SML1648

24(S)-Hydroxycholesterol

≥98% (HPLC)

• Synonym(s): 24S-Hydroxycholesterol, 5-Cholesten-3β,24(S)-diol, Cerebrosterin, Cerebrosterol, Cholest-5-ene-3β,24-diol
• Empirical Formula (Hill Notation): C₂₇H₄₆O₂
• CAS Number: 474-73-7
• Molecular Weight: 402.65
• UNSPSC Code: 12352211
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -45 to -52°, c = 1 in chloroform-d
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: 3 mg/mL, clear (warmed)
• storage temp.: −20°C
• SMILES string: O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CC[C@H](O)C(C)C)C)(CC3)C)CC=C2C1)C
• InChI: 1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1
• InChI key: IOWMKBFJCNLRTC-XWXSNNQWSA-N

Description

Biochem/physiol Actions

24(S)-Hydroxycholesterol is the major brain metabolite formed from cholesterol in the brain and is important for brain cholesterol homeostasis in addition to being an an endogenous agonist of the nuclear liver X receptors (LXRs).

24(S)-Hydroxycholesterol is the major brain metabolite formed from cholesterol in the brain and is important for brain cholesterol homeostasis in addition to being an an endogenous agonist of the nuclear liver X receptors (LXRs). Impairment of brain cholesterol metabolism has been associated with several neurodegenerative diseases, including multiple sclerosis, Alzheimer′s, and Huntington diseases. The exact role role of 24(S)-Hydroxycholesterol is unclear, and it may have differing effects depending on concentration. Low concentrations can protect neuronal cells against oxidative stress, while high concentrations induce necroptosis-like neuronal cell death. 24(S)-Hydroxycholesterol has also been found to be a potent allosteric modulator of N-methyl-d-aspartate receptors, potentiating NMDAR-mediated EPSCs in rat hippocampal neurons with an EC₅₀ of 1.2 μM.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable