JPS6152151B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel vitamin E ferulic acid ester (hereinafter referred to as VEF for convenience) obtained by reacting vitamin E (tocopherol) with ferulic acid.
). VEF has an antioxidant effect on fats and oils (lipids), and exhibits particularly excellent antioxidant effects on fats and oils under heating. Examples and experimental results of VEF will be shown and specifically described below. Example 1 Production method: 75 g of dl-α-tocopherol, 48 g of ferulic acid
, 300ml of dimethylformamide, 150ml of pyridine
Dissolve in a mixture of , put into a stirrer equipped with a reflux condenser, and gradually add 30 ml of diketene while stirring. Although the temperature of the reaction system increases due to the heat of reaction, the temperature is further maintained at 70 to 75°C using a water bath, and the reaction is continued for 2 hours.
Next, the reactant was cooled, and then poured into the water in Step 5, and 2.5 g of benzene was added to extract the reactant (ester) that had migrated to the benzene layer. For extraction, the benzene layer is washed with 2 portions of 1N hydrochloric acid and 2 portions of 1N sodium bicarbonate, washed several times with an appropriate amount of water, and then concentrated in vacuo under a nitrogen stream to obtain VEF. Example 2 Production method: 20 g of ferulic acid was placed in a 300 ml Erlenmeyer flask, 10 ml of dimethylformamide was added to dissolve it, 50 g of thionyl chloride was added, and the mixture was dissolved under stirring for 1 hour.
After refluxing for an hour, thionyl chloride was removed under reduced pressure.
Wash with appropriate amount of benzene and filter to obtain a precipitate in dry form. The obtained ferulic acid chloride hydrochloride was added to 40 ml of pyridine.
ml, add 200ml of benzene, and add dl−α−
Add 40 g of tocopherol dissolved in 100 ml of benzene and reflux for 2 hours. After refluxing, the mixture is cooled and filtered, and the filtrate is collected and concentrated in vacuo under a nitrogen stream to obtain VEF. The yield of VEF obtained in Examples 1 and 2 described above is 80 to 90 g in Example 1, which is a good yield. On the other hand, in Example 2, 40 to 50 g is obtained. [Experimental results] Obtained by the method shown in the above example
VEF has the UV absorption shown in FIG. 1, and the infrared absorption spectrum has the characteristics shown in FIG. The action (effect) of VEF lies in its antioxidant action, and looking at its effect on linoleic acid, for example, it is as shown in Table 1, and VEF
Similar to dl-α-tocopherol, it suppresses the increase in the peroxide value of linoleic acid, especially at 45°C.
It was found that VEF exhibited excellent antioxidant activity in a constant temperature bath.

〔safety〕

The VEF acute toxicity test was conducted on females weighing around 30g.
Oral administration of 4000mg/Kg and 8000mg/Kg using DD mice.
The experiment was conducted in two groups (3 animals per group) with oral administration of mg/Kg, but no deaths or symptoms of toxicity were observed. Therefore, the acute LD50 value of VEF is 8000
It was estimated to be more than mg/Kg. [Applications or fields of application] VEF can be used as an antioxidant in various oils and fats and foods containing oils and fats, cosmetics, medicines, feeds, etc., and is expected to have the effects of vitamin E. be done. In other words, since vitamin E, which is used as a starting material, was discovered as an anti-infertility vitamin, subsequent research has shown that
It suppresses the production of lipid peroxides in the living body, works to stabilize biological membranes, activates gonadal function, dilates peripheral blood vessels, acts on enzymes such as succinic oxidase, and favors material metabolism. As a result, it has come to be frequently used in the prevention and treatment of adult diseases such as arteriosclerosis, diabetes, and menopausal disorders. On the other hand, ferulic acid is a component contained in plants, particularly in grains. Ferulic acid has an antioxidant effect, and oral administration thereof is known to promote bile secretion. Therefore, the field of application of VEF is expected to be that after being absorbed into the body, it exerts the dual effects of vitamin E and ferulic acid, and in particular promotes bile secretion and prevents gallstones and liver damage. In addition, when blended into cosmetics, foods, feeds, etc., heating conditions are required during processing (formulation), but in such cases, the oils and fats in the formulation are Peroxide values often increase rapidly. Especially under high temperature and high humidity conditions in the summer, the effects on the product become stronger, resulting in the strong rancid odor characteristic of fats and oils, but when VEF is added, these effects can be prevented.

[Brief explanation of the drawing]

FIG. 1 shows the ultraviolet absorption spectrum of VEF. A is dl-α-tocopherol, B is
It is VEF. Figure 2 shows the infrared absorption spectrum of VEF.

Claims (1)

[Claims] 1. dl-α-tocopherol and ferulic acid are dissolved in a mixed solvent consisting of dimethyl formalde and pyridine, placed in a stirrer equipped with a reflux condenser, and diketene is gradually dissolved under stirring. Then, the temperature in the stirrer was maintained at 70 to 75°C and the mixture was reacted. After the reaction, the mixture was poured into water, and then benzene was added.
A method of tocopherol ferulic acid ester represented by the general formula [1], which comprises the steps of transferring the reactant to a benzene layer, separating it, washing it, and concentrating it in vacuum under a nitrogen stream. Manufacturing method.