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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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Certificates of Analysis (COA)

Lot/Batch Number
0000548967
0000548967
0000443959
0000443959
0000429130

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Articles

Cholesterol Biosynthesis Regulation

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

胆固醇生物合成调节

肝脏中胆固醇的合成量由饮食中的胆固醇水平来严格调节。LDL受体调节富含脂质的低密度脂蛋白（LDL）颗粒的细胞转运。

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)
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
View All Related Papers

Global Trade Item Number

SKUGTIN
H1015-10MG04061833663769
H1015-100MG04061833076415
H1015-25MG04061833663776