SML2042

27-hydroxycholesterol

≥98% (HPLC)

• Synonym(s): (25R)-26-Hydroxycholesterol, (25R)-Cholest-5-ene-3b,26-diol, 25(R)-27-hydroxy Cholesterol, 27-OHC
• Empirical Formula (Hill Notation): C₂₇H₄₆O₂
• CAS Number: 20380-11-4
• Molecular Weight: 402.65
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -25 to -35°, c = 0.5 in chloroform-d
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (warmed)
• storage temp.: −20°C
• InChI: 1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChI key: FYHRJWMENCALJY-YSQMORBQSA-N

Description

General description

27-hydroxycholesterol induces glutathione depletion, apoptosis, reactive oxygen species (ROS) generation and inflammation.

Biochem/physiol Actions

27-hydroxycholesterol is a peripherally derived oxysterol that that is produced by the enzyme CYP27A1. There has beeen increasing interest in the oxysterols, especially in the brain. Impairment of brain cholesterol metabolism has been associated with several neurodegenerative diseases. 27-hydroxycholesterol crosses the blood brain barrier and have been associated with Alzheimer′s disease. It is an activator of LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM and an inhibitor of cholesterol synthesis. 27-hydroxycholesterol has also been shown to bind to estrogen receptor-α (ERα) and Erβ, acting as an endogenous selective estrogen receptor modulator (SERM). In murine models of breast cancer 27-hydroxycholesterol significantly increased tumor growth and metastasis.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable