All Photos(2)

700059P

Avanti

27-hydroxycholesterol-d6

25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol, powder

Synonym(s):
25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol; 27-hydroxycholest-5-en-3-ol(d6); 111011
Empirical Formula (Hill Notation):
C27H40D6O2
CAS Number:
Molecular Weight:
408.69
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700059P-1mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCC[C@@]([2H])(C([2H])([2H])[2H])C(O)([2H])[2H]

General description

27-hydroxycholesterol (27-HC) is synthesized from cholesterol by the action of sterol 27-hydroxylase in the liver. It is an abundant oxysterol in the circulation ranging from 0.15 to 0.73 μM. 27-HC serves as a substrate for bile synthesis. 27-hydroxycholesterol-d6 is a deuterated form of 27-hydroxycholesterol.

Application

27-hydroxycholesterol-d6 has been used:
  • as an internal standard in isotope dilution-mass spectrometry analysis of heart mitochondria samples
  • as an internal standard in gas chromatography-mass spectrometry (GC–MS) for plasma sterol quantification
  • as a deuterated internal standard for spiking plasma samples for liquid chromatography with tandem mass spectrometry (LC-MS-MS) analysis

Biochem/physiol Actions

27-hydroxycholesterol (27-HC) is a weak liver X receptor (LXR) agonist and a selective estrogen receptor modulator (SERM). Elevated levels of 27-HC is observed in hypercholesterolemia. 27-HC is implicated in breast cancer tumor and glioblastoma progression. 27-HC may help in treating non-alcoholic steatohepatitis. Elevated levels of 27-HC is associated with atherosclerotic lesions.

Packaging

5 mL Amber Glass Screw Cap Vial (700059P-1mg)

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificate of Analysis

Certificate of Origin

Shaneabbas Raza et al.
Cancer cell international, 17, 52-52 (2017-05-16)
For every six men, one will be diagnosed with prostate cancer (PCa) in their lifetime. Estrogen receptors (ERs) are known to play a role in prostate carcinogenesis. However, it is unclear whether the estrogenic effects are mediated by estrogen receptor...
Michihisa Umetani et al.
Cell metabolism, 20(1), 172-182 (2014-06-24)
Oxysterols are cholesterol metabolites that serve multiple functions in lipid metabolism, including as liver X receptor (LXR) ligands. 27-hydroxycholesterol (27HC) is an abundant oxysterol metabolized by CYP7B1. How 27HC impacts vascular health is unknown. We show that elevations in 27HC...
Di Li et al.
Obesity (Silver Spring, Md.), 26(4), 713-722 (2018-02-25)
Although 27-hydroxycholesterol (27-HC) has been reported as a potent regulator of lipid homeostasis, its role in hepatic lipogenesis remains obscure. The present study was designed to investigate the impact of 27-HC on sterol regulatory element-binding protein 1 (SREBP-1) and hepatic...
Erik R Nelson et al.
Science (New York, N.Y.), 342(6162), 1094-1098 (2013-11-30)
Hypercholesterolemia is a risk factor for estrogen receptor (ER)-positive breast cancers and is associated with a decreased response of tumors to endocrine therapies. Here, we show that 27-hydroxycholesterol (27HC), a primary metabolite of cholesterol and an ER and liver X...
Julien Musman et al.
Biochemical pharmacology, 142, 87-95 (2017-06-25)
A major cause of cell death during myocardial ischemia-reperfusion is mitochondrial dysfunction. We previously showed that the reperfusion of an ischemic myocardium was associated with an accumulation of cholesterol into mitochondria and a concomitant strong generation of auto-oxidized oxysterols. The...

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