145-15-3

Basic information

• Product Name: 4-PREGNEN-20-BETA-OL-3-ONE
• Synonyms: 20-BETA-HYDROXYPROGESTERONE;20-BETA-HYDROXY-4-PREGNEN-3-ONE;4-PREGNEN-20-BETA-OL-3-ONE;(20r)-20-hydroxypregn-4-en-3-one;(20-r)-pregn-4-en-3-on;20-beta-dihydroprogesterone;20-beta-hydroxydihydroprogesterone;20-beta-hydroxy-pregn-4-en-3-on
• CAS NO: 145-15-3
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.48
• EINECS: 205-650-0
• Mol File: 145-15-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 158-160 °C
• Boiling Point: 451.7 °C at 760 mmHg
• Flash Point: 192.4 °C
• Appearance: /
• Density: 1.09 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Dichloromethane (Slightly), Meth
• PKA: 15.05±0.20(Predicted)
• CAS DataBase Reference: 4-PREGNEN-20-BETA-OL-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PREGNEN-20-BETA-OL-3-ONE(145-15-3)
• EPA Substance Registry System: 4-PREGNEN-20-BETA-OL-3-ONE(145-15-3)

Safety Data

• Hazardous Substances Data: 145-15-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 145-15-3 differently. You can refer to the following data:
1. 20β-Dihydroprogesterone is an impurity of Progesterone (P755900), a steroid hormone secreted by the corpus luteum. Progesterone have various significant physiological roles, such as inducing the matur ation and secretory activities of the uterine endothelium and the suppression of ovulation. Progesterone is also implicated in the etiology of breast cancer.
2. 20β-Dihydroprogesterone (Progesterone EP Impurity C) is an impurity of Progesterone (P755900), a steroid hormone secreted by the corpus luteum. Progesterone have various significant physiological roles, such as inducing the maturation and secretory activities of the uterine endothelium and the suppression of ovulation. Progesterone is also implicated in the etiology of breast cancer.

InChI:InChI=1/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1

Upstream product

• 28507-76-8 pregn-4-ene-3,20-diol 
• 57-83-0 Progesterone 
• 15780-23-1 pregn-4-ene-3,20-diol 
• 98774-50-6 3-benzylthiopregna-3,5-dien-20-one 
• 57-88-5 cholesterol 
• 145-13-1 Pregnenolone 
• 805-33-4 3-pyrrolidino-pregna-3,5-dien-20-one 
• 57-83-0 progesterone 

Downstream Products

• 57-83-0 Progesterone 
• 80-89-7 pregnadiol 
• 50909-89-2 Progesteron-3-(O-carboxymethyl)-oxim 
• 1159-72-4 20β_F-hydroxy-A-nor-pregn-3-en-2-one 
• 5062-62-4 20β_F-acetoxy-pregn-4-en-3-one 
• 2640-71-3 7α-methyl-4-pregnene-3,20-dione 

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.

Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury

Preclinical and clinical research findings have revealed that the hormone progesterone, when acutely administered, can dramatically reduce cerebral edema, inflammation, tissue necrosis, and programmed cell death following traumatic brain injury (TBI). The poor aqueous solubility of progesterone, however, limits its potential use as a therapeutic. Several chemically novel analogues of progesterone and its natural metabolite allopregnanolone have been synthesized and screened using both in vitro and whole animal models of TBI. The new derivatives demonstrated greatly improved solubility and select compounds have shown equivalent effectiveness to progesterone in reducing cerebral edema after TBI. 2009 American Chemical Society.