Lanosterol

Lanosterol

Names
IUPAC name lanosta-8,24-dien-3-ol
Identifiers
CAS Number	79-63-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16521 N
ChEMBL	ChEMBL225111 N
ChemSpider	216175 N
ECHA InfoCard	100.001.105
IUPHAR/BPS	2746
MeSH	Lanosterol
PubChem CID	246983
UNII	1J05Z83K3M N
CompTox Dashboard (EPA)	DTXSID1040744
InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1 N Key: CAHGCLMLTWQZNJ-BQNIITSRSA-N N InChI=1/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1 Key: CAHGCLMLTWQZNJ-BQNIITSRBP
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
Chemical formula	C30H50O
Molar mass	426.71 g/mol
Melting point	138 to 140 °C (280 to 284 °F; 411 to 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast plant steroids are produced via cycloartenol.

Role in biosynthesis of other steroids

Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.

Simplified version of the lanosterol synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP), and squalene shown. Some intermediates are omitted.

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

• Cycloartenol
• CYP51

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. PMID 5918046.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)