21-Hydroxy-20-methylpregn-4-en-3-one
[CAS# 60966-36-1]

Identification

• Name: 21-Hydroxy-20-methylpregn-4-en-3-one
• Synonyms: (8S,9S,10R,13S,14S,17R)-17-(1-hydroxypropan-2-yl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.50
• CAS Registry Number: 60966-36-1
• EC Number: 262-543-1
• SMILES: CC(CO)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.546, Calc.^*
• Boiling Point: 464.1±14.0 °C (760 mmHg), Calc.^*
• Flash Point: 197.5±12.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H351-H360-H362
• Safety Statements: P203-P260-P263-P264-P270-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Lact.	-	H362
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Repr.	1A	H360

Discovery and Applications

21-Hydroxy-20-methylpregn-4-en-3-one is a synthetic steroid compound that is closely related in structure to endogenous hormones. Its chemical formula is C22H32O2 and it is commonly referred to as 21-hydroxyprogesterone. The synthesis of 21-hydroxy-20-methylpregn-4-en-3-one is based on structural modifications of the essential hormone progesterone. In the mid-20th century, researchers sought to develop natural steroid derivatives with enhanced therapeutic properties or specific biological activities. The addition of a hydroxyl group (-OH) at position 21 and a methyl group at position 20 yields 21-hydroxy-20-methylpregn-4-en-3-one. These modifications are intended to enhance the stability of the compound and its interaction with steroid receptors.

21-Hydroxy-20-methylpregn-4-en-3-one has a modified pregnane skeleton characterized by the addition of a hydroxyl group at carbon 21 and a methyl group at carbon 20. This structure alters its interaction with biological systems compared to its parent molecule, progesterone. The compound's molecular structure enables it to bind to steroid hormone receptors and affect a variety of physiological processes.

Similar to other steroid hormones, 21-hydroxy-20-methylpregn-4-en-3-one exerts its effects by binding to specific intracellular receptors, influencing gene expression, and modulating a variety of biological responses. Its interaction with glucocorticoid and progesterone receptors is particularly important as it affects processes such as inflammation, metabolism, and reproductive function.

21-hydroxy-20-methylpregn-4-en-3-one has been intensively studied for its potential in hormone replacement therapy, particularly in cases where progesterone levels are insufficient or need to be regulated. Its structural similarity to the natural hormone allows it to effectively mimic or modulate hormonal activity in the body. It can be used to treat certain adrenal disorders, including congenital adrenal hyperplasia (CAH), where synthetic derivatives are needed to supplement or regulate deficient hormone secretion.

The compound's role in modulating reproductive function makes it a candidate for fertility treatment, particularly in cases where progesterone analogs are used to support pregnancy or address menstrual irregularities. Its potential for use in contraceptive formulations is also being investigated, as modifications to natural progesterone could enhance its effectiveness in preventing ovulation.

21-Hydroxy-20-methylpregn-4-en-3-one exhibits anti-inflammatory properties due to its interaction with the glucocorticoid receptor. This makes it a candidate for the treatment of inflammatory and autoimmune diseases. Ongoing studies explore its potential in the treatment of chronic diseases such as rheumatoid arthritis and inflammatory bowel disease, where modulation of the immune response is crucial.

References

2023. Production of 21-hydroxy-20-methyl-pregna-1,4-dien-3-one by modifying multiple genes in Mycolicibacterium. Applied Microbiology and Biotechnology, 107(4).
DOI: 10.1007/s00253-023-12399-2

2021. Production of 9,21-dihydroxy-20-methyl-pregna-4-en-3-one from phytosterols in Mycobacterium neoaurum by modifying multiple genes and improving the intracellular environment. Microbial Cell Factories, 20(1).
DOI: 10.1186/s12934-021-01717-w

2023. Current Trends and Perspectives in Microbial Bioconversions of Steroids. Methods in Molecular Biology, 2704.
DOI: 10.1007/978-1-0716-3385-4_1