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27-hydroxycholesterol

SIGMA/SML2042 - ≥98% (HPLC)

Synonym: (25R)-26-Hydroxycholesterol; (25R)-Cholest-5-ene-3b,26-diol; 25(R)-27-hydroxy Cholesterol; 27-OHC

CAS Number: 20380-11-4
Empirical Formula (Hill Notation): C27H46O2
Molecular Weight: 402.65
Linear Formula: C27H46O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML2042-5MG 5 mg
 $190.00
1/EA		 Add To Favorites
45-SML2042-25MG 25 mg
 $759.00
1/EA		 Add To Favorites

 

assay ≥98% (HPLC)
color white to beige
form powder
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
optical activity [α]/D -25 to -35°, c = 0.5 in chloroform-d
SMILES string O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CCC[C@H](CO)C)C)(CC3)C)CC=C2C1)C
solubility DMSO: 2 mg/mL, clear (warmed)
storage temp. −20°C
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.
General description: 27-hydroxycholesterol induces glutathione depletion, apoptosis, reactive oxygen species (ROS) generation and inflammation.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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