17alpha-Hydroxypregnenolone

Base Information

• Chemical Name: 17alpha-Hydroxypregnenolone
• CAS No.: 387-79-1
• Molecular Formula: C21H32O3
• Molecular Weight: 332.483
• European Community (EC) Number: 206-862-6
• UNII: 77ME40334S
• DSSTox Substance ID: DTXSID20894988
• Nikkaji Number: J22.718H
• Wikipedia: 17%CE%B1-Hydroxypregnenolone
• Wikidata: Q35666789
• NCI Thesaurus Code: C107138
• Pharos Ligand ID: YPDJLWSRB2Y5
• Metabolomics Workbench ID: 35393
• ChEMBL ID: CHEMBL408706
• Mol file: 387-79-1.mol

Synonyms:17 alpha Hydroxypregnenolone;17 alpha-Hydroxypregnenolone;17 Hydroxypregnenolone;17-alpha-Hydroxypregnenolone;17-Hydroxypregnenolone;17-Hydroxypregnenolone, (3alpha)-Isomer;17-Hydroxypregnenolone, (3beta,13alpha)-Isomer;17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-Isomer;17-Hydroxypregnenolone, (3beta,17alpha)-Isomer;17alpha Hydroxypregnenolone;17alpha-Hydroxypregnenolone;Hydroxypregnenolone

Chemical Property of 17alpha-Hydroxypregnenolone

Chemical Property:

• Vapor Pressure: 3.69E-11mmHg at 25°C
• Melting Point: 273℃
• Refractive Index: 1.567
• Boiling Point: 468.1 °C at 760 mmHg
• PKA: 13.02±0.70(Predicted)
• Flash Point: 251 °C
• PSA: 57.53000
• Density: 1.15g/cm³
• LogP: 3.63020
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 596

Purity/Quality:

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

17-Hydroxy Pregnenolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O
• Description: 17α-hydroxy Pregnenolone is a metabolite of pregnenolone and a precursor in the biosynthesis of dehydroepiandrosterone (DHEA; ). It is formed from pregnenolone by cytochrome P450 (CYP) isoform CYP17A1 hydroxylase activity and then converted to dehydroepiandrosterone by CYP17A1-mediated 17,20-lyase activity. Plasma levels of 17α-hydroxy pregnenolone are elevated in patients with type II 3β-hydroxysteroid dehydrogenase deficiency, a form of congenital adrenal hyperplasia.
• Uses: 17α-hydroxypregnenolone has been used as a substrate for the enzyme 3β‐hydroxysteroid dehydrogenase (3β‐HSD) expressed in COS1 cells.

Technology Process of 17alpha-Hydroxypregnenolone

There total 39 articles about 17alpha-Hydroxypregnenolone 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: 96.0%

pregn-5-ene-3β,17α-diol-20-one 17-acetate (2381-45-5) → 17-Hydroxypregnenolone (387-79-1)

Guidance literature:

With sodium hydroxide; water; for 3h; Heating;

DOI:10.1016/0039-128X(95)00170-U

Reference yield: 83.0%

3β-acetoxy-17α-hydroxy-5-pregnen-20-one (1863-39-4) → 17-Hydroxypregnenolone (387-79-1)

Guidance literature:

With potassium carbonate; In methanol; for 1h; Heating;

Reference yield: 21.0%

Pregnenolone (145-13-1) → dehydroepiandrosterone (53-43-0) + 17-Hydroxypregnenolone (387-79-1)

Guidance literature:

With potassium phosphate buffer; α-D-glucose 6-phosphate; NADP; phosphatidylcholine; Mechanism; pig 17α-hydroxylase-17,20-lyase, NADPH-cytochrome-P-450-reductase, glucose-6-phosphate dehydrogenase, pH 7.2; also in the presence of cytochrome b₅ or bovine tests microsomes; also 3β-hydroxyandrost-5-ene-17β-carbaldehyde;

DOI:10.1039/c39940001501

upstream raw materials:

Pregnenolone

16β-bromo-3β,17α-dihydroxypregn-5-ene-20-one

3β,17-dihydroxy-16β-iodo-pregn-5-en-20-one

5,6β-dichloro-3β,17-dihydroxy-5α-pregnan-20-one

Downstream raw materials:

dehydroepiandrosterone

3β,17α,21-trihydroxypregn-5-en-20-one

acetic acid

pregnenolone

Refernces

• 1、 Gardner,J.N. et al.. "-". . p. 1566 - 1570. Retrieved 1968.
• 2、 Julian,Meyer,Ryden. "". . . Retrieved 1950.
• 3、 Aubé, Jeffrey,Bart, Aaron G.,Scott, Emily E.,Vogt, Caleb D.,Yadav, Rahul. "Effects of fluorine substitution on substrate conversion by cytochromes P450 17A1 and 21A2". supporting information. p. 7664 - 7669. Retrieved 2021/09/22.
• 4、 -. "Further syntheses of cyproterone acetate". Page/Page column 16; 27; 29; 31. . Retrieved 2010/02/07.