JP5825803B2 - Oil composition - Google Patents

Description

  The present invention relates to an oil and fat composition that is liquid at room temperature.

Monoacylglycerol is a highly safe substance widely used as an emulsifier in foods, pharmaceuticals, cosmetics and the like.
In recent years, fats and oils having various functions focused on the structure of monoacylglycerol and the type of acyl group constituting monoacylglycerol have been proposed. An unsaturated fatty acid-containing oil and fat composition (Patent Document 1) in which emulsifiability is imparted to an oil and fat itself containing a highly unsaturated fatty acid in a high concentration has been reported. Moreover, the fats and oils (patent document 2) which contain 5 weight% or more of diglycerides and / or monoglycerides whose content of ω3 unsaturated acyl groups in the structural acyl group is 15% by weight or more, and ω3 having less than 20 carbon atoms as a constituent fatty acid. An oil composition (Patent Document 3) containing monoglyceride containing a specific amount of a series, ω9 and ω6 unsaturated fatty acid, and a diglyceride in a certain ratio to the monoglyceride has been reported.

On the other hand, oleic acid in fatty acid residues constituting fats and oils is considered to be a nutritionally preferable fatty acid, and edible fats and oils having a higher oleic acid ratio with increasing health consciousness are desired by consumers.
As for monoacylglycerol, 1-monoolein is known to have a serum triglyceride concentration lowering action and a postprandial GIP secretion inhibiting action (Patent Documents 4 and 5).

Japanese Patent Laid-Open No. 10-265795 JP 2001-247457 A JP 2002-53892 A JP-A-5-310567 JP 2007-290989 A

  However, since the conventional monoacylglycerol having a high oleic acid content in the constituent fatty acid is solid at room temperature, it must be dissolved by heating at the time of use, handling is not easy, and processing methods and applications are limited. There was a problem. In addition, when monoacylglycerol is contained as a part of food, crystals are precipitated and become non-uniform, making it difficult to ingest a desired amount and worsening the texture.

  Accordingly, an object of the present invention is to provide a fat and oil composition that is liquid at room temperature while containing monoacylglycerol having a high oleic acid content in the constituent fatty acids.

  As a result of intensive studies on the above problems, the present inventor has included specific amounts of monoacylglycerol, diacylglycerol, and triacylglycerol, respectively, and the content of monoacylglycerol and the content of diacylglycerol have a certain relationship. It was found that if the oil / fat composition is filled, crystallization is suppressed even at room temperature and the liquid state is maintained.

  That is, the present invention is an oil and fat composition that is liquid at room temperature, wherein 4 to 40% by mass of monoacylglycerol, 3 to 96% by mass of diacylglycerol, and triacylglycerol in which 60% by mass or more of the constituent fatty acids are oleic acid. An oil and fat composition containing 0 to 90% by mass of glycerol, and the content Y (% by mass) of monoacylglycerol and the content X (% by mass) of diacylglycerol satisfy the relationship of the following formula (1): It is to provide.

(Equation 1)
Y <X + 6 (1)

  According to the present invention, it is possible to obtain a liquid oil composition having a good appearance while maintaining transparency at room temperature while containing a high concentration of monoacylglycerol having a high oleic acid content in the constituent fatty acids.

It is a figure which shows the range of the content mass ratio of a monoacylglycerol, a diacylglycerol, and a triacylglycerol.

  The oil and fat composition of the present invention is liquid at room temperature. Here, room temperature shall be 23 degreeC. The liquid state is a state having fluidity.

  The oil and fat composition of the present invention may be made from either vegetable oil or animal fat. Specific raw materials include, for example, vegetable oils such as soybean oil, rapeseed oil, safflower oil, rice bran oil, corn oil, palm oil, sunflower oil, cottonseed oil, olive oil, sesame oil, perilla oil, fish oil, lard, Examples thereof include animal fats and oils such as beef tallow and butter fat, and fats and oils such as transesterified oil, hydrogenated oil and fractionated oil. These oils may be used alone or in combination as appropriate.

The oil and fat composition of the present invention contains monoacylglycerol and diacylglycerol. Triacylglycerol may also be included.
In the oil and fat composition, the content of monoacylglycerol is 4 to 40% by mass (hereinafter simply referred to as “%”), but is 4 to 39%, more preferably 10 to 39%, particularly 15 to 38%, and particularly 20 It is preferably -35% from the viewpoint of manifesting physiological effects, storage at low temperatures, and flavor.

Of the fatty acids constituting monoacylglycerol, the content of oleic acid is 60% or more. From the viewpoint of manifestation of physiological effects and oxidation stability, the content of oleic acid is preferably 78 to 95%, more preferably 80 to 85%.
The remaining constituent fatty acid may be either a saturated fatty acid or an unsaturated fatty acid, but 80 to 100% of the constituent fatty acids are preferably unsaturated fatty acids, more preferably 82 to 95%, and further 83. ˜90% is preferable in terms of appearance and industrial productivity of fats and oils. The number of carbon atoms of the unsaturated fatty acid is preferably 14 to 24, and more preferably 16 to 22 from the viewpoint of physiological effects.

  In addition, among fatty acids constituting monoacylglycerol, the content of saturated fatty acids is preferably 0 to 20%, more preferably 2 to 18%, and even more preferably 5 to 15%. From the viewpoint of industrial productivity of fats and oils. The saturated fatty acid is preferably those having 14 to 24 carbon atoms, particularly 16 to 22 carbon atoms.

  The content of trans-unsaturated fatty acids among the fatty acids constituting the monoacylglycerol is 0 to 4%, preferably 0.1 to 3.5%, and more preferably 0.2 to 3%. It is preferable in terms of flavor, physiological effect, appearance, and industrial productivity of fats and oils. Further, the content of oleic acid in trans form, that is, the content of elaidic acid is preferably 1% or less, more preferably 0.5% or less, and further preferably 0.3% or less from the viewpoint of physiological effects.

  In the oil and fat composition of the present invention, the content of diacylglycerol is 3 to 96%. From the viewpoint of improving the solubility of monoacylglycerol in the oil or fat composition, the content of diacylglycerol is preferably 10 to 90%, more preferably 30 to 90%, and particularly preferably 40 to 80%. The constituent fatty acid of diacylglycerol is preferably the same as monoacylglycerol from the viewpoint of manifesting physiological effects.

  In the oil and fat composition of the present invention, the monoacylglycerol content Y (%) and the diacylglycerol content X (%) satisfy the relationship of the following formula (1).

(Equation 2)
Y <X + 6 (1)

  That is, when the monoacylglycerol content Y (%) is smaller than the value obtained by the formula (1) from the diacylglycerol content X (%), it does not crystallize at room temperature and is a transparent and liquid oil composition. A thing is obtained.

Further, since the relationship between the monoacylglycerol content Y (%) and the diacylglycerol content X (%) satisfies the relationship of the following formula (2), the crystal is observed even at a temperature below room temperature, preferably 20 ° C. A transparent and liquid oil / fat composition is obtained.
(Equation 3)
Y <X-2 (2)

  Further, in the oil and fat composition of the present invention, the content of triacylglycerol is 0 to 90%, but 10 to 85%, more preferably 10 to 70%, in order to maximize the effect of monoacylglycerol. In particular, the content is preferably 15 to 60%. The constituent fatty acid of triacylglycerol is preferably the same as monoacylglycerol from the viewpoint of manifesting physiological effects.

  Moreover, the fat and oil composition of the present invention may contain a free fatty acid (salt), and the content thereof is preferably 5% or less, more preferably 0 to 2%, and particularly preferably 0 to 1%. From the viewpoint of industrial productivity.

The range of the mass ratio of monoacylglycerol (MAG), diacylglycerol (DAG), and triacylglycerol (TAG) in the oil and fat composition of the present invention is shown in the triangle diagram of the three components MAG, DAG, and TAG shown in FIG. , Point a (MAG = 4, DAG = 96, TAG = 0), point b (MAG = 40, DAG = 60, TAG = 0), point c (MAG = 40, DAG = 34, TAG = 26), point Range surrounded by d (MAG = 9, DAG = 3, TAG = 88), point e (MAG = 7, DAG = 3, TAG = 90) and point f (MAG = 4, DAG = 6, TAG = 90) Inside (however, the line segment connecting point c and point d is not included). By setting the mass ratio of the three components of MAG, DAG, and TAG within such a range, even if the oleic acid content in the fatty acid constituting monoacylglycerol is high, a liquid oil composition can be obtained at room temperature.
The range of the mass ratio of the MAG, DAG, and TAG is preferably point a (MAG = 4, DAG = 96, TAG) from the viewpoint of manifesting physiological effects, storage at low temperatures, and industrial productivity of fats and oils. = 0), point b (MAG = 40, DAG = 60, TAG = 0), point h (MAG = 40, DAG = 42, TAG = 18) and point f (MAG = 4, DAG = 6, TAG = 90) ) (But not on the line connecting point h and point f), more preferably point i (MAG = 10, DAG = 90, TAG = 0), point b (MAG = 40, DAG = 60, TAG = 0), point h (MAG = 40, DAG = 42, TAG = 18), point j (MAG = 28, DAG = 30, TAG = 42) and point k (MAG = 10) , DAG = 30, TAG = 60) And the point b (MAG = 20, DAG = 80, TAG = 0), point b (MAG = 40, DAG = 60, TAG = 0) are particularly preferable. , Point h (MAG = 40, DAG = 42, TAG = 18) and point m (MAG = 20, DAG = 42, TAG = 38).

  An antioxidant can be added to the oil and fat composition of the present invention for the purpose of improving storage stability and flavor stability. Antioxidants include natural antioxidants, tocopherols, ascorbyl palmitate, ascorbate stearate, BHT, BHA, phospholipids and the like.

  Moreover, the emulsifier etc. can be added to the oil-fat composition of this invention from points, such as the improvement of the food texture or flavor of cooking goods, and physiological function provision. Examples of additives include polyglycerin condensed ricinoleic acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, propylene glycol fatty acid ester and other polyol fatty acid esters, organic acid monoglycerides, plant sterols And plant sterol esters.

  The oil and fat composition of the present invention is liquid at room temperature, and since there are many nutritionally preferred oleic acids as acyl groups constituting monoacylglycerol, it is excellent in handleability and has excellent physiological activity. Has a low concentration and good flavor. Therefore, the oil and fat composition of the present invention can be used for foods, feeds and pharmaceuticals.

  As a food, the oil-and-fat composition can be used for an oil-and-fat-containing food containing the oil-and-fat composition as a part of the food in the same manner as a general edible oil and fat. Examples of such oil-containing foods include capsules, tablets, granules, powders containing such oil compositions; bakery foods such as bread, cakes, cookies; soups, sauces, dressings, mayonnaises; Examples include confectionery and beverages such as creams, chocolates, and candy. Such a fat-containing food can be produced by adding a food raw material generally used according to the type of the fat-containing food, in addition to the above fat composition. The amount of the oil / fat composition of the present invention to be added to food varies depending on the type of food, but is generally 0.1 to 100%, particularly preferably 1 to 80%.

  As feed, for example, feed for livestock used for cattle, pigs, chickens, sheep, horses, goats, etc., feed for small animals used for rabbits, rats, mice, etc., feed for seafood used for eel, Thailand, hamachi, shrimp, etc. Examples include pet foods used for dogs, cats, small birds, squirrels, etc., and can be produced by mixing together with feed ingredients generally used in addition to the oil and fat composition of the present invention. Although the compounding quantity to the feed of the fat composition of this invention changes with uses etc., generally 1-30%, especially 1-20% are preferable.

  Examples of pharmaceuticals include solid preparations such as powders, granules, capsules, pills and tablets, and oral administration agents such as liquids such as liquids, suspensions and emulsions. In addition to the oil and fat composition described above, this oral administration agent includes excipients, disintegrants, binders, lubricants, surfactants, alcohols, water, water-soluble high-concentration agents that are generally used depending on the form of the oral administration agent. Molecules, sweeteners, flavoring agents, acidulants and the like can be added for production. Examples of the orally administered drug include a brain function improving agent. The blending amount of the oil and fat composition of the present invention into a pharmaceutical product for oral administration varies depending on the use and form of the pharmaceutical product, but is generally 0.1 to 100%, particularly preferably 1 to 80%. Moreover, it is preferable to administer 0.1-50g per day as an oil-fat composition divided into 1 to several times.

[Analysis method]
(I) Glyceride composition About 10 mg of an oil and fat sample and 0.5 mL of a trimethylsilylating agent (“silylating agent TH”, manufactured by Kanto Chemical) were added to a glass sample bottle, sealed, and heated at 70 ° C. for 15 minutes. To this, 1.0 mL of water and 1.5 mL of hexane were added and shaken. After standing, the upper layer was analyzed by gas chromatography (GLC).

(Ii) Composition fatty acid composition Sample prepared by preparing fatty acid methyl ester in accordance with “Preparation method of fatty acid methyl ester (2.4.1.-1996)” in “Standard analysis method for fats and oils” edited by Japan Oil Chemists' Society Of American Oil Chemists. It was measured by Society Official Method Ce 1f-96 (GLC method).

[Preparation of raw oil and fat]
564 g of fatty acid obtained by hydrolyzing rapeseed oil and 92 g of glycerin were mixed, and an esterification reaction was carried out using immobilized 1,3-position selective lipase (manufactured by Novoldisk Industries) as a catalyst. After the lipase preparation was separated by filtration, the finished product was subjected to molecular distillation, further decolorized, washed with water, and deodorized to obtain a diacylglycerol-containing oil. This was used as the raw oil B. The analytical values are shown in Table 1.
Moreover, as raw material fats and oils A and C, fats and oils having the compositions shown in Table 1 were used.

  Raw material fats and oils A to C were mixed and dissolved to prepare respective fat and oil compositions. Table 2 shows the glyceride composition of each oil and fat composition and the fatty acid composition of monoacylglycerol.

[Appearance evaluation]
After each oil and fat composition was prepared, the appearance after storage at 20 ° C. and 23 ° C. for 1 day was visually evaluated according to the following criteria. The results are shown in Table 2.

Appearance evaluation criteria 1: Clear state 2: Slightly wrinkled state 3: State of some crystals precipitated or solidified

  As is clear from the results shown in Table 2, the oil and fat composition of the present invention contains a monoacylglycerol having a high oleic acid content in the constituent fatty acids, but is liquid at room temperature of 23 ° C. and has transparency. The keeping appearance was good.

Claims (5)

It is a fat and oil that is liquid at room temperature, and is composed of 7 to 40% by mass of monoacylglycerol, 3 to 80% by mass of diacylglycerol, and 10 to 90% by mass of triacylglycerol in which 60% by mass or more of the constituent fatty acid is oleic acid, And the fats and oils whose content Y (mass%) of the monoacylglycerol whose 60 mass% or more of a constituent fatty acid is an oleic acid, and content X (mass%) of a diacylglycerol satisfy | fill the following formula (1).
(Equation 1)
Y <X + 6 (1)   The fat or oil according to claim 1, wherein 0 to 20% by mass of the fatty acid constituting the monoacylglycerol is a saturated fatty acid.   The oil-and-fat composition containing 0-5 mass% of liquid fats and free fatty acids at room temperature of Claim 1 or 2.   Furthermore, the oil-fat composition of Claim 3 containing an antioxidant and / or an emulsifier.   Oil-containing food containing the oil composition according to claim 3 or 4.

Images