20998-18-9

Basic information

• Product Name: 1-hydroxydehydroepiandrosterone
• Synonyms: 1-hydroxydehydroepiandrosterone
• CAS NO: 20998-18-9
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.42382
• Mol File: 20998-18-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 471.4°Cat760mmHg
• Flash Point: 253°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 7.23E-11mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 1-hydroxydehydroepiandrosterone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-hydroxydehydroepiandrosterone(20998-18-9)
• EPA Substance Registry System: 1-hydroxydehydroepiandrosterone(20998-18-9)

Safety Data

• Hazardous Substances Data: 20998-18-9(Hazardous Substances Data)

Usage

General Description

1-Hydroxydehydroepiandrosterone, also known as 7beta-hydroxy-DHEA, is an endogenous metabolite of dehydroepiandrosterone (DHEA) - a steroid hormone produced by the adrenal glands. It functions as a biologically active intermediate in the conversion of DHEA to other hormones. 1-Hydroxydehydroepiandrosterone is believed to possess certain biological properties, including acting as an anti-glucocorticoid, inhibiting the growth of human cancer cells, and potentially having anti-aging effects. It is often used as an ingredient in dietary supplements. However, its long-term health effects are not entirely understood, and more research is needed to ascertain its safety and efficacy.

InChI:InChI=1/C19H28O3/c1-18-8-7-15-13(14(18)5-6-16(18)21)4-3-11-9-12(20)10-17(22)19(11,15)2/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13+,14+,15+,17+,18+,19+/m1/s1

Upstream product

• 7745-40-6 3β-hydroxy-17,17-ethylenedioxo-5-androstene 
• 80239-57-2 (17,17-Aethylendioxy-5-androsten-1α,3β-diol)-diacetat 
• 75678-18-1 17,17-Aethylendioxy-1α,2α-epoxy-4,6-androstadien-3-on 
• 14507-81-4 17,17-ethylenedioxyandrost-1,4,6-trien-3-one 
• 50556-47-3 17,17-ethylenedioxyandrost-5-ene-1α,3β-diol 
• 114028-19-2 1α,3α-diacetoxyandrost-5-ene-17-one 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 81089-21-6 [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one 
• 152397-54-1 (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-hydroxy-3-methylbuthyloxy)pregn-5-ene 
• 142785-61-3 1α,3β-dihydroxy-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7-diene 

Relevant articles and documents

Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone

A novel recyclable Pd/C catalyst mediated dehydrogenation of sterols is developed. The conversion of sterols to 1,4,6-trien-3-ones is best achieved with Pd/C as a catalyst (10%) in the presence of six equivalents of allyl diethyl phosphate (ADP) and excess amount of sodium carbonate in DMF under vigorous reflux conditions. This transformation gives 17,17-ethylenedioxyandrost-1,4,6- trien-3-one in better yield than that of DDQ oxidation and thus provides an improved synthesis of 1α-hydroxydehydroepiandrosterone from DHEA.

An Efficient Procedure for Preparing 1α,3β-Dihydroxy-Δ5-sterois by Reduction of 1α,2α-Epoxy-4,6-dien-3-ones with Lithium in Ammonia

A number of 1α,3β-dihydroxy-Δ5-steroids of the cholestane, (20S)-20-methylpregnane (23,24-dinorcholane), pregnane and androstane series were synthesized from common steroidal precursors.A process originally reported by Barton et aI., based on 1,4,6-trien-3-ones as intermediates, was used for the introduction of the lα-hydroxyl function.The last step of this process, consisting of lithium/ammonia reduction of 1α,2α-epoxy-4,6-dien-3-ones, was found to be crucial and therefore subjected to particular study.A reproducible procedure permitting high-yield conversion was developed. lt consists of first reducing the epoxydienone with an approximately stoichiometric amount of lithium in ammonia to give, after protonation with ammonium chloride, a 1α-hydroxy-5-en-3-one.This intermediate is then further reduced by repeated alternating treatment with ammonium chloride and an equivalent amount of lithium.