Lanosterol (Technical Grade)

• CAT Number: R021377
• CAS Number: 79-63-0
• Molecular Formula: C30H50O
• Molecular Weight: 426.729
• Purity: ≥95%
• Synonyms: Lanosterin; Lanster; Lanosta-8,24-dien-3β-ol; Lanostadien-3β-ol; 3β-Hydroxy-lansota-8,24-dien-21-oic Acid; 3β-Hydroxylanosta-8,24-diene; 4,4,14α-Trimethylcholesta-8,24-dien-3β-ol; 5α-Lanosta-8,24-dien-3β-ol; Lanosta-8,24-dienol; NSC 60677
• Target: Endogenous Metabolite
• Storage: -20°C
• IUPAC Name: (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• 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
• InChIKey: CAHGCLMLTWQZNJ-BQNIITSRSA-N
• SMILES: CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C

Lanosterol (Cat.No:R021377) is a naturally-occurring sterol and biosynthetic precursor of several animal, fungal, and protozoan steroids, including cholesterol and ergosterol. Defects in the processing of lanosterol contribute to a wide variety of disorders, including the formation of cataracts. Similarly, certain fungicides act by blocking lanosterol processing by fungi.

Reference

1. M. Kimura et al. “Protostadienol synthase from Aspergillus fumigatus: Functional conversion intolanosterol synthase” Biochemical and Biophysical Research Communications, Vol. 391 pp. 899-902, 2010
2. K. Ohyama et al. “Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis” PNAS, Vol. 106(3) pp. 725-730, 2009
3. L. Lim et al. “Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson’s disease” Cell Death and Differentiation, Vol. 19 pp. 416-427, 2012
4. C. Sheng et al. “Three-Dimensional Model of Lanosterol 14-alpha-Demethylase from Cryptococcus neoformans: Active-Site Characterization and Insights into Azole Binding” Antimicrobial Agents and Chemotherapy, Vol. 53(8) pp. 3487-3495, 2009