Asiatic acid

Base Information

• Chemical Name: Asiatic acid
• CAS No.: 464-92-6
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.708
• Hs Code.: 29181990
• European Community (EC) Number: 482-720-9
• UNII: 9PA5A687X5
• DSSTox Substance ID: DTXSID901019207
• Nikkaji Number: J11.338G
• Wikidata: Q15478109
• NCI Thesaurus Code: C63703
• RXCUI: 1551574
• Metabolomics Workbench ID: 49975
• ChEMBL ID: CHEMBL404313
• Mol file: 464-92-6.mol

Synonyms:asiatic acid

Chemical Property of Asiatic acid

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 2.13E-17mmHg at 25°C
• Melting Point: 325-330 °C(lit.)
• Refractive Index: 1.579
• Boiling Point: 609.446 °C at 760 mmHg
• PKA: 4.66±0.70(Predicted)
• Flash Point: 336.403 °C
• PSA: 97.99000
• Density: 1.19 g/cm³
• LogP: 5.03270
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble1mg/mL, clear, colorless
• Water Solubility.: Soluble in dimethyl sulfoxide, ethanol and dimethylformamide. Sparingly soluble in water
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 488.35017463
• Heavy Atom Count: 35
• Complexity: 930

Purity/Quality:

≥97%, ^*data from raw suppliers

Asiatic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O
• Uses: wound healing, experimental carcinogen Asiatic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Asiatic Acid is a neuroprotectant and induces of apoptosis in HepG2 human hepatoma cells. Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties. It is a starting material for asiatic acid derivative synthesis for use as anticancer agents, glycogen phosphorylase inhibitors and and hepatoprotectants.

Technology Process of Asiatic acid

There total 10 articles about Asiatic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.08%

asiaticoside (16830-15-2) → asiatic acid (464-92-6,89786-83-4,103974-74-9,106327-64-4,114580-55-1,116348-15-3,143839-02-5)

Guidance literature:

With water; sodium dodecyl-sulfate; sodium hydroxide; at 20 ℃; for 0.25h; under 760.051 Torr;

Reference yield: 92.0%

asiaticoside → asiatic acid (464-92-6,89786-83-4,103974-74-9,106327-64-4,114580-55-1,116348-15-3,143839-02-5)

Guidance literature:

With water; sodium hydroxide; In methanol; Reflux;

DOI:10.1248/cpb.c13-00328

Reference yield: 47.0%

Asiaticoside → asiatic acid (464-92-6,89786-83-4,103974-74-9,106327-64-4,114580-55-1,116348-15-3,143839-02-5) + 2α,3β,23α-trihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside

Guidance literature:

With α-L-rhamnosidase from Fusarium oxysporum CCF906; In phosphate buffer; at 35 ℃; for 48h; pH=6.0;

DOI:10.1002/adsc.200505047

upstream raw materials:

asiaticoside

Downstream raw materials:

N-(2α,3β,23-triacetoxyurs-12-ene-28-oyl)benzylamine

N-(2α,3β,23-triacetoxyurs-12-ene-28-oyl)p-toluidine

methyl 2α-hydroxy-3β,23-isopropylidenedioxyurs-12-ene-28-oate

methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Refernces

• 1、 Huang, Ri-Zhen,Wang, Cai-Yi,Li, Jian-Fei,Yao, Gui-Yang,Pan, Ying-Ming,Ye, Man-Yi,Wang, Heng-Shan,Zhang, Ye. "Synthesis, antiproliferative and apoptosis-inducing effects of novel asiatic acid derivatives containing α-aminophosphonates". . p. 62890 - 62906. Retrieved 2016/07/16.
• 2、 Li, Yong,Yang, Fang,Yuan, Mingxing,Jiang, Lijuan,Yuan, Li,Zhang, Xiaowei,Li, Ying,Dong, Lin,Bao, Xu,Yin, Shufan. "Synthesis and evaluation of asiatic acid derivatives as anti-fibrotic agents: Structure/activity studies". . p. 44 - 49. Retrieved 2015/02/19.