700059P
Avanti
27-hydroxycholesterol-d6
Avanti Polar Lipids
Synonym(s):
25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol; 27-hydroxycholest-5-en-3-ol(d6); 111011
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C27H40D6O2
CAS Number:
Molecular Weight:
408.69
UNSPSC Code:
41141804
NACRES:
NA.25
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description
25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700059P-1mg)
manufacturer/tradename
Avanti Polar Lipids
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)
WGK
WGK 3
Flash Point(F)
No data available
Flash Point(C)
No data available
Certificates of Analysis (COA)
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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
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
Plasma oxysterol levels in luminal subtype breast cancer patients are associated with clinical data.
Alzbeta Kloudova-Spalenkova et al.
The Journal of steroid biochemistry and molecular biology, 197, 105566-105566 (2019-12-25)
Oxygenated metabolites of cholesterol (oxysterols) have been previously demonstrated to contribute to progression of various cancers and to modulate resistance to breast cancer endocrine therapy in vitro. We measured prognostic roles of circulating levels of seven major oxysterols in the
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
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