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7α-Hydroxy-4-cholesten-3-one (CAS 3862-25-7)

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Alternate Names:
(7α)-7-Hydroxycholest-4-en-3-one; 7α-Hydroxycholest-4-en-3-one
Application:
7α-Hydroxy-4-cholesten-3-one is a metabolite of cholesterol
CAS Number:
3862-25-7
Molecular Weight:
400.64
Molecular Formula:
C27H44O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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7α-Hydroxy-4-cholesten-3-one (7alpha-HC) is a naturally occurring oxysterol and a metabolic intermediate within the cholesterol biosynthesis pathway. This compound not only acts as a potent agonist of the Liver X Receptor (LXR) but is a key regulator of cholesterol metabolism. By exerting its agonistic effects on the LXR, 7alpha-HC initiates events that lead to the upregulation of genes responsible for cholesterol efflux and the concomitant downregulation of genes involved in cholesterol uptake and biosynthesis. This response results in a reduction in cholesterol levels. It exhibits anti-inflammatory and antioxidant effects.


7α-Hydroxy-4-cholesten-3-one (CAS 3862-25-7) References

  1. Significance of plasma 7alpha-hydroxy-4-cholesten-3-one and 27-hydroxycholesterol concentrations as markers for hepatic bile acid synthesis in cholesterol-fed rabbits.  |  Honda, A., et al. 2004. Metabolism. 53: 42-8. PMID: 14681840
  2. Coffee oil consumption increases plasma levels of 7alpha-hydroxy-4-cholesten-3-one in humans.  |  Boekschoten, MV., et al. 2005. J Nutr. 135: 785-9. PMID: 15795435
  3. Highly sensitive quantification of 7alpha-hydroxy-4-cholesten-3-one in human serum by LC-ESI-MS/MS.  |  Honda, A., et al. 2007. J Lipid Res. 48: 458-64. PMID: 17093295
  4. Novel LC-MS/MS method for assay of 7alpha-hydroxy-4-cholesten-3-one in human plasma. Evidence for a significant extrahepatic metabolism.  |  Lövgren-Sandblom, A., et al. 2007. J Chromatogr B Analyt Technol Biomed Life Sci. 856: 15-9. PMID: 17561450
  5. Correlation between plasma levels of 7alpha-hydroxy-4-cholesten-3-one and cholesterol 7alpha-hydroxylation rates in vivo in hyperlipidemic patients.  |  Bertolotti, M., et al. 2008. Steroids. 73: 1197-202. PMID: 18582481
  6. ESI-MS/MS quantification of 7alpha-hydroxy-4-cholesten-3-one facilitates rapid, convenient diagnostic testing for cerebrotendinous xanthomatosis.  |  DeBarber, AE., et al. 2010. Clin Chim Acta. 411: 43-8. PMID: 19808031
  7. An efficient synthesis of 7α,12α-dihydroxy-4-cholesten-3-one and its biological precursor 7α-hydroxy-4-cholesten-3-one: Key intermediates in bile acid biosynthesis.  |  Ogawa, S., et al. 2013. Steroids. 78: 927-37. PMID: 23707572
  8. Bile acid malabsorption assessed by 7 alpha-hydroxy-4-cholesten-3-one in pediatric inflammatory bowel disease: correlation to clinical and laboratory findings.  |  Gothe, F., et al. 2014. J Crohns Colitis. 8: 1072-8. PMID: 24666974
  9. Measurement of serum 7α-hydroxy-4-cholesten-3-one as a marker of bile acid malabsorption in dogs with chronic diarrhoea: a pilot study.  |  Kent, AC., et al. 2016. Vet Rec Open. 3: e000163. PMID: 27110372
  10. Comparison of simple extraction procedures in liquid chromatography-mass spectrometry based determination of serum 7α-hydroxy-4-cholesten-3-one, a surrogate marker of bile acid synthesis.  |  LeníĿek, M., et al. 2016. J Chromatogr B Analyt Technol Biomed Life Sci. 1033-1034: 317-320. PMID: 27598558
  11. LC-MS/MS quantification of 7α-hydroxy-4-cholesten-3-one (C4) in rat and monkey plasma.  |  Kang, L., et al. 2017. J Chromatogr B Analyt Technol Biomed Life Sci. 1064: 49-55. PMID: 28915417
  12. A dysregulated bile acid-gut microbiota axis contributes to obesity susceptibility.  |  Wei, M., et al. 2020. EBioMedicine. 55: 102766. PMID: 32408110
  13. Pegbelfermin selectively reduces secondary bile acid concentrations in patients with non-alcoholic steatohepatitis.  |  Luo, Y., et al. 2022. JHEP Rep. 4: 100392. PMID: 34977519
  14. Serum concentrations of 7alpha-hydroxy-4-cholesten-3-one reflect bile acid synthesis in humans.  |  Sauter, G., et al. 1996. Hepatology. 24: 123-6. PMID: 8707250

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

7α-Hydroxy-4-cholesten-3-one, 1 mg

sc-210660
1 mg
$557.00

7α-Hydroxy-4-cholesten-3-one, 5 mg

sc-210660A
5 mg
$2092.00

7α-Hydroxy-4-cholesten-3-one, 10 mg

sc-210660B
10 mg
$4086.00

7α-Hydroxy-4-cholesten-3-one, 25 mg

sc-210660C
25 mg
$6636.00

which lot number is available online for sale?

Asked by: Anonymous
Thank you for your question. Please reach out to our technical service team directly so we can provide this information to you.
Answered by: Tech Support Europe
Date published: 2020-07-09

What is the desired solvent of this compoun: water, methanol or a mix of both solvents?

Asked by: two2igm05
This compound has a solubility in chloroform of about 3 mg/mL.
Answered by: Chemical Support 4
Date published: 2017-02-25
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Rated 5 out of 5 by from MignarriMignarri, A. et al. (PubMed 26153518) used 7 -Hydroxy-4-cholesten-3-one, a metabolite of cholesterol, as a marker for cerebrotendinous xanthomatosis (CTX). -SCBT Publication Review
Date published: 2015-03-08
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7α-Hydroxy-4-cholesten-3-one is rated 5.0 out of 5 by 1.
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