5508-55-4

Basic information

• Product Name: 21-hydroxypregna-1,4-diene-3,20-dione
• CAS NO: 5508-55-4
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.4452
• Mol File: 5508-55-4.mol

Chemical Properties

• Boiling Point: 490.8°C at 760 mmHg
• Flash Point: 264.7°C
• Density: 1.17g/cm³
• Vapor Pressure: 1.08E-11mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 21-hydroxypregna-1,4-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 21-hydroxypregna-1,4-diene-3,20-dione(5508-55-4)
• EPA Substance Registry System: 21-hydroxypregna-1,4-diene-3,20-dione(5508-55-4)

Safety Data

• Hazardous Substances Data: 5508-55-4(Hazardous Substances Data)

Usage

Chemical Type

Synthetic steroid hormone

Derived From

Progesterone

Role in Biosynthesis

Acts as an intermediate in the biosynthesis of glucocorticoids and mineralocorticoids in the adrenal glands

Physiological Importance

Crucial for the production of cortisol and aldosterone

Functions

Regulates various physiological processes including metabolism, immune response, and electrolyte balance

Medical Research

Used in medical research to study hormone synthesis pathways and mechanisms

Pharmaceutical Development

Utilized in the development of pharmaceuticals for treating endocrine disorders and related conditions

Upstream product

• 1162-54-5 pregna-1,4-diene-3,20-dione 
• 64-85-7 21-Hydroxyprogesterone 
• 1171-90-0 3,20-dioxo-pregna-1,4-dien-21-yl acetate 
• 57-83-0 progesterone 

Relevant articles and documents

CYP260B1 acts as 9α-hydroxylase for 11-deoxycorticosterone

Steroids and their oxyfunctionalized counterparts are valuable compounds for the pharmaceutical industry; however, the regio- and stereoselective introduction of oxygen is a challenging task for the synthetic chemistry. Thus, cytochromes P450 play an important role for the functionalization of steroidal compounds. In this study, we elucidated the main product of 11-deoxycorticosterone conversion formed by CYP260B1 from Sorangium cellulosum So ce56 as 9α-OH 11-deoxycorticosterone by NMR spectroscopy. This is, to the best of our knowledge, the first identification of a 9α-hydroxylase for this substrate. In addition, the major side product was identified as 21-OH pregna-1,4-diene-3,20-dione. Studies using 1α-OH 11-deoxycorticosterone as substrate suggested that the major side product is formed via dehydrogenation reaction. This side reaction was considerably decreased by employing the CYP260B1-T224A mutant, which showed an increased selectivity of about 75% compared to the 60% of the wild type for the 9α-hydroxylation. To scale up the production, an E. coli based whole-cell system harboring the CYP260B1-T224A variant as well as two heterologous redox partners was used. Employing growing cells in minimal medium led to a productivity of about 0.25 g/l/d at a 50 ml scale showing the biotechnological potential of this system.

Biotransformation of corticosteroids by Penicillium decumbens ATCC 10436

The biotransformation of a series of corticosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the corresponding 5α-dihydroxteroid was observed for all the Δ4-3-ketosteroids studied with the exception of deoxycorticosterone, which was converted to a Δ14-diene. Deoxycorticosterone acetate was, however, converted to a 5α- dihydro product concomitant with ester hydrolysis. Other substrates carrying a C-21 acetoxy group were also hydrolyzed to the alcohol. In two cases (resulting from deoxycorticosterone acetate and 11-deoxycortisone) the 5α- 3-keto-product was further reduced to the 3β-alcohol. No reduction of δ14-dienes was observed.