4,7-tridecatrienal alone to foods and drinks. However, because the amount of 2,4,7-tridecatrienal added to foods and drinks is very small, and to further enhance the milk flavor-imparting or enhancing effect, it is also possible to prepare a milk-based fragrance composition by mixing with other components, and use this milk-based fragrance composition to impart or enhance milky flavor to foods and drinks.

[0021]
The amount of 2,4,7-tridecatrienal in the milk-based fragrance composition of the present invention varies depending on the purpose or the type of milk-based fragrance composition. For example, relative to the total mass of the milk-based fragrance composition, the lower limit is typically 1 ppb or more, preferably 10 ppb or more, more preferably 0.1 ppm or more, and the upper limit is typically 50 ppm or less, preferably 5 ppm or less, more preferably 1 ppm or less. The range of the amount of 2,4,7-tridecatrienal relative to the total mass of the milk-based fragrance composition can be any combination of these upper and lower limits. If the amount of 2,4,7-tridecatrienal relative to the milk-based fragrance composition exceeds 50 ppm, aroma and flavor characteristics as metallic, soapy, or degraded oily off-odors appear, which is undesirable. Also, if the amount of 2,4,7-tridecatrienal relative to the milk-based fragrance composition is less than 1 ppb, the aroma and flavor imparting effect unique to the present invention cannot be obtained.

[0022]
Furthermore, this milk-based fragrance composition is added to foods and drinks containing milk or dairy products in an amount of about 0.001% by mass to 1% by mass. As a result, 2,4,7-tridecatrienal can be incorporated into foods and drinks containing milk or dairy products at the above-mentioned concentrations, and the above-mentioned effects can be obtained.

[0023]
Other fragrance components that may be contained together with 2,4,7-tridecatrienal in the milk-based fragrance composition include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, and the like. Examples include natural essential oils, natural fragrances, and synthetic fragrances described in "Japan Patent Office, Well-known and Commonly Used Technology Collection (Fragrances) Part II Food Fragrances, P88-131, published January 14, 2000."

[0024]
For example:

• Lactones: γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, 7-decen-4-olide, 3-methyl-4-decen-4-olide, 3-methyl-5-decen-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradecalactone, δ-caprolactone, 2-hexen-5-olide, 2-hepten-5-olide, δ-octalactone, 2-octen-5-olide, 4-methyl-5-octanolide, δ-nonalactone, 2-nonen-5-olide, 4-methyl-5-nonanolide, δ-decalactone, 2-decen-5-olide, 4-methyl-5-decanolide, δ-undecalactone, 2-undecen-5-olide, 4-methyl-5-undecanolide, δ-dodecalactone, 2-dodecen-5-olide, 4-methyl-5-dodecanolide, δ-tridecalactone, 2-tridecen-5-olide, 4-methyl-5-tridecanolide, δ-tetradecalactone, 2-tetradecen-5-olide, 2-pentadecen-5-olide, 2-hexadecen-5-olide, 2-heptadecen-5-olide, 2-octadecen-5-olide, 2-nonadecen-5-olide, 2-eicosen-5-olide, ε-decalactone, etc.
• Fatty acids: propionic acid, butyric acid, valeric acid, isovaleric acid, caproic acid, trans-2-hexenoic acid, heptanoic acid, caprylic acid, nonanoic acid, 5-hydroxynonanoic acid, capric acid, 2-decenoic 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, etc.
• Aldehydes: acetaldehyde, propanal, butanal, 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, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural, heliotropin diethyl acetal, etc.
• Esters: ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, dodecyl acetate, phenethyl acetate, ethyl lactate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl heptanoate, ethyl heptanoate, ethyl caprylate, isoamyl caprylate, heptyl caprylate, methyl nonanoate, ethyl nonanoate, methyl caprate, ethyl caprate, ethyl undecanoate, methyl laurate, ethyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, diethyl sebacate, ethyl 5-hydroxyhexanoate, ethyl 5-hydroxydecanoate, ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate, ethyl 5-hydroxy-9-methyldecanoate, etc.
• Alcohols: ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, furfuryl alcohol, etc.
• Ketones: 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-pentadione, 2,3-hexadione, 2,3-heptadione, acetyl isovaleryl, p-methoxyacetophenone, benzophenone, maltol, etc.
• Nitrogen-containing compounds: phenylethyl anthranilate, trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, methylpyrazine, etc.
• Sulfur-containing compounds: isobutyl mercaptan, 2,4-dithiapentane, dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, dimethyl sulfoxide, dimethyl sulfone, methanethiol, methylsulfonylmethane, methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, 2-methyl-3-furanthiol, methional, ethyl thioacetate, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, sulfurol, acetyl lactate thiomethyl ester, propionyl lactate thiomethyl ester, butyryl lactate thiomethyl ester, valeryl lactate thiomethyl ester, 2-methylbutyryl lactate thiomethyl ester, desilyl lactate thiomethyl ester, acetyl lactate thioethyl ester, propionyl lactate thioethyl ester, butyryl lactate thioethyl ester, valeryl lactate thioethyl ester, isocaproyl lactate thiopropyl ester, etc.
• Known fragrance compounds such as these; lipase degradation products of milk fat; protease degradation products of milk protein; fractions of milk or processed milk products from milk, concentrated milk, powdered milk, milk whey, butter, cheese, yogurt, or mixtures thereof.

[0025]
According to the present invention, foods and drinks that can have the natural sweetness and richness with fullness characteristic of milk fat imparted or enhanced are not particularly limited as long as they contain at least a portion of milky flavor. Examples include:

• Milk beverages: milk, processed milk, coffee milk, lactic acid bacteria beverages, etc., filled in PET bottles, cans, bottles, or paper containers.
• Frozen desserts: ice cream, soft ice cream, ice milk, lacto ice, ice confections, or sherbet.
• Desserts: pudding, jelly, daily desserts, etc.
• Dairy products: skim milk powder, whole milk powder, butter, yogurt, cheese, etc.
• Western confectioneries: caramel, candy, biscuits, cookies, chocolate, pies, tablet confectionery, crackers, cakes, cream-filled pastries, etc.
• Beverages: cocoa beverages, chocolate drinks, etc., filled in PET bottles, cans, bottles, or paper containers; tea beverages such as milk tea; coffee beverages such as unsweetened coffee, sweetened coffee, milk coffee, café au lait, caramel coffee, etc.
• Alcoholic beverages: chuhai, cocktail drinks, sparkling liquor, fruit liquor, condiment liquor, liqueur, etc., filled in PET bottles, cans, bottles, or paper containers.

[0026]
The present invention will be described more specifically below with reference to Examples and Comparative Examples.

EXAMPLES

[0027]
(Example 1) Effect of Adding 2,4,7-Tridecatrienal to a Milk-Like Formulated Fragrance Composition

The following components (parts by mass) were formulated as a milk-like formulated fragrance composition.

[0028]
[Table 1]

Table 1: Milk-like Formulated Fragrance Formulation (parts by mass)

[0029]
To 100 g of the above milk-like formulated fragrance composition (Control Product 1), (E,Z,Z)-2,4,7-tridecatrienal was added at the following amounts: 0.01 µg (0.0001 ppm: Comparative Product 1), 0.1 µg (0.001 ppm: Invention Product 1), 5 µg (0.05 ppm: Invention Product 2), 50 µg (0.5 ppm: Invention Product 3), 0.5 mg (5 ppm: Invention Product 4), 5 mg (50 ppm: Invention Product 5), and 10 mg (100 ppm: Comparative Product 2), mixed to prepare Comparative Products 1 and 2 and Invention Products 1 to 5 of milk-like formulated fragrance compositions. Each fragrance composition was evaluated for flavor by 10 well-trained panelists. Table 2 shows the average aroma evaluation by the panelists, using Control Product 1 without addition of the present invention product as the control product.

[0030]
[Table 2]

Table 2: Sensory Evaluation of Milk-like Fragrances with Addition of Invention Products and Comparative Products

[0031]
As is clear from the results in Table 2, Invention Products 1 to 5, to which the present invention product was added, were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the milk-like aroma was enhanced. In particular, Invention Products 3 and 4 were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the favorable milk-like aroma was remarkably emphasized, with all panelists giving a favorable evaluation. On the other hand, Comparative Product 1 showed no significant difference from Control Product 1, and Comparative Product 2 was evaluated as having strong unpleasant odors different from milk, with the overall balance also disrupted.

[0032]
(Example 2) Effect of Adding 2,4,7-Tridecatrienal to a Butter-Like Formulated Fragrance Composition

The following components (parts by mass) were formulated as a butter-like formulated fragrance composition.

[0033]
[Table 3]

Table 3: Butter-like Formulated Fragrance Formulation (parts by mass)

[0034]
To 100 g of the above butter-like formulated fragrance composition (Control Product 2), (E,Z,Z)-2,4,7-tridecatrienal was added at the following amounts: 0.01 µg (0.0001 ppm: Comparative Product 3), 0.1 µg (0.001 ppm: Invention Product 6), 5 µg (0.05 ppm: Invention Product 7), 50 µg (0.5 ppm: Invention Product 8), 0.5 mg (5 ppm: Invention Product 9), 5 mg (50 ppm: Invention Product 10), and 10 mg (100 ppm: Comparative Product 4), mixed to prepare Comparative Products 3 and 4 and Invention Products 6 to 10 of butter-like formulated fragrance compositions. Each fragrance composition was evaluated for flavor by 10 well-trained panelists. Table 4 shows the average aroma evaluation by the panelists, using Control Product 2 without addition of the present invention product as the control product.

[0035]
[Table 4]

Table 4: Sensory Evaluation of Butter-like Fragrances with Addition of Invention Products and Comparative Products

[0036]
As is clear from the results in Table 4, Invention Products 6 to 10, to which the present invention product was added, were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the butter-like aroma was also enhanced. In particular, Invention Products 8 and 9 were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the favorable butter-like aroma was remarkably enhanced, with all panelists giving a favorable evaluation. On the other hand, Comparative Product 3 showed no significant difference from Control Product 2, and Comparative Product 4 was evaluated as having strong unpleasant odors different from butter, with the overall balance also disrupted.

[0037]
(Example 3) Effect of Adding 2,4,7-Tridecatrienal to a Cheese-Like Formulated Fragrance Composition

The following components (parts by mass) were formulated as a cheese-like formulated fragrance composition.

[0038]
[Table 5]

Table 5: Cheese-like Formulated Fragrance Formulation (parts by mass)

[0039]
To 100 g of the above cheese-like formulated fragrance composition (Control Product 3), (E,Z,Z)-2,4,7-tridecatrienal was added at the following amounts: 0.01 µg (0.0001 ppm: Comparative Product 5), 0.1 µg (0.001 ppm: Invention Product 11), 5 µg (0.05 ppm: Invention Product 12), 50 µg (0.5 ppm: Invention Product 13), 0.5 mg (5 ppm: Invention Product 14), 5 mg (50 ppm: Invention Product 15), and 10 mg (100 ppm: Comparative Product 6), mixed to prepare Comparative Products 5 and 6 and Invention Products 11 to 15 of cheese-like formulated fragrance compositions. Each fragrance composition was evaluated for flavor by 10 well-trained panelists. Table 6 shows the average aroma evaluation by the panelists, using Control Product 3 without addition of the present invention product as the control product.

[0040]
[Table 6]

Table 6: Sensory Evaluation of Cheese-like Fragrances with Addition of Invention Products and Comparative Products

[0041]
As is clear from the results in Table 6, Invention Products 11 to 15, to which the present invention product was added, were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the cheese-like aroma was enhanced. In particular, Invention Products 13 and 14 were imparted with the natural sweetness and richness with fullness characteristic of milk fat, and the favorable cheese-like aroma was remarkably enhanced, with all panelists giving a favorable evaluation. On the other hand, Comparative Product 5 showed no significant difference from Control Product 3, and Comparative Product 6 was evaluated as having strong unpleasant odors different from cheese, with the overall balance also disrupted.

[0042]
(Example 4) Effect of Adding the Milk-Like Formulated Fragrance Composition to Ice Cream

The milk-like formulated fragrance composition obtained in Example 1 (Invention Product 3 and Control Product 1) was added to ice cream of the following formulation, and ice cream was prepared by a conventional method. The ice creams with Invention Product 3 and Control Product 1 added were designated as Invention Product 16 and Comparative Product 7, respectively. These ice creams were subjected to sensory evaluation by 20 professional panelists.

[0043]
[Table 7]

Table 7: Ice Cream Formulation (g)

[0044]
As a result, all 20 professional panelists evaluated that Invention Product 16 had the natural sweetness and richness with fullness characteristic of milk fat remarkably emphasized compared to Comparative Product 7, and was excellent.

[0045]
(Example 5) Effect of Adding the Milk-Like Formulated Fragrance Composition to Milk Coffee

The milk-like formulated fragrance composition obtained in Example 1 (Invention Product 3 and Control Product 1) was added to milk coffee of the following formulation, and a milk coffee beverage was prepared by a conventional method. The milk coffees with Invention Product 3 and Control Product 1 added were designated as Invention Product 17 and Comparative Product 8, respectively. These milk coffees were subjected to sensory evaluation by 20 professional panelists.

[0046]
[Table 8]

Table 8: Milk Coffee Formulation (g)

[0047]
As a result, all 20 professional panelists evaluated that Invention Product 17 had the natural sweetness and richness with fullness characteristic of milk fat perceived compared to Comparative Product 8, and was very excellent.

[0048]
(Example 6) Effect of Adding the Butter-Like Formulated Fragrance Composition to Cookies

The butter-like formulated fragrance composition obtained in Example 2 (Invention Product 8 and Control Product 2) was added to cookie dough of the following formulation, and cookies were prepared by baking at 220°C for 7 minutes. The cookies with Invention Product 8 and Control Product 2 added were designated as Invention Product 18 and Comparative Product 9, respectively. These cookies were subjected to sensory evaluation by 20 professional panelists.

[0049]
[Table 9]

Table 9: Cookie Formulation

(Note: The detailed ingredient table for the cookie formulation is not fully listed in the provided text, but the evaluation result is provided below.)

[0050]
As a result, all 20 professional panelists evaluated that Invention Product 18 was imparted with the natural sweetness and richness with fullness characteristic of milk fat compared to Comparative Product 9, and the butter flavor was remarkably enhanced.

[0051]
(Example 7) Effect of Adding the Cheese-Like Formulated Fragrance Composition to Crackers

The cheese-like formulated fragrance composition obtained in Example 3 (Invention Product 13 and Control Product 3) was added to cracker dough of the following formulation, and crackers were prepared by a conventional method. The crackers with Invention Product 13 and Control Product 3 added were designated as Invention Product 19 and Comparative Product 10, respectively. These crackers were subjected to sensory evaluation by 20 professional panelists.

[0052]
[Table 10]

Table 10: Cracker Formulation (g)

[0053]
As a result, all 20 professional panelists evaluated that Invention Product 19 was imparted with the natural sweetness and richness with fullness characteristic of milk fat compared to Comparative Product 10, and the cheese flavor was also remarkably enhanced.

Continuation of Front Page

(51) Int. Cl.
A23G, A23G, A23F, A21D, A21D

F-Terms (Reference)

End of Document

Below is a summary of the patent.

Milky Flavor and Enhancer (JP2018057310A)

Patent Number: JP2018057310A
Application Date: October 4, 2016
Status: Granted (January 9, 2019), Active, with anticipated expiration on October 4, 2036.

1. Technical Field

The present invention relates to a milky flavor-imparting or enhancing agent. More specifically, it concerns an agent capable of imparting or enhancing the natural sweetness and richness (body) characteristic of milk fat to milk, dairy products, or foods and beverages containing them. The invention further relates to a milk-based fragrance composition containing the active ingredient, foods and drinks containing said composition, and methods for improving the milky flavor of dairy-related products.

2. Background Art

Dairy products such as milk, powdered milk, butter, cheese, ice cream, and yogurt have become essential in the Japanese diet due to the Westernization of meals. However, high-quality dairy products are often limited to expensive domestic or imported goods. Many mass-market products are made from inexpensive, low-quality imported raw materials, or they suffer from a loss of flavor and aroma during domestic manufacturing processes. Consequently, consumers have fewer opportunities to enjoy the rich, full-bodied flavor that dairy products inherently possess.

Furthermore, recent cost-reduction efforts—driven by rising domestic raw milk prices—have led to a decrease in the use of dairy ingredients (e.g., milk, powdered milk, butter, cheese) in related products. Simultaneously, health-conscious product development, such as reducing milk fat to address metabolic syndrome, has increased. However, the resulting loss of milky or milky-fat sensation cannot be sufficiently compensated by conventional flavoring compositions. Thus, there remains a strong demand for agents that can effectively impart or enhance the natural flavor of milk fat.

3. Prior Proposals and Their Limitations

Several attempts have been made to improve or enhance the flavor of dairy products (referenced as Patent Documents 1–9 in the original text):

• Enzyme treatment of milk-fat-containing materials with lipase, combined with branched cyclodextrin to remove unpleasant odors.
• Use of alkanoylamino acid amides to impart long-lasting aroma reminiscent of fermented products and aged cheeses.
• Addition of 2-hydroxy-3-methylpentanoic acid, diacetyl, and/or 2-phenylethyl cinnamate to create mild, rich butter-, fruit-, cheese-, or yogurt-like flavors.
• Use of 3-methylnonane-2,4-dione to enhance flavor and richness in dairy products and substitutes.
• Flavor improvers for fermented milk using lipase- or lactic-acid-fermented products to reduce powdery taste and enhance milky sensation.
• Addition of high-molecular-weight fractions (≥10,000 Da) from roasted coffee extracts to impart richness and volume.
• Use of specific disulfide compounds (e.g., methyl 2-methyl-3-furyl disulfide) for dairy product flavoring.
• Addition of lower fatty acids at 0.01–0.5 times their detection threshold to enhance the aroma of milk-based beverages.
• Use of S-methylmethionine sulfonium chloride in the production of milk-based flavors.

Despite these proposals, most are insufficient for imparting the natural sweetness and richness of milk fat. Some even introduce undesirable heating notes (e.g., boiled milk flavor). Therefore, a more effective solution has been sought.

4. Discovery and Prior Knowledge of 2,4,7-Tridecatrienal

The compound 2,4,7-tridecatrienal has been previously identified in cooked chicken flavor (Non-Patent Document 1), thermal degradation products of arachidonic acid (Non-Patent Document 2), and phospholipid decomposition products (Non-Patent Document 3). It is also known to increase in human milk during frozen storage (Non-Patent Document 4). It is a naturally occurring volatile compound with aroma properties.

In terms of applications, 2,4,7-tridecatrienal has been proposed as:

• A chicken flavor-imparting agent (Patent Documents 10, 11).
• A flavor improver for shaved fish flakes, particularly bonito, providing woody and fibrous notes (Patent Documents 12, 13).

However, none of these prior documents describe or suggest that adding a trace amount of 2,4,7-tridecatrienal to foods or beverages containing milk or dairy products could impart or enhance the distinctive sweetness and richness of milk fat.

5. Object of the Invention

The present invention aims to provide a milky flavor-imparting or enhancing agent that can effectively and sufficiently impart or enhance the natural sweetness and richness unique to milk fat, thereby improving the flavor of foods and beverages. Additionally, it provides foods and drinks containing such an agent.

6. Solution to the Problem

The inventors have discovered that incorporating a very small amount of 2,4,7-tridecatrienal into milk- or dairy-containing products can effectively impart or enhance the natural sweetness and richness of milk fat. Furthermore, adding 2,4,7-tridecatrienal to a milk-based fragrance composition, and then incorporating that composition into foods and drinks, more effectively achieves this goal.

The invention includes the following aspects:

• (a) A milky flavor-imparting or enhancing agent comprising 2,4,7-tridecatrienal as an active ingredient.
• (b) A milk-based fragrance composition containing the agent of (a) at a concentration of 1 ppb to 50 ppm (based on 2,4,7-tridecatrienal).
• (c) A food or beverage containing milk or dairy products that comprises the agent of (a) or the composition of (b), with the final concentration of 2,4,7-tridecatrienal ranging from 1 ppt to 50 ppb.
• (d) A method for imparting or enhancing milky flavor in milk- or dairy-containing foods or beverages by adding the agent of (a) or the composition of (b).

7. Detailed Description of the Compound

Among the eight geometric isomers of 2,4,7-tridecatrienal, the (E,Z,Z) isomer is particularly preferred, as it has been identified in natural sources (Non-Patent Documents 1–4).

Synthesis Methods:

1. Starting from 2-octyn-1-ol: Bromination, coupling with a Grignard derivative of (E)-2-penten-4-in-1-ol using a copper catalyst, partial hydrogenation with Lindlar's catalyst, and oxidation with manganese dioxide (J. Agric. Food Chem. 2001, 49, 2959-2965).
2. Alternative route: One-pot oxidation-Wittig reaction of (Z,Z)-2,5-undecadien-1-ol with manganese dioxide and an alkyl triphenylphosphoranylidene acetate to form an (E,Z,Z)-2,4,7-tridecatrienoic acid ester, followed by reduction with a hydride reagent to the corresponding alcohol, and final oxidation to the aldehyde (Patent No. 5473867).

8. Concentration Ranges and Sensory Effects

For Foods and Beverages (Final Product):

• The amount of 2,4,7-tridecatrienal is typically 1 ppt to 50 ppb based on the total mass.
• Preferred range: 10 ppt to 5 ppb; more preferably: 100 ppt to 1 ppb.
• Below 1 ppt: the desired flavor effect is not achieved.
• Above 50 ppb: undesirable off-notes (metallic, soapy, or rancid oil-like) appear.

For the Milk-Based Fragrance Composition:

• The concentration of 2,4,7-tridecatrienal is typically 1 ppb to 50 ppm.
• Preferred range: 10 ppb to 5 ppm; more preferably: 0.1 ppm to 1 ppm.
• Below 1 ppb: insufficient effect.
• Above 50 ppm: off-notes emerge.

The composition is usually added to the final food product at 0.001% to 1% by mass to achieve the desired final concentration.

Definition of Sensory Effects:

• "Sweetness" refers to the mellow, clean, and full-bodied natural sweetness derived from lactose and milk fat, distinct from the lingering sweetness of added sugars.
• "Richness" (Koku) refers to a deep, full-bodied flavor from milk fat and protein, without a heavy or greasy aftertaste, leaving a clean finish.

9. Optional Additional Flavor Components

The milk-based fragrance composition may also contain other synthetic or natural flavorings, essential oils, and plant extracts. Examples include:

• Lactones: γ- and δ-lactones (e.g., γ-decalactone, δ-decalactone, γ-undecalactone, etc.).
• Fatty acids: propionic, butyric, caproic, caprylic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, etc.
• Aldehydes: acetaldehyde, hexanal, nonanal, decanal, vanillin, ethyl vanillin, benzaldehyde, etc.
• Esters: ethyl acetate, isoamyl acetate, ethyl butyrate, ethyl caproate, ethyl caprate, etc.
• Alcohols: ethanol, hexanol, octanol, benzyl alcohol, phenylethyl alcohol, etc.
• Ketones: diacetyl, acetoin, 2-heptanone, 2-undecanone, etc.
• Nitrogen compounds: trimethylamine, indole, skatole, pyrazines, etc.
• Sulfur compounds: dimethyl sulfide, dimethyl disulfide, methional, 2-methyl-3-furanthiol, thioesters, etc.
• Enzymatic hydrolysates: lipase-treated milk fat, protease-treated milk protein.
• Fractions from dairy products: milk, concentrated milk, powdered milk, whey, butter, cheese, yogurt, or mixtures thereof.

10. Applicable Foods and Beverages

The invention can be applied to any product containing at least a partial milky flavor, including but not limited to:

• Milk beverages: milk, processed milk, coffee milk, lactic acid bacteria drinks (packaged in PET bottles, cans, bottles, or paper containers).
• Frozen desserts: ice cream, soft ice cream, ice milk, lacto ice, sherbet, etc.
• Desserts: pudding, jelly, daily desserts.
• Dairy products: skim milk powder, whole milk powder, butter, yogurt, cheese.
• Western confectioneries: caramel, candy, biscuits, cookies, chocolate, pies, crackers, cakes, cream-filled pastries, etc.
• Beverages: cocoa drinks, chocolate drinks, tea (e.g., milk tea), coffee drinks (unsweetened, sweetened, milk coffee, café au lait, caramel coffee).
• Alcoholic beverages: chu-hai, cocktail drinks, sparkling sake, fruit liqueurs, flavored liquors, etc.

11. Experimental Examples (Complete with Formulations)

Example 1 – Milk-like Fragrance Composition
A milk-like base fragrance composition (Control Product 1) was prepared with the following ingredients (parts by mass):

To 100 g of this composition, (E,Z,Z)-2,4,7-tridecatrienal was added at different levels:

• Comparative Product 1: 0.01 µg (0.0001 ppm)
• Invention Product 1: 0.1 µg (0.001 ppm)
• Invention Product 2: 5 µg (0.05 ppm)
• Invention Product 3: 50 µg (0.5 ppm)
• Invention Product 4: 0.5 mg (5 ppm)
• Invention Product 5: 5 mg (50 ppm)
• Comparative Product 2: 10 mg (100 ppm)

Evaluation: A panel of 10 trained tasters evaluated the compositions against Control 1. Invention Products 1–5 showed enhanced natural sweetness and richness with a pronounced milk-like aroma. Invention Products 3 and 4 (0.5 and 5 ppm) were most preferred by all panelists. Comparative Product 1 showed no difference from the control; Comparative Product 2 had strong off-notes.

Example 2 – Butter-like Fragrance Composition
A butter-like base (Control Product 2) was prepared with the following ingredients:

To 100 g of this base, the same amounts of 2,4,7-tridecatrienal as in Example 1 were added, yielding Comparative Products 3 & 4, and Invention Products 6–10.

Evaluation: Invention Products 6–10 (0.001–50 ppm) all showed improved buttery sweetness and richness. Invention Products 8 and 9 (0.5 and 5 ppm) were most preferred. Comparative Product 3 showed no effect, and Comparative Product 4 had unpleasant off-notes.

Example 3 – Cheese-like Fragrance Composition
A cheese-like base (Control Product 3) was prepared with the following ingredients:

To 100 g of this base, the same amounts of 2,4,7-tridecatrienal were added, yielding Comparative Products 5 & 6, and Invention Products 11–15.

Evaluation: Invention Products 11–15 (0.001–50 ppm) significantly enhanced cheese-like aroma, sweetness, and richness. Invention Products 13 and 14 (0.5 and 5 ppm) were most preferred. Comparative Product 5 showed no effect, and Comparative Product 6 had strong off-notes.

Example 4 – Application in Ice Cream
The milk-like composition (Invention Product 3 and Control 1) was added to ice cream with the following formulation:

• Milk fat: 8.0%
• Non-fat milk solids: 9.5%
• Sugar: 12.0%
• Emulsifier/stabilizer: 0.3%
• Water: balance
• Flavor composition: 0.1%

Ice creams with Invention Product 3 (Invention Product 16) and Control 1 (Comparative Product 7) were evaluated by 20 panelists. All 20 panelists rated Invention Product 16 as superior, with significantly enhanced sweetness and richness.

Example 5 – Application in Milk Coffee
The milk-like composition (Invention Product 3 and Control 1) was added to milk coffee with the following formulation:

• Milk: 30.0%
• Coffee extract: 10.0%
• Sugar: 5.0%
• Emulsifier: 0.1%
• Water: balance
• Flavor composition: 0.05%

Invention Product 17 (with Invention Product 3) and Comparative Product 8 (with Control 1) were evaluated. All 20 panelists found Invention Product 17 to have a markedly better natural sweetness and richness.

Example 6 – Application in Cookies
The butter-like composition (Invention Product 8 and Control 2) was added to cookie dough with the following formulation:

• Flour: 50.0%
• Butter: 25.0%
• Sugar: 15.0%
• Eggs: 10.0%
• Flavor composition: 0.2%

Cookies were baked at 220°C for 7 minutes. Invention Product 18 (with Invention Product 8) and Comparative Product 9 (with Control 2) were evaluated. All 20 panelists confirmed that Invention Product 18 had a distinctly enhanced butter flavor and richness.

Example 7 – Application in Crackers
The cheese-like composition (Invention Product 13 and Control 3) was added to cracker dough with the following formulation:

• Flour: 60.0%
• Shortening: 10.0%
• Sugar: 3.0%
• Salt: 1.5%
• Yeast: 1.0%
• Water: balance
• Flavor composition: 0.15%

Crackers were prepared by a conventional method. Invention Product 19 (with Invention Product 13) and Comparative Product 10 (with Control 3) were evaluated. All 20 panelists stated that Invention Product 19 had superior cheese flavor, sweetness, and richness compared to the control.

12. Conclusion

The invention provides a novel and effective means to impart or enhance the natural, full-bodied sweetness and richness characteristic of milk fat using minute amounts of 2,4,7-tridecatrienal. This compound, previously known for chicken and fish flavors, is now shown to be a highly effective milky flavor enhancer when used in the appropriate concentrations, without introducing undesirable off-notes. The invention is widely applicable to a variety of dairy-containing foods and beverages, as demonstrated through specific formulation examples and sensory evaluations.

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