Production Method 1

5508-58-7

42895-58-9

1020673-18-0

955428-65-6

869807-57-8

4176-97-0

1020673-19-1

1262950-29-7

919120-75-5

Reaction Conditions

1.1 Solvents: Water ;  96 h, 28 °C

Reference

Cytotoxic biotransformed products from andrographolide by Rhizopus stolonifer ATCC 12939

He, Xiangjiu; et al, Journal of Molecular Catalysis B: Enzymatic, 2010, 62(3-4), 242-247

14-Deoxy-11,12-didehydroandrographolide Raw materials

• Andrographolide

14-Deoxy-11,12-didehydroandrographolide Preparation Products

• 12(S),13(S)-12-hydroxyandrographolide (1020673-18-0)
• 3-Oxoandrographolide (955428-65-6)
• Andropanolide (869807-57-8)
• 14-Deoxyandrographolide (4176-97-0)
• 12(R),13(R)-12-hydroxyandrographolide (1020673-19-1)
• 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,8aS)-decahydro-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-6-oxo-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3Z,4S)- (1262950-29-7)
• 3-[(1E)-2-[(1R,4aS,5R,8aR)-Decahydro-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-6-oxo-1-naphthalenyl]ethenyl]-2(5H)-furanone (919120-75-5)
• 14-Deoxy-11,12-didehydroandrographolide (42895-58-9)

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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Diterpene lactones
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Diterpene lactones
• Diterpenoids
• Other Chemical Reagents

Compound CAS No. 42895-58-9: 14-Deoxy-11,12-didehydroandrographolide

The compound CAS No. 42895-58-9, also known as 14-deoxy-11,12-didehydroandrographolide, is a highly specialized chemical entity that has garnered significant attention in the fields of pharmacology and natural product research. This compound is a derivative of andrographolide, a well-known diterpenoid lactone isolated from the plant *Andrographis paniculata*, which has been extensively studied for its pharmacological properties.

Andrographolide itself is renowned for its anti-inflammatory, antiviral, and anticancer activities, and the structural modifications in 14-deoxy-11,12-didehydroandrographolide have been shown to enhance certain bioactivities while potentially reducing toxicity. Recent studies have focused on the chemical structure of this compound, particularly the removal of the hydroxyl group at position 14 and the introduction of a double bond between positions 11 and 12, which significantly alters its physicochemical properties.

One of the most intriguing aspects of CAS No. 42895-58-9 is its pharmacokinetic profile. Researchers have reported improved solubility and bioavailability compared to its parent compound, making it a promising candidate for drug development. This improvement is attributed to the structural changes that reduce steric hindrance and enhance lipophilicity, which are critical factors in drug delivery systems.

The synthesis of 14-deoxy-11,12-didehydroandrographolide has been optimized through various methodologies, including semisynthesis from natural sources and total synthesis using advanced organic chemistry techniques. These methods have not only facilitated the production of this compound but also provided insights into the stereochemistry and regioselectivity of related diterpenoids.

Recent advancements in biological activity studies have highlighted the potential of CAS No. 42895-58-9 as an anticancer agent. Preclinical trials have demonstrated its ability to induce apoptosis in various cancer cell lines while sparing normal cells, suggesting a high therapeutic index. Additionally, this compound has shown synergistic effects when combined with conventional chemotherapeutic agents, which could pave the way for novel cancer treatment strategies.

In terms of therapeutic applications, CAS No. 42895-58-9 is being explored for its potential in treating chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease. Its anti-inflammatory properties are thought to be mediated through modulation of key signaling pathways like NF-kB and MAPK.

Another area of active research is the mechanism of action of this compound at the molecular level. Studies using advanced techniques such as X-ray crystallography and molecular docking have provided insights into how it interacts with target proteins, offering a deeper understanding of its pharmacodynamics.

The development of analytical methods for the characterization and quantification of CAS No. 42895-58-9 has also been a focus area. Techniques such as high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy have been employed to ensure precise analysis and quality control during synthesis and formulation.

Looking ahead, the future prospects for CAS No. 42895-58-9 are promising. Collaborative efforts between academia and industry are expected to accelerate its progression from preclinical studies to clinical trials. Furthermore, ongoing research into its biosynthesis could unlock new avenues for sustainable production methods.

In conclusion, CAS No. 42895-58-9, or 14-deoxy-11,12-didehydroandrographolide, represents a significant advancement in natural product chemistry with immense potential in drug discovery and development.

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• 160498-02-2(2(5H)-Furanone,5-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]-1-(2,5-dihydro-2-oxo-3-furanyl)ethyl]-3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]-(9CI))
• 162762-94-9(2(5H)-Furanone,3-[(1E)-2-[(1S,4R,4aS,8aR)-decahydro-4-hydroxy-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]ethenyl]-)
• 160498-01-1(2(5H)-Furanone,5-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]-1-(2,5-dihydro-2-oxo-3-furanyl)ethyl]-3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]-(9CI))
• 72601-38-8((7aS,8S)-8-hydroxy-6,6,8-trimethyl-5,6,7,7a,8,9-hexahydroazuleno[5,6-c]furan-3(1H)-one)
• 76958-99-1(Kalii Dehydrographolidi Succinas)
• 160498-00-0(Bisandrographolide)
• 1207722-88-0(19-O-acetyl-14-deoxy-11,12-didehydroandrographolide)
• 160598-92-5(2(5H)-Furanone,3-[(1E)-2-[(1S,4aS,8aS)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]ethenyl]-)