Veratraldehyde

Chemical properties

White to brown or blue-gray needle crystal (crystallization in ether); sweet woody fragrance, fragrant grass aroma and strong flavor of vanilla blue; oxidized into odorless 3,4-dimethoxybenzoic acid (veratric acid) in the air; Melting point 43~45℃; Insoluble in cold water; soluble in hot water, ethanol and oil.
Natural products exist in the Java citronella oil and Hu Xanthium parsley oil and so on.
Use GB 2760 a 1996 provisions for the use of food spices.

Application

• This product is the intermediate of organic synthesis. In pharmaceutical industry, it is used to synthesize methamphetamine and also used in the production of veterinary drug sulfonamide synergist. Adding 0.02% (weight) of this veterinary drug into feed can increase the efficiency of the iodine drug synergistic added in feed, which can prevent and control the poultry bacterial infection.
• Used as pharmaceutical intermediate and mainly used for antibiotic drug synthesis.

Preparation

It can be derived from the reaction of 3-methoxy-4-hydroxybenzaldehyde (vanillin) and dimethyl sulfate, or derived from the methylation of dimethyl sulfate with vanillin in alkaline conditions.

Chemical Properties

off-white crystalline solid

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.

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.

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.

Uses

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.]