JP2011229525A - Nicotinic acid amide-containing oil and fat composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oil and fat composition containing nicotinic acid amide at a high concentration.SOLUTION: In the oil and fat composition containing 1,000-20,000 ppm of the nicotinic acid amide, and having a hydroxyl value of 9-100 mg-KOH/g, the content C (ppm) of the nicotinic acid amide and the hydroxyl value X (mg-KOH/g) satisfy the relationship represented by the following formula (1): [Ln(C/850)]/X≤0.038 (wherein Ln is a natural logarithm) (1).

Description

  The present invention relates to a nicotinamide-containing oil and fat composition.

Oils and fats are important nutrients along with proteins and carbohydrates, and are particularly useful as energy sources. In addition, fats and oils are used as a heat medium for cooking. Moreover, it is an important material that imparts the good flavor of the oil itself. Against the background of health orientation in recent years, attempts have been made to enhance the appeal of products by strengthening nutritional components in edible oils, for example, stabilized tocopherol containing α-, β-tocopherol with high physiological activity at a high content An oil-and-fat composition (Patent Document 1) and the like have been reported.
The tocopherol is a kind of vitamin E, which is a fat-soluble vitamin, and is a component originally contained in fats and oils as a natural component. However, many of the nutritional components are insoluble in oil, and many of them cannot add the amount that they originally want to strengthen.

  On the other hand, nicotinamide is one of water-soluble vitamins collectively called niacin (vitamin B3) together with nicotinic acid. Nicotinamide is nicotinamide amide adenine dinucleotide (NAD) and nicotinamide amide adenine dinucleotide phosphate (NADP). Carbohydrate metabolism and normalization of nerve function as coenzymes of carbohydrate, lipid and protein metabolic systems. It is important to take an appropriate amount of nicotinamide for maintaining human health, but it tends to be deficient due to an increase in missing food rate and dependence on processed foods. When supplementing nicotinamide with nutrient-enriched foods, it is desirable to be able to consume more than 1/3 of the daily requirement based on the "6th revised Japanese nutritional requirement".

JP-A-8-173035

The inventor has tried to dissolve nicotinamide in edible oil that has been used in the past and contains triacylglycerol as a main component, but has found that the amount to be strengthened cannot be dissolved.
Therefore, the subject of this invention is providing the fats and oils composition which melt | dissolves nicotinamide in high concentration.

  As a result of intensive studies, the present inventor has found that when the hydroxyl value (OHV) of the oil and fat composition is not less than a certain value and the dissolved amount of nicotinic acid amide and the value of the hydroxyl value satisfy a certain relationship, nicotine It has been found that acid amides can be dissolved at a high concentration.

That is, the present invention is an oil / fat composition containing 1,000 to 20,000 ppm of nicotinamide and having a hydroxyl value of 9 to 100 mg-KOH / g, the content of nicotinamide being C (ppm) The oil and fat composition having a hydroxyl value X (mg-KOH / g) satisfying the relationship of the following formula (1) is provided.
(Equation 1)
[Ln (C / 850)] / X ≦ 0.038 (Ln: natural logarithm) (1)

  ADVANTAGE OF THE INVENTION According to this invention, the oil-and-fat composition which melt | dissolves and contains a high concentration nicotinic acid amide can be provided.

The oil and fat composition according to the present invention has a hydroxyl value (OHV) of 9 to 100 mg-KOH / g, particularly 20 to 100 mg-KOH / g, particularly 40 to 100 mg-KOH / g. It is preferable from the viewpoint of improving solubility.
Here, the hydroxyl value is a value measured by “hydroxyl number (pyridine-acetic anhydride method 2.3.6.2-1996)” in “Standard Oil Analysis Test Method 2003 Edition” edited by Japan Oil Chemists' Society.
Details of the method for measuring the hydroxyl value are described in Examples.

The oil and fat composition having a hydroxyl value (OHV) of 9 to 100 mg-KOH / g according to the present invention can be prepared by combining oils and emulsifiers alone or appropriately so that the hydroxyl value is in the above range. It is preferable to use one having a high content of glycerol and / or diacylglycerol.
In the present invention, “oil / fat” includes one or more of triacylglycerol, diacylglycerol, and monoacylglycerol.
In the oil and fat composition of the present invention, the content of diacylglycerol is preferably 10% by mass (hereinafter simply referred to as “%”) or more, more preferably 20% or more, particularly 40% or more. It is preferable from the point of improvement of property. The upper limit is not particularly defined, but is preferably 99% or less, more preferably 98% or less, and still more preferably 97% or less.
Further, the content of monoacylglycerol is preferably 0 to 5%, more preferably 0 to 2%, particularly 0.1 to 2%, in terms of improving the solubility of nicotinic acid amide, and flavor as an edible oil. From the viewpoint of industrial productivity.

  The fats and oils in the fat and oil composition of the present invention may be made from either vegetable oils or animal fats. 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, Animal fats and oils such as beef tallow and butter fats, or fats and oils such as transesterified oils, hydrogenated oils and fractionated oils can be mentioned, but those that are not hydrogenated constitute edible fats and oils This is preferable from the viewpoint of reducing the content of trans-unsaturated fatty acids in the total fatty acids.

  Fatty acids constituting the fats and oils in the fat and oil composition of the present invention are not particularly limited, and may be either saturated fatty acids or unsaturated fatty acids, but 40 to 100% are preferably unsaturated fatty acids, more It is preferably 80 to 100%, more preferably 90 to 100% from the viewpoint 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.

  Moreover, it is preferable that content of a saturated fatty acid is less than 60% among the fatty acids which comprise the fats and oils in an oil-fat composition, More preferably, it is 0-20%, Furthermore, it is 0-10%, an external appearance, It is preferable in terms of physiological effects and 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.

  Of the fatty acids constituting the fats and oils in the fat and oil composition, the content of trans-unsaturated fatty acids is 0 to 4%, preferably 0.1 to 3.5%, and more preferably 0.2 to 3%. From the viewpoint of physiological effect, appearance, and industrial productivity of fats and oils.

  As the emulsifier used in the oil and fat composition of the present invention, in addition to monoacylglycerol and diacylglycerol, polyglycerin condensed ricinoleic acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, Examples include polyol fatty acid esters such as propylene glycol fatty acid esters.

  The oil and fat composition according to the present invention contains 1,000 to 20,000 ppm of nicotinamide, but the content thereof is further 1,000 to 15,000 ppm, particularly 1,000 to 6,000 ppm, and even more preferably 1. 4,000 to 4,500 ppm is preferable from the viewpoints of stability and physiological effects. The content of nicotinamide in the oil / fat composition can be measured by the method described in Examples.

  In the present invention, commercially available nicotinamide can be used.

In the oil and fat composition of the present invention, the content C (ppm) of nicotinamide and the hydroxyl value X (mg-KOH / g) satisfy the relationship of the following formula (1).
(Equation 1)
[Ln (C / 850)] / X ≦ 0.038 (1)
Ln: natural logarithm

In addition, the oil and fat composition according to the present invention can be obtained by the content C (ppm) of nicotinic acid amide and the hydroxyl value X (mg-KOH / g) satisfying the relationship of the following formula (2). The amount of nicotinic acid amide dissolved can be further increased.
(Equation 2)
[Ln (C / 679)] / X ≦ 0.039 (2)
C: Same as above Ln: Same as above

Furthermore, the content C (ppm) of nicotinamide and the hydroxyl value X (mg-KOH / g) satisfy the following formula (3), so that only the amount of nicotinamide dissolved in the oil and fat composition is increased. The present inventors have found that the bitter taste derived from nicotinamide can be suppressed.
(Equation 3)
[Ln (C / 854)] / X ≦ 0.031 (3)
C: Same as above Ln: Same as above

Furthermore, it is the present invention that the bitterness derived from nicotinamide can be further suppressed by satisfying the following formula (4) with the content C (ppm) of nicotinamide and the hydroxyl value X (mg-KOH / g). Found.
(Equation 4)
[Ln (C / 859)] / X ≦ 0.024 (4)
C: Same as above Ln: Same as above

That is, in the present invention, the amount of nicotinamide that dissolves varies depending on the hydroxyl value of the oil or fat composition. Specifically, when the content of nicotinic acid amide is 1,000 ppm or more and 20,000 ppm or less, the hydroxyl value of the oil and fat composition is 9 mg-KOH / g or more and 100 mg-KOH / g or less. When the content of 2,000 ppm or more and 20,000 ppm or less, the hydroxyl value is preferably 28 mg-KOH / g or more, and is 35 mg-KOH / g or more from the viewpoint of solubility of nicotinamide and bitterness suppression. More preferably it is.
When the content of nicotinic acid amide is 5,000 ppm or more and 20,000 ppm or less, the hydroxyl value is preferably 51 mg-KOH / g or more, and more preferably 73 mg-KOH / g or more. To preferred. When the content of nicotinic acid amide is 6,000 ppm or more and 20,000 ppm or less, the hydroxyl value is preferably 55 mg-KOH / g or more, and more preferably 80 mg-KOH / g or more from the same point. .

In the present invention, in view of solubility of nicotinic acid amide and bitterness suppression, when the content of nicotinic acid amide is 2,000 ppm or more and 20,000 ppm or less, the hydroxyl value is 22 mg-KOH / g or more. It is preferably 27 mg-KOH / g or more.
From the viewpoint of solubility, when the nicotinamide content is 5,000 ppm or more and 20,000 ppm or less, the hydroxyl value is preferably 46 mg-KOH / g or more. From the same point, when the content of nicotinamide is 6,000 ppm or more and 20,000 ppm or less, the hydroxyl value is preferably 51 mg-KOH / g or more.

The oil and fat composition of the present invention may further contain a vitamin B1 derivative or a salt thereof. Vitamin B1, like nicotinamide, has a small amount of dissolution in fats and oils mainly composed of triacylglycerol. Examples of vitamin B1 derivatives or salts thereof include bisbenchamine disulfide, benfotiamine, fursultiamine, octothiamine, dibenzoylthiamine, chicotiamine, sulbutiamine, acetylamine, dicetiamine, or salts thereof. The salt may be a pharmaceutically acceptable salt, for example, a mineral salt such as nitrate, hydrochloride, sulfate, etc .; acetate, propionate, tartrate, fumarate, maleate, malic acid Organic acid salts such as salt, citrate, methanesulfonate, p-toluenesulfonate, trifluoroacetate and the like can be mentioned. Of these, vitamin B1 derivatives, particularly bisbenchamine disulfide, are preferred in terms of solubility and physiological effects.
The content of the vitamin B1 derivative or a salt thereof is preferably 44 ppm or more in terms of thiamine, more preferably 44 to 5,000 ppm, particularly 44 to 3,000 ppm, and particularly preferably 44 to 2,000 ppm from the viewpoint of physiological effects.

  An antioxidant may be added to the oil and fat composition of the present invention from the viewpoint of improving the storage stability and flavor stability, as in the case of general edible oils and fats. Antioxidants include natural antioxidants, tocopherols, BHT, BHA, phospholipids, organic carboxylic acids, polyphenols and the like.

  The water content in the oil and fat composition of the present invention is preferably 15,000 ppm or less, more preferably 10,000 ppm or less, particularly 3,000 or less, in terms of storage stability and usability during cooking. To preferred.

  The oil and fat composition of the present invention can be used in the same manner as general edible oils and fats, and can also be used for various foods and drinks, feeds and pharmaceuticals. Examples of foods and drinks include oil-in-water processed foods such as drinks, desserts, ice creams, dressings, toppings, mayonnaise and grilled meat; water-in-oil processed foods such as margarine and spreads; peanut butter Processed fats and oils such as baking shortenings; processed foods such as potato chips, snacks, cakes, cookies, pies, breads, chocolates; bakery mixes; processed meat products; frozen entrées;

[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) Fatty acid composition Fatty acid methyl ester was prepared in accordance with “Preparation method of fatty acid methyl ester (2.4.1.-1996)” in “Standard oil analysis test method” edited by Japan Oil Chemists' Society. , American Oil Chemists. It was measured by Society Official Method Ce 1f-96 (GLC method).

(Iii) Hydroxyl value In accordance with “Hydroxyl number (pyridine-acetic anhydride method 2.3.6.2-1996)” in “Standard fat analysis test method” edited by Japan Oil Chemists' Society, a fat sample of about 5 g was weighed, 5 ml of acetylating reagent was added, a small funnel was placed on the neck of the flask, and the bottom of the flask was submerged in a heating bath to a depth of about 1 cm and heated to 95-100 ° C. After 1 hour, the flask was taken out of the heating bath, cooled, 1 ml of distilled water was added from the funnel, and again placed in the heating bath and heated for 10 minutes. The solution was cooled again to room temperature, and the liquid condensed on the funnel and the neck of the flask was washed into the flask with 5 ml of neutral ethanol and titrated with a 0.5 mol / L potassium hydroxide-ethanol standard solution using a phenolphthalein indicator. In addition, the blank test was performed in parallel with this test, and the value calculated from the titration result based on the following formula was defined as “hydroxyl value (mg-KOH / g)” (OHV).
Hydroxyl value = (A−B) × 28.05 × F / C + acid number (A: 0.5 mol / L potassium hydroxide-ethanol standard solution used in blank test (ml), B: 0.5 mol of this test) / L potassium hydroxide-ethanol standard solution usage (ml), F: factor of 0.5 mol / L potassium hydroxide-ethanol standard solution, C: sampling amount (g))

(Iv) Determination of nicotinic acid amide 2 g of methanol was added to 1 g of an oil and fat sample and stirred well with a vortex mixer. After phase separation, the methanol phase was collected. To the residual liquid, 2 ml of methanol was added and extracted in the same manner. The extraction operation was performed three times with methanol, and the methanol phases were combined and dried under a nitrogen stream at room temperature. After dissolving in 1 ml of acetonitrile, it was washed 3 times with 1 ml of hexane. The acetonitrile phase after washing was dried at room temperature under a nitrogen stream, dissolved and fixed in acetonitrile again, and subjected to HPLC.
HPLC conditions:
Column: ODS-3 (4.6 ID × 250 mm), GL Sciences column temperature: 40 ° C.
Mobile phase: 0.05N-mixed solvent gradient of sodium dihydrogen phosphate (A) / methanol (B): A / B = 95/5 (0 min) → A / B = 5/95 (50 min)
Mobile phase flow rate: 0.5 ml / min
Injection volume: 20 μl
Detection: UV detector 260 nm

(V) Quantification of bisbenchamine disulfide 0.3 g of Tween 80, 5 ml of acetic acid buffer solution, and 1 ml of 10% thiourea solution were added to 0.5 g of an oil and fat sample to adjust the pH to 4.5.
3 ml of 2.5% -Takadiastase solution was added and left overnight at 40 degrees. 5 ml of 2N hydrochloric acid and 70 ml of ethanol were added and treated at 70 ° C. for 30 minutes with occasional stirring. The extract was adjusted to a volume of 100 ml with distilled water and filtered. 1 ml of 0.7% -cysteine solution was added to 5 ml of the extract, and 1 ml of 4N-sodium hydroxide solution was added and reacted at room temperature for 30 minutes, and then 1 ml of 4N-hydrochloric acid was added and the volume was adjusted to 20 ml with distilled water. Was subjected to HPLC.
HPLC conditions:
Column: ODS-3 (4.6 ID × 250 mm), GL Sciences column temperature: 40 ° C.
Mobile phase: (0.01 mol-sodium dihydrogen phosphate + 0.15 mol / L-sodium perchlorate) mixed solution (pH 2.2): methanol = 95: 5
Mobile phase flow rate: 1 ml / min
Injection volume: 20 μl
Detection: Fluorescence detector Ex = 375 nm, Em = 440 nm
Reaction solution: 0.05% potassium ferricyanide + 15% -sodium hydroxide Reaction solution flow rate: 0.4 ml / min

(Vi) Measurement of water content The water content of the oil and fat composition was measured by the Karl Fischer coulometric titration method using Tightland 851 (manufactured by Metrohm Japan).

[Preparation of raw oil and fat (1)]
A mixed fatty acid of soybean oil fatty acid: rapeseed oil fatty acid = 7: 3 (mass ratio) and 15 parts by mass of glycerin were mixed, and an esterification reaction was performed with an enzyme to obtain a diacylglycerol-containing fat. Fatty acid and monoacylglycerol were removed from the resulting esterified product by distillation, acid-treated (2% of 10% aqueous citric acid solution was added), washed with water, and deodorized to obtain oil (1). Table 1 shows the glyceride composition and the fatty acid composition.

  Rapeseed oil (manufactured by Nisshin Oillio Group Co., Ltd.) was used as the raw material fat and oil (2), and glycerin fatty acid monoester (O-95R, manufactured by Kao Corporation) was used as the raw material fat and oil (3). Table 1 shows the glyceride composition and fatty acid composition of the raw oils and fats (2) and (3).

  The fats and oils A to G were prepared by mixing the raw fats and oils (1) to (3) at a mass ratio shown in Table 2. Table 2 shows the glyceride composition and hydroxyl value of the fats and oils A to G.

[Solubility test]
The state after leaving the oil / fat composition after heating and stirring at room temperature for 24 hours was observed, and the solubility was evaluated according to the following criteria.
○: Dissolved transparently ×: Turbid and undissolved

〔sensory evaluation〕
The fat and oil compositions 1 to 2 g were eaten with a specialized panel, and the bitterness was evaluated according to the following criteria.
3: Bitter 2: Slightly bitter 1: Not bitter

Example 1
Oil and fat composition by adding nicotinamide (manufactured by Sigma-Aldrich) to fats and oils A to G at a mass ratio shown in Table 3 and heating and stirring in a hot water bath at 80 ° C. for 2 hours. 1-22 were prepared. The analytical values are shown in Tables 3 and 4.

  Next, the above-described solubility test and bitterness sensory evaluation were performed using each oil and fat composition. The results are shown in Tables 3 and 4.

As can be seen from Table 3, the oil and fat composition of the present invention was able to contain nicotinamide in a high concentration. In oil composition 16-22, undissolved nicotinamide was observed.
Furthermore, the fat and oil compositions 4, 6 to 15, particularly the fat and oil compositions 4, 7, 8, and 10 to 15 were preferable as edible oils because the bitter taste derived from nicotinamide was suppressed.

Example 2
Nicotinamide (manufactured by Sigma-Aldrich) and bisbenchamine disulfide (manufactured by Mitsubishi Tanabe Seiyaku) are added to fats and oils C or G at a mass ratio shown in Table 5 for 2 hours in a water bath at 80 ° C Oil composition 23-26 was prepared by heating and stirring. The analytical values are shown in Table 5.

  Next, using the oil and fat compositions 23 to 26, a solubility test and a bitter taste sensory evaluation were performed in the same manner as described above. The results are shown in Table 5.

  As can be seen from Table 5, the oil-and-fat composition of the present invention can contain a vitamin B1 derivative dissolved in a high concentration in addition to nicotinamide, and has little bitterness.

Claims (8)

An oil composition containing 1,000 to 20,000 ppm of nicotinamide and a hydroxyl value of 9 to 100 mg-KOH / g, wherein the content C (ppm) of nicotinamide and the hydroxyl value X (mg- An oil and fat composition in which KOH / g) satisfies the relationship of the following formula (1).
(Equation 1)
[Ln (C / 850)] / X ≦ 0.038 (Ln: natural logarithm) (1) The oil and fat composition according to claim 1, wherein the content C (ppm) of nicotinamide and the hydroxyl value X (mg-KOH / g) satisfy the relationship of the following formula (2).
(Equation 2)
[Ln (C / 679)] / X ≦ 0.039 (Ln: natural logarithm) (2) The fat and oil composition according to claim 1, wherein the content C (ppm) of nicotinic acid amide and the hydroxyl value X (mg-KOH / g) satisfy the relationship of the following formula (3).
(Equation 3)
[[Ln (C / 854)] / X ≦ 0.031 (Ln: natural logarithm) (3) The fat and oil composition according to claim 1, wherein the content C (ppm) of nicotinamide and the hydroxyl value X (mg-KOH / g) satisfy the relationship of the following formula (4).
(Equation 4)
[Ln (C / 859)] / X ≦ 0.024 (Ln: natural logarithm) (4)   The oil or fat composition according to claim 3 or 4, which contains 1,000 to 4,500 ppm of nicotinic acid amide.   Furthermore, the fats and oils composition of any one of Claims 1-5 containing a vitamin B1 derivative or its salt.   The fat and oil composition according to claim 6, wherein the vitamin B1 derivative is bisbenchamine disulfide.   It is an edible oil, The oil-fat composition of any one of Claims 1-7.