Veratraldehyde

Химические свойства

Veratraldehyde is a crystalline solid (mp 44.5–45°C) with a woody, vanillalike odor.
Veratraldehyde can be prepared by methylation of vanillin. It is used in oriental and warm, woody fragrances, as well as in flavor compositions for vanilla notes. It is an intermediate in, for example, the synthesis of pharmaceuticals.

Вхождение

Reported among the constituents of the essential oils of Cymbopogon javanensis and Eryngium poterium. Also reported found in raspberry, ginger, peppermint oil, Bourbon vanilla and mastic gum oil.

Использование

Veratraldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane. It was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity. It forms 1:1 inclusion complexes with cyclodextrins. It reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.

Подготовка

Prepared from vanillin by methylation of vanillin with dimethylsulfate under mildly alkaline conditions.

Общее описание

Needles or chunky light peach powder. Has an odor of vanilla beans.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

Veratraldehyde is incompatible with strong oxidizing agents and strong bases. . Veratraldehyde is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).

Пожароопасность

Veratraldehyde is probably combustible.

Методы очистки

Crystallise the ether from diethyl ether, pet ether, CCl4 or toluene. [Beilstein 8 IV 1765.]