20248-18-4

Usage

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

• 1380518-01-3 3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A 
• 3614-61-7 23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid 
• 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 academic research and scientific papers

Activity of 3-ketosteroid 9α-hydroxylase (KshAB) indicates cholesterol side chain and ring degradation occur simultaneously in Mycobacterium tuberculosis

Mycobacterium tuberculosis (Mtb), a significant global pathogen, contains a cholesterol catabolic pathway. Although the precise role of cholesterol catabolism in Mtb remains unclear, the Rieske monooxygenase in this pathway, 3-ketosteroid 9α-hydroxylase (KshAB), has been identified as a virulence factor. To investigate the physiological substrate of KshAB, a rhodococcal acyl-CoA synthetase was used to produce the coenzyme A thioesters of two cholesterol derivatives: 3-oxo-23,24-bisnorchol-4- en-22-oic acid (forming 4-BNC-CoA) and 3-oxo-23,24-bisnorchola- 1,4-dien-22-oic acid (forming 1,4-BNC-CoA). The apparent specificity constant (kcat/Km) of KshAB for the CoA thioester substrates was 20-30 times that for the corresponding 17-keto compounds previously proposed as physiological substrates. The apparent KmO2 was 90 ± 10 μM in the presence of 1,4-BNC-CoA, consistent with the value for two other cholesterol catabolic oxygenases. The Δ1 ketosteroid dehydrogenase KstD acted with KshAB to cleave steroid ring B with a specific activity eight times greater for a CoA thioester than the corresponding ketone. Finally, modeling 1,4-BNC-CoA into the KshA crystal structure suggested that the CoA moiety binds in a pocket at the mouth of the active site channel and could contribute to substrate specificity. These results indicate that the physiological substrates of KshAB are CoA thioester intermediates of cholesterol side chain degradation and that side chain and ring degradation occur concurrently in Mtb. This finding has implications for steroid metabolites potentially released by the pathogen during infection and for the design of inhibitors for cholesterol-degrading enzymes. The methodologies and rhodococcal enzymes used to generate thioesters will facilitate the further study of cholesterol catabolism.

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.

Synthesis of 20-Carbaldehydes and 20-Carbonitriles of the Pregnane Series Starting with (20S)-20-Hydroxymethylpregna-1,4-dien-3-one

An efficient six-step approach to 3-protected (20S)-3β-hydroxypregna-1,5-diene-20-carbaldehydes 8 with potential importance in the synthesis of vitamin D analogues was developed starting with (20S)-20-hydroxymethylpregna-1,4-dien-3-one (1).Oxidation of the 22-hydroxy group of 1 by means of periodinane 2 (Dess-Martin reagent) furnished the aldehyde 3 without epimerization. 3 was protected selectively at C-22 as dimethyl acetal 5.Isomerization to 6 and subsequent reduction of the 3-carbonyl group with calcium borohydride furnished the 3β-alcohol 7a with high stereoselectivity.Cleavage of the acetal to 8a occurred in a homogeneous solution of acetic acid in the presence of small amounts of water and trifluoroacetic acid.After protection of the 3-OH group 8b-d were obtained in 54percent overall yield.The in situ generated aldehyde N,N-dimethylhydrazones of 3, 8a, and 8b were converted in high yields with excellent chemoselectivity into the nitriles 12, 15a, and 15b with magnesium monoperoxyphthalate hexahydrate.The uniform (20S) stereochemistry of 3 and 8a-d was elucidated by 1H-NMR investigations. - Key Words: Pregnanes / Steroids

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.