SQUALENE (synonym spinacene) — acyclic polyunsaturated hydrocarbon in a transconfiguration, C 30 H 50 , belonging to triterpena of a fatty series, is an important intermediate product in biosynthesis of cyclic triterpen (a lanosterin, amirin) and steroid connections, including cholesterol, steroid hormones, bile acids, etc.
S. represents one of the most important chemical components of skin of the person, contains in fat of the person and animals, in a liver of the majority of animals, especially fishes, in yeast and vegetable oils. The name of this squalene connection came from a specific name of family of sharks of Squalus, in a liver to-rykh S. collects in large numbers because of blocking of its oxidation in cholesterol (see) and from where it was allocated in 1916. It is synthesized by Karrer (P. Karrer) in 1931.
The page represents a colorless oily liquid with a pleasant smell, t°kip 284 ° (at 25 mm w.g.), t°zamerz — 20 °, is easily ether-soluble, acetone, is badly alcohol-soluble. Forms a complex with thiourea. At S.'s hydrogenation saturated hydrocarbon squalane turns out (C 30 H 62 ), to-ry apply to calibration of devices during the determination of index of refraction of light, viscosity, etc., and also as a liquid phase at gas-liquid chromatography (see).
The page is synthesized from an active form acetic acid (see) atsetil-KOA through education mevalonovy to - you, an isopentylpyrophosphate and headlights-nezilpirofosfata. Further transformation of S. in fabrics of the majority of animals consists in its oxidation by molecular oxygen under the influence of the fermental system localized in microsomes, cyclization of the N who is formed 2,3 epoxysqualenes in lanosternn transformation of the last into cholesterol, to-ry is one of the main biosynthetic predecessors, including. steroid hormones (see), bile acids (see), etc.
Bibliography: Mayo P. Terpenoids, the lane with English, M., 1963; Aspects of terpenoid chemistry and biochemistry, ed. by T.W. Goodwin, L. — N. Y., 1971.
H. H. Chernov.