20248-18-4

Basic information

• Product Name: 20-carboxy-1,4-pregnadien-3-one
• Synonyms: 20-carboxy-1,4-pregnadien-3-one;3-oxo-23,24-bisnorchola-1,4-dien-22-oic acid
• CAS NO: 20248-18-4
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.47
• Mol File: 20248-18-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 507.8°Cat760mmHg
• Flash Point: 275°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.1E-11mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 20-carboxy-1,4-pregnadien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 20-carboxy-1,4-pregnadien-3-one(20248-18-4)
• EPA Substance Registry System: 20-carboxy-1,4-pregnadien-3-one(20248-18-4)

Safety Data

• Hazardous Substances Data: 20248-18-4(Hazardous Substances Data)

Usage

Description

20-carboxy-1,4-pregnadien-3-one is a steroid acid that is 23,24-bisnor-chol-1,4-dien-22-oic acid bearing an additional oxo substituent at position 3. It is a derivative of the steroid hormone pregnenolone, which plays a crucial role in the synthesis of other steroid hormones, including cortisol, aldosterone, and testosterone.

Uses

Used in Pharmaceutical Industry:
20-carboxy-1,4-pregnadien-3-one is used as a pharmaceutical intermediate for the synthesis of various steroidal drugs. It serves as a key building block in the production of corticosteroids, which have anti-inflammatory and immunosuppressive properties, and are used to treat a wide range of conditions, such as asthma, allergies, and autoimmune disorders.
Used in Hormone Replacement Therapy:
20-carboxy-1,4-pregnadien-3-one is used as a precursor in the synthesis of hormone replacement therapies, particularly for conditions related to menopause, adrenal insufficiency, and certain genetic disorders. It helps in maintaining hormonal balance and alleviating symptoms associated with hormonal imbalances.
Used in Research and Development:
20-carboxy-1,4-pregnadien-3-one is utilized as a research compound in the development of new drugs and therapies targeting various diseases and conditions. Its unique structure and properties make it a valuable tool for studying the mechanisms of action and potential applications of steroid hormones and their analogs.
Used in Cosmetic Industry:
20-carboxy-1,4-pregnadien-3-one is used as an active ingredient in some cosmetic products, particularly those targeting skin aging and rejuvenation. Its hormone-like properties may contribute to improved skin elasticity, hydration, and overall skin health.

InChI:InChI=1/C22H30O3/c1-13(20(24)25)17-6-7-18-16-5-4-14-12-15(23)8-10-21(14,2)19(16)9-11-22(17,18)3/h8,10,12-13,16-19H,4-7,9,11H2,1-3H3,(H,24,25)/t13-,16-,17+,18-,19-,21-,22+/m0/s1

Upstream product

• 3614-61-7 23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid 
• 1380518-01-3 3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A 
• 81201-82-3 (20S)-3-oxopregna-1,4-diene-20-carboxaldehyde 
• 35525-27-0 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one 

Downstream Products

• 115208-40-7 2-((8R,9S,10S,13S,14S)-10,13-Dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-propionic acid 
• 3614-61-7 3-Keto-bis-norchol-4-enoic acid 

Relevant articles and documents

Microbial production of 3-oxobisnorchola-1,4-dien-22-oic acid

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Isolation, biological significance, synthesis, and cytotoxic evaluation of new natural parathiosteroids A-C and analogues from the soft coral Paragorgia sp

(Chemical Equation Presented) Three unusual new steroid thioesters, parathiosteroids A-C (1a-3a), were isolated from the 2-propanol extract of the soft coral Paragorgia sp. collected in Madagascar. Their structures, determined by detailed spectroscopic analysis, were confirmed by synthesis and represent the first isolation of natural steroids bearing a C22 thioester in their side chain. These compounds displayed cytotoxicity against a panel of three human tumor cell lines at the micromolar level. The preparation of several analogues revealed structure/activity relationships in this type of steroids, for example, that the XCH2CH2NHCOCH3 moiety (X = S, O, NH) in the side chain is essential for the antiproliferative activity, and a low degree of oxidation in the A-ring results in higher bioactivity. These natural products could be biosynthetic intermediates in the steroid side chain degradation pathway involving activation with CoA and β-oxidations.

BIODEGRADATION OF CHOLESTEROL BY A MUTANT OF THE Mycobacterium SPECIES

The biodegradation of cholesterol by the Mycobacterium mutant CCM 3528 gave rise to 22-hydroxy-23,24-bisnorchola-1,4-diene-3-one (I) as the main product.The identified by-products were 24-norchola-1,4-diene-3,22-dione (IX), androsta-1,4-diene-3,17-dione (XV) and their unsaturated analogues, X and XVI respectively.