LANOSTEROL

LANOSTEROL Basic information
Description Source Function Biosynthesis pathway
Product Name:LANOSTEROL
Synonyms:Lanosterol (Isocholesterol);(3-beta)-lanosta-24-dien-3-ol;(3-beta)-lanosta-8,24-dien-3-ol;lanosta-8,24-dien-3-beta-ol;Lanosta-8,24-dien-3beta-ol;Lanosta-8,24-dien-3-ol;Lanosta-8,24-dien-3-ol, (3beta)-;Lanosta-8,24-dienol
CAS:79-63-0
MF:C30H50O
MW:426.73
EINECS:201-214-9
Product Categories:Biochemistry;Hydroxysteroids;Miscellaneous Natural Products;Organics;Steroids;N-Boc-3-pyrroli
Mol File:79-63-0.mol
LANOSTEROL Structure
LANOSTEROL Chemical Properties
Melting point 137 °C
alpha D20 +62.0° (chloroform)
Boiling point 482.1°C (rough estimate)
density 0.9600 (rough estimate)
refractive index 1.4910 (estimate)
storage temp. -20°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
pka15.16±0.70(Predicted)
form powder
color white
Odorat 100.00?%. bland
Merck 5360
InChIKeyCAHGCLMLTWQZNJ-BQNIITSRSA-N
LogP10.521 (est)
CAS DataBase Reference79-63-0(CAS DataBase Reference)
Safety Information
WGK Germany 1
RTECS OE3360000
MSDS Information
ProviderLanguage
SigmaAldrich English
LANOSTEROL Usage And Synthesis
DescriptionLanosterol occurs naturally in the eyes of mammals and has been shown to dissolve cataracts by revitalizing damaged cataract-causing crystallin proteins. Lanosterol’s amphipathic nature is believed to play a large role in its ability to prevent and reverse cataract formation.
Lanosterol
SourceLanosterol is the first sterol in lipid biosynthetic pathway, which is initially converted by acetyl-CoA. The complex process of lanosterol synthesis involves several enzymes, including 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, squalene epoxidase, and lanosterol synthase (LSS). LSS is a microsomal enzyme that functions as a downstream element in the lanosterol biosynthetic pathway, catalyzing the cyclization of the linear 2,3-monoepoxysqualene to lanosterol.
FunctionA cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid (PubMed:20149798, PubMed:8619637). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase.
Biosynthesis pathwayThe lanosterol pathway refers to a segment of the cholesterol biosynthesis pathway comprising twelve enzymes, namely acetyl-CoA acetyltransferase, hydroxymethylglutaryl-CoA synthase, hydroxymethylglutaryl-CoA reductase, mevalonate kinase, phosphomevalonate kinase, diphoshomevalonate decarboxylase, isopentenyl-diphosphate delta isomerase, geranylgeranyl diphosphate synthase, farnesyl diphosphate synthase, squalene synthase, squalene monooxygenase and lanosterol synthase. The lanosterol pathway describes the stages of cholesterol biosynthesis between the conversion of substrates acetyl CoA and acetoacetyl CoA to (S)-3-hydroxy-3-methylglutaryl-CoA, through to the formation of intermediate metabolite lanosterol, the precursor of cholesterol. Metabolites of the lanosterol pathway are either directed to the synthesis of cholesterol and other sterols, or to side branches of the pathway through which they are converted to isoprenoids and other non-sterols.
DescriptionLanosterol 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.
UsesLanosterol 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

DefinitionChEBI: A tetracyclic triterpenoid that is lanosta-8,24-diene substituted by a beta-hydroxy group at the 3beta position. It is the compound from which all steroids are derived.
General DescriptionLanosterol, an amphipathic molecule, that is produced by?lanosterol?synthase (LSS). It is enriched in the lens.
Biochem/physiol ActionsCholesterol precursor sterol.Lanosterol serves as an endogenous selective modulator of macrophage immunity.
Purification MethodsIf very impure, then it should be acetylated, converted to the dibromide acetate [crystallised from EtOAc with slow cooling, m 168-170o, [] D +214o (CHCl3)], de-brominated with Zn dust to give the acetate (below) which is recrystallised from 3-4 parts of Me2CO/MeOH (4:1) and hydrolysed as for stigmasterol (below). Recrystallise it from anhydrous MeOH. Dry it in vacuo over P2O5 for 3hours at 90o. The purity is checked by proton magnetic resonance. The acetate crystallises from MeOH with m 131-133o and [ ] 25D +62o (c 1,CHCl3). [Block & Urech Biochemical Preparations 6 32 1958. van Tamelen et al. J Am Chem Soc 104 6479, 6480 1982, Beilstein 6 III 2880, 6 IV 4188.]
LANOSTEROL Preparation Products And Raw materials
1-BUTENYLCYCLOPENTANE 1,3-DIMETHYLCYCLOHEXENE 2,2,4-TRIMETHYL-3-HEXENE 1-CYCLOHEXYLCYCLOHEXENE 2,2,4,6,6-PENTAMETHYL-3-HEPTENE LANOSTEROL, [3-3H] CIS-2,5-DIMETHYL-3-HEXENE 3,5-DIMETHYL-3-HEPTENE 1,10-UNDECADIENE VINYLCYCLOPENTANE 2,3-DIMETHYL-2-OCTENE 2-(3-cyclohexenyl)ethanol VINYLCYCLOHEXANE trans-4,4-Dimethyl-2-hexene TRANS-5-DECEN-1-OL 1,9-DECADIENE 2,3-DIMETHYL-2-HEPTENE p-menth-3-ene

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