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H1015 Sigma-Aldrich

25-Hydroxycholesterol

≥98%

Synonym: 5-Cholestene-3β,25-diol

  • CAS Number 2140-46-7

  • Empirical Formula (Hill Notation) C27H46O2

  • Molecular Weight 402.65

  •  Beilstein/REAXYS Number 3161259

  •  MDL number MFCD00057815

  •  eCl@ss 39023139

  •  PubChem Substance ID 329815150

  •  NACRES NA.77

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Properties

Related Categories Anti-Proliferative Agents, Antitumor Agents, Bile Acid Metabolism, Biochemicals and Reagents, Cancer Research,
Quality Level   200
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

Description

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

BACSMLS Online Plate Map

BACSMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arran...
Keywords: Metabolites

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. When dietary intake of cholesterol is high, synthesis is decreased and when dietary inta...
BioFiles 2007, 2.7, 6.
Keywords: Gene expression, Transcription

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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