L5768
Lanosterol
≥93%, powder
Synonym(s):
3β-Hydroxy-8,24-lanostadiene, 8,24-Lanostadien-3β-ol
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About This Item
Empirical Formula (Hill Notation):
C30H50O
CAS Number:
Molecular Weight:
426.72
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
EC Number:
201-214-9
MDL number:
Quality Level
assay
≥93%
form
powder
color
white to off-white
storage temp.
−20°C
SMILES string
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC3)[C@H](C)CC\C=C(/C)C
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
InChI key
CAHGCLMLTWQZNJ-BQNIITSRSA-N
General description
Lanosterol, an amphipathic molecule, that is produced by lanosterol synthase (LSS). It is enriched in the lens.
Application
Lanosterol has been used:
- as a standard in HPLC for the quantification in testis samples
- in S-adenosyl-L-methionine:Δ24-sterol-C-methyltransferase (SMT) assay
- to treat wild-type cells growing in rich medium to know its effects on Sre1 protein
Biochem/physiol Actions
Cholesterol precursor sterol.
Lanosterol serves as an endogenous selective modulator of macrophage immunity.
Lanosterol serves as an endogenous selective modulator of macrophage immunity.
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Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Lanosterol reverses protein aggregation in cataracts
Zhao L, et al.
Nature, 523(7562), 607-607 (2015)
Identification and Characterization of an S-Adenosyl-L-methionine:-Sterol-C-methyltransferase cDNA from Soybean
Shi J, et al.
The Journal of Biological Chemistry, 271(16), 9384-9389 (1996)
Lorena Fernández-Cabezón et al.
Frontiers in microbiology, 9, 958-958 (2018-06-06)
Nowadays steroid manufacturing occupies a prominent place in the pharmaceutical industry with an annual global market over $10 billion. The synthesis of steroidal active pharmaceutical ingredients (APIs) such as sex hormones (estrogens, androgens, and progestogens) and corticosteroids is currently performed