Phytolaccoside E (Esculentoside A)

Base Information

• Chemical Name: Phytolaccoside E (Esculentoside A)
• CAS No.: 65497-07-6
• Molecular Formula: C₄₂H₆₆O₁₆
• Molecular Weight: 826.976
• Hs Code.: 29389090
• European Community (EC) Number: 683-197-1
• Wikidata: Q105379796
• Mol file: 65497-07-6.mol

Synonyms:esculentoside A

Chemical Property of Phytolaccoside E (Esculentoside A)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 936.7 ºC
• PKA: 4.39±0.70(Predicted)
• Flash Point: 275.3 ºC
• PSA: 262.36000
• Density: 1.42 g/cm^3/sup>
• LogP: 0.61740
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 9
• Exact Mass: 826.43508601
• Heavy Atom Count: 58
• Complexity: 1610

Purity/Quality:

98%,99%, ^*data from raw suppliers

Esculentoside A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)C2C1)C)C(=O)O)C(=O)OC
• General Description: Esculentoside A (EsA) is a triterpene saponin known for its anti-inflammatory properties and selective inhibition of cyclooxygenase-2 (COX-2). Structural modifications, particularly the introduction of aromatic rings at the C-28 position, have been shown to enhance its COX-2 inhibitory activity while reducing haemolytic toxicity, making it a promising candidate for developing more effective and safer anti-inflammatory agents.

Refernces

Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A

10.1016/j.bmcl.2007.10.006

The research focused on the synthesis and evaluation of derivatives of Esculentoside A (EsA), a triterpene saponin with notable anti-inflammatory properties and selective inhibitory activity towards cyclooxygenase-2 (COX-2). The purpose was to optimize EsA's structure to enhance its biological activity while reducing its haemolytic toxicity. A series of derivatives were synthesized by converting the C-28 carboxylic acid group of EsA into amides using HOBt and DCC in DMF, followed by the addition of various amines (aliphatic, aromatic, and amino acid esters). The study concluded that introducing aromatic rings significantly improved COX-2 inhibitory activity, with compound 23 exhibiting higher inhibitory rates than both EsA and Celecoxib, while also demonstrating lower haemolytic toxicity. The findings suggest that structural modifications of EsA can lead to more effective COX-2 inhibitors with reduced side effects.