Cas no 13027-33-3 (5α-hydroxy-6-keto Cholesterol)

5α-hydroxy-6-keto Cholesterol is a steroidal derivative of cholesterol, characterized by hydroxylation at the 5α-position and a ketone group at the 6-position. This compound serves as a valuable intermediate in steroid biosynthesis research and metabolic studies, particularly in investigating enzymatic pathways involving cholesterol oxidation. Its structural modifications make it useful for probing sterol metabolism, enzyme specificity, and the biochemical mechanisms of steroidogenesis. The compound is synthesized under controlled conditions to ensure high purity, making it suitable for analytical applications, including LC-MS and NMR studies. Researchers utilize 5α-hydroxy-6-keto Cholesterol to explore lipid signaling pathways and oxidative transformations in biological systems.
5α-hydroxy-6-keto Cholesterol structure
5α-hydroxy-6-keto Cholesterol structure
Product Name:5α-hydroxy-6-keto Cholesterol
CAS No:13027-33-3
MF:C27H46O3
MW:418.652348995209
CID:174692
PubChem ID:159461
Update Time:2025-06-08

5α-hydroxy-6-keto Cholesterol Chemical and Physical Properties

Names and Identifiers

    • 3b,5a-Dihydroxycholestan-6-one
    • 5ALPHA-CHOLESTAN-3BETA,5ALPHA-DIOL-6-ONE
    • 5α-hydroxy-6-keto Cholesterol
    • Cholestan-6-one,3,5-dihydroxy-, (3b,5a)-
    • 5ALPHA-HYDROXY-6-KETO CHOLESTEROL
    • CHOLESTANE-6-OXO-3,5-DIOL
    • CHOLESTANE-6-OXO-3BETA,5ALPHA-DIOL
    • yakkasterone
    • YS-64
    • 3β,5-Dihydroxy-5α-cholestan-6-one
    • CHOLESTAN-3-BETA, 5-ALPHA-DIOL-6-ONE
    • Q27896404
    • 13027-33-3
    • 5
    • HY-123349
    • 3.beta.,5.alpha.-Dihydroxycholestan-6-one
    • Cholestan-6-one, 3,5-dihydroxy-, (3.beta.,5.alpha.)-
    • SR-01000946790-1
    • 3,5-DIHYDROXYCHOLESTAN-6-ONE, (3BETA,5ALPHA)-
    • UNII-YO7G6S09N3
    • BDBM50045538
    • 5.ALPHA.-HYDROXY-6-KETOCHOLESTANOL
    • Cholestan-6-one, 3,5-dihydroxy-, (3beta,5alpha)-
    • 6-Oxo-3,5-diol
    • PD020294
    • HMS3650I05
    • 5 alpha -hydroxy-6-keto Cholesterol
    • (3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
    • YS 64
    • 5??-Hydroxy-6-keto cholesterol
    • 3beta,5alpha-Dihydroxycholestan-6-one
    • DTXSID80926658
    • 3beta,5-dihydroxy-5a-cholestan-6-one
    • 5.alpha.-Cholestan-6-one, 3.beta.,5-dihydroxy-
    • J-005776
    • (3S,5R,8S,9S,10R,13R,14S,17R)-3,5-Dihydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)tetradecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one
    • 3,5-Dihydroxycholestan-6-one
    • CHEMBL1277915
    • 3,5-DIHYDROXYCHOLESTAN-6-ONE, (3.BETA.,5.ALPHA.)-
    • 5-Hydroxy-6-keto cholesterol
    • CHOLESTANE-3.BETA.,5.ALPHA.-DIOL-6-ONE
    • YO7G6S09N3
    • cholestan-6-oxo-3,5-diol
    • AKOS022180753
    • CHEBI:166811
    • A-hydroxy-6-keto Cholesterol
    • SCHEMBL2130218
    • CS-0082542
    • SR-01000946790
    • 3beta, 5alpha-dihydroxycholestan-6-one
    • cholestane-3beta,5alpha-diol-6-one
    • 5ALPHA-CHOLESTAN-6-ONE, 3BETA,5-DIHYDROXY-
    • Inchi: 1S/C27H46O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-23,28,30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,25-,26-,27+/m1/s1
    • InChI Key: SJZZRXMQSAXCFD-ZCBMJONGSA-N
    • SMILES: O[C@]12C[C@H](CC[C@]1(C)[C@H]1CC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC2=O)O

Computed Properties

  • Exact Mass: 418.34500
  • Monoisotopic Mass: 418.345
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 5
  • Complexity: 659
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 9
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 7
  • Topological Polar Surface Area: 57.5?2

Experimental Properties

  • Color/Form: Not available
  • Density: 1.061
  • Melting Point: Not available
  • Boiling Point: 528.9°Cat760mmHg
  • Flash Point: 287.7°C
  • Refractive Index: 1.53
  • PSA: 57.53000
  • LogP: 5.76250
  • Vapor Pressure: 0.0±3.2 mmHg at 25°C

5α-hydroxy-6-keto Cholesterol Security Information

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Additional information on 5α-hydroxy-6-keto Cholesterol

Recent Advances in the Study of 5α-hydroxy-6-keto Cholesterol (CAS: 13027-33-3)

5α-hydroxy-6-keto Cholesterol (CAS: 13027-33-3) is an oxysterol derivative that has garnered significant attention in recent years due to its potential roles in various biological processes and disease pathways. Oxysterols, which are oxidized derivatives of cholesterol, are known to play critical roles in cell signaling, lipid metabolism, and inflammation. This research briefing aims to provide an overview of the latest findings related to 5α-hydroxy-6-keto Cholesterol, focusing on its chemical properties, biological activities, and potential therapeutic applications.

Recent studies have highlighted the unique structural features of 5α-hydroxy-6-keto Cholesterol, which distinguish it from other oxysterols. The compound's molecular structure, characterized by a hydroxyl group at the 5α position and a keto group at the 6 position, confers specific reactivity and interaction capabilities with cellular receptors and enzymes. Researchers have employed advanced spectroscopic techniques, including NMR and mass spectrometry, to elucidate its conformation and stability under physiological conditions. These studies have provided valuable insights into the compound's behavior in biological systems.

One of the most significant findings in recent research is the role of 5α-hydroxy-6-keto Cholesterol in modulating lipid metabolism and inflammation. In vitro and in vivo studies have demonstrated that this oxysterol can influence the activity of key enzymes involved in cholesterol biosynthesis, such as HMG-CoA reductase. Additionally, it has been shown to interact with nuclear receptors like LXR (liver X receptor) and RORγt, which are implicated in immune regulation and metabolic homeostasis. These interactions suggest potential therapeutic avenues for metabolic disorders, autoimmune diseases, and even cancer.

Another area of active investigation is the involvement of 5α-hydroxy-6-keto Cholesterol in neurodegenerative diseases. Oxysterols are known to accumulate in the brain and have been linked to the pathogenesis of conditions like Alzheimer's disease and multiple sclerosis. Preliminary studies indicate that 5α-hydroxy-6-keto Cholesterol may contribute to neuroinflammation and oxidative stress, although the exact mechanisms remain under investigation. Researchers are exploring whether targeting this oxysterol could offer neuroprotective benefits.

In the context of drug development, 5α-hydroxy-6-keto Cholesterol presents both opportunities and challenges. Its ability to modulate critical metabolic and immune pathways makes it an attractive candidate for therapeutic intervention. However, its stability, bioavailability, and potential off-target effects require careful consideration. Recent advances in synthetic chemistry have enabled the production of analogs with improved pharmacokinetic properties, paving the way for preclinical studies. Collaborative efforts between academic and industrial researchers are expected to accelerate the translation of these findings into clinical applications.

In conclusion, 5α-hydroxy-6-keto Cholesterol (CAS: 13027-33-3) represents a promising area of research in the field of chemical biology and medicine. Its multifaceted roles in metabolism, inflammation, and disease pathogenesis underscore its potential as a therapeutic target. Future studies should focus on elucidating its mechanisms of action, optimizing its pharmacological properties, and exploring its efficacy in disease models. As the scientific community continues to uncover the complexities of oxysterol biology, 5α-hydroxy-6-keto Cholesterol is poised to play a pivotal role in advancing our understanding and treatment of various health conditions.

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