Skatole

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skatole

[′ska‚tōl]
(organic chemistry)
C9H9N A white, crystalline compound that melts at 93-95°C, dissolves in hot water, and has an unpleasant feceslike odor. Also known as 3-methylindole.

Skatole

 

(also beta-methylindole), a foul-smelling substance occurring as colorless crystals and having the structural formula

Skatole has a melting point of 95 °C and a boiling point of 265°C; it is insoluble in water and soluble in organic solvents. Extremely dilute solutions of the compound have a pleasant floral odor. Skatole is present in small amounts in coal tar and secretions of the civet cat. It is formed from tryptophan during the splitting of proteins by putrefactive bacteria in the colon, hence the fecal odor.

Synthetic skatole is obtained by, for example, heating phe-nylhydrazone of propionaldehyde (C6H5NH—N=CHC2H5) with ZnCl2 and is used in perfumery. [23–1481–]

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