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–]

References in periodicals archive ?
Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes.
In order to detect it in individual pigs cheaply and efficiently, DeRosa's test strips employ aptamers, which are short synthetic strands of DNA that specifically bind to pre-selected molecular targets--in this case androstenone and skatole.
Source skatole indole p-cresol dimethly dimethyl trisulfide disulfide Pre-cond 5.
This therefore reduces the production of androstenone and skatole, hormonal substances which release a strong odour, which is highly unpleasant for consumers.
The effect of feeding system, lysine level and gilt contact on performance, level skatole and economy of entire male pigs.
20) Nonsulfur containing compounds such as cadaverine, putrescine, indole, and skatole have also been implicated in oral malodor.
Enterobacterioaceae in the intestinal tract have mostly unpleasant properties since they generate smelly chemicals of the type of skatole and related indoles.
Skatole is detected in pork from boars, barrows, and gilts.
The unpleasant odor of some flatus is the result of trace gases, such as hydrogen sulfide, indole, and skatole, which are produced when foods decompose in the colon.
There are many types of gas butthe main ones are sulphur - which gives a stink bomb its pong; putrecine;cadaverine; skatole and indole.
The prime suspects are skatole and indole (by-products of protein digestion) and sulfide gases, which are responsible for the smell of rotten eggs.