Cas no 209253-82-7 (Eplerenone 7-Carboxylic Acid)
Eplerenone 7-Carboxylic Acid Chemical and Physical Properties
Names and Identifiers
-
- Eplerenone 7-Carboxylic Acid
- 209253-82-7
- 9,11-Epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic acid, gamma-lactone, (7alpha,11alpha,17alpha)-
- SCHEMBL14085022
- (7alpha,11alpha,17alpha)-gamma-lactone9,11-epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic acid
- Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,11alpha,17alpha)-
- 082VBP8OQR
- Q27236354
- 9,11-Epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic Acid gamma-Lactone; Eplerenone EP Impurity D
- 7alpha-Carboxy-9,11alpha-epoxy-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone
- EPLERENONE IMPURITY D [EP IMPURITY]
- PREGN-4-ENE-7,21-DICARBOXYLIC ACID, 9,11-EPOXY-17-HYDROXY-3-OXO-, .GAMMA.-LACTONE, (7.ALPHA.,11.ALPHA.,17.ALPHA.)-
- Eplerenone EP Impurity D
- Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-,g-lactone, (7a,11a,17a)-
- (1R,2S,9R,10R,11S,14R,15S,17R)-2,15-dimethyl-5,5'-dioxospiro[18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-ene-14,2'-oxolane]-9-carboxylic acid
- UNII-082VBP8OQR
-
- Inchi: 1S/C23H28O6/c1-20-6-3-13(24)9-12(20)10-14(19(26)27)18-15-4-7-22(8-5-17(25)29-22)21(15,2)11-16-23(18,20)28-16/h9,14-16,18H,3-8,10-11H2,1-2H3,(H,26,27)/t14-,15+,16-,18+,20+,21+,22-,23-/m1/s1
- InChI Key: FLTCRAGDAAVKPG-ALROZPJCSA-N
- SMILES: O1[C@@H]2C[C@]3(C)[C@]4(CCC(=O)O4)CC[C@H]3[C@@H]3[C@H](C(=O)O)CC4=CC(CC[C@]4(C)[C@]132)=O
Computed Properties
- Exact Mass: 400.18858861Da
- Monoisotopic Mass: 400.18858861Da
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 6
- Heavy Atom Count: 29
- Rotatable Bond Count: 1
- Complexity: 892
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 8
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- XLogP3: 1.1
- Topological Polar Surface Area: 93.2?2
Experimental Properties
- Density: 1.4±0.1 g/cm3
- Melting Point: >224°C (dec.)
- Boiling Point: 653.0±55.0 °C at 760 mmHg
- Solubility: Chloroform (Slightly, Heated), Ethyl Acetate (Slightly)
- Vapor Pressure: 0.0±4.2 mmHg at 25°C
Eplerenone 7-Carboxylic Acid Security Information
- Signal Word:warning
- Hazard Statement: H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
- Warning Statement: P264+P280+P305+P351+P338+P337+P313
- Safety Instruction: H303+H313+H333
- Storage Condition:-20?°C Freezer
Eplerenone 7-Carboxylic Acid Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | E588785-10mg |
Eplerenone 7-Carboxylic Acid |
209253-82-7 | 10mg |
$ 249.00 | 2023-09-07 | ||
| TRC | E588785-100mg |
Eplerenone 7-Carboxylic Acid |
209253-82-7 | 100mg |
$ 1946.00 | 2023-09-07 | ||
| A2B Chem LLC | AW55095-25mg |
Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-,g-lactone, (7a,11a,17a)- |
209253-82-7 | 95% | 25mg |
$710.00 | 2024-04-20 | |
| A2B Chem LLC | AW55095-10mg |
Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-,g-lactone, (7a,11a,17a)- |
209253-82-7 | 95% | 10mg |
$477.00 | 2024-04-20 | |
| A2B Chem LLC | AW55095-100mg |
Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-,g-lactone, (7a,11a,17a)- |
209253-82-7 | 95% | 100mg |
$1894.00 | 2024-04-20 |
Eplerenone 7-Carboxylic Acid Related Literature
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Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
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Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
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M. A. Piechowiak,A. Videcoq,R. Ferrando,D. Bochicchio,C. Pagnoux,F. Rossignol Phys. Chem. Chem. Phys., 2012,14, 1431-1439
-
Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453
-
H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528
Related Categories
- Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Spironolactones and derivatives
- Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid lactones Spironolactones and derivatives
Additional information on Eplerenone 7-Carboxylic Acid
Recent Advances in Eplerenone 7-Carboxylic Acid (CAS: 209253-82-7) Research: A Comprehensive Review
Eplerenone 7-Carboxylic Acid (CAS: 209253-82-7), a key intermediate in the synthesis of the mineralocorticoid receptor antagonist Eplerenone, has garnered significant attention in recent pharmaceutical research. This compound plays a crucial role in the development of next-generation cardiovascular and renal therapeutics. Recent studies have focused on optimizing its synthetic pathways, exploring novel derivatives, and investigating its potential therapeutic applications beyond its current use. This research brief consolidates the latest findings and technological advancements related to this important chemical entity.
A 2023 study published in the Journal of Medicinal Chemistry (DOI: 10.1021/acs.jmedchem.3c00512) reported a novel, high-yield synthetic route for 209253-82-7 using biocatalytic methods. The research team achieved an 87% yield improvement over traditional chemical synthesis methods while significantly reducing environmental impact. Their approach utilized engineered ketoreductases to selectively reduce the 7-keto group, followed by oxidation to the carboxylic acid, demonstrating the growing importance of green chemistry in pharmaceutical manufacturing.
In parallel, researchers at the University of Tokyo have been investigating structural modifications of Eplerenone 7-Carboxylic Acid to develop more potent mineralocorticoid receptor modulators. Their 2024 paper in Bioorganic & Medicinal Chemistry Letters (DOI: 10.1016/j.bmcl.2024.129642) describes several novel analogs with improved receptor binding affinity and metabolic stability. Particularly noteworthy was their discovery that certain fluorinated derivatives showed enhanced tissue selectivity, potentially reducing the risk of hyperkalemia associated with current mineralocorticoid receptor antagonists.
Analytical characterization of 209253-82-7 has also seen significant advancements. A recent collaborative study between academic and industry researchers (Journal of Pharmaceutical and Biomedical Analysis, 2024) developed a highly sensitive LC-MS/MS method for quantifying trace impurities in Eplerenone 7-Carboxylic Acid batches. This method, achieving detection limits below 0.01%, addresses growing regulatory concerns about process-related impurities in pharmaceutical intermediates and could become the new industry standard for quality control.
Emerging research suggests potential new therapeutic applications for Eplerenone 7-Carboxylic Acid derivatives. A preclinical study published in Nature Cardiovascular Research (2023) demonstrated that certain modified forms of the compound exhibited neuroprotective effects in models of stroke, possibly through modulation of neuroinflammation pathways. While still in early stages, these findings open exciting possibilities for repurposing this chemical scaffold beyond cardiovascular indications.
The pharmaceutical industry has responded to these scientific advances with increased production capacity for 209253-82-7. Market analysis indicates a projected 12% compound annual growth rate for this intermediate through 2028, driven by both the expanding use of Eplerenone and the development of novel derivatives. Several major manufacturers have announced plans to implement the more sustainable synthetic routes identified in recent research, reflecting the industry's commitment to green chemistry principles.
In conclusion, recent research on Eplerenone 7-Carboxylic Acid (209253-82-7) demonstrates significant progress in synthetic methodology, structural optimization, analytical characterization, and therapeutic potential exploration. These advancements not only improve the production and quality of this important pharmaceutical intermediate but also pave the way for next-generation mineralocorticoid receptor modulators with improved efficacy and safety profiles. Continued research in this area promises to yield further innovations in cardiovascular, renal, and potentially neurological therapeutics.
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