621-59-0

Preparation

Synthesis of isovanillin: 4-Hydroxybenzaldehyde is used as raw material, firstly react with bromine to obtain 3-bromo-4-hydroxybenzaldehyde, then react with methyl iodide to obtain 3-bromo-4-methoxybenzaldehyde, and then hydrolyzed under the action of sodium hydroxide and cuprous chloride to produce isovanillin. The yield was 64.1%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1596, 1980 DOI: 10.1021/jo01297a010

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.]

General Description

Isovanillin, also known as 3-hydroxy-4-methoxybenzaldehyde, is a versatile aromatic aldehyde used in organic synthesis, particularly in the preparation of sweetening agents and bioactive compounds. It serves as a key intermediate in the copper(I)-catalyzed synthesis of 1,4-benzodioxines, yielding sweetening derivatives significantly sweeter than sucrose. Additionally, it has been employed in the synthesis of bactericidal arylidenedeoxyvasicinones, though these compounds exhibited only moderate to low antimicrobial activity. Its functional groups allow for diverse chemical modifications, making it valuable in pharmaceutical and flavoring applications.

Application

Isovanillin is a kind of fragrance and isomer of vanillin. it has unique properties than vanillin, its fragrance can change with the change of ambient temperature, so it is especially suitable for special cosmetics and some special fragrance industries. Isovanillin is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which could make it a candidate drug for use in alcohol aversion therapy.