Cortolone

Base Information

• Chemical Name: Cortolone
• CAS No.: 516-42-7
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498
• NSC Number: 59872
• UNII: 3J9D9J550A
• DSSTox Substance ID: DTXSID10904343
• Nikkaji Number: J6.310J
• Wikidata: Q27106233
• Metabolomics Workbench ID: 38254
• ChEMBL ID: CHEMBL1908042
• Mol file: 516-42-7.mol

Synonyms:cortolone;cortolone, (3alpha,5alpha,20S)-isomer;cortolone, (3alpha,5beta,20R)-isomer

Chemical Property of Cortolone

Chemical Property:

• Melting Point: 208-209°
• Boiling Point: 564.1°Cat760mmHg
• Flash Point: 309°C
• PSA: 97.99000
• Density: 1.248g/cm³
• LogP: 1.65330
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 366.24062418
• Heavy Atom Count: 26
• Complexity: 593

Purity/Quality:

98%min ^*data from raw suppliers

α-Cortolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(=O)CC4(C3CCC4(C(CO)O)O)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4([C@H](CO)O)O)C)O
• Uses: α-Cortolone is a human urinary metabolite of Cortisol ((H714615), a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.

Technology Process of Cortolone

There total 9 articles about Cortolone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3α,21-diacetoxy-17-hydroxy-5β-pregnane-11,20-dione (28439-40-9) → Cortolone (516-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; platinum / Hydrogenation.Behandlung der nach der Abtrennung von 17.20β_F-Dihydroxy-3α.21-diacetoxy-5β-pregnanon-(11) verbliebenen Anteile des Reaktionsprodukts mit Acetanhydrid und Pyridin

With acetic acid; platinum;

Reference yield:

C24H38O6 → Cortolone (516-42-7)

Guidance literature:

With hydrogenchloride; In methanol; Heating;

DOI:10.1016/S0040-4020(01)82212-2

Reference yield:

methyl 20β-acetoxy-3α-tert-butyldimethylsilyloxy-17α-hydroxy-11-oxo-5β-pregnan-21-oate (93206-77-0) → Cortolone (516-42-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 410 mg / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 250 mg / pyridine / Ambient temperature

3: 110 mg / 10percent CrO₃-pyridine complex / pyridine / 1 h / Ambient temperature

4: 60 mg / 50percent H₂SO₄ / acetone / 0.17 h / Ambient temperature

5: saponification

With lithium aluminium tetrahydride; chromium trioxide-pyridine complex; sulfuric acid; In pyridine; diethyl ether; acetone;

DOI:10.1248/cpb.32.4023

upstream raw materials:

3α,20α_F,21-triacetoxy-17-hydroxy-5β-pregnan-11-one

20α-cortolone 20,21-diacetate

methyl 20β-acetoxy-3α-tert-butyldimethylsilyloxy-17α-hydroxy-11-oxo-5β-pregnan-21-oate

20α-cortol 3-tert-butyldimethylsilyl ether

Refernces