60966-95-2

Basic information

• Product Name: 4-Pregnene-3-alpha,20-beta-diol
• Synonyms: 4-Pregnene-3-alpha,20-beta-diol
• CAS NO: 60966-95-2
• Molecular Formula: C21H34O2
• Molecular Weight: 318.49346
• Mol File: 60966-95-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Pregnene-3-alpha,20-beta-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pregnene-3-alpha,20-beta-diol(60966-95-2)
• EPA Substance Registry System: 4-Pregnene-3-alpha,20-beta-diol(60966-95-2)

Safety Data

• Hazardous Substances Data: 60966-95-2(Hazardous Substances Data)

Upstream product

• 57-83-0 Progesterone 
• 25680-68-6 3α-hydroxy-4-pregnen-20-one 
• 104528-39-4 3α-hydroxy-17α-pregn-4-en-20-one 

Relevant articles and documents

Substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase

In this study, we examined the substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase (AKR1C5), which plays a role in the termination of pregnancy by progesterone inactivation. AKR1C5 moderately reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β- ol-17-one) and tocolytic 5β-pregnane-3,20- dione. In addition to the progesterone inactivation, the formation of estrogens and metabolism of the tocolytic steroid by AKR1C5 may be related to its role in rabbit parturition. AKR1C5 also reduced various non-steroidal carbonyl compounds, including isatin, an antagonist of the C-type natriuretic peptide receptor, and 4-oxo-2-nonenal, suggesting its roles in controlling the bioactive isatin and detoxification of cytotoxic aldehydes. AKR1C5 was potently and competitively inhibited by flavonoids such as kaempferol and quercetin, suggesting that its activity is affected by ingested flavonoids.

SYNTHESIS AND CHARACTERISTICS OF ALLYLIC 4-PREGNENE-3,20-DIOLS FOUND IN GONADAL AND BREAST TISSUES

Recently several allylic steroids have been found in gonadal and breast tissues.In order to establish their presence and identity in tissues and determine the possible biological properties, a method for the synthesis of 4-pregnene-3α,20α-diol, 4-pregnene-3α,20β-diol, 4-pregnene-3β,20α-diol, and 4-pregnene-3β,20β-diol was developed using 4-pregnene-3,20-dione (progesterone) as substrate and freshly-prepared aluminum isopropoxide in isopropyl alcohol as reducing agent.The yields were about 19percent, 30percent, 13percent, and 38percent for the 3α,20α-, 3α,20β-, 3β,20α-, and 3β,20β-diols, respectively.The structures and stereochemistry of these diols were established using proton and carbon NMR spectroscopy and infrared and mass spectrometry.