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

Irundika H K Dias et al.
Redox biology, 16, 139-145 (2018-03-04)
Oxysterols (OHC) are biologically active cholesterol metabolites circulating in plasma that may be formed enzymatically (e.g. 24S-OHC, 25-OHC and 27-OHC) or by autoxidative mechanisms (e.g. 7-ketocholesterol, 7β-OHC and 25-OHC). Oxysterols are more soluble than cholesterol and are reported to exert...
Lu Liu et al.
Oncology letters, 18(4), 3623-3629 (2019-10-04)
Glioblastoma is the most frequent primary malignant brain tumor in adults. Oxysterols are oxidation products of cholesterol generated by enzymatic reactions. 27-hydroxycholesterol (27-HC), an oxysterol, is an abundant metabolite of cholesterol. 27-HC significantly accelerates mammary cancer growth, proliferation and progression...
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...
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...

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