16alpha-Hydroxyandrostenedione

Base Information

• Chemical Name: 16alpha-Hydroxyandrostenedione
• CAS No.: 63-02-5
• Molecular Formula: C19H26 O3
• Molecular Weight: 302.40794
• UNII: JN8H7214IR
• DSSTox Substance ID: DTXSID20331500
• Nikkaji Number: J337.168I
• Wikipedia: 16%CE%B1-Hydroxyandrostenedione
• Wikidata: Q27103209
• Metabolomics Workbench ID: 35346
• ChEMBL ID: CHEMBL1908014
• Mol file: 63-02-5.mol

Synonyms:16 alpha-hydroxyandrost-4-en-3,17-dione;16-hydroxyandrost-4-en-3,17-dione;16-hydroxyandrost-4-en-3,17-dione, (16alpha)-isomer;16-hydroxyandrost-4-en-3,17-dione, (16beta)-isomer;16alpha-hydroxyandrostenedione;16alpha-OHAD

Chemical Property of 16alpha-Hydroxyandrostenedione

Chemical Property:

• Vapor Pressure: 4.95E-11mmHg at 25°C
• Boiling Point: 475.3°C at 760 mmHg
• Flash Point: 255.4°C
• PSA: 54.37000
• Density: 1.19g/cm³
• LogP: 3.05820
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 302.18819469
• Heavy Atom Count: 22
• Complexity: 577

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CC(C4=O)O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3C[C@H](C4=O)O)C
• General Description: **4-ANDROSTEN-16A-OL-3,17-DIONE (16α-Hydroxyandrostenedione)** is a steroid derivative characterized by a hydroxyl group at the 16α position and ketone groups at the 3 and 17 positions. It serves as a key intermediate in the biosynthesis of estriol during pregnancy and can be synthesized via chemical routes such as hydrazone formation or oxidation, with yields varying depending on the method. Its structural features make it a significant precursor in steroid metabolism and hormonal synthesis.

Technology Process of 16alpha-Hydroxyandrostenedione

There total 15 articles about 16alpha-Hydroxyandrostenedione 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: 89.0%

16α-bromo-4-androstene-3,17-dione (61145-69-5) → [3H]-16-alpha-Hydroxyandrostenedione (63-02-5)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1021/jo00142a004

Reference yield: 30.0%

Androstenedione (63-05-8) → [3H]-16-alpha-Hydroxyandrostenedione (63-02-5)

Guidance literature:

In ethanol; for 24h;

DOI:10.1248/cpb.40.1839

Reference yield:

→ 16α-Hydroxy-4-androsten-3,17-dion (63-02-5,5746-45-2,59685-30-2)

Guidance literature:

Aethylendithioketal 37, HgCl2/CaCO3;

upstream raw materials:

Androstenedione

16α-bromo-4-androstene-3,17-dione

16α-Hydroxy-3-ethoxy-androstadien-(3,5)-on-(17)

16α-Acetoxy-3β-formyloxy-androst-5-en-17-on

Downstream raw materials:

Androstenedione

Androst-4-en-3,16-dion

16-Keto-testosterone

Refernces

10.1016/0039-128X(78)90063-6

The research aims to develop a more efficient chemical synthesis method for 16α-hydroxylated androgens, which are crucial intermediates in the formation of estriol during pregnancy. Key chemicals used include 16α-bromoandrostenedione, which is converted to the hydrazone of 16α-hydroxyandrostenedione and then hydrolyzed to yield the desired compound. 16α-Hydroxyandrostenedione (16α-hydroxyandrost-4-ene-3,17-dione) is a steroid with a hydroxyl group at the 16α position and a ketone group at the 3 and 17 positions. The total yield of 16α-hydroxyandrostenedione from dehydroepiandrosterone is 38% via the hydrazone route, and 24% via the Jones' reagent oxidation route. 16α-Hydroxytestosterone (16α,17β-dihydroxyandrost-4-en-3-one) is a steroid with hydroxyl groups at the 16α and 17β positions and a ketone group at the 3 position. 16α-Hydroxydehydroepiandrosterone 3-sulfate (3β,16α-dihydroxyandrost-5-en-17-one 3-monosulfate) is a steroid with hydroxyl groups at the 3β and 16α positions, a ketone group at the 17 position, and a sulfate ester at the 3 position.