Lanosterol

Lanosterol

Ball-and-stick model of lanosterol
Names
IUPAC name lanosta-8,24-dien-3-ol
Identifiers
CAS Number	79-63-0 Y
ChEBI	CHEBI:16521 N
ChEMBL	ChEMBL225111 N
ChemSpider	216175 N
IUPHAR/BPS	2746
Jmol 3D model	Interactive image
MeSH	Lanosterol
PubChem	246983
UNII	1J05Z83K3M N
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)
Vapor pressure	{{{value}}}
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 fungi steroids are derived. By contrast plant steroids are produced via cycloartenol.

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.

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.

Recent research suggests that lanosterol might be instrumental in prevention of formation of cataracts in mammals.

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)	400px	(step 2)

Clinical significance

Preliminary studies in dogs and rabbits have shown that lanosterol can prevent and even reverse cataract formation.

See also

• Cycloartenol
• CYP51