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H1015

Sigma-Aldrich

25-Hydroxycholesterol

≥98%

Synonym(s):
5-Cholestene-3β,25-diol
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
Beilstein:
3161259
MDL number:
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic (organic)

assay

≥98%

form

powder

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)(O)C

InChI

1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI key

INBGSXNNRGWLJU-ZHHJOTBYSA-N

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Application

25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.

Packaging

10, 25, 100 mg in poly bottle

Biochem/physiol Actions

25-Hydroxycholesterol is a side-chain oxysterol that reportedly triggers activation of a number of cholesterol molecules. This triggers their movement from cell membrane to the endoplasmic reticulum (ER). 25-Hydroxycholesterol affects the immune system and has a key role in the pathogenesis of atherosclerosis.
Suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). 25-Hydroxycholesterol induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases.

Preparation Note

A stock solution of 25-Hydroxycholesterol may be prepared in ethanol and dissolved in cell culture medium to give a final concentration of 1 mg/ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Brett N Olsen et al.
Biophysical journal, 100(4), 948-956 (2011-02-16)
Side-chain oxysterols are enzymatically generated oxidation products of cholesterol that serve a central role in mediating cholesterol homeostasis. Recent work has shown that side-chain oxysterols, such as 25-hydroxycholesterol (25-HC), alter membrane structure in very different ways from cholesterol, suggesting a
Ulf Diczfalusy
Biochimie, 95(3), 455-460 (2012-06-27)
The oxysterol 25-hydroxycholesterol is a widely used compound displaying an array of pharmacological actions in in vitro systems and cell based experimental systems. In spite of the frequent use of this compound over the last few decades and a large number
Alastair G Kerr et al.
The Journal of pharmacology and experimental therapeutics, 361(3), 417-428 (2017-04-01)
Hypercholesterolemia remains one of the leading risk factors for the development of cardiovascular disease. Many large double-blind studies have demonstrated that lowering low-density lipoprotein (LDL) cholesterol using a statin can reduce the risk of having a cardiovascular event by approximately
Giulia Parisio et al.
Journal of the American Chemical Society, 134(29), 12198-12208 (2012-06-29)
The transverse motion of molecules from one leaflet to the other of a lipid bilayer, or flip-flop, represents a putative mechanism for their transmembrane transport and may contribute to the asymmetric distribution of components in biomembranes. However, a clear understanding
Kenji Ohgane et al.
Chemistry & biology, 20(3), 391-402 (2013-03-26)
Niemann-Pick type C1 (NPC1) is a polytopic endosomal membrane protein required for efflux of LDL-derived cholesterol from endosomes, and mutations of this protein are associated with Niemann-Pick disease type C, a fatal neurodegenerative disease. At least one prevalent mutation (I1061T)

Articles

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. LDL receptors regulate the cellular transport of lipid rich low density lipoprotein (LDL) particles.

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