700019P
Avanti
25-hydroxycholesterol
Avanti Polar Lipids
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All Photos(2)
Synonym(s):
110816
Empirical Formula (Hill Notation):
C27H46O2
Recommended Products
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 Polar Lipids
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)
also commonly purchased with this product
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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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
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
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
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
Anita Wnętrzak et al.
The journal of physical chemistry. B, 124(6), 1104-1114 (2020-01-24)
In this study, 25-hydroxycholesterol (25-OH), a biamphiphilic compound with a wide range of biological activities, has been investigated at the air/water interface. We were interested in how two hydroxyl groups attached at distal positions of the 25-OH molecule (namely, at
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