7ALPHA-HYDROXYCHOLESTEROL-25,26,26,26,27,27,27-D7

7ALPHA-HYDROXYCHOLESTEROL-25,26,26,26,27,27,27-D7 Property

storage temp. 

-20°C

solubility 

DMF: 2 mg/ml; DMSO: 0.1 mg/ml; Ethanol: 20 mg/ml

form 

A solid

color 

White to off-white

Hazard and Precautionary Statements (GHS)

7ALPHA-HYDROXYCHOLESTEROL-25,26,26,26,27,27,27-D7 Chemical Properties,Usage,Production

Description

7α-hydroxy Cholesterol-d₇ is intended for use as an internal standard for the quantification of 7α-hydroxy cholesterol by GC- or LC-MS. 7α-hydroxy Cholesterol is an oxysterol and a precursor in the biosynthesis of the bile acids cholic acid (CA; ) and chenodeoxycholic acid (CDCA; ). It is formed via the oxidation of cholesterol by cholesterol 7α-hydroxylase/CYP7A1 in rat liver microsomes. 7α-hydroxy Cholesterol (40 μM) increases levels of the adhesion molecules ICAM-1, VCAM-1, and E-selectin in human umbilical vein endothelial cells (HUVECs). It increases secretion of chemokine (C-C motif) ligand 2 (CCL2) and matrix metalloproteinase-9 (MMP-9) in serum-deprived THP-1 cells when used at a concentration of 5 μg/ml. 7α-hydroxy Cholesterol has been found in macrophages isolated from atherosclerotic lesions in rabbits fed a high-cholesterol diet.

Uses

7α-hydroxycholesterol-d7 has been used as an internal standard for cholesterol and oxysterol measurement by gas chromatography-mass spectrometry (GC/MS).

General Description

7α-hydroxycholesterol is an oxysterol synthesized by the oxidation of the side chain of cholesterol. It is the precursor of bile acid.

References

[1] K A MITROPOULOS  S B. Cholesterol 7 -hydroxylase in rat liver microsomal preparations.[J]. Biochemical Journal, 1972, 128 1: 1-9. DOI: 10.1042/bj1280001
[2] CHIANG J Y L. Bile acid metabolism and signaling in liver disease and therapy[J]. Liver Research, 2017, 1 1: Pages 3-9. DOI: 10.1016/j.livres.2017.05.001
[3] STéPHANIE LEMAIRE. Different patterns of IL-1β secretion, adhesion molecule expression and apoptosis induction in human endothelial cells treated with 7α-, 7β-hydroxycholesterol, or 7-ketocholesterol[J]. FEBS Letters, 1998, 440 3: Pages 434-439. DOI: 10.1016/s0014-5793(98)01496-3
[4] SUN-MI KIM . 7α-Hydroxycholesterol induces inflammation by enhancing production of chemokine (C–C motif) ligand 2[J]. Biochemical and biophysical research communications, 2015, 467 4: Pages 879-884. DOI: 10.1016/j.bbrc.2015.10.050
[5] L M HULTéN. Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages.[J]. Journal of Clinical Investigation, 1996, 97 2: 461-468. DOI: 10.1172/jci118436