没食子酸プロピル

外観

白色〜わずかにうすい赤褐色, 結晶性粉末〜粉末

定義

本品は、没食子酸(*)のプロピルエステルであり、次の化学式で表される。
参照表示名称：没食子酸

溶解性

水に不溶。熱湯, エタノールに易溶。エタノールに溶け、水に溶けにくい。

用途

油脂およびバターの酸化防止剤

化粧品の成分用途

酸化防止剤、香料

効能

酸化防止剤

説明

Propyl gallate is an antioxidant with antimicrobial activity. It is hepatoprotective in vitro and in vivo, preventing CCl₄ induced lipoperoxidation and reduction in polysomes in rat liver. Propyl gallate (100 mg/kg, i.p.) increases expression of HIF-1α, EPO, and VEGF mRNA levels and the number of normal neurons in rat brains after 8 minutes of forebrain ischemia. Propyl gallate in combination with potassium sorbate is bactericidal and bacteriostatic against S. aureus strains known to produce enterotoxins in food. Propyl gallate is commonly added to foods to prevent autoxidation and microbial growth.

使用

Propyl Gallate is a known inhibitor of Tyrosinase, a polyphenol oxidase, which is an important enzyme in pigment biosynthesis in various organisms. It has also recently been seen to boost biodiesel li pid biosynthesis in cultures.

製造方法

Produced commercially by the esterification of gallic acid with propyl alcohol followed by distillation to remove the excess alcohol.

一般的な説明

Fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150°C. Insoluble in water. Slightly bitter taste.

空気と水の反応

Insoluble in water.

反応プロフィール

Propyl gallate can react with oxidizing agents. Incompatible with strong acids, strong bases and strong reducing agents. Darkens in the presence of iron and iron salts. Contact with metals should be avoided .

危険性

Use in foods restricted to 0.02% of fat con- tent.

火災危険

Propyl gallate is combustible.

接触アレルゲン

This gallate ester (E 311) is an antioxidant frequently used in the food, cosmetic, and pharmaceutical industries to prevent the oxidation of unsaturated fatty acids into rancid-smelling compounds. It causes cosmetic dermatitis mainly from lipsticks and induced contact dermatitis in a baker, and in a female confectioner, primarily sensitized by her night cream, who fried doughnuts the margarine probably containing gallates.

毒性学

Propyl gallate (n-propyl-3,4,5-trihydroxybenzoate) is used in vegetable oils and butter. When 1.2 or 2.3% propyl gallate was added to feed for rats, loss of weight was observed. This may be due to the rats reluctance to eat food that was contaminated with the bitter taste of propyl gallate. When it was given for 10 to 16 months at the 2 to 3% level, 40% of the rats died within the first month and the remainder showed severe growth inhibition. Autopsies of rats indicated kidney damage resulting from the ingestion of propyl gallate. However, no other animal studies show serious problems and further studies indicated that propyl gallate does not cause serious chronic toxicities.

安全性プロファイル

Poison by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.

安全性

Propyl Gallate currently is used as an antioxidant in a reported 167 cosmetic products at maximum concentrations of 0.1%. Propyl Gallate is a generally recognized as safe (GRAS) antioxidant to protect fats, oils, and fat-containing food from rancidity that results from the formation of peroxides.

純化方法

Crystallise the ester from aqueous EtOH or *C6H6 (m 146-146.5o). [Beilstein 10 III 2078, 10 IV 2003.]