Veratraldehyde

Chemical properties

off-white crystalline solid

Chemical properties

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.

Chemical properties

Veratraldehyde has a very sweet, woody, vanilla-like odor with a warm, sweet, vanilla-like taste. This compound gets oxidized in air to odorless veratric acid.

Occurrence

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.

The Uses of Veratraldehyde

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.

Preparation

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

Definition

ChEBI: Veratraldehyde is a dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4. It is found in peppermint, ginger, raspberry, and other fruits. It has a role as an antifungal agent. It is a member of benzaldehydes and a dimethoxybenzene.

Aroma threshold values

Aroma characteristics at 1.0%: phenolic, sweet vanilla, powdery, slightly woody with a candy and cocoa creaminess.

Taste threshold values

Taste characteristics at 50 ppm: phenolic, vanilla, sweet powdery cocoa, creamy, cherry-like with phenolic and balsamic nuances..

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2070, 1947 DOI: 10.1021/ja01200a517
Organic Syntheses, Coll. Vol. 2, p. 619, 1943
Tetrahedron Letters, 20, p. 975, 1979

General Description

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

Air & Water Reactions

Insoluble in water.

Reactivity Profile

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).

Fire Hazard

Veratraldehyde is probably combustible.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Taste at 50 ppm

Purification Methods

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