Cas no 566-35-8 (11-Epihydrocortisone)

11-Epihydrocortisone is a synthetic corticosteroid derivative with structural similarities to hydrocortisone, featuring an epimerized configuration at the C-11 position. This modification influences its biological activity, potentially altering receptor binding affinity and metabolic stability. The compound is of interest in pharmaceutical research due to its potential anti-inflammatory and immunosuppressive properties, which may offer advantages in therapeutic applications where tailored glucocorticoid activity is desired. Its precise pharmacological profile depends on the specific stereochemistry and functional group interactions, making it a subject of study for optimizing corticosteroid efficacy and minimizing off-target effects. Further investigation is required to fully characterize its clinical potential.
11-Epihydrocortisone structure
11-Epihydrocortisone structure
Product Name:11-Epihydrocortisone
CAS No:566-35-8
MF:C21H30O5
MW:362.459907054901
MDL:MFCD00200339
CID:367800
PubChem ID:229860
Update Time:2025-10-05

11-Epihydrocortisone Chemical and Physical Properties

Names and Identifiers

    • Pregn-4-ene-3,20-dione,11,17,21-trihydroxy-, (11a)-
    • 11-Epihydrocortisone
    • 11-Epicortisol
    • 4-PREGNEN-11A,17A,21-TETROL-3,20-DIONE
    • 11-Epihydrocortison
    • 17-Hydroxy-corticosteron
    • 4-PREGNEN-11ALPHA,17ALPHA,21-TETROL-3,20-DIONE
    • Cortisonalkohol
    • EPI COMPOUND ''F''
    • Hydrocortisol
    • Pregn-4-ene-11,17,21-triol-3,20-dione
    • Tetrahydrocortisol
    • 11.ALPHA.-CORTISOL
    • GW7CPD2E7K
    • 566-35-8
    • DTXSID80858945
    • NSC-23903
    • 11.ALPHA.,17,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE
    • NS00087964
    • 60103-17-5
    • PREGN-4-ENE-3,20-DIONE, 11,17,21-TRIHYDROXY-, (11.ALPHA.)-
    • Epicortisol
    • 11-alpha,17-alpha,21-Trihydroxypregn-4-ene-3,20-dione
    • 11.ALPHA.-EPICORTISOL
    • NSC23903
    • CHEBI:178075
    • 11-ISOCORTISOL
    • 11alpha,17,21-Trihydroxypregn-4-ene-3,20-dione (Epihydrocortisone)
    • UNII-GW7CPD2E7K
    • JYGXADMDTFJGBT-MKIDGPAKSA-N
    • NSC27390
    • EINECS 262-053-8
    • Pregn-4-ene-3,20-dione, 11,17,21-trihydroxy-, (11alpha)-
    • (1R,3aS,3bS,9aR,9bS,10R,11aS)-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
    • 11alpha-hydrocortisone
    • (11.ALPHA.)-11,17,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE
    • (8S,9S,10R,11R,13S,14S,17R)-11,17-Dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
    • Q63409214
    • (8S,9S,10R,11R,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
    • NSC-27390
    • (Cortisol)
    • EN300-19744553
    • 11alpha-Cortisol
    • HYDROCORTISONE IMPURITY M [EP IMPURITY]
    • EPI-HYDROCORTISONE
    • epihydrocortisone
    • 11-epi-cortisol
    • 11alpha,17,21-Trihydroxypregn-4-ene-3,20-dione
    • SCHEMBL143922
    • NSC 23903
    • U-1676
    • 11-ALPHA-HYDROCORTISONE
    • G90872
    • MDL: MFCD00200339
    • Inchi: 1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16+,18+,19-,20-,21-/m0/s1
    • InChI Key: JYGXADMDTFJGBT-MKIDGPAKSA-N
    • SMILES: O[C@]1(C(CO)=O)CC[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3[C@@H](C[C@@]21C)O)=O

Computed Properties

  • Exact Mass: 362.20900
  • Monoisotopic Mass: 362.20932405g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 2
  • Complexity: 684
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 7
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 94.8?2

Experimental Properties

  • Density: 1.2±0.1 g/cm3
  • Melting Point: 200-209°C
  • Boiling Point: 391.7±52.0 °C at 760 mmHg
  • PSA: 94.83000
  • LogP: 1.78160
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

11-Epihydrocortisone Security Information

11-Epihydrocortisone Pricemore >>

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11-Epihydrocortisone Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Ethanol ,  Water ;  3 d, 40 °C
Reference
Progesterone transformations by three species of Humicola
Zohri, A. A.; et al, Folia Microbiologica (Prague), 1999, 44(3), 277-282

11-Epihydrocortisone Raw materials

11-Epihydrocortisone Preparation Products

Additional information on 11-Epihydrocortisone

11-Epihydrocortisone (CAS No. 566-35-8): A Comprehensive Guide to Its Properties and Applications

11-Epihydrocortisone (CAS No. 566-35-8) is a steroid derivative that has garnered significant attention in the fields of biochemistry and pharmaceuticals. This compound, structurally related to cortisol, plays a crucial role in metabolic processes and has potential therapeutic applications. In this article, we delve into the chemical properties, biological significance, and emerging trends surrounding 11-Epihydrocortisone.

The molecular formula of 11-Epihydrocortisone is C21H30O5, and it belongs to the class of corticosteroids. Unlike its more well-known counterpart, cortisol, 11-Epihydrocortisone exhibits unique stereochemical properties due to the epimerization at the 11-position. This subtle structural difference can significantly influence its biological activity and metabolic pathways.

Recent studies have highlighted the potential of 11-Epihydrocortisone in modulating inflammatory responses. Researchers are particularly interested in its role as a biomarker for certain metabolic disorders. For instance, elevated levels of 11-Epihydrocortisone have been observed in patients with adrenal insufficiency, making it a valuable diagnostic tool.

One of the most frequently asked questions about 11-Epihydrocortisone is its difference from cortisol. While both compounds share a similar backbone, the epimerization at the 11-position in 11-Epihydrocortisone alters its receptor binding affinity. This makes it less potent than cortisol in activating glucocorticoid receptors but potentially useful in specific therapeutic contexts where milder effects are desired.

The synthesis of 11-Epihydrocortisone involves several steps, starting from readily available steroid precursors. Modern synthetic routes often employ enzymatic transformations to achieve high stereoselectivity at the 11-position. These methods are not only efficient but also environmentally friendly, aligning with the growing demand for sustainable chemistry practices.

In the pharmaceutical industry, 11-Epihydrocortisone is being explored for its anti-inflammatory properties. Preliminary studies suggest that it may offer a safer alternative to traditional corticosteroids, which are known for their side effects. This has led to increased interest in developing 11-Epihydrocortisone-based therapies for chronic inflammatory conditions.

Another area of research focuses on the role of 11-Epihydrocortisone in metabolic regulation. Some studies indicate that it may influence glucose metabolism and lipid homeostasis, making it a potential target for managing metabolic syndrome. These findings are particularly relevant in the context of the global rise in obesity and diabetes.

The analytical characterization of 11-Epihydrocortisone typically involves techniques such as HPLC, mass spectrometry, and NMR spectroscopy. These methods are essential for ensuring the purity and identity of the compound, especially in pharmaceutical applications where quality control is paramount.

From a commercial perspective, the demand for 11-Epihydrocortisone is expected to grow as its therapeutic potential becomes more apparent. Suppliers and manufacturers are increasingly offering high-purity grades of this compound to meet the needs of research institutions and pharmaceutical companies.

In conclusion, 11-Epihydrocortisone (CAS No. 566-35-8) is a fascinating steroid derivative with diverse applications in medicine and biochemistry. Its unique structural features and biological activities make it a subject of ongoing research, particularly in the fields of inflammation and metabolic disorders. As scientific understanding of this compound deepens, its role in therapeutic development is likely to expand, offering new opportunities for innovation in healthcare.

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