JPS59169464A - Production of oil-soluble flavor - Google Patents

Abstract

PURPOSE:To obtain an oil-soluble flavor for use as food additives, having improved storage stability with volatilization of low-boiling volatile aromatic components prevented, by treating an aqueous solution containing a natural aromatic component containing a water-miscible organic solvent in a specific proportion with a porous polymer resin or liquid triglyceride, etc. CONSTITUTION:(A) An aqueous solution containing a natural aromatic component (containing <=10wt% water-miscible organic solvent) is treated with (B) a porous polymer resin or chemically bonded type silical gel, and (C) a liquid triglyceride is then added thereto to give the aimed oil-soluble flavor. EFFECT:The aimed oil-soluble flavor can be obtained in high yield with retained improved aroma balance without hydrolysis and dehydration, etc. of the natural aromatic component. USE:For additives in drinks, tobacco, medicines, feeds, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is capable of eliminating the invasion of natural aroma components without accompanying changes in the aroma components present in natural products such as undesirable side reactions such as hydrolysis and dehydration of natural aroma components. Industrially advantageous and easy manipulation of natural aroma components from an aqueous solution (which may contain up to about 10% by weight of a water-miscible organic solvent) while maintaining a desired aroma balance. The present invention relates to a method for producing an oil bath flavor that can be selectively separated into an oil phase with high yield.

More specifically, the present invention involves treating an aqueous bath containing natural aroma acids (which may contain up to about 10% by weight of a water-miscible organic solvent) with a porous polymeric resin or a chemically bonded silica shell. The present invention relates to a method for producing an oil bath flavor, which comprises adsorbing the natural aroma components using a liquid triglyceride, and then eluting the aroma components using a liquid triglyceride.

In order to prevent the dissipation of volatile aroma components with low boiling points, one aroma acid is dissolved in an oil-soluble bath agent such as animal and vegetable oils to improve the retention (volatility adjustment) of the aroma components. Oil-soluble flavors have an important meaning in that they can provide dispersibility to products such as foods, and furthermore, they can impart heat resistance.

Conventionally, oil bath flavors in which natural aroma components are dissolved in animal and vegetable oils and fats, etc., are produced by, for example, (1) extracting natural aroma components directly from natural products such as cooked and processed products using animal and vegetable oils, etc.). Alternatively, a complicated method has been adopted in which the aroma component is obtained in advance from the natural product by a method such as steam distillation, fractional distillation, or solvent extraction, and then the soluble portion from the aroma component is extracted again into animal or vegetable oil or fat.

However, the above-mentioned extraction using animal and vegetable oils has a poor extraction rate of aroma components, and the animal and vegetable oil layer after the extraction process is
It tends to form an emulsion, and its separation is extremely difficult.

Further, as a method for collecting aroma components from natural products in advance, for example, in the fruit juice industry, a method for recovering aroma components by fractional distillation has been put into practical use.

However, in practice, it is difficult to collect aroma components ranging from low boiling points to high boiling points existing in a natural product while maintaining an excellent and desirable aroma balance of the natural aroma components by employing such a distillation method. This is impossible, and furthermore, changes in the components due to heat during the distillation operation are unavoidable.

On the other hand, when a solvent extraction method is adopted, although the extraction operation itself can be carried out at low temperatures, the resulting extract can only be obtained after being diluted with a solvent, resulting in weak aroma and unsatisfactory aroma. This is usually the result. When removing the solvent from such a bath agent extract to obtain an aroma component concentrate, there are disadvantages such as changes in the components due to heat during the solvent removal operation and changes in the aroma balance due to loss of components due to volatilization. However, it has the disadvantage that the aroma component is far from the original natural aroma component.

In order to improve the above-mentioned drawbacks, a natural aromatic component such as fruit is adsorbed onto a porous polymer resin such as styrene/divinylbenzene copolymer resin, and then a hydrophilic bath agent such as ethanol, propylene glycol or its water content is adsorbed. A method for producing natural fragrances has been proposed in which the components are eluted and recovered using the following method (Japanese Patent Publication No. 34234/1983). However, even with this proposed method using a porous styrene/divinylbenzene polymer resin, the excellent and favorable aroma balance of natural aroma components can be maintained satisfactorily. It was difficult to transfer it into an oil-soluble bath agent, and the operation was also complicated.

The present inventors have conducted research in order to develop an improved oil bathing method for collecting natural aroma components using an adsorption-bathing method.

As a result, an aqueous solution (which may contain up to about 10% by weight of a water-miscible organic solvent) containing natural fragrance ingredients is brought into contact with a porous polymeric resin and a chemically bonded silica cell. Alternatively, the natural aroma components are adsorbed onto the silica gel, and then the aroma components are eluted using liquid triglyceride. Having discovered that a satisfactory oil bath with a favorable aroma balance and a high yield of natural aroma components can be obtained all at once from an aqueous bath solution, it is therefore an object of the present invention to: An object of the present invention is to provide an excellent improvement method capable of collecting a high concentration of an oil-bathable natural aroma component having excellent thermal stability and unilytic decomposition properties for oily aromas.

The above objects and many other objects and advantages of the present invention will become more apparent from the following description.

The aqueous solution containing the natural fragrance component in the present invention (approximately 1
(which may contain up to 0% by weight of a water-miscible organic solvent) include natural source animal and plant materials 1 natural source animal + xr monoguhiro juice 1 extract, dilutions thereof - distillates of natural source animal and plant materials Examples include aqueous liquids containing natural aroma components (which may contain up to about 10 volumes of water-miscible organic solvents) produced by membrane separation methods such as reverse osmosis and ultrafiltration. Such natural source animal and plant materials include, for example, fruits, vegetables,
Coffee) Tea leaves, spices, herbal medicines, seafood, dairy products,
Examples include mixtures thereof.

In the present invention, an aqueous solution containing the above-mentioned natural source material or a natural aroma component derived from the material is brought into contact with a porous polymer resin and/or a chemically bonded silica shell. Aqueous bath liquids containing such naturally sourced materials or natural aroma components derived from them (water-miscible organic solvents at about 10% by weight, e.g. methanol, ethanol, n-propanol, ingropanol). It may also contain water-miscible organic solvents such as acetone to globylene dalicol, glycerin, and mixtures of two or more thereof. Furthermore, cine-soluble substances can be separated and removed from the aqueous solution by an appropriate solid-liquid separation means such as filtration or centrifugation, if desired.

The porous polymeric resins used in the present invention are known per se, such as polymers, eg Itf, styrene and duvinylbenzene copolymers, ethylvinylbenzene and sovinylbenzene copolymers,
Examples include a polymer of 2,6-diphenyl-9-phenylene oxide and a polycondensation polymer of methacrylic acid and duol. A preferable example of such a porous polymer resin has a specific surface area of about 500 y/f.
Porous polymer resins having a pore size of preferably about 700 m'/1 or more and a pore distribution of preferably about 10X to about 500X can be exemplified.

In fact, the chemically bonded silica gel used in the present invention itself is known, and is a type of silica gel in which alcohols, amines, silanes, etc. are chemically bonded using the reactivity of the silanol groups on the silica gel surface. For example, silanol groups present on the surface of silica gel are substituted with 01 or more alkylsilanes such as octadecylsilane, octylsilane, aminopropylsilane, cyanopropylsilane, and γ-glycidoxyprobylsilane. An example of such a chemically bonded silica gel is a chemically bonded silica gel having a pore diameter of about 50X to about 5000X, more preferably about 50X to about 500X, and a specific surface area of about 5
0rr? /7 or more, more preferably about 1 o o m
A chemically bonded porous silica gel having a particle diameter of about 6 μm to about 1 cTn1, preferably about 5 μm to about 1 cTn1, is preferred.

Furthermore, in the present invention, the liquid triglyceride can be used under elution conditions that can be used to desorb and release the natural aroma components adsorbed on the porous polymer resin and/or chemically bonded silica cell as exemplified above. Triglycerides that are liquid at room temperature, such as rapeseed oil, safflower oil, 1 part soybean oil, 1 part sunflower oil, 1 part seed oil, 1 part coma oil, corn oil, bran oil, cottonseed oil, olive oil, coffee bean oil, castor oil, 1 part saturated medium-chain fatty acid triglyceride. Examples include triglycerides such as cacao butter, palm oil, beef tallow, lard, peanut oil, fish oil, which become liquid when heated, and any mixture thereof.

According to a preferred embodiment of the method of the invention, in a few seconds:
A porous polymer resin and/or an aqueous liquid containing a natural aroma component (which may contain up to about 101% by weight of a water-temperature organic solvent) such as a juice extract or a distillate of a natural animal or plant material as exemplified above. The resin or the silica gel is allowed to adsorb natural aroma components by flowing down through a column filled with chemically bonded silica gel, and then, preferably, after passing through an inert gas such as nitrogen gas or spring acid gas, water is drained.
One-liquid triglyceride is passed through the solution as a Tanide bath medium at room temperature or under heating conditions, for example heated to about 100°C or less)
By bathing out the aroma components and sensory checking the solution flowing out from the bottom of the column, and collecting the fraction in which the desired aroma can be felt, ~ without changing the aroma components present in natural products, and '-1: Maintaining a favorable aroma balance: Since triglycerides are absorbed into the skin, oil-soluble flavors can be collected at a high yield.

In addition, the oil-soluble flavor may be prepared by removing residual water (immobilized matter) by using appropriate means such as FJr washing and centrifugation. In addition to using the active flavor as is, for example, 1 starch,
It can be used as an emulsion emulsified with polysaccharide and/or protein materials such as dextrin, gum arabic, pectin) xanthan gum, gelatin, casein, soy protein and any mixtures thereof; The liquid can also be dried using any drying method such as spray drying, freeze drying, fluidized bed drying, etc., and used as a powder or granules.

The oil bath flavor collected by the method of the present invention maintains an excellent and favorable aroma balance of the natural aroma components contained in the original natural source material, and has an aroma several times that of the natural source material. ~Several six times stronger aroma) beverages,
Western sweets) Fermentation hole 1 It can be advantageously used for frozen desserts, bakery products, dairy products, snacks, flavorings, tobacco, cosmetics, health and hygiene products, feed, etc.

Some embodiments of the method of the present invention will be explained in more detail with reference to Examples below.

Example 1 1.000 t of roasted and ground mixed coffee was packed into a glass column and steam distilled using a conventional method to collect 20,001 nl of distillate and 100'Oml of the distillate.
, porous polymer resin Eno Ibolus Polymer HP-2
0 (trade name, Mitsubishi Chemical Industries, Ltd.)] 5- from the top of a glass column (inner diameter 6 m x height 200 ++I+++) at about 50 sv to adsorb aroma components. Next, after draining the water by flowing nitrogen gas for about 10 minutes, the rapeseed was poured from the top of the column to about α2 Kq/c.
50 tons of the initial distillate was collected by pressure-feeding to extract aroma components, and was then dehydrated and over-treated to create a storage-stable coffee with a light palatability characteristic of roasted coffee and a strong aroma. An oil bath coffee flavor 451 was obtained.

Example 2 11 raw garlic cloves were cut into approximately 1 m pieces, immediately immersed in 5% lactic acid water bath solution 1.00 Of, left overnight at room temperature, and then decanted to obtain acid-treated waste liquid 9502 of 1 raw garlic. The obtained nucleic acid treatment waste liquid was treated with chemically bonded silica cell [Lichrosorb RP18 (trade name,
A glass column (manufactured by Merck) packed with 18rnl (
SVV2O3 was passed through a tube (inner diameter 8m x height 250mm) to adsorb aroma components.Then, after passing the gas for about 10 minutes and draining, 1°1τ Approximately 0.5 Ky of Aki triglyceride mixture
/crA pressure to extract aroma components, collect the first extracted portion 502, and further pass through a dehydrator to obtain an oil bath-based garlic flake with a strong aroma and concentrated fresh garlic aroma. -452 was obtained.

Example 6 After adding warm water to 1.000 y of crushed mustard and allowing myrosinase to act on the mixture at about 4D° C., steam distillation was carried out using a conventional method to collect 500 y of distillate. Next, the distillate was treated with a porous polymer resin [Porapack Q (trade name, Wate
rB), 15m7! The liquid was passed through a column packed with KSV of about 10 to adsorb and mix the aromatic components.

After draining with nitrogen gas, the mustard and mustard seed oil was pumped to extract the aromatic components. This oil-bathed mustard flavor had a very strong and sharp flavor unique to allyl mustard oil, which affected its storage stability.

Claims (1)

[Claims] 1. An aqueous bath solution containing natural aroma components (approximately 1 (may contain up to +wt% water-miscible organic solvent) is treated with a porous polymer resin or chemically bonded silica gel to adsorb the natural aroma components. A method for producing an oil bath flavor, which comprises: