21-Hydroxypregn-4-ene-3,11-20-trione

Base Information

• Chemical Name: 21-Hydroxypregn-4-ene-3,11-20-trione
• CAS No.: 72-23-1
• Molecular Formula: C21H28 O4
• Molecular Weight: 344.451
• European Community (EC) Number: 200-776-2
• NSC Number: 9702
• Wikipedia: 11-Dehydrocorticosterone
• Mol file: 72-23-1.mol

Synonyms:Dehydrocorticosterone;Dehydrocortocicosterone;11-Dehydrocorticosteron;72-23-1;21-Hydroxypregn-4-ene-3,11-20-trione;21-Hydroxypregn-4-en-3,11,20-trion;delta-4-pregnen-21-ol-3,11,20-trione;SCHEMBL13026136;NSC9702;PD133480;Pregn-4-ene-3,20-trione, 21-hydroxy-;FT-0607216;C05490

Chemical Property of 21-Hydroxypregn-4-ene-3,11-20-trione

Chemical Property:

• Vapor Pressure: 1.9E-13mmHg at 25°C
• Melting Point: 183.5°C
• Refractive Index: 1.4430 (estimate)
• Boiling Point: 530°C at 760 mmHg
• PKA: 12.95±0.10(Predicted)
• Flash Point: 288.4°C
• PSA: 71.44000
• Density: 1.21g/cm³
• LogP: 2.87490
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 677

Purity/Quality:

99% ^*data from raw suppliers

11-Dehydrocorticosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4C(=O)CO)C
• Uses: 11-Dehydrocorticosterone is a precursor to corticosterone (C695700), converted by 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) which plays a role in glucocorticoid-induced insulin resistance.

Technology Process of 21-Hydroxypregn-4-ene-3,11-20-trione

There total 14 articles about 21-Hydroxypregn-4-ene-3,11-20-trione 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: 27.0%

Cortisone (53-06-5) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Guidance literature:

With trimethylsilyl iodide; In chloroform; for 3h; Ambient temperature;

DOI:10.1248/cpb.34.3722

Reference yield: 7.0%

21-(Trityloxy)pregn-4-ene-3,11,20-trione (129786-20-5) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Guidance literature:

With methanol; trimethylsilyl iodide; In acetonitrile; for 2.5h; Ambient temperature;

DOI:10.1021/jo00001a062

Reference yield: 4.0%

21-Methoxypregn-4-ene-3,11,20-trione (129786-19-2) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Guidance literature:

With methanol; trimethylsilyl iodide; In acetonitrile; for 10h; Ambient temperature;

DOI:10.1021/jo00001a062

upstream raw materials:

11-Ketoprogesterone

21-acetoxy-pregn-4-ene-3,11,20-trione

Cortisone

Pregnenolone

Downstream raw materials:

21-(Trityloxy)pregn-4-ene-3,11,20-trione

(20R)-20.21-dihydroxy-pregnene-(4)-dione-(3.11)

11-Ketoprogesterone

5α-dihydro-Kendall's A

Refernces

• 1、 Cobice, Diego F.,Logan MacKay,Goodwin, Richard J. A.,McBride, Andrew,Langridge-Smith, Patrick R.,Webster, Scott P.,Walker, Brian R.,Andrew, Ruth. "Mass spectrometry imaging for dissecting steroid intracrinology within target tissues". . p. 11576 - 11584. Retrieved 2014/01/06.
• 2、 Numazawa,Nagaoka,Kunitama. "Regiospecific deoxygenation of the dihydroxyacetone moiety at C-17 of corticoid steroids with iodotrimethylsilane.". . p. 3722 - 3726. Retrieved 2007/10/02.