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H1015

Sigma-Aldrich

25-Hydroxycholesterol

≥98%

Synonym(s):

5-Cholestene-3β,25-diol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
2140-46-7
Molecular Weight:
402.65
Beilstein:
3161259
MDL number:
MFCD00057815
UNSPSC Code:
41141804
eCl@ss:
39023139
PubChem Substance ID:
329815150
NACRES:
NA.77

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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25-hydroxycholesterol enhances cytokine release and toll-like receptor 3 response in airway epithelial cells
Koarai A et al
Respiratory Research, 13, doi: 10-doi: 10 (2012)
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
Joseph Longo et al.
Molecular metabolism, 25, 119-130 (2019-04-27)
The statin family of cholesterol-lowering drugs has been shown to induce tumor-specific apoptosis by inhibiting the rate-limiting enzyme of the mevalonate (MVA) pathway, HMG-CoA reductase (HMGCR). Accumulating evidence suggests that statin use may delay prostate cancer (PCa) progression in a
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)
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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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