JP6283510B2 - Method for producing triterpene alcohol-containing fats and oils - Google Patents

Description

  The present invention relates to a method for producing triterpene alcohol-containing fats and oils.

  Triterpene alcohol is a tetracyclic compound having 30 or 31 carbon atoms, and is a component contained in cereal oil such as rice bran oil. Triterpene alcohol is also a main component of the alcohol moiety constituting γ-oryzanol. There are various reports on the physiological functions of triterpene alcohols, such as blood cholesterol lowering action, lipid absorption inhibitory action, adiponectin secretion promoting action, etc. (Non-patent Document 1, Patent Documents 1 and 2).

Against the background of health orientation in recent years, it is required to effectively obtain the physiological action of these triterpene alcohols. In order to satisfy the demand, a form that can be easily and easily ingested through daily cooking such as oil is desirable. Furthermore, it is desirable to take triterpene alcohol as a free form.
However, most of the triterpene alcohols in ordinary rice bran oil exist as ferulic acid esters or fatty acid esters, and the free form accounts for only about 0.2% by mass.

Then, the trial which mix | blends the triterpene alcohol which hydrolyzed and extracted and isolate | separated (gamma) -oryzanol with cooking oil is made | formed (for example, patent document 1).
The triterpene alcohol can be extracted and separated by alkaline hydrolysis of crude oryzanol, followed by extraction with acetone and benzene, followed by recrystallization from methanol and purification (Patent Document 3), or after alkaline hydrolysis of crude oryzanol. , Extraction with ether or precipitation in ice water (Patent Document 4), alkali hydrolysis of γ-oryzanol, extraction with low polarity organic solvent, heating and melting triterpene alcohol in water, cooling, etc. It has been reported (Patent Document 5).

JP 2006-257064 A JP 2005-68132 A Japanese Patent Publication No.55-2440 JP 2006-273762 A JP 2012-41304 A

“Arteriosclerosis”, 1985, Vol. 13, no. 2 June, p. 273-278

As shown in Patent Documents 3 to 5, conventionally, in order to separate triterpene alcohol released from γ-oryzanol, solvent extraction with acetone, benzene or the like has been required. However, when using triterpene alcohols for food applications, it is desirable to reduce or avoid the use of organic solvents. In consideration of handling, special equipment is required to convert the extracted and separated triterpene alcohol into a solid state, and there is a concern about purification load and environmental load.
Therefore, the present invention intends to provide a new method for producing fats and oils containing triterpene alcohol at a high concentration.

  The inventors of the present invention have intensively studied in view of the above-mentioned problems. After the alkali hydrolysis of γ-oryzanol, the triterpene alcohol liberated using fats and oils can be easily extracted and separated by neutralizing the remaining alkali under certain conditions. Further, it was found that the obtained fats and oils have a good appearance at room temperature and excellent low-temperature resistance while containing a high concentration of triterpene alcohol.

That is, the present invention includes the following steps (1), (2) and (3):
(1) a step of subjecting a γ-oryzanol-containing raw material to alkaline hydrolysis,
(2) The step of neutralizing the hydrolyzate obtained in step (1) with an acid so that the degree of neutralization is in the range of 0.9 to 1.05 with respect to the residual alkali amount,
(3) The step of mixing the neutralized product and fat obtained in step (2) to obtain a fat containing triterpene alcohol,
The manufacturing method of the triterpene alcohol containing fats and oils containing this is provided.

  According to the present invention, it is possible to obtain fats and oils containing triterpene alcohol at a high concentration, having a good appearance at room temperature, and excellent low-temperature resistance. Since the method of the present invention can be refined with normal oil refining equipment, it is possible to reduce the purification load and the environmental load.

The method for producing a triterpene alcohol-containing fat according to the present invention includes the following steps (1), (2) and (3):
(1) a step of subjecting a γ-oryzanol-containing raw material to alkaline hydrolysis,
(2) The step of neutralizing the hydrolyzate obtained in step (1) with an acid so that the degree of neutralization is in the range of 0.9 to 1.05 with respect to the residual alkali amount,
(3) The step of mixing the neutralized product and fat obtained in step (2) to obtain a fat containing triterpene alcohol,
including.

Step (1) of the present invention is a step of subjecting the γ-oryzanol-containing raw material to alkaline hydrolysis.
γ-Oryzanol is a substance present in rice bran oil, corn oil, and other cereal oils. Ferulic acid (3-methoxy-4-hydroxycinnamic acid) ester of triterpene alcohol and feruler of plant sterol other than triterpene alcohol A general term for acid esters.

γ-oryzanol is contained in a large amount in deoxidized foots (alkali oil separated in the deoxidizing step) produced during the production process of the rice bran oil and the like. For this reason, the γ-oryzanol-containing raw material often contains a large amount of triacylglycerol, fatty acid and fatty acid salt. The γ-oryzanol-containing raw material can be either a crude product or a refined product from the oil, but it is neutralized after extraction with a lower alcohol from a deoxidized foot, particularly a deoxidized foot from rice bran oil. It is preferable from the viewpoint of industrial productivity and cost to use a crude product of oryzanol obtained by recrystallization.
The content of triterpene alcohol ferulic acid ester in the γ-oryzanol-containing raw material is 45 to 95% by mass (hereinafter simply referred to as “%”), and further 50 to 90% from the viewpoint of industrial productivity and cost. Is preferred.
Commercially available products can be used as the γ-oryzanol-containing raw material.

  Alkaline hydrolysis can be performed according to a conventional method. Examples of the alkali include hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, ammonia, and amines. Of these, alkali metal hydroxides are preferable from the viewpoint of handleability, and potassium hydroxide is more preferable.

From the viewpoint of sufficiently hydrolyzing the triterpene alcohol ferulic acid ester, the amount of alkali used is preferably 1 to 20 equivalents, more preferably 5 to 10 equivalents, relative to the saponification value of the γ-oryzanol-containing raw material. The saponification value of the γ-oryzanol-containing raw material can be measured, for example, according to the method described in the standard fat analysis method 2.3.2.
The concentration of alkali is from the viewpoint of fully hydrolyzed triterpene alcohol ferulic acid ester, 1 mol / dm ³ or more, further 1.5 mol / dm ³ or more, further 2 mol / dm ³ or more. The concentration of the alkali, from the viewpoint of performing the neutralization after hydrolysis efficiently, preferably 5 mol / dm ³ or less, more preferably 3 mol / dm ³ or less.

  Alkaline hydrolysis may be performed in the presence of an organic solvent. The organic solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include ethers such as dioxane and tetrahydrofuran; alcohols such as methanol and ethanol. These can be used alone or in combination of two or more. Of these, alcohols are preferable from the viewpoint of handleability, and ethanol is more preferable. The concentration of the alcohol is preferably 70% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and 98% by mass or less from the viewpoint of sufficiently hydrolyzing the triterpene alcohol ferulic acid ester. Is preferable, and 95 mass% or less is more preferable.

  Although reaction temperature is not specifically limited, From a viewpoint of fully hydrolyzing triterpene alcohol ferulic acid ester, 25-100 degreeC, Furthermore, 50-90 degreeC is preferable.

  The reaction time is appropriately selected from the alkali concentration and the reaction temperature. From the viewpoint of sufficiently hydrolyzing the triterpene alcohol ferulic acid ester, it is preferably 1 hour to 50 hours, more preferably 2 hours to 24 hours, and further 3 hours. ~ 15 hours is preferred.

In the step (2) in the method of the present invention, the alkali hydrolyzate obtained in the step (1) is neutralized with an acid so that the neutralization degree is in the range of 0.9 to 1.05 with respect to the residual alkali amount. It is a process of summing.
In the present specification, the residual alkali amount is the amount of alkali remaining without being used in the alkaline hydrolysis of the γ-oryzanol-containing raw material, and from the amount of alkali added in step (1), the γ-oryzanol-containing raw material This is a value obtained by subtracting the amount of alkali used for alkaline hydrolysis of the. The amount of residual alkali is the number of moles of added alkali (mol)-(number of moles of triterpene alcohol ferulic acid ester in the γ-oryzanol-containing raw material (mol) + number of moles of plant sterol ferulic acid ester in the γ-oryzanol-containing raw material. (Mol)).

The degree of neutralization is in the range of 0.9 to 1.05 with respect to the residual alkali amount. If it is 0.9 or more, hydrolysis of fats and oils by excess alkali can be prevented in the fat and oil extraction step (3) after neutralization, and if it is 1.05 or less, by-products generated by alkali hydrolysis are mixed. Therefore, it is possible to obtain a triterpene alcohol-containing oil and fat having a good appearance at room temperature and low temperature.
The degree of neutralization is preferably 0.92 or more, more preferably 0.93 or more, more preferably 1.02 or less, and further 0.99, from the viewpoint of the extraction efficiency of triterpene alcohol with the oil and fat after neutralization. The following is preferred. Further, the neutralization degree is preferably 0.92 to 1.02, more preferably 0.93 to 0.99, with respect to the residual alkali amount.
The degree of neutralization is the ratio of the amount of added acid (added acid amount (mol) × valence) and the amount of residual alkali base (residual alkali amount (mol) × valence) (added acid amount / residual alkali base amount). Represent.

  Known acids can be used, for example, inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, p-toluenesulfonic acid and methanesulfonic acid; organic acids such as formic acid, acetic acid, propionic acid, malic acid and citric acid Is mentioned. These can be used alone or in combination of two or more. Of these, sulfuric acid and citric acid are preferred from the viewpoint of handleability.

  The temperature during neutralization is preferably 25 to 70 ° C. from the viewpoint of industrial productivity.

Step (3) in the method of the present invention is a step of mixing the neutralized product obtained in step (2) with fats and oils, extracting triterpene alcohol, and obtaining fats and oils containing triterpene alcohol.
Examples of the fats and oils used in the present invention include soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, palm oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, pearl oil, wheat germ oil, perilla Oil, linseed oil, sesame oil, sacha inch oil, walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, coconut oil, tea seed oil, borage oil, palm oil, palm olein Vegetable oils such as palm stearin, palm oil, palm kernel oil, cacao butter, monkey butter, shea butter, algae oil, etc .; animal fats and oils such as fish oil, lard, beef tallow and butter butter; Examples thereof include fats and oils such as hydrogenated oil and fractionated oil. These oils may be used singly or may be used as a mixture, and among these oils and fats, it is preferable to use vegetable oils and fats from the viewpoint of triterpene alcohol extraction efficiency, and rapeseed oil, It is preferable to use rice oil or a combination thereof.

  From the viewpoint of triterpene alcohol extraction efficiency, the amount of oil used is preferably at least 2 times, more preferably at least 5 times the mass of the γ-oryzanol-containing material used as the alkali hydrolysis material in step (1). Moreover, from a viewpoint of industrial productivity and cost, 20 mass times or less, Furthermore, 15 mass times or less are preferable. The amount of oil used is preferably 2 to 20 times, more preferably 5 to 15 times the γ-oryzanol-containing raw material.

  Moreover, as for the temperature at the time of mixing a neutralized material and fats and oils, 25-100 degreeC is preferable from a viewpoint of triterpene alcohol extraction efficiency. The mixing time at this time can be appropriately set depending on the apparatus, but is preferably 30 minutes or more in order to obtain a sufficient extraction effect.

In this invention, it is preferable to perform the process of removing water and a solid part, after mixing a neutralized material and fats and oils. Examples of the method for removing water and the solid part include centrifugation and decantation.
Centrifugation conditions can be appropriately set depending on the state of separation.

Moreover, it is preferable to perform the process of making water contact the obtained fats and oil-water separation from a viewpoint of removing the by-product produced | generated by alkali hydrolysis. From the viewpoint of impurity removal efficiency, the amount of water used is preferably 0.2 to 2 times the mass of the oil.
Further, the temperature of water is preferably 25 to 90 ° C., more preferably 25 to 70 ° C., from the viewpoint of removal efficiency of by-products.
Washing with water may be performed once or a plurality of times, for example, twice or three times.

As a result of such treatment, triterpene alcohol is extracted from the fat and oil, and a triterpene alcohol-containing fat and oil having a high content of triterpene alcohol is obtained.
In the present specification, triterpene alcohol refers to tetracyclic triterpene alcohol having 30 or 31 carbon atoms. These triterpene alcohols are compounds that clearly differ from 4-desmethylsterols having 28 or 29 carbon atoms such as β-sitosterol, stigmasterol, campesterol and the like. Triterpene alcohols have a hydroxyl group at the C-3 position of the steroid nucleus, such as cycloartenol, 24-methylenecycloartanol, cyclobranol, cycloartanol, cyclosador, cyclolaudenol, butyrosperimol. , Parqueol etc. are included.

  In the triterpene alcohol-containing oil / fat of the present invention, the content of the triterpene alcohol is preferably 0.5% by mass or more, more preferably 1% by mass or more, and further preferably 2% by mass or more from the viewpoint of handleability. 10 mass% or less, Furthermore 8 mass% or less is preferable. Moreover, in triterpene alcohol containing fats and oils, content of triterpene alcohol is 0.5-10 mass%, Furthermore, 1-10 mass%, Furthermore, 2-8 mass% is preferable.

  The triterpene alcohol-containing fats and oils of this invention may perform the refinement | purification process normally used with respect to fats and oils. Specific examples include a degumming step, a dewaxing step, a deoxidizing step, a decolorizing step, and a deodorizing step.

  The triterpene alcohol-containing fats and oils of the present invention thus obtained are excellent in handleability and can be used in a wide range of applications. For example, it can mix | blend and use for fats and oils or foodstuffs.

Aspects and preferred embodiments of the present invention are shown below.
<1> Next steps (1), (2) and (3):
(1) a step of subjecting a γ-oryzanol-containing raw material to alkaline hydrolysis,
(2) The step of neutralizing the hydrolyzate obtained in step (1) with an acid so that the degree of neutralization is in the range of 0.9 to 1.05 with respect to the residual alkali amount,
(3) The step of mixing the neutralized product and fat obtained in step (2) to obtain a fat containing triterpene alcohol,
A method for producing a triterpene alcohol-containing fat or oil.

<2> The content of the triterpene alcohol ferulic acid ester in the γ-oryzanol-containing raw material is preferably 45% by mass or more, more preferably 50% by mass or more, and preferably 95% by mass or less, more preferably 90%. The manufacturing method of the triterpene alcohol containing fats and oils as described in <1> which is the mass% or less.
<3> The alkali is preferably one or more selected from alkali metal hydroxides, ammonia and amines, more preferably one or more selected from alkali metal hydroxides. Yes, More preferably, it is potassium hydroxide, The manufacturing method of the triterpene alcohol containing fats and oils as described in <1> or <2>.
<4> In any one of <1> to <3>, the amount of alkali used is preferably 1 equivalent to 20 equivalents, more preferably 5 equivalents to 10 equivalents, relative to the saponification value of the γ-oryzanol-containing raw material. The manufacturing method of fats and oils containing triterpene alcohol of description.
<5> the concentration of the alkali is preferably 1 mol / dm ³ or more, more preferably 1.5 mol / dm ³ or more, more preferably 2 mol / dm ³ or more, preferably 5 mol / dm ³ or less, more preferably Is 3 mol / dm < ³ > or less The manufacturing method of the triterpene alcohol containing fats and oils of any one of <1>-<4>.
<6> Alkaline hydrolysis is preferably an organic solvent, more preferably alcohols, more preferably ethanol, still more preferably 70% by mass or more, still more preferably 80% by mass or more, further preferably 90% by mass or more, The method for producing a triterpene alcohol-containing oil or fat according to any one of <1> to <5>, which is performed in the presence of ethanol having a concentration of 98% by mass or less, more preferably 95% by mass or less.
<7> The method for producing a triterpene alcohol-containing fat / oil according to any one of <1> to <6>, wherein the alkali hydrolysis is preferably performed at a reaction temperature of 25 to 100 ° C, more preferably 50 to 90 ° C.
<8> The alkaline hydrolysis is preferably performed for a reaction time of 1 hour to 50 hours, more preferably 2 hours to 24 hours, and further 3 hours to 15 hours, according to any one of <1> to <7>. A method for producing triterpene alcohol-containing fats and oils.
<9> The degree of neutralization is preferably 0.92 or more, more preferably 0.93 or more, and preferably 1.02 or less, more preferably 0.99 or less with respect to the residual alkali amount <1. The manufacturing method of the triterpene alcohol containing fats and oils of any one of>-<8>.
<10> Described in any one of <1> to <8>, wherein the degree of neutralization is preferably 0.92 to 1.02 and more preferably 0.93 to 0.99 with respect to the residual alkali amount. Of producing triterpene alcohol-containing fats and oils.
<11> The acid is preferably one or more selected from hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, p-toluenesulfonic acid, methanesulfonic acid, formic acid, acetic acid, propionic acid, malic acid and citric acid. More preferably, the method for producing a triterpene alcohol-containing fat according to any one of <1> to <10>, which is sulfuric acid, citric acid, or a combination thereof.
<12> Fats and oils are preferably used in an amount of 2 mass times or more, more preferably 5 mass times or more with respect to the γ-oryzanol-containing raw material, and preferably 20 mass times or less, more preferably 15 times the γ-oryzanol-containing raw material. The method for producing a triterpene alcohol-containing oil or fat according to any one of <1> to <11>, which is used at a mass ratio or less.
<13> Oils and fats are preferably vegetable oils and fats, animal oils and fats, transesterified oils, hydrogenated oils or fractionated oils, more preferably vegetable oils and fats, more preferably rapeseed oil, rice oils or these The method for producing a triterpene alcohol-containing oil or fat according to any one of <1> to <12>, which is a combination of the above.
<14> The method for producing a triterpene alcohol-containing fat / oil according to any one of <1> to <13>, including a step of oil / water separation in which water is brought into contact with the fat / oil after the step (3).
<15> The method for producing a triterpene alcohol-containing oil or fat according to <14>, wherein water is preferably used in an amount of 0.2 to 2 times the oil or fat.
<16> The process according to any one of <1> to <15>, wherein one or more treatments selected from a degumming step, a dewaxing step, a deoxidizing step, a decoloring step, and a deodorizing step are further performed after the step (3). Of producing triterpene alcohol-containing fats and oils.
The content of <17> triterpene alcohol is preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 2% by mass or more, and preferably 10% by mass or less, more preferably 8% by mass. The method for producing a triterpene alcohol-containing oil or fat according to any one of <1> to <16>, which is not more than mass%.
<18> A triterpene alcohol-containing fat obtained by the production method according to any one of <1> to <17>.
The content of <19> triterpene alcohol is preferably 0.5% by mass or more, more preferably 1% by mass or more, still more preferably 2% by mass or more, and preferably 10% by mass or less, more preferably 8% by mass. The triterpene alcohol-containing fat / oil according to <18>, which is not more than mass%.

[Analysis method]
(1) Triterpene alcohol The oil and the triterpene alcohol fraction were separated by a solid phase extraction column. About 25 mg of the separated triterpene alcohol fraction was taken and made up to 10 mL with chloroform. 1 μL of this was injected into the GC and analyzed. The conditions of GC analysis are as follows.
Solid phase extraction column: Sep-Pak syika 5g
Column: Capillary GC column DB-1 (J & W), 30 mx 0.25 mm, film thickness 0.25 μm
Carrier gas: He, 2.30 mL / min
Injector: Split (40: 1), T = 300 ° C.
Detector: FID, T = 300 ° C
Oven temperature: held at 150 ° C. for 1.5 minutes, raised to 250 ° C. at 15 ° C./minute, raised to 320 ° C. at 5 ° C./minute, held for 3 minutes

(2) γ-Oryzanol The sample was made up with ethyl acetate so that it would be 0.2 to 0.8 mg / 10 mL as oryzanol, and after complete dissolution and mixing, analysis was performed using HPLC.
Column: Inersil ODS-3 (Φ4.6 × 250 μm)
Method: wavelength 325 nm, analysis time 60 minutes, column temperature 40 ° C., flow rate 1.2 mL / min

[Appearance evaluation of triterpene alcohol-containing fats and oils]
Triterpene alcohol-containing fats and oils were diluted with rapeseed oil, and the content of triterpene alcohol was adjusted to 4% by mass. Five panelists observed the turbidity at 25 ° C. immediately after dilution in a 20 mL screw vial (NEG screw vial SV-20), and evaluated according to the following criteria. The average value was used as the score for appearance evaluation.
3: No turbidity 2: Slightly turbid 1: Turbid

[Evaluation of low-temperature resistance of triterpene alcohol-containing fats and oils]
Triterpene alcohol containing fats and oils were diluted with rapeseed oil, and the content of triterpene alcohol was adjusted to 0.4 mass%. Five panel members observed the appearance when stored in a quartz cell having an optical path length of 1 cm and stored at 0 ° C. for 3 days, and evaluated according to the following criteria. The average value was used as a score for low temperature resistance evaluation.
3: No turbidity 2: Slightly turbid 1: Turbid

Example 1
52.8 g of potassium hydroxide was dissolved in 400 mL of 90% by mass ethanol aqueous solution. 80 g of γ-oryzanol-containing raw material (manufactured by Tsukino Food Industry Co., Ltd., content of triterpene alcohol ferulic acid ester 53.4% by mass, saponification value 115) was added and the temperature was raised to 80 ° C. under stirring conditions of 400 r / min. The mixture was warmed and stirred for about 5 hours for hydrolysis. Thereafter, it was cooled to 45 ° C., and neutralized by adding 410 g of a 10% aqueous citric acid solution to obtain a neutralized product. The degree of neutralization with respect to the remaining alkali amount was 0.92.
To the neutralized product, 720 g of rapeseed oil 9 times as much as the γ-oryzanol-containing raw material was added, and the mixture was heated to 70 ° C. under a stirring condition of 400 r / min, and triterpene alcohol was extracted. The obtained oil / water mixed solution was centrifuged at 6000 r / min for 20 minutes at an operating temperature of 40 ° C. using a small cooling centrifuge (manufactured by Hitachi Koki Co., Ltd.) to obtain an oil phase. Subsequently, the oily phase was washed with water three times using 1 mass times distilled water. The obtained fats and oils were subjected to deodorization treatment for 34 minutes under reduced pressure of 260 Pa and at 150 ° C. with water vapor (3% / h-to-oil) to obtain triterpene alcohol-containing fats and oils.

Example 2
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 1 except that the degree of neutralization with respect to the residual alkali amount was 0.97.

Example 3
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 1 except that the degree of neutralization with respect to the residual alkali amount was 0.93 and the deodorization treatment was performed at 200 ° C.

Example 4
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 3 except that the degree of neutralization with respect to the residual alkali amount was 0.98.

Example 5
A triterpene alcohol-containing fat was obtained in the same manner as in Example 3 except that the degree of neutralization with respect to the residual alkali amount was 1.02.

Example 6
The triterpene alcohol-containing fats and oils were obtained in the same manner as in Example 3 except that the degree of neutralization with respect to the residual alkali amount was 0.96 and 560 g of rapeseed oil seven times as much as the γ-oryzanol-containing raw material was added.

Example 7
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 3 except that the neutralization degree with respect to the residual alkali amount was 0.96 and 880 g of rapeseed oil 11 times as much as the γ-oryzanol-containing raw material was added.

Example 8
A triterpene alcohol-containing fat / oil was obtained in the same manner as in Example 1 except that the degree of neutralization with respect to the residual alkali amount was 0.93 and rice oil was used as the extracted fat / oil.

Example 9
A triterpene alcohol-containing fat was obtained in the same manner as in Example 8 except that the degree of neutralization with respect to the residual alkali amount was 0.99.

Example 10
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 1 except that 330 g of 10% sulfuric acid aqueous solution was used instead of 10% citric acid aqueous solution and the neutralization degree with respect to the remaining alkali amount was 0.97.

Comparative Example 1
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 1 except that the degree of neutralization with respect to the residual alkali amount was 1.09.

Comparative Example 2
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 3 except that the degree of neutralization with respect to the residual alkali amount was 1.09.

Comparative Example 3
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 10 except that the degree of neutralization with respect to the residual alkali amount was 0.80.

Comparative Example 4
A triterpene alcohol-containing oil and fat was obtained in the same manner as in Example 10 except that the degree of neutralization with respect to the residual alkali amount was 1.09.

  Table 1 shows the conditions of each step of Examples and Comparative Examples, the content of triterpene alcohol (TTA) in the triterpene alcohol-containing oil and fat, the results of appearance evaluation, and low-temperature resistance evaluation.

  As can be seen from Table 1, according to the method of the present invention, it was possible to obtain fats and oils containing triterpene alcohol at a high concentration, having a good appearance at room temperature, and excellent low-temperature resistance. On the other hand, Comparative Example 3 with a low degree of neutralization and Comparative Examples 1, 2, and 4 with a high degree of neutralization were able to extract triterpene alcohol liberated from γ-oryzanol in fats and oils, but turbidity at normal and low temperatures. It was seen.

Claims (5)

Next steps (1), (2) and (3):
(1) a step of subjecting a γ-oryzanol-containing raw material to alkaline hydrolysis,
(2) The step of neutralizing the hydrolyzate obtained in step (1) with an acid so that the degree of neutralization is in the range of 0.9 to 1.05 with respect to the residual alkali amount,
(3) After mixing the neutralized product and fats and oils obtained in step (2), separating the oil and water to obtain fats and oils containing triterpene alcohol,
A method for producing a triterpene alcohol-containing fat or oil.   The method for producing a triterpene alcohol-containing oil or fat according to claim 1, wherein the acid is citric acid or sulfuric acid.   The manufacturing method of the triterpene alcohol containing fats and oils of Claim 1 or 2 which uses fats and oils at 2 mass times or more and 20 mass times or less of a gamma-oryzanol containing raw material in a process (3).   The manufacturing method of the triterpene alcohol containing fats and oils of any one of Claims 1-3 whose fats and oils are rapeseed oil and / or rice oil in a process (3). The manufacturing method of the triterpene alcohol containing fats and oils of any one of Claims 1-4 which further includes the process of making water contact the fats and oils containing a triterpene alcohol and performing oil-water separation after a process (3).