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41719

Sigma-Aldrich

(3S)-2,3-Oxidosqualene

≥97.5% (HPLC)

Synonyme(s) :

(S)-2,3-Epoxy-2,3-dihydrosqualene, (S)-22,23-Epoxy-2,6,10,15,19,23-hexamethyl-2,6,10,14,18-tetracosapentaene, (S)-Squalene 2,3-epoxide, (S)-Squalene 2,3-oxide

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About This Item

Formule empirique (notation de Hill):
C30H50O
Numéro CAS:
54910-48-4
Poids moléculaire :
426.72
Numéro MDL:
MFCD28100799
Code UNSPSC :
12352204
ID de substance PubChem :
329756144
Nomenclature NACRES :
NA.28

Pureté

≥97.5% (HPLC)

Forme

liquid

Pureté optique

enantiomeric excess: ≥90.0%

Adéquation

conforms to structure for Proton NMR spectrum

Température de stockage

−20°C

Chaîne SMILES 

CC1(C)O[C@H]1CC/C(C)=C/CC/C(C)=C/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C

InChI

1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1

Clé InChI

QYIMSPSDBYKPPY-RSKUXYSASA-N

Application


  • Schizophrenic behavior of 2,3-Oxidosqualene Sterol Cyclase from pig liver towards 2,3-oxidosqualene analogues. Alain Krief and colleagues discuss the variable catalytic behaviors of oxidosqualene cyclase when interacting with different oxidosqualene analogues, suggesting implications for sterol production efficiency and specificity (Krief et al., 2021).


Actions biochimiques/physiologiques

(S)-2,3-Epoxysqualene is an intermediate of many metabolic pathways such as the steroid biosynthesis, sesquiterpenoid and triterpenoid biosynthesis, biosynthesis of plant secondary metabolites, biosynthesis of terpenoids and steroids, biosynthesis of plant hormones, biosynthesis of secondary metabolites, and biosynthesis of antibiotics.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Z Shi et al.
Proceedings of the National Academy of Sciences of the United States of America, 91(15), 7370-7374 (1994-07-19)
The ERG7 gene encoding oxidosqualene-lanosterol cyclase [(S)-2,3-epoxysqualene mutase (cyclizing, lanosterol forming), EC 5.4.99.7] from Saccharomyces cerevisiae has been cloned by genetic complementation of a cyclase-deficient erg7 strain. The DNA sequence of this gene has been determined and found to contain
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Cellular microbiology, 16(6), 797-815 (2014-02-21)
We recently showed that Mycobacterium leprae (ML) is able to induce lipid droplet formation in infected macrophages. We herein confirm that cholesterol (Cho) is one of the host lipid molecules that accumulate in ML-infected macrophages and investigate the effects of
Deletion of the Gly600 residue of Alicyclobacillus acidocaldarius squalene cyclase alters the substrate specificity into that of the eukaryotic-type cyclase specific to (3S)-2,3-oxidosqualene.
Tsutomu Hoshino et al.
Angewandte Chemie (International ed. in English), 43(48), 6700-6703 (2004-12-14)
Dorianne A Castillo et al.
Journal of the American Chemical Society, 135(15), 5885-5894 (2013-04-11)
Plants allocate an estimated 15-25% of their proteome to specialized metabolic pathways that remain largely uncharacterized. Here, we describe a genome mining strategy for exploring such unknown pathways and demonstrate this approach for triterpenoids by functionally characterizing three cytochrome P450s
Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes.
Abe, I., et al.
Chemical Reviews, 93, 2189-2206 (1993)
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