Pregnenoic acid

Base Information

• Chemical Name: Pregnenoic acid
• CAS No.: 2681-57-4
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• DSSTox Substance ID: DTXSID70949614
• Nikkaji Number: J39.799G
• Wikidata: Q82927535
• Mol file: 2681-57-4.mol

Synonyms:4-pregnene-3,20-dione-21-oic acid;pregnenoic acid

Chemical Property of Pregnenoic acid

Chemical Property:

• Vapor Pressure: 4.15E-11mmHg at 25°C
• Boiling Point: 494°Cat760mmHg
• Flash Point: 266.7°C
• PSA: 71.44000
• Density: 1.21g/cm³
• LogP: 3.78820
• XLogP3: 3.6
• 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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)C(=O)O)CCC4=CC(=O)CCC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)C(=O)O)CCC4=CC(=O)CC[C@]34C

Technology Process of Pregnenoic acid

There total 6 articles about Pregnenoic acid 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: 62.0%

Desoxycorticosterone (64-85-7,3562-14-9,5716-95-0,109361-92-4) → 20-Hydroxy-3-oxo-pregn-4-en-21-oic acid (2681-54-1,2681-56-3,75197-03-4,91200-16-7) + 3,20-Dioxopregn-4-en-21-oic acid (2681-57-4)

Guidance literature:

With water; triphenyltetrazolium chloride; Yield given. Multistep reaction; 1.) EtOH, 2.) 0.5 h, room temp.,(aqueous phase);

DOI:10.1055/s-1980-29195

Reference yield: 53.0%

3,20-dioxo-4-pregnen-21-al (853-27-0) → 3,20-dioxopregn-4-en-21-oic acid (2681-57-4)

Guidance literature:

With sodium hydroxide; silver(l) oxide; for 1h;

DOI:10.1016/0039-128X(83)90118-6

Reference yield: 16.0%

21-Hydroxyprogesterone (64-85-7) → 3,20-dioxopregn-4-en-21-oic acid (2681-57-4)

Guidance literature:

With lumiflavin; In ethanol; Irradiation; pH > 11; var. reag.: 3-methyllumiflavin, 8-carboxylumiflavin;

DOI:10.1016/S0040-4039(00)98908-1

upstream raw materials:

Desoxycorticosterone

21-Hydroxyprogesterone

3,20-dioxo-4-pregnen-21-al

Refernces

• 1、 Monder, Carl,Han, C. Arthur. "AN IMPROVED METHOD FOR THE CHEMICAL SYNTHESIS OF STEROIDAL 20-OXO-21-OIC ACIDS". . p. 549 - 554. Retrieved 1983.
• 2、 Smoczkiewicz, Maria A.,Jasiczak, Jan. "Organic Compounds with Reversible Red-Ox Potential as Oxidizers in Steroid Chemistry; I. Tetrazolium Salts". . p. 739 - 740. Retrieved 2007/10/02.