Madecassic acid Chemical Properties

Melting point:

270°C (dec.)

Boiling point:

641.7±55.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Sparingly), Methanol (Slightly, Heated)

form 

Solid

pka

4.63±0.70(Predicted)

color 

White to Pale Red

InChI

InChI=1/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/s3

InChIKey

PRAUVHZJPXOEIF-MRQYELSVNA-N

SMILES

C[C@]12C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]1([H])[C@H](O)C[C@]1([C@@]3(CC[C@]4(CC[C@@H](C)[C@H](C)[C@@]4([H])C3=CC[C@]21[H])C(=O)O)C)C |&1:1,3,5,7,11,13,16,17,20,23,25,27,32,r|

LogP

4.321 (est)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HS Code 

29389090

Madecassic acid Usage And Synthesis

Description

Madecassic acid is a triterpenoid that has been found in C. asiatica and has diverse biological activities. It inhibits LPS-induced production of nitric oxide (NO), prostaglandin E₂ (PGE₂; ), TNF-α, IL-1β, and IL-6 in RAW 264.7 macrophages when used at a concentration of 150 μg/ml. Madecassic acid (0.05 and 0.1% in the diet) decreases plasma levels of fibrinogenin and triglycerides, as well as heart and kidney levels of reactive oxygen species (ROS), in a mouse model of diabetes induced by streptozotocin (STZ; ). It decreases tumor growth in a CT26 murine colon cancer model in a dose-dependent manner.

Chemical Properties

White powder

Uses

wound healing

Uses

Madecassic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Madecassic Acid displays anti-inflammatory properties as a result of iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-kappaB activation in RAW 264.7 macrophage cells. Madecassic Acid is found in cosmetic products due to its skin-protective activities.

Definition

ChEBI: A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2alpha,3beta,6beta stereoisomer).

Madecassic acid(18449-41-7)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• ORIENTIN
• AURANTIO-OBTUSIN
• CALYCOSIN
• Stearic acid
• Centella asiatica extract
• Asiaticoside
• Citric acid
• Folic acid
• Ascoric Acid
• Asiatic acid
• 3,3,5,5-TETRAMETHYLCYCLOHEXANOL
• Madecassic acid
• Centella asiatica whole plant
• MADECASSIC ACID(SECONDARY STANDARD)
• MADECASSIC ACID(SH)
• MADECASSIC ACID 95%
• MADECASSIC ACID(PRIMARY STANDARD)