JPWO2017188161A1 - Flavor improver - Google Patents

Abstract

A flavor improving material comprising, as an active ingredient, a partial hydrolyzate of animal and vegetable oils and fats brought into contact with an adsorbent. The adsorbent preferably has a pH of 3.0 to 8.0, and silica gel is preferred as the adsorbent. Moreover, it is preferable that the partial hydrolyzate of the animal and vegetable fats and oils is obtained by a column-type enzymatic decomposition method. It is preferable that the enzyme decomposition method uses an immobilized enzyme using an ion exchange resin as a carrier. The step of performing an oxidation treatment so that the peroxide value of the partial hydrolyzate of animal and vegetable oils and fats is 5 to 60 before or after the partial hydrolyzate of the animal and vegetable oils and fats contacts with the adsorbent ( It is preferable that the material has undergone A).

Description

  The present invention relates to a flavor improving material capable of imparting a rich taste to food and drink.

  In recent years, with increasing consumer preference for processed foods, the demands have been diversified and sophisticated. In particular, there is a demand not only for flavors that directly affect the taste, such as sweetness, saltiness, and acidity, but also for secondary flavors that can be obtained only by processing raw materials in general, such as richness. On the other hand, the flavor sensation such as richness is considered to involve different components for each raw material, so that it has been generally studied according to the material and use. Therefore, there has been a demand for a material that can raise the characteristics of the raw material and give a rich taste to a wide range of uses. In order to solve such problems, various methods have been studied so far.

As one of the techniques, utilization of a partial hydrolyzate of animal and vegetable oils and fats has been studied.
The partial hydrolyzate of animal and vegetable oils and fats is obtained by allowing alkali and lipolytic enzymes to act on edible animal and vegetable oils and fats, and in addition to fatty acids and glycerin, it contains a variety of flavor components derived from these. It is.
In the food industry, the technology of using a partial hydrolyzate of animal and vegetable oils and fats as an effective flavor component of flavor improvers is to provide animal foods and fats for the purpose of imparting a rich and rich flavor to foods and drinks. Regardless of the type of vegetable oils and fats, it has been studied conventionally.

  For example, Patent Document 1 proposes a dairy flavor in which a lipolytic enzyme produced by a specific microorganism is allowed to act. In patent document 2, the flavor improving material of the food / beverage products which uses a whey protein degradation product and a milk fat degradation product as an active ingredient is proposed. In patent document 3, the flavor modifier which uses the alkaline hydrolysis product of milk fat as an active ingredient is proposed. Patent Document 4 proposes an enzyme hydrolyzate of vegetable oil containing abundant oleic acid as a constituent fatty acid. In patent document 5, the impact material of food-drinks and the improvement material of mouthfeel which use the diglyceride fraction of the hydrolyzate of animal and vegetable fats and oils as an active ingredient are proposed.

However, in the method of Patent Document 1, the protein contained in the enzyme-treated product is heated by the heating at the time of deactivation of the enzyme after the milk fat-containing food material is treated with the enzyme, and it is easy to impart a taste.
In the method of Patent Document 2, the production efficiency is low because it is necessary to separately prepare and mix the whey protein decomposed product and the milk fat decomposed product, and further, the foreign matter derived from both the whey protein decomposed product and the milk fat decomposed product. There was also a problem that a good flavor would be imparted to the added food or drink.
In the method of Patent Document 3, there is a problem that neutralization treatment with an acid is required, the purification process becomes complicated, and more facilities are required.

Further, in the method of Patent Document 4, the disclosed decomposition rate is low, and it is necessary to add a large amount in order to exhibit a sufficient effect, and there is a possibility that the texture of the food or drink will be changed if an amount that exhibits the effect is added. there were.
In the method of Patent Document 5, a rich and creamy texture is imparted, but this method improves mouthfeel and mouthfeel called mouthfeel, that is, the physical characteristics of the added food and drink. Because it is a change, it did not improve the taste itself of food and drink.

In addition, these methods generally produce and coexist with a good flavor component, a component that leads to a strange odor and a component that easily exhibits an irritating taste, and the off-flavor odor is directly imparted to the food or beverage. There was a risk of lowering.
Therefore, when considering the use of a partial hydrolyzate of animal and vegetable fats and oils as an active ingredient of the flavor improving material, after partial hydrolysis, the ingredients and stimulant tastes that lead to off-flavors from the partial hydrolyzate of animal and vegetable fats and oils are exhibited. It has been necessary to reduce, remove, or modify the facile components to adjust the flavor of the partial hydrolyzate of animal and vegetable fats and oils to a preferred flavor.

  For example, Patent Document 6 proposes a composition in which a branched cyclodextrin is blended with a processed product obtained by treating a milk fat-containing food material with a lipolytic enzyme or with a lipolytic enzyme. A method for producing a milk fat decomposition product has been proposed in which milk fat hydrolyzed is irradiated with ultraviolet rays to enhance the flavor and suppress an irritating decomposition odor.

  However, in the method of Patent Document 6, it has been shown that it is necessary to use protease, fractase or the like in combination in order to impart a rich taste with excellent palatability to foods and drinks. Therefore, the problem of residual enzyme activity was likely to occur. Moreover, although it is suggested in the Examples that it is effective in improving the aftertaste and decomposition odor of stimulating last presumed to be derived from intermediate fatty acids or higher fatty acids, it has a low boiling point and is particularly likely to be a source of off-flavors. There is no description or suggestion regarding lower fatty acids.

  In addition, the method of Patent Document 7 shows that it is necessary to further irradiate ultraviolet rays for 24 to 100 hours after long-term enzymatic degradation, and there is a problem that the production efficiency is high and the production efficiency is very low. It was. Moreover, since strong milk system flavor and oxidation odor coexisted as a result, it could not be said to give a favorable flavor to food and drink.

JP-A 64-002549 Japanese Patent Laid-Open No. 9-037735 JP 58-175468 A JP 2011-223842 A US5695802 (A) JP-A-6-125733 US5753281 (A)

  The object of the present invention is to provide a flavor improving material comprising a partial hydrolyzate of animal and vegetable oils and fats, which can impart a sufficient rich taste to foods and drinks without imparting an off-flavor or pungent taste, and its It is to provide a manufacturing method.

  As a result of diligent research on the subject of partial hydrolyzate of animal and vegetable fats and oils, such as the off-flavor odor and pungent taste associated with the degradation, surprisingly, the present inventors found that partial hydrolysates of animal and vegetable fats and oils It discovered that the said subject was solved by making it contact with adsorption agent, and the improvement of the richness and flavor of the food / beverage products contained and the improvement of flavor intensity | strength can be aimed at.

  This invention is made | formed based on the said knowledge, and provides the flavor improving material which uses the partial hydrolyzate of animal and vegetable fats and oils contacted with the adsorption agent as an active ingredient, and its manufacturing method.

  In addition, as for the partial hydrolyzate of animal and vegetable oils and fats, which is an active ingredient of the flavor improving material of the present invention, the reaction system of hydrolysis is inhomogeneous because the animal and vegetable oils and fats that are the substrate of the lipolytic enzyme are insoluble in water. Therefore, reaction kinetic analysis was difficult. Although the present inventors tried diligently, it was difficult to grasp the actual behavior of the enzyme, and as a result, the partial hydrolyzate of animal and vegetable oils and fats could not be directly identified by the structure or characteristics.

  Hereinafter, it explains in full detail based on preferable embodiment of this invention.

First, a partial hydrolyzate of animal and vegetable oils and fats will be described (hereinafter, animal and vegetable oils and fats may be simply referred to as fats and oils, and animal and vegetable oils and fats may be simply referred to as partial hydrolysates).
The partial hydrolyzate of animal and vegetable fats and oils in the present invention is not limited to animal fats and oils and vegetable fats and oils, and acts on any edible fats and oils by causing alkali or lipolytic enzyme to act on them to partially hydrolyze the fats and oils (hereinafter simply referred to as “fat hydrolysates”). Fatty components derived from fats and oils such as fatty acids, glycerin, monoglycerides, diglycerides, and triglycerides, and organic acids, hydrocarbons, and alcohols that are secondarily produced during the decomposition process. , Aldehydes, esters, sulfur-containing compounds, ketones, fatty acids, fatty acid esters, aromatic compounds, lactones and the like.

  The partial hydrolysis of animal and vegetable fats and oils can be carried out by conventional methods. As the partial hydrolyzate of animal and vegetable fats and oils used in the present invention, commercially available products can be used, or those produced by the production method described below. Although it can also be used, in the present invention, in order to obtain a flavor improving material with less off-flavor odor and pungent taste, it is preferable to use one produced by the production method described below.

The preferable manufacturing method of the partial hydrolyzate of the animal and vegetable fats and oils in this invention is described below.
In the production of the partial hydrolyzate of animal and vegetable fats and oils, the fats and oils used as a substrate are not particularly limited as long as they are edible, and any edible fats and oils can be used. For example, palm oil, palm kernel oil, palm oil, microalgae oil, corn oil, cottonseed oil, soybean oil, rapeseed oil, rice oil, sunflower oil, safflower oil, olive oil, canola oil, beef tallow, milk fat, lard, sheep 1 or 2 selected from various vegetable oils and animal fats and oils such as fat, cacao butter, shea fat, mango kernel oil, monkey fat, iripe fat, fish oil, whale oil, phospholipid, and hydrogenation, fractionation and transesterification Processed fats and oils made of one or more selected from the processed fats and oils that have been subjected to the above treatment, and foods that are processed as a part of the raw oils such as cream, butter, cheese, margarine, and shortening. Etc. are mentioned as substrates used in the present invention.

  In particular, since the effect of imparting a rich taste and richness is high, animal fats such as pork fat, beef tallow and milk fat, or processed fats and oils obtained by subjecting these animal fats to one or more of the above treatments in the substrate It is preferable to include. Even when using a vegetable oil or fat, or a processed oil or fat obtained by subjecting the vegetable oil or fat to one or more of the above-mentioned treatments, it is possible to impart a richer taste and richness than those of conventional products. However, animal fats and oils are often more complex in composition of fatty acids that constitute fats and oils than vegetable fats and oils, and the hydrolysis described later yields partial hydrolysates having a very complex composition of aroma components. As a result, the effect of imparting a rich taste and richness to the food and drink is increased, which is preferable.

  Moreover, the fats and oils used as a substrate can be changed according to the food / beverage products which are the object of flavor improvement. In particular, it is preferable to add a partial hydrolyzate of fats and oils to the foods and drinks containing the fats and oils used as the substrate, since the flavor of the food and drinks is further enhanced.

  Furthermore, an antioxidant such as tocopherol can be contained in advance in an amount of 50 to 1000 ppm with respect to the substrate in order to prevent oxidative degradation of the animal or vegetable oil that is the substrate during the hydrolysis reaction.

  The hydrolysis method for obtaining the partial hydrolyzate is not particularly limited, and examples thereof include a hydrolysis method using an alkali treatment and a hydrolysis method using a lipolytic enzyme (hereinafter sometimes simply referred to as an enzyme). However, since a partial hydrolyzate can be produced under mild conditions, a hydrolysis method using a lipolytic enzyme is preferably selected.

  As the above-mentioned lipolytic enzyme, any of lipolytic enzymes derived from animals and lipolytic enzymes derived from microorganisms can be used without particular limitation, for example, derived from Candida, Aspergillus, Mucor, Chromobacterium genus, Penicillium genus, Rhizopus sp., Rhizomucor sp. Lipolytic enzyme produced by microorganisms derived from origin, Arthrobacter genus, Achromobacter genus, lipolytic enzyme obtained from the pancreas of livestock animals, lipolysis obtained from oral secretory glands such as goats, sheep and calves An enzyme etc. are mentioned. As the lipolytic enzyme, any of a random enzyme and a 1,3-position specific enzyme can be used.

  The above lipolytic enzymes can be used alone or in any combination. Among the above lipolytic enzymes, in particular, enzymes derived from Mucor, Rhizopus, Rhizomucor, and Candida are used. It is preferable to use it from the viewpoint that a partial hydrolyzate with suppressed stimulating flavor derived from lower fatty acids can be obtained.

  Examples of the method for containing the lipolytic enzyme in the animal or vegetable oil or fat as a substrate include a method of containing the lipolytic enzyme itself in the form of a powder or an aqueous solution, and a method using an immobilized lipolytic enzyme (an immobilized enzyme). In addition, microorganisms such as molds and yeasts capable of producing lipolytic enzymes can also be used, but they can be easily separated from the reaction solution, and the enzyme activity in the resulting flavor improving material remains. A method using an immobilized enzyme is preferable because it is difficult to perform recovery and is easy to recover from the system. When an immobilized enzyme is used, the method for immobilizing the enzyme is not particularly limited, and any of a carrier binding method, a crosslinking method, and a comprehensive method is possible, but there are two methods of reducing residual enzyme activity and maintaining enzyme activity. From the viewpoint, it is preferable to select a carrier binding method.

  As the carrier used for the immobilized enzyme, regardless of organic or inorganic, Celite, diatomaceous earth, kaolinite, pentonite, silica gel, molecular sieves, porous glass, activated carbon, calcium carbonate, ceramics, hydroxyapatite and other inorganic carriers, Examples thereof include organic polymers such as polyvinyl alcohol, polypropylene, chitosan, ion exchange resin, hydrophobic adsorption resin, chelate resin, and synthetic adsorption resin. Among these, an ion exchange resin is preferably selected because high enzyme activity and production efficiency are obtained, and among these ion exchange resins, a nonion exchange resin can be selected because of its high ability to retain lipolytic enzymes. preferable.

  About the particle size of a support | carrier, it is preferable that it is 150-1000 micrometers, It is more preferable that it is 200-800 micrometers, It is most preferable that it is 200-600 micrometers. When the particle size of the carrier is less than 150 μm, pressure loss may occur or the separation process may be difficult. Moreover, when it exceeds 1000 micrometers, there exists a possibility that the contact surface of a substrate and an immobilized enzyme may decrease, and it may take time for decomposition | disassembly of animal and vegetable fats and oils. Moreover, it is preferable that the carrier particle of a particle size of 200-600 micrometers is 90% or more on a volume basis.

  In the present invention, the enzymatic reaction process for obtaining a partial hydrolyzate of animal and vegetable fats and oils using a lipolytic enzyme can be a batch type in which the lipolytic enzyme is directly added to the animal and vegetable fats and oils to be subjected to hydrolysis. It is possible to use a column type in which a lipolytic enzyme is packed into a cylindrical container (column) and the animal and vegetable oils and fats to be hydrolyzed are passed through in a liquid state. From the point that adjustment of the reaction rate of the hydrolysis reaction and termination of the hydrolysis reaction can be easily performed by adjusting the amount of liquid fed, and that these operations can be continuously performed by circulation or the like. The column method is preferably selected as the enzymatic decomposition method.

In partially hydrolyzing animal and plant fats and oils selected from the aforementioned fats and oils group, in the present invention, it is necessary to contain a certain amount of water in the fats and oils that are substrates during the hydrolysis step. In the present invention, at the start of hydrolysis, the oil is preferably contained in an amount of 500 to 30000 ppm, more preferably 650 to 15000 ppm, and most preferably 800 to 4000 ppm.
When the moisture content in the fats and oils used as a substrate is less than 500 ppm, the transesterification reaction of fats and oils in equilibrium with the fats and oils decomposition reaction tends to proceed more predominately than the target animal and plant fats and oils decomposition reaction. Therefore, the effect as a flavor improving material may be difficult to obtain. When the water content in fats and oils is more than 30000 ppm, it takes time for the dehydration process to be described later, so that there is a risk that many flavor components that are easily volatilized in the partial hydrolyzate are lost.

As a method of adding water to fats and oils, it is also possible to use animal and vegetable oils and fats whose water has been adjusted in advance, but the contained water gradually decreases due to a hydrolysis reaction with a lipolytic enzyme. After adding water of about 30% by mass or less to 100% by mass of the oil and fat and leaving it to stand still, and confirming the two-phase separation of the animal and vegetable oil and water, the stirring blade is floated from the oil and water interface to the animal and vegetable oil and fat side. After stirring the animal and vegetable oils and fats so as not to disturb the above-mentioned preferable water content, it is possible to continue supplying water to the animal and vegetable oils and fats during the hydrolysis process by taking a method of starting the hydrolysis reaction as it is. This is preferable in terms of efficient hydrolysis of the substrate.
The agitation of animal and vegetable oils and fats is preferably carried out at an arbitrary stirring speed of 300 rpm or less, more preferably 5 to 150 rpm, using a stirring blade or the like.

  In the course of hydrolysis of the fats and oils used as the substrate, the water content is adjusted to 10000 ppm or less when the measured value of the acid value of the oil phase is less than 50, and 20000 ppm or less when the measured value is 50 or more. It is preferable.

  The amount of the above-mentioned lipolytic enzyme varies depending on the amount of fats and oils to be hydrolyzed as a substrate, the titer and type of the lipolytic enzyme, and is appropriately set in each system. Usually, based on the weight of fats and oils as a substrate, for example, in the case of a batch type, 0.01 to 10.0% by mass of fats and oils, preferably 0.01 to 5% by mass of fats and oils, more preferably fats and oils 0.01-1.0 mass% enzyme is contained. In addition, when the hydrolysis of animal and vegetable oils and fats is carried out in a column system, it is preferable to use an immobilized enzyme as the enzyme packed in the column. It is preferable to use 1 to 10% by mass, particularly 0.5 to 5% by mass with respect to fats and oils, for efficiently producing a partial hydrolyzate of animal and vegetable fats and oils.

The flow rate of the fats and oils flowing through the column is preferably set appropriately from the relationship with the enzyme amount. Specifically, the ratio of the flow rate of the animal and vegetable oils and fat to the immobilized enzyme (the flow rate of animal and vegetable oils and fats / Adjust immobilized enzyme weight, unit [/ hour]).
The control of the degree of decomposition of animal and vegetable oils and fats that greatly affect the flavor, and if the flow rate of oils and fats is too large relative to the amount of immobilized enzyme, the reaction does not proceed sufficiently and takes time and the reaction is incomplete. It is preferably 15 to 150 / hour, and more preferably 40 to 125 / hour, from the point of being easily damaged and avoiding deterioration under long-time heating conditions.

The reaction temperature at the time of enzymatic degradation of fats and oils, that is, the fat and oil temperature, is appropriately set according to the optimum temperature at which the activity of the selected enzyme is maximized, but is preferably 35 to 75 ° C as an example. More preferably, it is -70 degreeC, and it is most preferable that it is 45-65 degreeC.
If the oil temperature is less than 35 ° C., the activity of the enzyme may not be sufficient, and oils and fats selected as a substrate, such as oils and fats exhibiting solid properties at room temperature, may not have fluidity. It may be difficult to disassemble. On the other hand, if it exceeds 75 ° C., the protein constituting the enzyme may be denatured and the flavor of the resulting flavor improving material may be impaired due to thermal degradation of the fats and oils of the substrate.

The end point of the hydrolysis reaction for obtaining a partial hydrolyzate of fats and oils can be determined by the acid value (AV), and the reaction is preferably terminated when AV = 10 to 120 is reached. It is more preferable to end the reaction when reaching 30 to 100.
When the acid value is less than 10, the flavor improving material itself obtained has a weak flavor, and at the same time, the flavor improving effect tends to be poor. Moreover, when the acid value is more than 120, the flavor of the resulting flavor improving material itself has a strong taste such as acidity or metal taste, and gives an off-flavor to the contained food or drink. There is a fear.

After completion of the reaction, it is preferable to perform a dehydration treatment. The method for the dehydration treatment is not particularly limited. For example, after only the obtained partial hydrolyzate is taken out from the system by a conventional method, the pressure is reduced to 0.01 MPa or less and 70 to 100 ° C., preferably 80 to 100 ° C. The dehydration process in the partial hydrolyzate of animal and vegetable fats and oils can be performed by heating at 0 degreeC for about 0.5 to 1.0 hour.
In the case of not undergoing dehydration treatment, the activity of the adsorbent is reduced in the contact step with the adsorbent described below, and the flavor and richness imparting effect of the partial hydrolyzate of the obtained animal and plant oil / fat itself may be reduced. is there.

  After the dehydration treatment, a step of further deactivating / removing the enzyme can be performed. The enzyme deactivation condition is not particularly limited as long as the protein constituting the enzyme is denatured, and a method such as heating or changing the pH can be adopted, but preferably a deactivation treatment by heating is selected, For example, the enzyme added to the system can be inactivated by treating at 90 ° C. for 30 minutes with stirring.

  When an immobilized enzyme is used, the lipolytic enzyme is supported on the surface of the carrier and can be removed by filtration. Note that the deactivation treatment and the removal treatment by filtration can be performed together. The enzyme deactivation / removal step can be performed before or after the contact treatment with the adsorbent described later.

Next, the process of contacting the partial hydrolyzate of animal and vegetable fats and oils with an adsorbent will be described.
In this invention, it is preferable to use the partial hydrolyzate of the animal and vegetable fats and oils detailed above as an active ingredient of a flavor improvement material by making it contact with adsorption agent.
Although the principle is unknown at this stage, it is possible to reduce and remove the off-flavor and pungent taste of the partial hydrolyzate of animal and vegetable oils and fats immediately after decomposition by the step of contacting with the adsorbent, and a preferable aroma. Is granted.

  Examples of the adsorbent used in the present invention include adsorbents that are also used as food additives, such as silicates such as zeolite, silica gel, talc, and kaolin, activated alumina, anhydrous calcium carbonate, and anhydrous sodium sulfate. Of these, silicate is preferably selected, silica gel and zeolite are more preferably selected, and silica gel is most preferably selected.

  The adsorbent used is preferably in the form of fine particles in order to improve the contact efficiency, and the shape may be powder or spherical, but the effect of reducing the pungent odor and off-flavor of the decomposition products is particularly high. Therefore, it is preferably in a powder form.

The average particle size of the adsorbent to be used is preferably 3 to 60 μm, and more preferably 10 to 40 μm.
When the average particle size is less than 3 μm, the eyes are easily clogged at the time of filtration, and the filtration efficiency tends to decrease. When the average particle diameter is larger than 60 μm, the particle surface area becomes small, so that the effect of reducing the pungent odor and off-flavor of the decomposed product tends to be low, and the effect of the flavor improving material obtained by the present invention is hardly obtained. There is a fear.

The specific surface area of the adsorbent to be used is preferably 250 meters ² / g or more, more preferably 300 meters ² / g or more, most preferably 400 to 800 m ² / g.
When the specific surface area of the adsorbent used is less than 250 m ² / g, the contact efficiency between the partial hydrolyzate of animal and vegetable fats and oils and the adsorbent is low, and the flavor improving material of the present invention is contained in food and drink. There is a risk that the richness obtained when the potato is used is poor.

  When silica gel is used as an adsorbent that is brought into contact with a partial hydrolyzate of animal or vegetable fats and oils, it is possible to use either unmodified or chemically modified silica gel. Those subjected to physical and physical modification can also be used.

Further, the pH of the silica gel used is preferably 3.0 to 8.0, more preferably 5.0 to 8.0, and most preferably 6.5 to 8.0.
Even if the pH of the silica gel is more acidic than 3.0, the off-flavor odor can be sufficiently reduced, but the flavor components are decomposed due to the acidity of the silica gel, which is the purpose of the present invention. There exists a possibility that the provision effect and the flavor improvement effect may become weak.
In addition, examples of silica gel having a pH of more than 8.0 include aminated silica gel and the like. However, these silica gels themselves are expensive and particularly attract aldehydes, ketones, and fatty acids that contribute to flavor. The flavor improving effect of the partial hydrolyzate of animal and vegetable oils and fats may be poor.

  The step of bringing the partial hydrolyzate of animal and vegetable oils and fats into contact with the adsorbent can be carried out in a batch manner or by a method in which the adsorbent is packed into the column and passed through. Is preferable because the amount of the partial hydrolyzate of animal and vegetable fats and oils that can be purified at a time increases. Compared with before and after hydrolysis of fats and oils, the viscosity is likely to increase after the hydrolysis of fats and oils, and accordingly, the column type also tends to increase the pressure, so it is difficult to perform contact treatment efficiently because of the batch type. Is preferred.

The amount of the adsorbent to be brought into contact with the partial hydrolyzate of animal and vegetable oils and fats is appropriately selected according to the type of adsorbent and the flavor strength required for the flavor improving material, but 100 parts by mass of the partial hydrolyzate of animal and vegetable oils and fats. 1 to 20 parts by mass is preferable, 1 to 18 parts by mass is more preferable, and 3 to 10 parts by mass is most preferable.
When the amount of the adsorbent is less than 1 part by mass with respect to 100 parts by mass of the partial hydrolyzate, there is a possibility that the pungent taste and off-flavor that the partial hydrolyzate has cannot be reduced. Moreover, when the amount of the adsorbent is more than 20 parts by mass with respect to 100 parts by mass of the partially hydrolyzed product, there is a possibility that a strong taste and miscellaneous taste may occur.
Moreover, it is preferable to use the adsorbent after releasing moisture by heating or the like before the contacting step to enhance its activity.

When the adsorbent is brought into contact with the partial hydrolyzate of animal and vegetable fats and oils, the property of the partial hydrolyzate must be fluid to liquid for the purpose of increasing the contact area between the adsorbent and the partial hydrolyzate. It is preferable that it is liquid.
For this reason, when the adsorbent and the partial hydrolyzate are brought into contact with each other, it is necessary to adjust the temperature of the partial hydrolyzate to a temperature at which the partial hydrolyzate becomes fluid to liquid, in order to prevent the loss and alteration of the preferred flavor components. It is preferable to adjust the temperature to less than 100 ° C.

  During the contact with the adsorbent, it is necessary to make the partial hydrolyzate uniform, but as long as it is in a uniform state, any method such as shaking or stirring can be used. In particular, in contact with the adsorbent in a batch type, the adsorbent may be settled, and therefore, for example, it is preferable to stir at about 350 rpm using a stirring blade.

  Moreover, it is preferable to make a partial hydrolyzate and an adsorbent contact in a pressure-reduced state, More preferably, it is made to contact at 0.01 Mpa or less. Thereby, the off-flavor and odor of the obtained flavor modifier are particularly reduced.

  The end point of the contact step with the adsorbent can be determined as an end point at which the effect of the present invention can be obtained, but “(1) contact time with the adsorbent” or “(2) described below”. By judging on the basis of any one or more of “the amount of change in the analytical value due to contact with the adsorbent”, a flavor improving material is obtained in which the off-flavor odor and gummy taste are sufficiently reduced and the effect of imparting a rich taste is high. Therefore, it is preferable.

(1) Contact time with adsorbent The contact time is preferably 5 minutes to 5 hours, more preferably 15 minutes to 2 hours. When the contact time is less than 5 minutes, the effect of reducing off-flavors and irritation caused by contact with the adsorbent may not be obtained. Moreover, when contact time exceeds 5 hours, there exists a possibility that an undesirable flavor change may arise by excessive heating.

(2) Amount of change in analytical value due to contact with adsorbent When judging the amount of change in analytical value due to contact with adsorbent as a criterion for the end point, the partial hydrolyzate is analyzed by a conventional method as appropriate. It is preferable from the viewpoint of obtaining a flavor improving material with reduced off-flavor and odor to be judged based on either or both of (i) monoglyceride (MG) content and (ii) moisture content of the partial hydrolyzate. .

  (I) When based on the monoglyceride (MG) content, based on the MG content of the partial hydrolyzate before the contact step, the MG content of the partial hydrolyzate after the contact step is 75% or less, particularly It is preferable to determine a point that is in the range of 30 to 70% as an end point in order to obtain a flavor improving material with reduced off-flavor and odor. When the MG content is more than 75%, the off-flavor and savory taste are not sufficiently reduced, and the flavor of the added food or drink may be deteriorated.

  In addition, when (ii) the moisture content is used as a reference, it is preferable to determine the point at which the moisture content in the partial hydrolyzate after the contact step is 1500 ppm or less as an end point, and the point is 50 to 300 ppm. Is more preferably determined as the end point. When the water content in the partial hydrolyzate is higher than 1500 ppm, the off-flavor and odor of the obtained flavor improving material is not sufficiently reduced, and the deterioration of the flavor over time may be promoted during storage. In addition, it is preferable that the water | moisture content in the partial hydrolyzate which passed through the contact process is fully reduced within the range with which the effect of this invention is acquired from the said viewpoint.

  When the partial hydrolyzate and the adsorbent are contacted in a batch manner, the adsorbent is removed by filtration after a contact step with the adsorbent. As a filtration method, natural filtration, suction filtration, pressure filtration, centrifugal separation, or the like can be used, and a filter press using a membrane filter or a filter cloth is preferably selected.

  The flavor improving material of the present invention is obtained by using the partial hydrolyzate of animal and vegetable oils and fats obtained as described above in contact with the adsorbent as an active ingredient, and this is used as it is as the flavor improving material of the present invention. If necessary, water, edible animal and vegetable oils, emulsifiers, antioxidants, sugars and sugar alcohols, thickeners, starch, flour, inorganic salts and organic acid salts, gelling agents, dairy products , Egg products, flavorings, seasonings, colorants, preservatives, pH adjusters, and other food materials can be mixed to provide the flavor improving material of the present invention. In the flavor improving material of the present invention, the content of other food materials is particularly limited as long as it is in a range that does not impair the richness imparting effect and flavor improving effect of the partial hydrolyzate of animal and vegetable oils and fats brought into contact with the adsorbent. However, it is usually 20 parts by mass or less with respect to 100 parts by mass of the partially hydrolyzed product.

  When the flavor improving material of the present invention obtained as described above is blended into a food or drink, compared with the case where a flavor improving material containing a conventional oil / fat decomposed product is blended into a food or drink, the occurrence of off-flavor odor is suppressed, And it has the characteristics that the richness imparting effect and the flavor improving effect are good. Therefore, it is excellent as a food material that imparts a rich taste to food and drink.

  Here, in the product design of food and drink, there is a case where only a small amount of flavor improving material can be added due to the balance with other ingredients, and there is a case where a stronger flavor is required for food and drink. When an improving material is added, a flavor improving material having a stronger effect of imparting richness and a rich feeling is desired.

Therefore, the effect of imparting the richness and richness of the flavor improving material having the active ingredient of the partial hydrolyzate of animal and vegetable oils and fats brought into contact with the adsorbent obtained by the above method is preferably enhanced. The material and the method of obtaining it are described.
Specifically, before the partial hydrolyzate of animal and vegetable fats and oils comes into contact with the adsorbent, or after contact with the adsorbent, the effect of imparting richness and richness by applying the following step (A) It becomes possible to obtain a flavor improving material preferably enhanced.
Moreover, the partial hydrolyzate of the animal and vegetable fats and oils which passed through the process (A) performs the following process (B), and can obtain the flavor improving material in which the effect which provides a more rich taste and a rich feeling was reinforced. It becomes possible.
Hereinafter, the partially hydrolyzed product brought into contact with the adsorbent may be described as an adsorption-treated product.
(A) Step of performing oxidation treatment so that the peroxide value of the partial hydrolyzate of animal and vegetable fats and oils is 5 to 60 (B) The excessive hydrolyzate of animal and vegetable fats and oils that have undergone the step (A) contains Step of reducing oxide with hydrogen

Oxidation treatment to be described later, preferably by performing reduction treatment after oxidation treatment, so that not only animal fats and processed fats and oils are used as a substrate, but also vegetable oils and processed fats and oils that are relatively weak in flavor are used as substrates. Even in the case of an adsorption-treated product, it is possible to obtain a flavor improving material having a rich taste and richness with a preferable strength.
In addition, when selecting vegetable oils and fats as a substrate for the flavor improving agent of the present invention, as described above, the type is not particularly limited, but by using liquid oil or palm oils and fats, an oily feeling is imparted. This is preferable because a rich taste and richness can be imparted to the food and drink without having to.

First, (A) a step of performing an oxidation treatment so that the peroxide value becomes 5 to 60 (hereinafter referred to as an oxidation treatment, the oxidation treatment is performed regardless of whether it is in contact with the adsorbent or after contact). The partly hydrolyzed product of animal and vegetable oils and fats that have been passed may be described as an oxidized product).
In the present invention, the oxidation treatment method and its conditions are not particularly limited, and known methods and conditions can be employed. Specifically, the oxidation treatment can be performed by thermal oxidation, photooxidation, or the like. Moreover, the partial hydrolyzate of the said animal and vegetable fats and oils may be oxidized naturally and may be oxidized artificially.
In addition, in the case of artificially oxidizing the partial hydrolyzate of the above-mentioned animal and vegetable fats and oils, there is no particular limitation on the method for oxidizing the fats and oils, but it can be efficiently oxidized and the value of the peroxide value. From the point that it is easy to adjust to the specific range described below, it is preferable to perform thermal oxidation by heat treatment.
In any method, it is desirable to perform the oxidation treatment while stirring so that the oxidation treatment is uniformly performed.

  In addition, about the heating conditions in the case of thermal oxidation, it will not specifically limit if the peroxide value of an oxidation treatment product can satisfy | fill the below-mentioned range, However, Preferably heating temperature is 80-180 degreeC, More preferably, it is 80-160. ° C, more preferably 80 to 140 ° C. The heating time varies depending on the heating temperature and may be appropriately selected. For example, the heating temperature is preferably in the range of 5 minutes to 30 minutes at 180 ° C. and 6 to 48 hours at 80 ° C.

When the partial hydrolyzate of animal and vegetable fats and oils undergoes an oxidation treatment, it is sufficient to oxidize so that the peroxide value of the oxidation-treated product is in the range of 5 to 60. It is necessary from the viewpoint of strengthening.
Here, it is preferable to oxidize until the peroxide value of the oxidation-treated product becomes 10 to 40, and it is more preferable to oxidize until the peroxide value becomes 20 to 35.
When oxidized until the value of the peroxide value of the oxidized product exceeds 60, when the obtained flavor improving material is used in a food or drink, the effect of imparting a rich taste and a rich feeling can be obtained. In addition, there is a possibility that the off-taste accompanying oxidation is strongly expressed.
In addition, when oxidized so that the value of the peroxide value of the oxidized product is less than 5, when the obtained flavor improving material is used in a food or drink, it is compared with before and after the oxidation treatment to give a rich taste Differences are hardly seen in the effect and the effect of giving a rich feeling, and there is a possibility that a significant effect cannot be obtained.
In the present invention, the peroxide value of fats and oils can be measured, for example, in accordance with [Japan Oil Chemists' Society established standard fat analysis method 2.5.2.1-2013].

Further, at the end point of the oxidation treatment, the above peroxide value range is satisfied, and the anisidine value is preferably 35 or less, more preferably 30 or less, and most preferably 25 or less. The lower limit of the anisidine value is preferably 10 or more, more preferably 15 or more, and most preferably 18 or more.
If the anisidine value of the oxidized product is more than 35, an off-flavor tends to occur in the flavor of the food or drink using the obtained flavor improving material. Moreover, when the anisidine value of the oxidation-treated product is less than 10, the oxidation treatment is not sufficient, and there is a fear that the enhancement of the effect of imparting the rich taste and the effect of providing a rich feeling may be insufficient.
In this invention, the anisidine value of fats and oils can be measured based on, for example, [The Japan Oil Chemists' Society establishment standard fat and oil analysis test method 2.5.3-2013].

In addition, it is preferable to add an antioxidant such as tocopherol to the oxidation-treated product after the oxidation treatment because further oxidation during the process and oxidation deterioration during storage can be suppressed. Here, when subjecting the partial hydrolyzate of animal and vegetable fats and oils to contact with the adsorbent, the antioxidant may be contained in the partial hydrolyzate before contacting with the adsorbent. It may be contained in the partial hydrolyzate after contact with the agent. Moreover, when performing the reduction process (process (B)) by the hydrogen mentioned later with respect to an oxidation treatment product, an antioxidant can be contained at the following timing. That is, when the steps (A) and (B) are applied to the partial hydrolyzate of animal and vegetable oils and fats that have been brought into contact with the adsorbent, the antioxidant is applied after the step (A) and before the step (B). An agent may be contained, and an antioxidant may be contained after performing the step (A) and the step (B). When the steps (A) and (B) are performed on the partial hydrolyzate of animal and vegetable oils and fats before being brought into contact with the adsorbent, the antioxidant is applied after the step (A) and before the step (B). An antioxidant may be added after the steps (A) and (B) and before contacting with the adsorbent, and the steps (A) and (B) may be added. An antioxidant may be added after application and after contact with the adsorbent. Prior to contacting with the adsorbent, the step (A) was applied to the partial hydrolyzate of animal and vegetable fats and oils, and the partial hydrolyzate subjected to the step (A) was brought into contact with the adsorbent and contacted with the adsorbent. When the step (B) is applied to the partially hydrolyzed product, an antioxidant may be contained before contacting with the adsorbent, and the antioxidant is added before the subsequent step (B) after contacting with the adsorbent. In some cases, an antioxidant may be added after the step (B).
The content of the antioxidant in the oxidation-treated product may be 50 ppm or more, preferably 100 ppm or more, but is preferably 1000 ppm or less in the oxidation-treated product, more preferably 700 ppm or less, and 500 ppm or less. Most preferred.

  In the present invention, the step (A) may be applied before the contact between the partial hydrolyzate of animal and vegetable fats and oils and the adsorbent, and the partial hydrolyzate contacted with the adsorbent is subjected to the step (A). May be applied. Whether to perform the step (A) before contacting with the adsorbent or to perform the step (A) after contacting with the adsorbent depends on the strength and quality of the desired flavor, In particular, when it is desired to enhance the aftertaste, it is preferable to perform the step (A) before contacting with the adsorbent. In particular, when it is desired to enhance the taste, it is preferable to perform the step (A) after contacting with the adsorbent.

Next, (B) a step of reducing the contained peroxide with hydrogen (hereinafter sometimes referred to as a reduction treatment, and after undergoing the reduction treatment may be referred to as a reduction treatment product) will be described.
By applying the step (A) to the partial hydrolyzate of animal and vegetable fats and oils, the effect of imparting the rich taste and richness of the obtained flavor improving material is strengthened, but the oxidized product obtained through the step (A) By passing through a process (B), it becomes possible to obtain the flavor improving material in which the effect which provides a richer taste and a rich feeling was further reinforced.
In addition, when performing a process (A) to the partial hydrolyzate of the animal and vegetable fats and oils before adsorbent processing, a process (B) may be performed before adsorbent processing, and a process is performed after adsorbent processing. (B) may be applied. It is preferable to perform the step (B) prior to the adsorbent treatment because the effect of imparting richness and richness can be more easily obtained.

Specifically, the reduction treatment in the present invention is performed by heating the oxidation-treated product together with a hydrogenation catalyst at 60 to 130 ° C. in the presence of hydrogen gas. The purpose of the reduction treatment in the present invention is to reduce the peroxide produced in the partial hydrolyzate through the step (A) without fluctuation in iodine value, and to preferably obtain a flavor component.
In the present invention, “with no change in iodine value” means that the iodine value before the reduction step is compared with the iodine value after the reduction step, and the change rate of the iodine value is preferably 5% or less, more preferably It indicates 3% or less.

Here, the hydrogenation catalyst used for the reduction treatment will be described.
The hydrogenation catalyst used in the present invention is not particularly limited as long as the peroxide in the oxidation-treated product can be reduced by hydrogen, and a nickel catalyst, a platinum catalyst, a palladium catalyst, or the like can be selected. . Among these hydrogenation catalysts, it is particularly preferable to select a nickel catalyst because it is inexpensive and can stably reduce the peroxide even in a low temperature range. The nickel catalyst may be a nickel catalyst having selectivity or a nickel catalyst having non-selectivity.
Further, the shape of the hydrogenation catalyst may be in the form of powder and may be in the form of flakes, but the flake form is preferred because it can be added to the oil without scattering.

  The addition amount of the hydrogenation catalyst is preferably 0.01 to 0.5% by mass, more preferably 0.05 to 0.3% by mass, with respect to the oil / fat decomposed product after the step (A). More preferred. If the hydrogenation catalyst is added in an amount of less than 0.01% by mass, the peroxide contained in the oxidation-treated product may not be efficiently reduced. Moreover, when a hydrogenation catalyst exceeds 0.5 mass%, the multiple bond of the fatty acid which comprises the glycerol fatty acid ester contained in an oxidation process goods will be reduced, and it will become easy to produce trans fatty acid.

Further, the reduction step in the present invention is performed in the presence of hydrogen gas. At this time, hydrogen gas is pressurized and injected in a pressure range of 0.5 to ^2.5 kg / cm ^2. It is preferable because the fluctuation of the value is minimized and only the peroxide in the oxidized product is easily reduced. The hydrogen gas is more preferably pressurized and injected in a pressure range of 0.5 to 1.7 kg / cm ² , most preferably 0.6 to 1.5 kg / cm ² .
In addition, it is preferable from the viewpoint of suppressing the fluctuation of the iodine value before and after the reduction treatment, by sufficiently replacing the air in the head space in the vessel in which the reduction reaction is performed with hydrogen gas and setting the pressure within the above pressure range.

  During the reduction step using the nickel catalyst, the temperature of the oxidation-treated product is preferably heated to be in the temperature range of 60 to 130 ° C, and is preferably heated to be in the temperature range of 70 to 120 ° C. It is more preferable to heat so that it may become a temperature range. When the temperature of the oxidized product is less than 60 ° C., the peroxide and carbonyl compound in the oxidized product cannot be sufficiently reduced, and depending on the type of oil selected as the raw material for the adsorption-treated product, fat crystals are formed. There is a risk that. If the temperature of the oxidized product exceeds 130 ° C., the peroxide or carbonyl compound may not be reduced while controlling the iodine value so as not to fluctuate.

In addition, in this invention, since a peroxide and a carbonyl compound can be reduce | restored efficiently by stirring at the time of the heating of a reduction process, it is preferable.
About stirring at the time of heating in the reduction step, stirring is preferably performed at a speed of 100 to 750 rpm, more preferably at a speed of 150 to 600 rpm, and stirring at a speed of 200 to 500 rpm. Is most preferred. When the stirring speed at the time of heating is less than 100 rpm, hydrogen gas is not sufficiently contained in the oxidized product, and the progress of the reduction reaction of the peroxide or the carbonyl compound may be extremely slow. Moreover, when the stirring speed at the time of heating exceeds 750 rpm, hydrogen gas will be included excessively and it may become difficult to control a reductive reaction.

The end point of the reduction step is based on the iodine value of the oxidized product before the reduction step, and preferably the peroxide value is within a range where the fluctuation rate of the iodine value is 5% or less, more preferably 3% or less. A point that is 15 or less is preferably the end point, a point that is 10 or less is more preferably the end point, and a point that is 1 or less is most preferably the end point. When the end point is a range in which the fluctuation rate of iodine value exceeds 5%, the physical properties of the obtained reduction-treated product and further the flavor improving material may be changed and may be easily solidified. For this reason, when added to food or drink, there is a risk of localization. Moreover, when the fluctuation rate of iodine value is within the range of 5% or less, but the end point is that the peroxide value is more than 5, there is a risk that deterioration of the obtained reduction-treated product and further the flavor improving material will be accelerated. There is.
From the viewpoint of obtaining a preferable reduction-treated product, the anisidine value is preferably 20 or less, more preferably 15 or less, at the end point of the reduction process determined by the peroxide value. When the adsorption process is performed after the reduction process, the fluctuation rate of the iodine value is calculated based on the iodine value of the partially hydrolyzed product subjected to the adsorption process. Similarly, the peroxide value and the anisidine value of the partially hydrolyzed product that has undergone the reduction process are the peroxide value and the anisidine value of the partially hydrolyzed product that has been subjected to the adsorption process when the adsorption process is performed after the reduction process.

After the reduction step, it is necessary to remove the hydrogenation catalyst from the system. The method for removing the hydrogenation catalyst is not particularly limited, and may be filtered off with a filter cloth or the like as it is, or a filter aid such as silica gel, celite, or activated carbon may be used.
In addition, when using a filter aid such as silica gel, celite, activated carbon or the like to remove the hydrogenation catalyst, the amount used is not particularly limited as long as the hydrogenation catalyst is removed. By using 0.5-5 mass% with respect to a reduction | restoration process goods, a hydrogenation catalyst can be fully removed preferably from a system.

The adsorption-treated product, oxidation-treated product, and reduction-treated product thus obtained may be further subjected to one or more of purification such as decolorization and deodorization and processing such as fractionation and transesterification. . These treatments can be performed according to a conventional method.
In particular, decolorization and deodorization are preferably performed under mild temperature conditions from the viewpoint of preventing the dissipation of flavor components and aroma components. Specifically, for decolorization, the measurement temperature is 80 to 100 ° C. The deodorization is preferably performed so that the measurement temperature is 180 to 220 ° C.

  The flavor improving material of the present invention will be further described in detail based on specific examples and the like. In addition, this invention is not limited to the Example described below at all.

[Example 1]
After 3000 g of melted purified milk fat was weighed into a 5000 mL four-necked flask, 300 g of ion-exchanged water was added, separated into two phases, an oil phase and an aqueous phase, and allowed to stand until the oil / water interface settled. Next, an anchor type stirring blade was placed slightly floating from the interface so as not to disturb the oil / water interface, stirred at 100 rpm for 90 minutes, and the oil / fat was allowed to contain water at 1000 ppm. During this time, heating was continued so that the temperature of the oil and fat was about 60 ° C.

  Next, in a state where the fat flow rate and the amount of the immobilized enzyme to be filled are adjusted so that the ratio of the fat flow rate to the immobilized enzyme amount packed in the column is 50 / hour, the fat portion in the four-necked flask A line was connected so that only the oil passed through the column and then returned to the flask, and was circulated with a pump. All the lines through which the fats and oils passed were treated so that the temperature of the fats and oils could be maintained at about 60 ° C. Further, the immobilized enzyme was a lipolytic enzyme derived from the genus Rhizomucor (Rhizomucor meihei).

While circulating this system, the acid value of the oil and fat portion was appropriately measured, and when the acid value exceeded 70, the liquid passage was stopped and only the partial hydrolyzate was transferred to another flask.
Next, the liquid temperature in the flask was adjusted to 90 ° C. while reducing the pressure so that the pressure in the flask containing the partially hydrolyzed product was 0.01 MPa or less, and the mixture was stirred at 250 rpm and dehydrated for 60 minutes. .
After that, the pressure is once returned to normal pressure, 250 g of pH 7.5 silica gel (Fuji Silysia silopute 130) is added as an adsorbent, and the pressure is reduced again to 0.01 MPa or less. The stirring speed is 350 rpm and the fat temperature is 90 ° C. Made contact. While making contact, the monoglyceride content in the partial hydrolyzate is appropriately measured, and the monoglyceride content of the partial hydrolyzate after the contacting step is 60% or less based on the monoglyceride content of the partial hydrolyzate before contact. At that time, the end point was reached, the decompression was released, and the silica gel (adsorbent) was filtered off as it was without lowering the temperature. In this way, a partial hydrolyzate (hereinafter referred to as milk fat decomposed product) obtained by partially enzymatically degrading milk fat was obtained.

[Example 1-2]
The milk fat degradation product produced in Example 1 was weighed into a four-necked flask with a capacity of 5000 mL, and 2000 g was weighed, and the fat temperature was 90 ° C. with a mantle heater while blowing dry air at 3.0 L / min without closing the mouth. Then, the mixture was further stirred using an anchor type stirring blade at 300 rpm and oxidized until the peroxide value reached 6. 300 ppm of tocopherol as an antioxidant was added to the oxidized milk fat decomposition product to obtain a milk fat decomposition product (Ox).
The milk fat decomposed product (Ox) had an iodine value of 35.5, a peroxide value of 6.3, an anisidine value of 3.1, and a trans fatty acid content of 2.5% by mass.

[Example 2]
Using 3000 g of purified tallow, the same operation as in Example 1 was performed to obtain a partial hydrolyzate (hereinafter referred to as tallow decomposed product) obtained by partially enzymatically degrading tallow.

[Example 2-2]
The pork fat decomposition product produced in Example 2 was oxidized by the same method as in Example 1-2 until the peroxide value reached 6, to obtain pork fat decomposition product (Ox).
The iodine value of the pork fat decomposition product (Ox) was 65.0, the peroxide value was 6.5, the anisidine value was 2.5, and the trans fatty acid content was 2.1% by mass.

Example 3
For the mixed oil obtained by uniformly mixing 900 g of oil obtained by random transesterification of palm fraction soft part oil (palm olein) of IV = 57.0 and 2100 g of milk fat, the same operation as in Example 1 was performed to perform partial hydrolysis. A decomposition product (hereinafter referred to as “mixed oil decomposition product A”) was obtained.

[Example 3-2]
2000 g of the mixed fat / oil decomposition product A (untreated) produced in the same manner as in the method of Comparative Example 3 described below was weighed into a four-necked flask having a volume of 5000 mL. The liquid temperature in the flask was adjusted to 90 ° C. while reducing the pressure to be 01 MPa or less, and the mixture was stirred at 250 rpm and dehydrated for 60 minutes. Then, while blowing dry air at 3.0 L / min without closing the mouth, it was heated with a mantle heater so that the oil temperature became 120 ° C. and oxidized until the peroxide value reached 25. During this time, stirring was performed at 300 rpm using an anchor type stirring blade.
Furthermore, 150 g of silica gel was added, the pressure was reduced to 0.01 MPa or less, and the monoglyceride content was appropriately measured while contacting with silica gel (Fuji Silysia Silopup 130) at a stirring speed of 350 rpm and an oil temperature of 90 ° C. Based on the monoglyceride content of the previous partial hydrolyzate, based on the monoglyceride content of the milk fat hydrolyzate (untreated) before contact, the point where the monoglyceride content after the contacting step is 50% or less is the end point, and the vacuum is reduced. The silica gel (adsorbent) was filtered off as it was without releasing the temperature, and 300 ppm of tocopherol was added as an antioxidant to obtain a mixed fat and oil decomposition product A (α1).
The mixed fat / oil decomposition product A (α1) had an iodine value of 35.5, a peroxide value of 24.5, an anisidine value of 17.4, and a trans fatty acid content of 2.5% by mass.

[Example 3-3]
In a four-necked flask with a capacity of 5000 mL, 2000 g of the mixed fat / oil decomposition product A produced in Example 3 was weighed, and the oil temperature was 90 ° C. with a mantle heater while blowing dry air at 3.0 L / min without closing the mouth. Then, the mixture was further stirred using an anchor type stirring blade at 300 rpm and oxidized until the peroxide value reached 25. 300 ppm of tocopherol as an antioxidant was added to the oxidized mixed fat / oil decomposition product A to obtain a mixed fat / oil decomposition product A (α2).
The mixed oil and fat decomposition product A (α2) had an iodine value of 35.7, a peroxide value of 27.3, an anisidine value of 18.1, and a trans fatty acid content of 2.7% by mass.

[Example 3-4]
In a four-necked flask with a capacity of 5000 mL, 2000 g of the mixed fat / oil decomposition product A (untreated) produced in the same manner as in the method of Comparative Example 3 described below was weighed. The liquid temperature in the flask was adjusted to 90 ° C. while reducing the pressure to be 01 MPa or less, and the mixture was stirred at 250 rpm and dehydrated for 60 minutes. Then, while blowing dry air at 3.0 L / min without closing the mouth, heat the oil and fat temperature to 120 ° C. with a mantle heater, and further stir at 300 rpm using an anchor-type stirring blade, and peroxidize It was oxidized until the price reached 25. Here, the oxidized mixed oil decomposition product A (untreated) had an iodine value of 35.5, a peroxide value of 25.6, an anisidine value of 16.8, and a trans fatty acid content of 2.5% by mass. .
Next, 1000 g of the oxidized mixed fat / oil decomposition product A (untreated) was transferred to a pressure vessel, 0.1 mass% of a curing nickel catalyst (manufactured by Sakai Chemical) was added as a hydrogenation catalyst, and the headspace portion was hydrogen gas. After sufficient substitution, the mixture was heated to 90 ° C., and the hydrogen pressure in the pressure vessel was 1.0 kg / cm ² and stirred at 300 rpm using an anchor type stirring blade. During the sampling, the peroxide value was analyzed, and the hydrogenation catalyst was filtered off when the peroxide value became 10 or less for the first time. The filtrate was transferred to a 3000 ml four-necked flask, decompressed to 0.01 MPa or less, and the monoglyceride content was appropriately measured while contacting with silica gel at a stirring speed of 350 rpm and an oil temperature of 90 ° C. With the monoglyceride content of the partial hydrolyzate as the standard, the monoglyceride content of the milk fat decomposed product (untreated) before contact is the standard, and the point where the monoglyceride content after the contact process is 50% or less is the end point, and the decompression is released. Silica gel (adsorbent) was filtered off as it was without lowering the temperature, and 300 ppm of tocopherol was added as an antioxidant to obtain a mixed fat and oil decomposition product A (β1). The mixed fat / oil decomposition product A (β1) had an iodine value of 33.2, a peroxide value of 4.5, an anisidine value of 11.1, and a trans fatty acid content of 3.0% by mass.

[Example 3-5]
Weigh 1000 g of the mixed fat and oil decomposition product A (α2) produced in Example 3-3 into a pressure vessel, add 0.1% by mass of a curing nickel catalyst (manufactured by Sakai Chemical) as a hydrogenation catalyst, After sufficiently substituting with gas, the mixture was heated to 90 ° C., and the hydrogen pressure in the pressure vessel was 1.0 kg / cm ² and stirred at 300 rpm using an anchor type stirring blade. During the sampling, the peroxide value was analyzed, and when the peroxide value became 10 or less for the first time, the hydrogenation catalyst was removed by filtration, 300 ppm of tocopherol was added as an antioxidant, and the mixed oil and fat decomposition product A (β2 ) The obtained mixed fat and oil decomposition product A (β2) had an iodine value of 34.5, a peroxide value of 4.2, an anisidine value of 10.0, and a trans fatty acid content of 3.0% by mass.

Example 4
The same operation as in Example 1 was performed on the mixed fat obtained by uniformly mixing 900 g of soybean hardened oil having an iodine value of 5 or less and 2100 g of milk fat, and then partially hydrolyzed (hereinafter referred to as mixed fat and oil decomposed substance B). )

Example 5
The same operation as in Example 1 was performed on 3000 g of sweet butter (no salt used) manufactured by Yotsuba Dairy Co., Ltd. to obtain a partially hydrolyzed product (hereinafter referred to as butter decomposed product).

Example 6
The same operation as in Example 1 was performed on 3000 g of palm oil having an iodine value of 51.0 to obtain a partially hydrolyzed product (hereinafter, palm oil decomposed product).

[Example 6-2]
For the palm oil degradation product (untreated) produced by the same method as in Comparative Example 6 described below, the same operation as in Example 3-2 is performed, and after the decomposition with the immobilized enzyme, the oxidation treatment is performed. A palm oil decomposition product (α1) brought into contact with the adsorbent was obtained.
The palm oil decomposed product (α1) had an iodine value of 51.0, a peroxide value of 25.3, an anisidine value of 17.5, and a trans fatty acid content of 0.8% by mass.

[Example 6-3]
Palm oil produced by the same method as in Example 6 is subjected to the same operation as in Example 3-3, and after decomposition with an immobilized enzyme, it is brought into contact with an adsorbent and subjected to oxidation treatment. An oil breakdown product (α2) was obtained.
The palm oil decomposition product (α2) had an iodine value of 51.0, a peroxide value of 26.8, an anisidine value of 18.3, and a trans fatty acid content of 0.8% by mass.

[Example 6-4]
For the palm oil degradation product (untreated) produced by the same method as in Comparative Example 6 described below, the same operation as in Example 3-4 is performed, the degradation with the immobilized enzyme, the oxidation treatment, The peroxide generated by the oxidation treatment was reduced with hydrogen and then contacted with an adsorbent to obtain a palm oil decomposition product (β1).
The oxidized palm oil decomposed product (untreated) had an iodine value of 51.0, a peroxide value of 25.3, an anisidine value of 17.5, and a trans fatty acid content of 0.8% by mass. It was. The palm oil decomposed product (β1) had an iodine value of 49.8, a peroxide value of 5.8, an anisidine value of 12.1, and a trans fatty acid content of 1.3% by mass.

[Example 6-5]
Palm oil decomposition | disassembly which reduced the peroxide produced by performing operation similar to Example 3-5 with respect to the palm oil decomposition product ((alpha) 2) manufactured in Example 6-3 with the oxidation process, and hydrogen. A product (β2) was obtained.
The palm oil decomposition product (β2) had an iodine value of 50.1, a peroxide value of 6.2, an anisidine value of 13.3, and a trans fatty acid content of 1.2% by mass.

[Comparative Example 1]
Although the refined milk fat was partially hydrolyzed in the same manner as in Example 1, the partially hydrolyzed product that was not subjected to the contact treatment with silica gel was defined as a milk fat decomposed product (untreated).

[Comparative Example 2]
Although refined pork fat was partially hydrolyzed in the same manner as in Example 1, the partially hydrolyzed product that was not subjected to the contact treatment with silica gel was defined as pork fat decomposed product (untreated).

[Comparative Example 3]
In the same operation as in Example 1, partial hydrolysis of the mixed fat and oil having the same composition as in Example 3 was performed, but the partial hydrolyzate that was not subjected to contact treatment with silica gel was mixed with the mixed fat and oil decomposed product A ( Untreated).

[Comparative Example 4]
In the same operation as in Example 1, partial hydrolysis of the mixed fat and oil having the same composition as in Example 4 was performed, but the partial hydrolyzate which was not subjected to contact treatment with silica gel was mixed with the mixed fat and oil decomposed product B ( Untreated).

[Comparative Example 5]
Butter was hydrolyzed in the same manner as in Example 1, but the partially hydrolyzed product that was not subjected to the contact treatment with silica gel was defined as the butter decomposed product (untreated).

[Comparative Example 6]
Although the palm oil was hydrolyzed by the same operation as in Example 1, the partially hydrolyzed product that was not subjected to the contact treatment with silica gel was defined as a palm oil decomposed product (untreated).

[Evaluation example 1] Flavor evaluation with compound whipped cream 100 parts by weight of compound whipped cream ("Pure Blend Whip 20" manufactured by ADEKA, milk fat content 20% by mass) and 7 parts by weight of white sucrose are added to a mixer bowl. After adding 0.03 parts by mass of the milk fat degradation product prepared in Example 1 as a flavor improving material of the present invention, it was set in a tabletop mixer and whipped at high speed for 6 minutes to obtain whipped cream A containing the milk fat degradation product. Obtained.
Similarly, whipped cream B containing milk fat degradation product (untreated) and whipped cream C containing milk fat degradation product (Ox) were obtained.
On the other hand, whipped cream D was obtained by whipping only the above compound whipped cream without containing a milk fat decomposition product.
Each of the obtained whipped creams A to D was put in a squeezed bag equipped with a star-shaped mouthpiece, squeezed into a polycup, and evaluated for flavor. As a result, especially in whipped cream A, compared with whipped cream D, a rich milk flavor was sufficiently felt, and the richness of milk remaining from the middle to the last was enhanced. In addition, the whipped cream B has an unpleasant taste because it has an irritating taste and taste from the top to the last after eating, and the effect of enhancing the milk flavor and richness is poor. In addition, the whipped cream C had a stronger milk flavor at the top than the whipped cream A, and the richness was further increased.

[Evaluation example 2] Flavor evaluation in hamburger 39.0 parts by weight of minced meat (7: 3 beef pork), 0.7 parts by weight of salt and pepper, 0.1 part by weight of nutmeg, 30.8 parts by weight of saute onion, egg 5.1 parts by weight, 6.1 parts by weight of water, 3.1 parts by weight of milk, 5.1 parts by weight of bread crumbs, and 9.8 parts by weight of tallow are put into a mixer bowl, and at low speed using a desktop mixer. After mixing for 1 minute, 0.2 parts by weight of the pork fat decomposition product prepared in Example 2 was added as a flavor improving material of the present invention, and further mixed at a low speed for 1 minute to obtain a meat dough. The obtained meat dough was baked in a fixed oven (set temperature 190 ° C.) for 10 minutes to obtain hamburger A.
Similarly, hamburger B containing pork fat decomposition product (untreated) and hamburger C containing pork fat decomposition product (Ox) were obtained.
On the other hand, the pork fat decomposition product was replaced with pork fat, and hamburger D containing 10 parts by mass of pork fat and not containing pork fat decomposition product was obtained.
When flavor evaluation was performed on the obtained hamburgers A to D, in the hamburger A containing the pork fat decomposition product, compared with the hamburger C not containing the pork fat decomposition product, the thickness of the taste from the middle to the last It was confirmed that the spread was further felt and the aftertaste had a rich feeling and richness, and had a flavor improving effect. In the hamburger B, a particularly pungent taste was felt, and the effect of enhancing the rich taste was poor. In the hamburger C, the thickness of the middle to the last and the rich feeling of the aftertaste similar to the hamburger A are felt, and the taste is preferably enhanced.

[Evaluation Example 3] Flavor Evaluation in Rolls (Butter Roll Molding) Using the partial hydrolysates obtained in Examples 3-5 and Comparative Examples 3-5 as flavor improvers, the formulations shown in Table 1 and the following Roll bread (butter roll molding) was manufactured by the manufacturing method. About the obtained bread roll, flavor evaluation was performed by the following method. The evaluation results are shown in Table 2.

<Production method of roll bread (butter roll molding)>
All the raw materials mixed with the above medium seed dough were mixed with a vertical mixer for 3 minutes at low speed and for 2 minutes at medium speed to obtain a medium seed dough (kneading temperature 26 ° C.). The obtained medium seed dough was subjected to medium seed fermentation at 28 ° C. and a relative humidity of 80% for 120 minutes.
After mixing the above-mentioned medium-sized dough and main-powder dough with strong powder, sugar, salt, skim milk powder, whole egg and water with a vertical mixer for 3 minutes at low speed and 3 minutes at medium speed, then margarine with mix of mainland dough A mixture of various partial hydrolysates in advance was mixed, and further mixed at a low speed for 3 minutes and at a medium speed for 4 minutes to obtain a main body dough (kneading temperature 28 ° C.). The margarine used had a butter compound rate of 10%.
The obtained main body dough was 30 minutes in floor time, divided (45 g), rounded, taken 30 minutes in bench time, and then subjected to butter roll molding. This was placed on a top plate, taken at 38 ° C., 80% relative humidity, and 50 minutes proof, then baked in an oven at 190 ° C. for 13 minutes to obtain rolls A to F.
In addition, the roll bread was manufactured by the same manufacturing method without including a partial hydrolyzate in the main body dough mixing | blending, and it was set as control.

<Method of flavor evaluation>
The evaluation items are three items, “degree of off-season taste”, “degree of taste”, and “degree of richness”. Eight panelists evaluated roll bread manufactured by the above blending and manufacturing method according to the following evaluation criteria. Carried out. The average values of the obtained scores were compared. The degree of taste and richness was evaluated by comparison with a control product containing no partial hydrolyzate.
In addition, a taste means the preferable flavor with the swelling which can be felt immediately after eating. The rich taste means a rich flavor that is preferably felt in the oral cavity and nasal cavity immediately after swallowing during chewing.

Evaluation criteria (degree of off-season miscellaneous taste)
5 points Very good with no nuisance and miscellaneous taste.
3 points There is almost no off-taste and miscellaneous taste, and it is good.
1 point.
0 points The taste and taste are strong and poor.
(Degree of taste)
5 points An excellent taste compared to the control was felt.
A 3-point feel was felt compared to the control.
One point was the same as the control.
0 points The taste is not felt compared to the control.
(Degree of richness)
5 points Excellent body taste compared to the control.
3 points A rich taste was felt compared to the control.
1 point The taste was the same as the control.
0 point The taste is not felt compared to the control.

As a result of the flavor evaluation of the obtained rolls A to F, the flavor itself and the appearance of the flavor were different depending on the presence or absence of contact treatment with silica gel (adsorbent). In the bread rolls D to F using the partial hydrolyzate not subjected to the contact treatment with the silica gel (adsorbent), a taste of strange taste was uniformly felt, which resulted in greatly impairing the flavor of the bread roll. On the other hand, in the bread rolls A to C using the partial hydrolyzate subjected to the contact treatment with silica gel (adsorbent), almost no strange taste was felt. Moreover, in roll bread AC, compared with control and roll bread DF, generally the taste and richness were strengthened, and it confirmed that the flavor was improved. Furthermore, it confirmed that the tendency of flavor expression differed by the fats and oils type | mold used as the substrate of a partial hydrolyzate.
As can be seen from the flavor evaluation in Evaluation Examples 1 to 3, by using a flavor improving material containing a partial hydrolyzate of animal and vegetable oils and fats brought into contact with the adsorbent as an active ingredient, a rich feeling and richness are imparted to the food and drink. The Further, it was found that the contact treatment with the adsorbent can reduce the off-flavor and odor, and at the same time enhance the richness and richness imparting effect of the flavor improving material of the present invention.

[Evaluation Example 4] Flavor Evaluation in Sablé Using the partially hydrolyzed products obtained in Examples 3 to 3-5 and Comparative Example 3 and their processed products as flavor improvers, the formulations shown in Table 3 and the following Sables A to J were manufactured by the manufacturing method. For the obtained sables A to J, flavor evaluation was performed by 8 panelists in accordance with the above evaluation criteria, and the average values of the obtained scores were compared. The degree of taste and richness was evaluated by comparison with a control product containing no partial hydrolyzate. The evaluation results are shown in Table 4.

<Sablet manufacturing method>
70 parts of margarine (Sociel, ADEKA) and 5 parts of butter in advance and the partial hydrolyzate obtained in Comparative Example 1, Examples 3 to 3-5 or Comparative Example 3 as a flavor improver, A mixture obtained by adding the amount shown in 3 and mixing homogeneously and 40 parts of powdered sugar to a specific gravity of about 0.8 with a beater, and adding 10 parts of egg yolk were mixed to obtain a mixture. A dough was obtained by adding and mixing 100 parts of the weak flour that was sieved to the resulting mixture. The obtained dough was rested overnight in a refrigerator, rolled to 2.5 mm, punched out and fired at 160 ° C. for about 15 minutes to obtain sables A to J.

When using a partially hydrolyzed product obtained by simply hydrolyzing animal and vegetable oils and fats, that is, when looking at Sable A, it is slightly superior to the control Sable, but it has a slightly different taste and rich taste, It was not eaten preferably. Next, comparing the sables using the mixed fat and oil decomposed product A, the mixed fat and oil decomposed product A (α1) and the mixed fat and oil decomposed product A (α2), the partial hydrolyzate is subjected to oxidation treatment regardless of the order of the steps. As a result, it was found that the taste and richness were enhanced compared to those not subjected to oxidation treatment. On the other hand, the sable using the mixed fat and oil decomposed product A (α2) subjected to oxidation treatment at the end of the process is different from the sable using the mixed fat and oil decomposed product A (α1) subjected to silica gel treatment after oxidation. The score for miscellaneous tastes has dropped slightly. This suggests that, with the oxidation treatment, components preferable for imparting a taste and richness increase, and a component that is perceived as having an off-taste or a miscellaneous taste is slightly generated.
Next, the mixed oil / fat decomposed product A (β1) and the mixed oil / fat decomposed product A (β2) subjected to both the oxidation treatment and the reduction treatment with hydrogen gas are mixed oil / fat decomposed products subjected to only the oxidation treatment. Compared with the sable using, the taste of taste was almost unnoticeable, and the degree of taste and richness were further enhanced. This is considered to be because the mixed fat / oil decomposition product A (β1) and the mixed fat / oil decomposition product A (β2) have a complex aroma component composition and the flavor is preferably enhanced by the reduction treatment with hydrogen gas.
The sable using the mixed fat / oil decomposition product A (β2) obtained by subjecting the partial hydrolyzate treated with silica gel to both the oxidation treatment and the reduction treatment is applied to the partial hydrolyzate subjected to the combination of the oxidation treatment and the reduction treatment. Compared with the sable using the mixed fat / oil decomposition product A (β1) subjected to the silica gel treatment, a slightly different taste was produced. This suggests that the amount of a substance that can cause an unpleasant taste can be reduced by applying silica gel treatment.
In addition, Sable D, Sable F, Sable H and Sable J were prepared by reducing the amount of flavor improver added compared to Sable C, Sable E, Sable G and Sable I, respectively. In addition, a good taste and richness are obtained. This suggests that the flavor intensity is further increased by performing oxidation treatment or a combination of oxidation treatment and reduction treatment.

[Evaluation Example 5] Flavor Evaluation with Fry Oil and French Fries Palm oil decomposition produced in Examples 6 to 6-5 and Comparative Example 6 against palm fraction soft part oil (iodine value 56, manufactured by ADEKA Corporation) The product was added as a flavor improver, and this was used as frying oil. (See Table 5)
1 kg of the obtained frying oil was put in each pan and heated to 180 ° C., and 100 g of frozen fried potatoes (Oleida shredded fried potatoes (Shoestring), Heinz Japan) were fried for 3 minutes.
About the obtained french fries, flavor evaluation was performed by eight panelists in accordance with the above evaluation criteria, and the average values of the obtained scores were compared. The degree of richness was evaluated by comparison with a partial hydrolyzate-free product as a control. The evaluation results are shown in Table 6.

Even in French fries, using frying oil containing palm oil decomposition products that have not been subjected to oxidation treatment by frying using frying oil containing palm oil decomposition products subjected to oxidation treatment regardless of the order of the steps Compared with the fried food, it was confirmed that the richness was enhanced. In addition, the mixed fat and oil decomposed product obtained by combining the oxidation treatment and the reduction treatment with hydrogen gas hardly feels an unpleasant taste compared to the mixed fat and oil decomposed product obtained by performing only the oxidation treatment. The level of taste was further enhanced.
Moreover, it became clear that flavor intensity | strength further increases by performing oxidation treatment or combining oxidation treatment and reduction treatment regardless of the oil type.

  With the flavor improving material of the present invention, a rich taste and a rich feeling can be imparted without imparting an off-flavor and pungent taste to food and drink.

Claims (8)

  A flavor improving material comprising, as an active ingredient, a partial hydrolyzate of animal and vegetable oils and fats brought into contact with an adsorbent.   The flavor improving material according to claim 1, wherein the adsorbent has a pH of 3.0 to 8.0.   The flavor improving material according to claim 1 or 2, wherein the adsorbent is silica gel.   The flavor improving material according to any one of claims 1 to 3, wherein the partial hydrolyzate of the animal and vegetable fats and oils is obtained by a column-type enzymatic decomposition method.   The flavor improving material according to claim 4, wherein the enzyme decomposition method uses an immobilized enzyme having an ion exchange resin as a carrier. The flavor improvement material as described in any one of Claims 1-5 which passes through the following process (A), after the partial hydrolyzate of the said animal and vegetable fats and oils contacts with the said adsorbent.
(A) The process of performing an oxidation process so that the peroxide value of the partial hydrolyzate of the said animal and vegetable oil and fat may be 5-60. The flavor improving material of Claim 6 in which the partial hydrolyzate of the animal and vegetable fats and oils which passed through the said process (A) passes through the following process (B).
(B) The process of reducing the peroxide which the partial hydrolyzate of the animal and vegetable fats and oils which passed through the said process (A) contains with hydrogen. The manufacturing method of the flavor improving material including the process which makes the partial hydrolyzate of animal and vegetable oil and fat contact an adsorption agent.