516-58-5

Basic information

• Product Name: allopregnan-20beta-ol-3-one
• Synonyms: allopregnan-20beta-ol-3-one;(20R)-20-Hydroxy-5α-pregnan-3-one;5α-Pregnan-20α-ol-3-one;Allopregnan-20β-ol-3-one;Allopregnan-20b-ol-3-one;5alpha-pregan-20beta-ol-3-one
• CAS NO: 516-58-5
• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.49
• Mol File: 516-58-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 185°
• Boiling Point: 433.8±18.0 °C(Predicted)
• Appearance: /
• Density: 1.048±0.06 g/cm3(Predicted)
• PKA: 15.05±0.20(Predicted)
• CAS DataBase Reference: allopregnan-20beta-ol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: allopregnan-20beta-ol-3-one(516-58-5)
• EPA Substance Registry System: allopregnan-20beta-ol-3-one(516-58-5)

Safety Data

• Hazardous Substances Data: 516-58-5(Hazardous Substances Data)

Usage

Uses

5α-Pregnan-20β-ol-3-one is a metabolite of Progesterone (P755900), a steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

Definition

ChEBI: A 3-oxo steroid that is 5alpha-pregane-3-one carrying an additional hydroxy substituent at the 20beta-position.

Upstream product

• 432552-68-6 (20R)-3-oxo-5α-pregnan-20-yl benzoate 
• 5888-07-3 20β_F-acetoxy-5α-pregnan-3-one 
• 566-65-4 dihydroprogesterone 
• 516-52-9 isofuntumidine 
• 95564-96-8 3.3-Dimethoxy-20β-hydroxy-5α-pregnan 
• 516-53-0 (20R)-5α-Pregnandiol-(3β.20) 
• 566-58-5 5α-pregnane-3α,20α-diol 
• 6003-19-6 acetic acid-(3β-hydroxy-5α-pregnanyl-(20β_F)-ester) 
• 6057-94-9 3β,20β_F-diacetoxy-5α-pregnane 
• 474-45-3 (3α,5α)-3-aminopregnan-20-one 
• 18003-79-7 3,3-dimethoxy-5α-pregnan-20-one 
• 1011735-38-8 20(R)-formyloxy-5αH-pregnan-3-one 

Downstream Products

• 846-46-8 androstanedione 
• 432552-70-0 (20R)-3,3-difluoro-5α-pregnan-20-yl benzoate 
• 566-65-4 dihydroprogesterone 

Relevant articles and documents

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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.