700033P

Avanti

5β,6β-epoxycholestanol

cholestanol, 5β,6β-epoxy, powder

别名:
110805
Empirical Formula (Hill Notation):
C27H46O2
CAS号:
分子量:
402.65
NACRES:
NA.25
价格与库存信息目前不能提供

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (700033P-5mg)

mfr. no.

Avanti Polar Lipids, 700033P

shipped in

dry ice

storage temp.

−20°C

SMILES string

C[C@]12CC[C@H]([C@](CC[C@H](O)C3)(C)[C@]3(O4)[C@H]4C5)[C@@H]5[C@@H]1CC[C@@H]2[C@H](C)CCCC(C)C

InChI

1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1

InChI key

PRYIJAGAEJZDBO-DTLXENBRSA-N

General description

5β,6β-epoxycholestanol (5β,6β-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5α,6α-epoxycholestanol (5α,6α-EC).

Application

5β,6β-epoxycholestanol may be used as a oxy-mix component in treating human colorectal adenocarcinoma CaCo-2 cells to test its effect on toll-like receptor (TLR) expression, in the preparation of langmuir monolayers for isotherm studies, as an internal standard for gas chromatography-mass spectrometry (GC–MS) chromatograms

Biochem/physiol Actions

5β,6β-epoxycholestanol (5β,6β-EC) is associated with human carotid plaques and is not down-regulated by apolipoprotein A1 (apoA-I) protein. 5,6β-EC along with 5α,6α-epoxycholesterol and other oxysterols are reported to be associated with Alzheimer′s disease. It is catabolized by the enzyme cholesterol-5,6-epoxide hydrolase (ChEH) enzyme to 3β,5α,6β-triol. 5β,6β-EC elicits cytotoxic and inflammatory properties.

Packaging

5 mL PTFE Vial with Screw Cap (700033P-5mg)

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

A dietary mixture of oxysterols induces in vitro intestinal inflammation through TLR2/4 activation: The protective effect of cocoa bean shells
Rossin D, et al.
Antioxidants, 8(6), 151-151 (2019)
Changes in brain oxysterols at different stages of Alzheimer's disease: Their involvement in neuroinflammation
Testa G, et al.
Redox Biology, 10, 24-33 (2016)
Improvement of 5, 6alpha-epoxycholesterol, 5, 6beta-epoxycholesterol, cholestane-3beta, 5alpha, 6beta-triol and 6-oxo-cholestan-3beta, alpha-diol recovery for quantification by GC/MS
Soules R, et al.
Chemistry and Physics of Lipids, 207, 92-98 (2017)
Cholesterol Acceptors Regulate the Lipidome of Macrophage Foam Cells
Paul A, et al.
International Journal of Molecular Sciences, 20(15), 3784-3784 (2019)
Reduced condensing and ordering effects by 7-ketocholesterol and 5beta, 6beta-epoxycholesterol on DPPC monolayers
Telesford DM, et al.
Langmuir, 31(36), 9859-9869 (2015)

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