Lanosterol
From Wikipedia, the free encyclopedia
Lanosterol
IUPAC name lanosta-8,24-dien-3-ol
Identifiers
CAS number [79-63-0]
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC
[C@]2(C)C1CCC3=C2CC[C@H]
4C(C)(C)[C@@H](O)CC[C@]34C
[C@]2(C)C1CCC3=C2CC[C@H]
4C(C)(C)[C@@H](O)CC[C@]34C
Properties
Molecular formula C30H50O
Molar mass 426.70 g/mol
Melting point
138-140 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references
Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived.
[edit] Role in creation of steroids
Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-demethylation of lanosterol by CYP51 eventually yields cholesterol.
[edit] Biosynthesis
Description Illustration Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene 
squalene synthase
squalene synthase
2,3-oxidosqualene is converted to a protosterol cation and finally to lanosterol 
lanosterol synthase
lanosterol synthase(step 2) 
(step 2)
(step 2)[edit] See also
[edit] References
E. J. Corey, W. E. Russey, P. R. Ortiz de Montellano (1966). "2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene". Journal of the American Chemical Society 88 (20): 4750–4751. doi:. I. Abe, M. Rohmer, G. D. Prestwich (1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews 93 (6): 2189–2206. doi:. A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen". Helvetica Chimica Acta 38 (7): 1890–1904. doi:.
