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700019P

Avanti

25-hydroxycholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

110816

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
2140-46-7
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.25

description

cholest-5-ene-3β,25-diol

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (700019P-10mg)
pkg of 1 × 100 mg (700019P-100mg)
pkg of 1 × 5 mg (700019P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°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

General description

25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production.

Application


  • Inhibition Mechanism of SARS-CoV-2 Infection by a Cholesterol Derivative, Nat-20(S)-yne: This study explores how a cholesterol derivative, related to 25-hydroxycholesterol, inhibits SARS-CoV-2 infection, highlighting its potential in therapeutic applications for viral infections (Murae et al., 2024).

  • 25-hydroxycholesterol promotes proliferation and metastasis of lung adenocarcinoma cells by regulating ERβ/TNFRSF17 axis: Demonstrates the role of 25-hydroxycholesterol in cancer biology, particularly in enhancing tumor growth and metastasis, providing insights for targeted cancer therapies (He et al., 2024).

  • 25-Hydroxycholesterol regulates lysosome AMP kinase activation and metabolic reprogramming to educate immunosuppressive macrophages: Investigates how 25-hydroxycholesterol influences immune cells, particularly in the context of immune suppression and potential anti-inflammatory therapies (Xiao et al., 2024).

Packaging

5 mL Amber Glass Screw Cap Vial (700019P-100mg)
5 mL Amber Glass Screw Cap Vial (700019P-10mg)
5 mL Amber Glass Screw Cap Vial (700019P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

700019P-10MG:
700019P-VAR:
700019P-BULK:
700019P-100MG:
700019P-5MG:

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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Jason G Cyster et al.
Nature reviews. Immunology, 14(11), 731-743 (2014-10-18)
Cholesterol and components of the cholesterol biosynthetic pathway have fundamental roles in all mammalian cells. Hydroxylated forms of cholesterol are now emerging as important regulators of immune function. This involves effects on the cholesterol biosynthetic pathway and cell membrane properties
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
Leah N Makley et al.
Science (New York, N.Y.), 350(6261), 674-677 (2015-11-07)
Cataracts reduce vision in 50% of individuals over 70 years of age and are a common form of blindness worldwide. Cataracts are caused when damage to the major lens crystallin proteins causes their misfolding and aggregation into insoluble amyloids. Using
Andrea Reboldi et al.
Science (New York, N.Y.), 345(6197), 679-684 (2014-08-12)
Type I interferon (IFN) protects against viruses, yet it also has a poorly understood suppressive influence on inflammation. Here, we report that activated mouse macrophages lacking the IFN-stimulated gene cholesterol 25-hydroxylase (Ch25h) and that are unable to produce the oxysterol
Samantha A Hutchinson et al.
Nutrients, 11(11) (2019-11-07)
Interventions that alter cholesterol have differential impacts on hormone receptor positive- and negative-breast cancer risk and prognosis. This implies differential regulation or response to cholesterol within different breast cancer subtypes. We evaluated differences in side-chain hydroxycholesterol and liver X nuclear
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