27-Hydroxycholesterol | CAS 20380-11-4

Element: hydroxycholesterol

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C-S » Chemicals » hydroxycholesterol-PX84010

Identification

27-Hydroxycholesterol

CAS:

20380-11-4

EINECS:

Molecular Formula:

C₂₇H₄₆O₂

MDL:

MFCD00272990

SMILES:

C[C@H](CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)CO

Synonym:

(25r)-cholest-5-ene-3β,26-diol ; 27-ohc ; 5,25r-cholesten-3beta,26-diol ; 25(r)-27-hydroxy cholesterol ; 26-hydroxycholesterol (not deuterated) ; (3s,8s,9s,10r,13r,14s,17r)-17-[(2r)-7-hydroxy-6-methyl-heptan-2-yl]-10,13-d ; cholest-(25r)-5-ene-3,27-diol ; 26-hydroxycholesterol-26,26,27,27,27-d5 ; (25r)-cholest-5-en-3β,26β-diol

Description

27-Hydroxycholesterol, an oxysterol secreted from macrophages, has been shown to be capable of passing through the blood-brain barrier and entering the circulation via the brain. This compound has been shown to be a cholesterol oxidation metabolite that causes an increase in levels of GADD 153 and caspase-12 in ARPE-19 cells in vitro. 27-Hydroxycholesterol has also been reported to increase levels of Aβ peptide production, reduce mitochondrial membrane potential, and induce nuclear factor κB (NFκB) and heme-oxygenase 1 (HO-1). Overall, 27-Hydroxycholesterol displays apoptotic properties via reactive oxygen species (ROS) generation, glutathione depletion, and inflammation. 27-Hydroxycholesterol is an activator of LXR α and LXR β.