700017P
Avanti
25-hydroxycholesterol-3-sulfate
Avanti Polar Lipids
Synonym(s):
5-cholesten-3beta, 25-diol 3-sulfate; 25HC3S
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C27H45NaO5S
CAS Number:
Molecular Weight:
504.70
UNSPSC Code:
12352211
NACRES:
NA.25
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description
25-hydroxycholesterol-3-sulfate (sodium salt)
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 10 mg (700017P-10mg)
pkg of 1 × 5 mg (700017P-5mg)
manufacturer/tradename
Avanti Polar Lipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@@]12[C@]([C@](CC[C@H](OS(=O)([O-])=O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)(O)C.[Na+]
General description
25-hydroxycholesterol-3-sulfate (25OHC3S) is a nuclear oxysterol. It accumulates in hepatocyte nuclei upon steroidogenic acute regulatory protein (STARD1) overexpression.
Application
25-hydroxycholesterol-3-sulfate has been used to induce anti-inflammatory responses and understand its effect on lymphocyte migration. It has also been used as an oxysterol sulfate standard in mass spectroscopy and liquid chromatography methods.
Biochem/physiol Actions
25-hydroxycholesterol-3-sulfate (25OHC3S) is involved in lipid homeostasis in liver and is a lipid metabolism regulator. 25OHC3S acts on liver X receptor (LXR) and sterol regulatory element-binding protein (SREBP) and inhibits cholesterol synthesis by downregulating enzymes of the biosynthesis pathway in hepatocytes and macrophages. It also acts an agonist for peroxisome proliferator-activated receptor γ (PPAR-γ) and modulates the nuclear factor κ-light-chain-enhancer (NF-κB) based inflammatory response. 25OHC3S modulates tumor necrosis factor α (TNFα)-induced inflammatory response in hepatocytes.
Packaging
5 mL Amber Glass Screw Cap Vial (700017P-10mg)
5 mL Amber Glass Screw Cap Vial (700017P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
Certificates of Analysis (COA)
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Shunlin Ren et al.
Biochemical and biophysical research communications, 360(4), 802-808 (2007-07-13)
Recently, a novel oxysterol, 5-cholesten-3beta, 25-diol 3-sulfate (25HC3S) was identified in primary rat hepatocytes following overexpression of the cholesterol transport protein, StarD1. This oxysterol was also detected in human liver nuclei. In the present study, 25HC3S was chemically synthesized. Addition
Yongjie Ma et al.
American journal of physiology. Endocrinology and metabolism, 295(6), E1369-E1379 (2008-10-16)
The oxysterol receptor LXR is a key transcriptional regulator of lipid metabolism. LXR increases expression of SREBP-1, which in turn regulates at least 32 genes involved in lipid synthesis and transport. We recently identified 25-hydroxycholesterol-3-sulfate (25HC3S) as an important regulatory
Leyuan Xu et al.
American journal of physiology. Endocrinology and metabolism, 302(7), E788-E799 (2012-01-26)
The nuclear receptor peroxisome proliferator-activated receptors (PPARs) are important in regulating lipid metabolism and inflammatory responses in macrophages. Activation of PPARγ represses key inflammatory response gene expressions. Recently, we identified a new cholesterol metabolite, 25-hydroxycholesterol-3-sulfate (25HC3S), as a potent regulatory
Leyuan Xu et al.
Lipids, 45(9), 821-832 (2010-08-12)
Dysregulation of lipid metabolism is frequently associated with inflammatory conditions. The mechanism of this association is still not clearly defined. Recently, we identified a nuclear oxysterol, 25-hydroxycholesterol-3-sulfate (25HC3S), as an important regulatory molecule involved in lipid metabolism in hepatocytes. The
Tetsuya Sakurai et al.
Science signaling, 11(541) (2018-08-02)
Although immune responses are essential to protect the body from infection, they can also harm tissues. Certain tissues and organs, including the eye, constitute specialized microenvironments that locally inhibit immune reactivity. Dedicator of cytokinesis protein 2 (DOCK2) is a Rac-specific
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