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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

Contents

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)

See also

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.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Lanosterol". A list of authors is available in Wikipedia.
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