15780-16-2

Basic information

• Product Name: 4-Pregnene-3-alpha,20-alpha-diol
• Synonyms: 4-Pregnene-3-alpha,20-alpha-diol
• CAS NO: 15780-16-2
• Molecular Formula: C21H34O2
• Molecular Weight: 318.49346
• Mol File: 15780-16-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 449.5°C at 760 mmHg
• Flash Point: 199.5°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 5.72E-10mmHg at 25°C
• Refractive Index: 1.557
• PKA: 14.40±0.70(Predicted)
• CAS DataBase Reference: 4-Pregnene-3-alpha,20-alpha-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pregnene-3-alpha,20-alpha-diol(15780-16-2)
• EPA Substance Registry System: 4-Pregnene-3-alpha,20-alpha-diol(15780-16-2)

Safety Data

• Hazardous Substances Data: 15780-16-2(Hazardous Substances Data)

Usage

Description

4-Pregnene-3-alpha,20-alpha-diol, also known as (3α,20S)-Dihydroxy Progesterone, is a metabolite of Progesterone, a steroid hormone produced by the corpus luteum. It plays a crucial role in the reproductive system and has been linked to the etiology of breast cancer.

Uses

Used in Pharmaceutical Industry:
4-Pregnene-3-alpha,20-alpha-diol is used as a pharmaceutical compound for its ability to induce maturation and secretory activity of the uterine endothelium. It is also used for its suppressive effects on ovulation.
Used in Research and Development:
In the field of research and development, 4-Pregnene-3-alpha,20-alpha-diol is used as a key compound in studying the etiology of breast cancer and the role of Progesterone in the development of the disease.
Used in Hormone Therapy:
4-Pregnene-3-alpha,20-alpha-diol may be used as a component in hormone therapy, particularly for conditions related to the reproductive system, due to its effects on the uterine endothelium and ovulation.
Used in Drug Delivery Systems:
Similar to Gallotannin, 4-Pregnene-3-alpha,20-alpha-diol could potentially be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes in various applications, including hormone-related conditions and cancer treatment.

InChI:InChI=1/C21H34O2/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/h12-13,15-19,22-23H,4-11H2,1-3H3/t13-,15+,16-,17+,18-,19-,20-,21+/m0/s1

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 
• 145-14-2 (20S)-20-hydroxypregn-4-en-3-one 

Relevant articles and documents

Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds

3-Hydroxyhexobarbital dehydrogenase (3HBD) catalyzes NAD(P) +-linked oxidation of 3-hydroxyhexobarbital into 3-oxohexobarbital. The enzyme has been thought to act as a dehydrogenase for xenobiotic alcohols and some hydroxysteroids, but its physiological function remains unknown. We have purified rabbit 3HBD, isolated its cDNA, and examined its specificity for coenzymes and substrates, reaction directionality and tissue distribution. 3HBD is a member (AKR1C29) of the aldo-keto reductase (AKR) superfamily, and exhibited high preference for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D2, which were converted to 3α-, 17β- and 20α-hydroxysteroids and 9α,11β- prostaglandin F2, respectively. Especially, α-diketones (such as isatin and diacetyl) and lipid peroxidation-derived aldehydes (such as 4-oxo- and 4-hydroxy-2-nonenals) were excellent substrates showing low Km values (0.1-5.9 μM). In 3HBD-overexpressed cells, 3-oxohexobarbital and 5β-androstan-3α-ol-17-one were metabolized into 3-hydroxyhexobarbital and 5β-androstane-3α,17β-diol, respectively, but the reverse reactions did not proceed. The overexpression of the enzyme in the cells decreased the cytotoxicity of 4-oxo-2-nonenal. The mRNA for 3HBD was ubiquitously expressed in rabbit tissues. The results suggest that 3HBD is an NADPH-preferring reductase, and plays roles in the metabolisms of steroids, prostaglandin D2, carbohydrates and xenobiotics, as well as a defense system, protecting against reactive carbonyl compounds.

Synthesis of the allylic gonadal steroids, 3α-hydroxy-4-pregnen-20-one and 3α-hydroxy-4-androsten-17-one, and of 3α-hydroxy-5α-pregnan-20-one

A method for the convenient synthesis of the recently isolated allylic gonadal steroids, 3α-hydroxy-4-pregnen-20-one (3α-dihydroprogesterone; 3α-DHP) and 3α-hydroxy-4-androsten-17-one (3α-HA), was developed using 4-pregnene-3,20-dione (progesterone) and 4-androstene-3,17-dione as substrates and potassium trisiamylborohydride (KS-Selectride) as reducing agent. Similar reactions were also used for the reduction of 5α-pregnane-3,20-dione to 3α-hydroxy-5α-pregnan-20-one (3α-HP). The yields were about 15%, 50%, and >90% for 3α-DHP, 3α-HA and 3α-HP, respectively. Structures of the products, including the 3β-isomers and the 17α-epimer, formed in these reactions were determined by NMR and mass spectroscopic methods.