Schiff’s base with methyl anthranilate

SCHIFF S base Organic compound formed by reaction between an aldehyde or ketone with a primary amine, e.g. hydroxycitronellal forms a Schiff s base with methyl anthranilate to give Aurantiol . 

A new fashion was created when Dior introduced Poison in which the aldehyde component of the Schiff s base has a strident green character, creating a sharp contrast with the heavy sweetness of the methyl anthranilate. The pale yellow colour of methyl anthranilate is darkened when a Schiff s base is formed from it, because of the hypsochromic shift in the ultraviolet absorbtion maximum that results from the extension of conjugation. This colour has an effect on the colour of any fragrance in which it is incorporated and has to be taken into account if colour might be deleterious in the final product. Many Schiff s bases are available commercially, but some perfumers prefer to formulate their fragrances using aldehydes and free methyl anthranilate and allow the Schiff s base to form spontaneously in the perfume. 

However, since many natural oils and absolutes also possess a correspondingly high odour strength and quality, the ratio of the cost to strength and quality should always be considered carefully before removing them. In this case, it is difficult to justify inclusion of the broom absolute in the soap context, so in its place a small quantity of methyl anthranilate (the chemical that quantitatively dominated the headspace of broom) is added. Care should always be taken with anthranilates because of the possible formation of Schiff s bases upon reaction with aldehydes. Extra aldehydes will certainly be added to the soap version of the alcoholic perfume because of their excellent odour performance in covering the fatty smell of common soap bases. 

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