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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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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)
Joanna L Sharman et al.
Nucleic acids research, 41(Database issue), D1083-D1088 (2012-10-23)
The International Union of Basic and Clinical Pharmacology (IUPHAR) database, IUPHAR-DB (http://www.iuphar-db.org) is an open access, online database providing detailed, expert-driven annotation of the primary literature on human and rodent receptors and other drug targets, together with the substances that
Lanosterol modulates TLR4-mediated innate immune responses in macrophages
Araldi E, et al.
Testing, 19(13), 2743-2755 (2017)
Ying-Chi Du et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(8-9), 788-796 (2012-04-21)
Antrodia camphorata (AC) is a native Taiwanese mushroom which is used in Asian folk medicine as a chemopreventive agent. The triterpenoid-rich fraction (FEA) was obtained from the ethanolic extract of AC and characterized by high performance liquid chromatography (HPLC). FEA
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
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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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