1-hydroxydehydroepiandrosterone

Base Information

• Chemical Name: 1-hydroxydehydroepiandrosterone
• CAS No.: 20998-18-9
• Molecular Formula: C19H28 O3
• Molecular Weight: 304.43
• Mol file: 20998-18-9.mol

Synonyms:Androst-5-en-17-one,1a,3b-dihydroxy- (8CI); 1a-Hydroxydehydroepiandrosterone

Chemical Property of 1-hydroxydehydroepiandrosterone

Chemical Property:

• Vapor Pressure: 7.23E-11mmHg at 25°C
• Boiling Point: 471.4°Cat760mmHg
• Flash Point: 253°C
• PSA: 57.53000
• Density: 1.19g/cm³
• LogP: 2.85000

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-hydroxydehydroepiandrosterone

There total 11 articles about 1-hydroxydehydroepiandrosterone 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: 99.0%

17,17-ethylenedioxyandrost-5-ene-1α,3β-diol (50556-47-3) → 1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 40 ℃; for 10h; Inert atmosphere;

DOI:10.1016/j.steroids.2012.08.018

Reference yield: 87.5%

1α,3α-diacetoxyandrost-5-ene-17-one (114028-19-2) → 1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9)

Guidance literature:

With methanol; potassium hydroxide; In methanol; for 3h; Heating;

DOI:10.1002/hlca.19810640621

Reference yield:

17,17-ethylenedioxyandrost-1,4,6-trien-3-one (14507-81-4) → 1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / 10percent NaOH/MeOH, 30percent aq. H₂O₂ / methanol / 4.5 h / Ambient temperature

2: 1.) Li; 2.) Li/NH₄Cl / 1.) NH₃(l), Et₂O, THF, -33 deg C, 15 min; 2.) NH₃(l), Et₂O, THF, -33 deg C, 30 min

3: 71 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 48 h / Ambient temperature

4: 87 percent / 5percent HCl / methanol / 1 h / 50 °C

5: 87.5 percent / 10percent KOH/MeOH / methanol / 3 h / Heating

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium hydroxide; dihydrogen peroxide; lithium; ammonium chloride; In pyridine; methanol;

DOI:10.1002/hlca.19810640621

upstream raw materials:

dehydroepiandrosterone

1α,3α-diacetoxyandrost-5-ene-17-one

17,17-ethylenedioxyandrost-5-ene-1α,3β-diol

17,17-ethylenedioxyandrost-1,4,6-trien-3-one

Downstream raw materials:

17-methyl-androst-5-ene-1α,3β,17β-triol

1α,3β-dihydroxy-5α-androstan-17-one

Androsta-1,4-diene-3,17-dione

androst-5-ene-1α,3β,17β-triol

Refernces

• 1、 Kubodera,Miyamoto,Ochi,Matsunaga. "Synthetic studies of vitamin D analogues. VII. Synthesis of 20-oxa-21-norvitamin D3 analogues". . p. 2286 - 2289. Retrieved 2007/10/02.
• 2、 Kaneko,Sugimoto,Yamada,Ishikawa,Sasaki. "Hydroboration of steroidal 1,5 dien 3β ols: a general procedure for the introduction of a hydroxyl group at 1α position of the 3 oxygenated steroids". . p. 2101 - 2107. Retrieved 2007/10/10.