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MilliporeSigma

41719

Sigma-Aldrich

(3S)-2,3-Oxidosqualene

≥97.5% (HPLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C30H50O
Número de CAS:
Peso molecular:
426.72
Número MDL:
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
NACRES:
NA.28
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Ensayo

≥97.5% (HPLC)

Formulario

liquid

pureza óptica

enantiomeric excess: ≥90.0%

idoneidad

conforms to structure for Proton NMR spectrum

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

QYIMSPSDBYKPPY-RSKUXYSASA-N

Aplicación


  • 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).


Acciones bioquímicas o fisiológicas

(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.

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes.
Abe, I., et al.
Chemical Reviews, 93, 2189-2206 (1993)
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
Xudong Han et al.
Frontiers in oncology, 10, 1549-1549 (2020-10-20)
Glioblastoma, also known as glioblastoma multiforme (GBM), is the most malignant form of glioma and represents 81% of malignant brain and central nervous system (CNS) tumors. Like most cancers, GBM causes metabolic recombination to promote cell survival, proliferation, and invasion
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
Katherine A Mattos et al.
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

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