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H1015

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
NACRES:
NA.77
PubChem Substance ID:
329815150
eCl@ss:
39023139
UNSPSC Code:
41141804
MDL number:
MFCD00057815
Beilstein/REAXYS Number:
3161259
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biological source

synthetic (organic)

Quality Level

200

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

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Articles

Cholesterol Biosynthesis Regulation

Cholesterol synthesis regulation by dietary levels, LDL receptors control lipid-rich LDL particle transport in cells.