JPS60222476A - Tocopherol ferulate - Google Patents

Abstract

NEW MATERIAL:The ester of tocopherol with ferulic acid represented by the formula. USE:A drug for a preventing or curing adults diseases or promoting the secretion of bile. PREPARATION:For example, the reaction of dl-alpha-tocopherol (Vitamin E) with ferulic acid give the compound of the formula.

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 niferulic acid.

VEF has an antioxidant effect on oils and fats (lipids),
In particular, it shows excellent antioxidant effects on oils and fats under heating.

Examples and experimental results of VEF will be shown and specifically described below.

[Example-1] Production method: 75 g of dl-σ-tocopherol, 48 f of ferulic acid
, dimethylformamide 300,,l! , pyridine 150, . Dissolve the mixture in a mixture of 1 and 1, place the mixture in a stirrer equipped with a reflux condenser, and gradually add 30 ne of diketene while stirring. Although the temperature of the reaction system increases due to the heat of reaction, the temperature is maintained at 70 to 75 C0 using a water bath, and the reaction is continued for 2 hours. The reactants were then cooled and then lubricated into 5e water,
Benzene 2,5a was added and transferred to the benzene layer,
Extract the reactant (ester).

For extraction, the benzene layer was extracted with 2J of IN hydrochloric acid. , IN sodium bicarbonate 21, washed several times with an appropriate amount of water, and concentrated in vacuo under a nitrogen stream to obtain VEF.

[Example-2] Production method: Ferulic acid 209 was placed in a 300-e Erlenmeyer flask, dimethylformamide 10-1 was added and dissolved, then thionyl chloride 50 f was added and refluxed for 1 hour while stirring. After this, thionyl chloride is removed under reduced pressure, washed with an appropriate amount of benzene, and filtered to obtain a precipitate in a dry state. The ferulic acid chloride hydrochloride obtained here was taken in a colben (1e), and pyridine 40, l, benzene 200 -
To this, add dl-α-tocopherol 40
A solution of f in benzene 100 rLl is added, and the mixture is refluxed 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.

〔Experimental result〕

The VEF obtained by the method shown in the above-mentioned Examples has the U-absorption shown in FIG. 1, and the infrared absorption spectrum has the characteristics as shown in FIG. 2.

The action (effect) of VEF lies in its antioxidant action, and when looking at its effect on linoleic acid, for example, the first
As shown in the table, VEF suppresses the increase in the peroxide value of linoleic acid in the same way as dl-α-tocopherol, and especially in a 45C0 constant temperature bath, VEF
was found to exhibit excellent antioxidant effects.

(Table-1) Peroxide value (antioxidant effect) of VEF in the above table (
Conditions 11) were as follows: A sample was placed in a transparent glass container, left in a predetermined location, and the peroxide value was measured based on changes over time.

〔safety〕

The acute toxicity test of VEF was conducted using female DD mice weighing around 30 g, with oral administration of 4000 mf/h and 8000 mf/h.
Two groups (3 animals per group) of oral administration of mf/n were conducted, 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 'l/phantom.

[Application or application (utilization) field]

VEF can be used as an antioxidant in various oils and fats and foods containing oils and fats, cosmetics, medicines, feeds, etc., and is also expected to have the effects of vitamin E. In other words, since vitamin E, which is used as a starting substance, was discovered as an anti-infertility vitamin, subsequent research has shown that it suppresses the production of lipid peroxides in living organisms and works to stabilize biological membranes. Activates gonadal function, expands peripheral blood vessels, acts on enzymes such as succinidase, and has a positive effect on substance metabolism, thereby preventing adult diseases such as arteriosclerosis, diabetes, and menopausal symptoms. It has come to be frequently used for treatment. 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 application field of VEF is to exert the dual functions of vitamin E and ferulic acid after being absorbed into the body.
In particular, it is expected to promote bile secretion and prevent gallstones and liver damage. In addition, when blending into cosmetics, foods, feeds, etc., heating conditions are required during processing (formulation), but in such cases, the oils and fats in the formulation may be Peroxide values often increase rapidly. Especially under high temperature and high humidity conditions in the summer, the effect on the product becomes stronger, and as a result, the rancid odor characteristic of oils and fats appears strongly, but V
When EF is added, these effects can be prevented.

[Brief explanation of the drawing]

Figure 1 shows the ultraviolet absorption spectra of VE and F. Aftd6-σ-tocopherol, B is VEF
It is. FIG. 2 is an infrared absorption spectrum of VEF. Patent Applicant II/II. s2 diagram

Claims (1)

[Claims] (1) An ester of tocopherol and ferulic acid whose general formula is represented by [1]. Shii3