Key facts
CAS number:77058-74-3,
Purity:>95%,
Form:SolidSee storage information,
Molecular weight:400.6 Da,
Molecular formula:C27H44O2,
PubChem:3247059,
Nature:Synthetic,
Solubility:Soluble in ethanol to 25 mM,
Biochemical name:24,25-Epoxy-cholesterol,
Biological description:Endogenous cholesterol metabolite. Suppresses SREBP activation in the regulation of hepatic cholesterol metabolism in vivo.,
Canonical smiles:CC(CCC1C(O1)(C)C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C,
Isomeric smiles:C[C@H](CC[C@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C,
InChi:InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1,
InChiKey:OSENKJZWYQXHBN-XVYZBDJZSA-N,
IUPAC Name:(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Product details:
We recommend immediate use of this product following dissolution.
Although reported to be soluble in DMSO our analysis shows gentle heating is required to achieve this, leading to significant decomposition. The product is soluble in ethanol, however we found extended time or gentle warming once again led to some degree of decomposition.
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions--20°C, Appropriate long-term storage conditions--20°C, Storage information-Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
Liver X receptors known as LXR alpha and LXR beta are nuclear receptors that regulate cholesterol fatty acid and glucose metabolism. They also have alternate names like NR1H3 (LXR alpha) and NR1H2 (LXR beta). LXRs function as transcription factors activated by endogenous metabolites like oxysterols. LXR alpha is highly expressed in liver adipose tissue kidney and macrophages while LXR beta shows a more ubiquitous distribution. The mass of LXR alpha is approximately 50 kDa and both play important roles in lipid homeostasis.
Biological function summary
LXR receptors regulate genes involved in lipid metabolism cholesterol efflux and inflammation. They form permissive heterodimers with Retinoid X Receptors (RXRs) to influence metabolic and inflammatory pathways. LXRs enhance the expression of transporter proteins such as ATP-binding cassette (ABC) transporters supporting cholesterol efflux and maintaining lipid balance. LXR activation leads to suppression of inflammatory gene expression in macrophages highlighting its role in immune response modulation.
Pathways
LXRs play a significant role in the reverse cholesterol transport and lipid metabolism pathways. They interact intimately with proteins like ABC transporters and the sterol regulatory element-binding protein 1c (SREBP-1c) to mediate lipid homeostasis. LXRs influence the liver and adipose tissue lipid management and their activity affects cholesterol clearance and storage. Their role intertwines with other nuclear receptors emphasizing their importance in maintaining metabolic harmony.
Dysregulation of LXR activity links to atherosclerosis and metabolic syndrome. Dysregulated LXR signaling can lead to the accumulation of cholesterol in blood vessels enhancing atherosclerosis risk. Furthermore alterations in LXR-mediated lipid metabolism contribute to metabolic syndrome impacting glucose and fatty acid balance. In a disease context LXRs connect with proteins like RXRs and SREBPs suggesting potential targets for therapeutic intervention in lipid-related disorders.
