17alpha,21-Dihydroxypregnenolone

Base Information

• Chemical Name: 17alpha,21-Dihydroxypregnenolone
• CAS No.: 1167-48-2
• Molecular Formula: C21H32 O4
• Molecular Weight: 348.483
• UNII: 1644H18038
• DSSTox Substance ID: DTXSID801276254
• Nikkaji Number: J2.756.013J
• Wikidata: Q27103367
• Metabolomics Workbench ID: 35421
• Mol file: 1167-48-2.mol

Synonyms:17, 21-dihydroxypregnenolone

Chemical Property of 17alpha,21-Dihydroxypregnenolone

Chemical Property:

• Vapor Pressure: 2.98E-14mmHg at 25°C
• Boiling Point: 507.8°Cat760mmHg
• Flash Point: 275°C
• PSA: 77.76000
• Density: 1.204g/cm³
• LogP: 2.60260
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 348.23005950
• Heavy Atom Count: 25
• Complexity: 613

Purity/Quality:

98%,99%, ^*data from raw suppliers

17,21-Dihydroxypregnenolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1=CCC3C2CCC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
• Uses: 17,21-Dihydroxypregnenolone is the main precursor of cortisol. 17,21-Dihydroxypregnenolone can be formed by pregnenolone through human adrenal microsomal preparations.

Technology Process of 17alpha,21-Dihydroxypregnenolone

There total 3 articles about 17alpha,21-Dihydroxypregnenolone 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:

17-Hydroxypregnenolone (387-79-1) → dehydroepiandrosterone (53-43-0) + 3β,17α,21-trihydroxypregn-5-en-20-one (1167-48-2) + C21H32O4

Guidance literature:

With zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; In aq. phosphate buffer; at 37 ℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;

DOI:10.1074/jbc.RA117.000504

Reference yield:

Pregnenolone (145-13-1) → dehydroepiandrosterone (53-43-0) + 3β,17α,21-trihydroxypregn-5-en-20-one (1167-48-2) + C21H32O4

Guidance literature:

Multi-step reaction with 2 steps

1: zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish b5 enzyme; NADPH-P₄₅₀ reductase / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction

2: zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction

With zebrafish b5 enzyme; zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; NADPH-P₄₅₀ reductase; In aq. phosphate buffer;

DOI:10.1074/jbc.RA117.000504

Reference yield:

17α-Hydroperoxy-5-pregnen-3β-ol-20-on (34069-59-5) → dehydroepiandrosterone (53-43-0) + 3β,17α,21-trihydroxypregn-5-en-20-one (1167-48-2) + C21H32O4

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish P₄₅₀ 17A₂ enzyme / aq. phosphate buffer; ethanol; dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction

2: zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction

With zebrafish P₄₅₀ 17A₁ enzyme; zebrafish P₄₅₀ 17A₂ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; In aq. phosphate buffer; ethanol; dimethyl sulfoxide;

DOI:10.1074/jbc.RA117.000504

upstream raw materials:

17α-Hydroperoxy-5-pregnen-3β-ol-20-on

Pregnenolone

17-Hydroxypregnenolone

Downstream raw materials:

3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate

6β,17α,21-trihydroxypregn-4-ene-3,20-dione

17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one

Refernces