Asiatic acid Chemical Properties

Melting point:

325-330 °C(lit.)

Boiling point:

609.4±55.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

RTECS 

YU9580000

storage temp. 

2-8°C

solubility 

methanol: soluble1mg/mL, clear, colorless

form 

powder

pka

4.66±0.70(Predicted)

color 

white

biological source

Centella asiatica

Water Solubility 

Soluble in dimethyl sulfoxide, ethanol and dimethylformamide. Sparingly soluble in water

InChIKey

JXSVIVRDWWRQRT-UYDOISQJSA-N

LogP

5.748 (est)

CAS DataBase Reference

464-92-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

HS Code 

29181990

Hazardous Substances Data

464-92-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Asiatic acid Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from the whole grass of Centella asiatica (Centella asiatica), a plant of the genus Leiogangen, family Umbelliferae.

Uses

wound healing, experimental carcinogen

Uses

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.

Uses

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.

Definition

ChEBI: A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). It is isolated from Symplocos lancifolia and Vateria indica and exhibits anti-angiogenic activity.

General Description

Asiatic acid is a naturally occurring pentacyclic triterpenoid, obtained from Centella asiatica.

Biochem/physiol Actions

Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties.

Synthesis

1) 1 g of (2α,3β,4α)-3,4-dihydroxy-6-(hydroxymethyl)-5-((3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl 10,11-dihydroxy-9-(hydroxymethyl)-hexamethyl- Eicosanoid-4a-carboxylic acid ester (asiaticoside), 4.3×10^-2 mol sodium dodecyl sulfate and 0.02 mol NaOH were mixed, water was added to 1 L, and stirred until completely dissolved to obtain a mixed solution. The hydrolysis reaction was carried out at room temperature (25°C) and atmospheric pressure (1 atm) for 15 min to obtain the hydrolysate.2) The pH of the hydrolysate was adjusted to 5.0 with 1 M HCl solution and allowed to stand for 30 min, followed by filtration and collection of the precipitate.3) The precipitate was dissolved in 70% (v/v) aqueous ethanol at a ratio of 1 g:30 mL and filtered to remove insoluble matter. Crystallization was carried out by adding 16 times the volume of distilled water to the filtrate and allowed to stand overnight for complete crystallization. The crystallized product was collected by filtration and dried to constant weight in a vacuum drying oven at 40°C to obtain cumaric acid white crystals of 0.445 g. The product was analyzed by high-performance liquid chromatography (HPLC) with a purity of 95.8% and a yield of 93.08%.

target

TNF-α | IFN-γ | IL Receptor | Caspase | p21 | NOS | NADPH-oxidase | NO | HMG-CoA reductase | COX

References

[1] Patent: CN106349319, 2017, A. Location in patent: Paragraph 0017-0032
[2] Patent: WO2009/89365, 2009, A2. Location in patent: Page/Page column 6-7
[3] Steroids, 2015, vol. 96, p. 44 - 49
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4500 - 4504
[5] RSC Advances, 2016, vol. 6, # 67, p. 62890 - 62906

Asiatic acid(464-92-6)Related Product Information

• Citric acid
• Shikimic acid
• Calcium oxalate
• Ammonium oxalate monohydrate
• Dimethyl oxalate
• Ferrous oxalate
• Ethyl 2-(Chlorosulfonyl)acetate
• Hyaluronic acid
• Folic acid
• Ascoric Acid
• Madecassic acid
• niga-ichigoside F1
• Asiatic acid
• Centella asiatica whole plant
• ASIATIC ACID 95%
• 2,3,23-TRI(ACETYLOXY)-(2ALPHA,3BETA,4ALPHA)-URS-12-EN-28-OIC ACID
• ASIATIC ACID(RG)
• 2,3,23-TRI(ACETYLOXY)-(2ALPHA,3BETA,4ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER