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L5768

Sigma-Aldrich

Lanosterol

≥93%, powder

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Synonym(s):
3β-Hydroxy-8,24-lanostadiene, 8,24-Lanostadien-3β-ol
Empirical Formula (Hill Notation):
C30H50O
CAS Number:
79-63-0
Molecular Weight:
426.72
EC Number:
201-214-9
MDL number:
MFCD00021108
PubChem Substance ID:
24896417
NACRES:
NA.77

Quality Level

200

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

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Lanosterol reverses protein aggregation in cataracts
Zhao L, et al.
Nature, 523(7562), 607-607 (2015)
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
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
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 modulates TLR4-mediated innate immune responses in macrophages
Araldi E, et al.
Testing, 19(13), 2743-2755 (2017)
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Articles

Cholesterol Biosynthesis

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

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