Process for producing a fruity flavoring agent

Food or edible material: processes – compositions – and products – Fermentation processes – Of milk or milk product

Reexamination Certificate

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C426S035000, C426S534000, C426S650000

Reexamination Certificate

active

06242015

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a process for producing a flavoring agent having a strong fruity flavor which comprises treating milk or milk products with lipase and an ester-synthesizing enzyme, and to a use of said flavoring agent in foods, particularly processed foods.
BACKGROUND ART
Some methods are known for producing flavoring agents derived from milk or milk products: for example, a method in which fresh cream or milk is treated with an enzyme derived from animal pharynx (U.S. Pat. Nos. 3,469,993, 3,650,768); a method in which milk or cream is treated with lipase derived from a microorganism (Japanese Published Examined Patent Application No. 3187/70); a method in which butter is hydrolyzed and then treated with lipase derived from a microorganism in the presence of an alcohol [Journal of the Japanese Society for Food Science and Technology, Vol. 30, p. 572 (1983)]; a method in which vegetable fats and oils are hydrolyzed and then treated with lipase derived from a microorganism in the presence of an alcohol (Japanese Published Examined Patent Application No. 50554/81); and a method in which butter oil is treated with esterase derived from an animal in the absence of an alcohol and then treated with lipase (Japanese Published Unexamined Patent Application No. 66856/84). The flavoring agents derived from milk or milk products which are obtained by the above methods have a butter flavor or a cheese flavor, but do not have a rich fruity flavor.
It is known that large amounts of higher fatty acid ethyl esters are formed by treating, in the presence of ethanol, butter fat with lipase derived from a microorganism [Journal of the Japanese Society for Food Science and Technology, Vol. 30, p. 572 (1983)]. However, flavoring agents containing quantities of higher fatty acid alkyl esters have waxy smell and taste.
In another known method, an enzyme derived from animal liver or kidney having a high ester-synthesizing activity is brought into contact with foods and beverages to impart a fruit flavor thereto (WO 93/09681). However, the treatment of milk or milk products with only escerase derived from animal liver or kidney would produce rather grassy smell than a fruit flavor.
DISCLOSURE OF THE INVENTION
According to the present invention, flavoring agents having a fruity flavor can be produced by treating milk or milk products with lipase, and in the presence of an alcohol, with an animal-derived enzyme having the activity to produce an ester using an organic acid and an alcohol as substrates (hereinafter referred to as an ester-synthesizing enzyme or esterase).
Preferred flavoring agents with a rich flavor can be obtained by the use of an ester-synthesizing enzyme having the ethyl butyrate-synthesizing activity of 0.1 unit/mg protein or above when 0.5% ethanol and 2.6% butyric acid are used as substrates. The enzymatic treatment may be carried out first with lipase and then with an ester-synthesizing enzyme, or with both of them at the same time.
A fermentation step with a lactic acid bacterium may be added at any stage of the production process of the above flavoring agents to intensify the flavor thereof.
The flavoring agents obtained according to the above method contain milk fat and quantities of fatty acid alkyl esters, specifically large amounts of lower fatty acid alkyl esters. They have a rich flavor and are useful in processing foods.
Of the flavoring agents obtained according to the method of the present invention, those which contain fatty acid alkyl esters in the total amount of 20 &mgr;mol or more, preferably 27 &mgr;mol or more per gram, and in which 80% or more, preferably 90% or more of the fatty acid alkyl esters contained is lower fatty acid alkyl esters have particularly rich flavor.
Specifically, flavoring agents containing lower fatty acid alkyl esters of the following composition have a rich flavor:
composition by concentration: ethyl butyrate, 35-50%, preferably 38-46%; ethyl caproate, 15-30%, preferably 20-27%; ethyl caprylate, 5-10%, preferably 6-9%; ethyl caprate, 15-30%, preferably 20-26%;
composition by weight: ethyl butyrate, 20-40 parts by weight, preferably 25-35 parts by weight; ethyl caproate, 15-30 parts by weight, preferably 20-25 parts by weight;
ethyl caprylate, 3-15 parts by weight, preferably 5-10 parts by weight; ethyl caprate, 20-40 parts by weight, preferably 25-35 parts by weight.
Based on the analysis of the flavoring agents obtained by the enzyme reaction, the composition of mixtures of milk fat and fatty acid alkyl esters can be clarified, and thus the flavoring agents can be obtained only by mixing components without the enzyme reaction. However, flavoring agents obtained by the enzyme reaction have a richer flavor and are preferred.
In producing such mixtures, either saturated fatty acids or unsaturated fatty acids can be used as the fatty acid moieties of the fatty acid alkyl esters so long as they are constituents of milk fat.
In the present invention, the term lower fatty acids refers to fatty acids having 1-10 carbon atoms, and the term higher fatty acids refers to fatty acids having 11-32 carbon atoms.
Examples of the lower fatty acids which are constituents of milk fat are butyric acid, caproic acid, caprylic acid, and capric acid.
Examples of the higher fatty acids which are constituents of milk fat are lauric acid, myristic acid, pentadecylic acid, palmitic acid, palmitoleic acid, heptadecylic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, arachidonic acid, behenic acid, and lignoceric acid.
Examples of the alkyl moieties of the fatty acid alkyl esters are straight-chain or branched alkyl having 1-6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, and hexyl.
Examples of the raw milk for the milk and milk products used in the present invention are those from animals such as cows, goats, sheep, camels, reindeers, yaks, horses, and donkeys.
The term milk products means the products obtained by processing milk, and examples thereof are cream, butter, butter oil, cheese, concentrated whey, ice cream, ice cream [milk solid non fat (MSNF): over 10%, fat: over 3%)], ice cream (MSNF: over 3%), concentrated milk, defatted concentrated milk, nonfat condensed milk, nonsugar skim milk, condensed milk, condensed skim milk, whole dry milk, skim milk powder, cream powder, whey powder, sweetened dry milk, sweetened skim milk powder, adjusted dry milk, yogurt (fermented milk), lactic acid beverages, and milk beverages. They are used alone or as a mixture. Solid components such as dry milk can be used in the form of a solution or a dispersion in a solvent such as milk or water.
In the enzyme reaction, the milk fat is usually used at a concentration of 3-55%, preferably 18-45%.
As for the components of general milk or milk products, it is known that whole milk comprises about 3% each of fat and protein, about 5% of sugar, and 88% of water, cheese comprises 27-34% of fat, 25-31% of protein, and 33-40% of water, and butter comprises 81-84% of fat and 16% of water. The other components of the above milk products and the main components of other milk and milk products are also widely known [Food Additives & Food Ingredients Convenient Book, edited by Akio Sotoyama, The Food Science Co., Ltd. (1976)].
The milk fat content of milk or milk products can be determined according to an ordinary method, for example, the Röse-Gottlieb method [Official Methods of Analysis of the AOAC. 13th ed. 245 (1980)].
Preferred examples of the raw materials are milk, cream, whole fat sugarless yogurt, ice cream, ice cream (MSNF: over 10%, fat: over 3%), whole dry milk, adjusted dry milk, and cheese. Particularly preferred is cream.
Suitable cream to be used includes the following: fresh cream which is prepared by separating raw milk into cream and skim milk by centrifugation; fresh cream which is prepared by adding skim milk to fresh cream to adjust the milk fat content; compound cream which is prepared by r

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