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. The binding agents are laboratory-tested nucleic acid sequences that can then be coated on to gold nanoparticles that are infused into the strips.
Other nonsulphur gases are also known to be involved in causing bad breath as Volatile aromatic compounds like indole, skatole, organic acids like acetic and propionic and amines like cadaverin and putrescine.10, 12
En cada transecto se usaron cuatro metodos de captura diferentes: trampas Malaise, Van Someren Rydon, red entomologica y atrayente artificial (metil salicilato, metil cinnamate, vainillin, eugenol, dimetil, skatole, acetato de fentilo y cineole para abejas euglosinas).
However, the main advantage of dairy products is that they are "alive food." Lactic acid and bifidobacteria contained in them inhibit the growth and development of pathogenic and putrefactive micro-organisms that inhabit the intestines and poison the body with products of rotting and fermentation (phenol, indole, skatole, ammonia, etc.).
Source skatole indole p-cresol dimethly dimethyl trisulfide disulfide Pre-cond 5.8 2.3 1.0 947.3 428.5 Pre-cond 5.3 5.7 1.0 327.5 207.0 Pre-cond 0.78 0.06 1.0 5.5 5.1 Pre-cond 1.1 0.06 1.0 17.0 23.4 Phase 1 1.2 0.07 1.0 6.6 2.1 Downwind 0.03 0.10 1.0 0.5 1.8 The sampling method with SPME fibers may cause variation in chromatograph concentrations due to variations in length of exposure period, variations between individual SPME fibers and instrumentation changes.
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.
The flavor is produced by a testosterone derivative and by skatole, produced by intestinal microbial breakdown of the amino acid tryptophan.