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L5768

Sigma-Aldrich

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:
79-63-0
Molecular Weight:
426.72
EC Number:
201-214-9
MDL number:
MFCD00021108
UNSPSC Code:
12352211
PubChem Substance ID:
24896417
NACRES:
NA.77

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Marja-Riitta Taskinen et al.
Journal of clinical lipidology, 14(1), 77-87 (2020-01-10)
Monoclonal antibodies to proprotein convertase subtilisin/kexin type 9 (PCSK9) significantly lower the levels of low-density lipoprotein and very-low-density lipoproteins (VLDL), but their effect on postprandial lipoprotein metabolism in dyslipidemic subjects is unclear. This study aimed to investigate the effects of
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)
Lanosterol reverses protein aggregation in cataracts
Zhao L, et al.
Nature, 523(7562), 607-607 (2015)
Ergosterol regulates sterol regulatory element binding protein (SREBP) cleavage in fission yeast
Porter J R, et al.
The Journal of Biological Chemistry, 285(52), 41051-41061 (2010)
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Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

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