700053P

Avanti

25-hydroxycholesterol-d6

cholest-5-ene-3β,25-diol-d6, powder

Synonym(s):
26,26,26,27,27,27-hexadeuterocholest-5-ene-3β,25-diol; 25-hydroxycholest-5-en-3-ol(d6)
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 (700053P-1mg)

manufacturer/tradename

Avanti Polar Lipids 700053P

shipped in

dry ice

storage temp.

−20°C

General description

25-hydroxycholesterol (25HC) is synthesized from cholesterol in the presence of oxygen and enzyme cholesterol 25-hydroxylase and the conversion is dependent on nicotinamide adenine dinucleotide phosphate (NADPH) during toll-like receptor activation. 25HC is catabolized to 7α-hydroxylated sterol. 25-hydroxycholesterol-d6 is the deuterated form of 25-hydroxycholesterol.

Application

25-hydroxycholesterol-d6 has been used as an internal standard:
  • in the quantification of 25-OHC in jejunum samples by liquid chromatography with tandem mass spectrometry (LC-MS-MS)
  • in plasma samples by liquid chromatography-mass spectrometry analysis
  • for calibration curve generation for plasma oxysterol quantification

Biochem/physiol Actions

25-hydroxycholesterol is a liver X receptor ligand. This bioactive lipid regulates immune response and macrophages production from monocytes. 25-HC serves as an antiviral effector and may have therapeutic potential. It reduces cholesterol biosynthesis by inactivating sterol regulatory element binding protein and inhibits HMG-CoA reductase (HMGCR). 25-HC may play a protective role in myocardial ischemia-reperfusion injury by inhibiting apoptosis and regulating mitogen-activated protein kinase (MAPK) pathway.

Packaging

5 mL Amber Glass Screw Cap Vial (700053P-1mg)

storage_class_code

13 - Non Combustible Solids

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificate of Analysis

Certificate of Origin

Elizabeth S Gold et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(29), 10666-10671 (2014-07-06)
Cross-talk between sterol regulatory pathways and inflammatory pathways has been demonstrated to significantly impact the development of both atherosclerosis and infectious disease. The oxysterol 25-hydroxycholesterol (25HC) plays multiple roles in lipid biosynthesis and immunity. We recently used a systems biology...
Editorial: 25-Hydroxycholesterol: a new life in immunology.
Jeffrey G McDonald et al.
Journal of leukocyte biology, 88(6), 1071-1072 (2010-12-03)
Stian Solheim et al.
The Journal of steroid biochemistry and molecular biology, 192, 105309-105309 (2019-02-20)
Oxysterols can contribute to proliferation of breast cancer through activation of the Estrogen Receptors, and to metastasis through activation of the Liver X Receptors. Endogenous levels of both esterified and free sidechain-hydroxylated oxysterols were examined in breast cancer tumours from...
Ying Liu et al.
Journal of lipid research, 59(3), 439-451 (2018-01-05)
Cholesterol 25-hydroxylase (CH25H) catalyzes the production of 25-hydroxycholesterol (25-HC), an oxysterol that can play an important role in different biological processes. However, the mechanisms regulating CH25H expression have not been fully elucidated. In this study, we determined that CH25H is...
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...

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