145-14-2

Basic information

• Product Name: 4-PREGNEN-20-ALPHA-OL-3-ONE
• Synonyms: 20-ALPHA-DIHYDROPROGESTERONE;20-ALPHA-HYDROXY-4-PREGNEN-3-ONE;20-ALPHA-HYDROXYPROGESTERONE;4-PREGNEN-20-ALPHA-OL-3-ONE;(20s)-20-hydroxypregn-4-en-3-one;(20s)-pregn-4-en-3-on;20(s)-hydroxyprogesterone;20-alpha-hydroxydihydroprogesterone
• CAS NO: 145-14-2
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.48
• EINECS: 205-649-5
• Product Categories: Steroids;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 145-14-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 171-172 °C
• Boiling Point: 451.7°Cat760mmHg
• Flash Point: 192.4°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 4.65E-10mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 15.05±0.20(Predicted)
• CAS DataBase Reference: 4-PREGNEN-20-ALPHA-OL-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PREGNEN-20-ALPHA-OL-3-ONE(145-14-2)
• EPA Substance Registry System: 4-PREGNEN-20-ALPHA-OL-3-ONE(145-14-2)

Safety Data

• WGK Germany: 3
• RTECS: TU5559900
• Hazardous Substances Data: 145-14-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 145-14-2 differently. You can refer to the following data:
1. Δ4-Pregnen-20α-ol-3-one is the main metabolite of Progesterone (P755900). Studies shows regulation of estrogen receptor levels in breast cancer by Δ4-Pregnen-20α-ol-3-one and other progesterone metabolites.
2. Δ4-Pregnen-20α-ol-3-one (Progesterone EP Impurity B) is the main metabolite of Progesterone (P755900). Studies shows regulation of estrogen receptor levels in breast cancer by Δ4-Pregnen-20α-ol-3-one and other progesterone metabolites.

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+/m0/s1

Upstream product

• 57-83-0 progesterone 
• 6247-91-2 17β-androstane-4-ene-3-keto-17-formaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 499221-87-3 3-benzoyloxy-pregnadien-(3.5)-one-⁽²⁰⁾ 
• 57-83-0 Progesterone 
• 145-13-1 Pregnenolone 
• 1162-53-4 16-dehydropregnenolone 
• 5035-09-6 20α_F-acetoxy-pregn-4-en-3-one 
• 28507-76-8 pregn-4-ene-3,20-diol 
• 1379595-89-7 (+)-(20S)-20-O-caprinoylpregn-4-en-3-one 
• 1379595-88-6 (+)-(20S)-20-O-lauroylpregn-4-en-3-one 
• 1379595-90-0 (+)-(20S)-20-O-capryloylpregn-4-en-3-one 
• 15780-23-1 pregn-4-ene-3,20-diol 
• 58400-99-0 diosone 

Downstream Products

• 57-83-0 Progesterone 
• 15780-16-2 4-pregnene-3α,20S-diol 
• 2640-71-3 7α-methyl-4-pregnene-3,20-dione 

Relevant articles and documents

An analysis of the metabolites of progesterone produced by isolated Sertoli cells at the onset of gametogenesis

Sertoli cells isolated from 7 day old rats were maintained in culture and incubated with [14C]-progesterone for 20 h. The cells and media were extracted with ether/chloroform and the extracts chromatographed two-dimensionally on TLC and the radioactive metabolites visualized by autoradiography. Nine of the metabolites (constituting about 88% of total metabolite radioactivity) were identified by relative mobilities of the compounds and their derivatives in TLC and GC systems and by recrystallizations with authentic steroids as the following: 20α-hydroxypregn-4-en-3-one, 3α-hydroxy-5α-pregnan-20-one, 5α-pregnane-3α,20α-diol, 17β-hydroxy-5α-androstan-3-one, 5α-pregnane-3,20-dione, 17-hydroxypregn-4-ene-3,20-dione, testosterone, 5α-androstane-3α,17β-diol and androst-4-ene-3,17-dione. Over 71% of the metabolite radioactivity was due to 20α-hydroxypregn-4-en-3-one, the major metabolite. 5α-reduced pregnanes constituted about 12% and C19 steroids comprised about 2.9% of the radioactivity of the metabolites. Calculation of relative steroidogenic enzyme activities from initial reaction rates suggested the following activities in μunits/mg Sertoli cell protein: 20α-hydroxysteroid oxidoreductase (20α-HSO; 7.71), 5α-reductase (4.77), 3α-HSO (3.57), 17α-hydroxylase (0.93), 17β-HSO (0.34) and C17-C20 lyase (0.34). The relatively high rate of steroidogenic enzyme activities in the Sertoli cells of young rats may indicate that Sertoli cells are less dependent on Leydig cell steroidogenesis than has been assumed. Since nearly all the metabolites of progesterone and testosterone are now identified, it is possible to construct a picture of Sertoli cell steroidogenic activity.

Metabolism and Effects of Progesterone in the Human Endometrial Adenocarcinoma Cell Line HEC-1

Human endometrial adenocarcinoma cells (HEC-1 line) were incubated with 14C-progesterone.Four major labeled metabolites, 3β-hydroxy 5α-pregnan-20-one, 5α-pregnane-3β,20α-diol, 20α-hydroxy-4-pregnen-3-one and 5α-pregnane-3,20-dione were separated by thin layer chromatography, further purified by high pressure liquid chromatography, and finally identified by addition of carriers and crystallization to constant specific activity.Among these metabolites, 5α-pregnane-3β,20α-diol seems characteristic of this cell line since its formation from labeled progesterone was not detected in normal endometrium or in 2 specimens of endometrial adenocarcinoma.The growth of HEC cells was unaffected by either progesterone or medroxyprogesterone acetate, a slowly metabolized progestin, at about 10-6 M levels but was inhibited by about 10-5 M concentrations of these compounds.

Structure and bioassay of triterpenoids and steroids isolated from sinocalamus affinis

Five triterpenoids with a new 25-norfern carbon skeleton (1-5), a lupane triterpenoid (6), and four 20-hydroxyprogesterone acyl esters (7-10), together with 23 known compounds, were isolated from the stem (with skin removed) of Sinocalamus af f inis. The absolute configuration of compound 1 was confirmed by single-crystal X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1-5 exhibited inhibitory activity against protein tyrosine phosphatase 1B.

PROGESTERONE-CATIONIC LIPID HYBRID AS ANTICANCER AGENT AND THE PROCESS OF SYNTHESIS THEREOF

The present invention relates to the development of the cationic progesterone compounds of formula 6 as a novel anti-tumor agent. The present invention provides a method for the preparation of novel series of progesterone derivatives of formula 6. The invention also provides information related to highly selective anti-cancer activities of these compounds in wide range of cancer cell irrespective of their progesterone receptor status. Thus, the presently disclosed cationic progesterone compounds offer a viable option as anti-cancer therapeutics.

STEROID ANALOGUES FOR NEUROPROTECTION

Provided are steroid analogues functionalized with polar substituents at the C3 and/or C20 positions of the steroid ring system that exhibit improved water solubility. Also provided are pharmaceutical compositions comprising the steroid analogues and methods using the novel steroid analogues for the treatment and prevention of neurodegeneration in a patient following injury to the central nervous system.