My watch list

Lanosterol

Lanosterol


IUPAC name	lanosta-8,24-dien-3-ol
Identifiers
CAS number	79-63-0
MeSH	Lanosterol
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
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 disclaimer and references

Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived.

Additional recommended knowledge

Correct Test Weight Handling Guide: 12 Practical Tips

Essential Laboratory Skills Guide

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.

Biosynthesis

Description	Illustration	Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene		squalene synthase
Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide)		squalene monooxygenase
2,3-oxidosqualene is converted to a protosterol cation and finally to lanosterol		lanosterol synthase
(step 2)		(step 2)

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:10.1021/ja00972a056.
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:10.1021/cr00022a009.
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:10.1002/hlca.19550380728.