8768. Squalene
Nomenclature
Description and references
All trans isoprenoid contg six isoprene units. Found in large quantities in shark liver oil. Occurs in smaller amounts (0.1 to 0.7%) in olive oil, wheat germ oil, rice bran oil, and yeast. Intermediate in biosynthesis of cholesterol. Isoln: Heilbron et al., J. Chem. Soc. 1926, 1630. Structure: eidem, ibid. 1929, 873; Heilbron, Thompson, ibid. 883; Karrer et al., Helv. Chim. Acta 13, 1084 (1930); Karrer, Helfenstein, ibid. 14, 78 (1931); Karrer et al., ibid. 435. Crystal structure: J. Ernst et al., Angew. Chem. Int. Ed. 15, 778 (1976). Synthesis: Trippett, Chem. Ind. (London) 1956, 80; Dicker, Whiting, J. Chem. Soc. 1958, 1994; Cornforth et al., ibid. 1959, 2539; Johnson et al., J. Am. Chem. Soc. 92, 741 (1970); Hirai et al., Tetrahedron Lett. 1971, 4359; P. A. Grieco, Y. Masaki, J. Org. Chem. 39, 2135 (1974). Synthesis of squalene and trans-cis-trans-trans isomer: Biellmann, Ducep, Tetrahedron 27, 5861 (1971).
