18449-41-7

Basic information

• Product Name: Madecassic acid
• Synonyms: 6BETA-HYDROXYASIATIC ACID;(2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxy-urs-12-en-28-oic acid;MADECASSIC ACID;Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2.alpha.,3.beta.,4.alpha.,6.beta.)-;(1S,2R,4aS,6aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bR)-8,10,11-trihydroxy -9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,1 1,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid;Hydroxy asiaticoside;MADECASSIC ACID(P);2α,3β,6β,23-Tetrahydroxyurs-12-en-28-oic acid
• CAS NO: 18449-41-7
• Molecular Formula: C30H48O6
• Molecular Weight: 504.7
• Product Categories: Miscellaneous Natural Products;The group of Asiaticoside;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Cofactor;Inhibitors
• Mol File: 18449-41-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 270°C (dec.)
• Boiling Point: 641.7 °C at 760 mmHg
• Flash Point: 355.9 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 3.61E-19mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 4.63±0.70(Predicted)
• CAS DataBase Reference: Madecassic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Madecassic acid(18449-41-7)
• EPA Substance Registry System: Madecassic acid(18449-41-7)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• Hazardous Substances Data: 18449-41-7(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 18449-41-7 differently. You can refer to the following data:
1. wound healing
2. 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.
3. 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).

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+/m1/s1

Upstream product

• 23140-81-0 methyl 2α,3β,6β,23-tetrahydroxyurs-12-en-28-oate 

Related news

SHORT COMMUNICATIONSeparation and Determination of Madecassic acid (cas 18449-41-7) in Extracts of Centella asiatica Using High Performance Liquid Chromatography with β-Cyclodextrin as Mobile Phase Additive09/03/2019

Centella asiatica (L.) Urban is a tropical medicinal plant with a long history of therapeutic uses. Madecassic acid and terminolic acid, a pair of structural isomers, are two constituents of Centella asiatica. A method using reversed-phase high performance liquid chromatography in which β-cyclo...detailed

Madecassic acid (cas 18449-41-7) protects against hypoxia-induced oxidative stress in retinal microvascular endothelial cells via ROS-mediated endoplasmic reticulum stress09/02/2019

Madecassic acid (MA) is an abundant triterpenoid in Centella asiatica (L.) Urban. (Apiaceae) that has been used as a wound-healing, anti-inflammatory and anti-cancer agent. Up to now, the effects of MA against oxidative stress remain unclear. In this study, we investigated the effect of MA and i...detailed

A LC-ESI-MS method for the simultaneous determination of madecassoside and its metabolite Madecassic acid (cas 18449-41-7) in rat plasma: comparison pharmacokinetics in normal and collagen-induced arthritic rats09/01/2019

To develop a simple and highly sensitive high performance liquid chromatography with electrospray ionization mass spectrometric (LC-ESI-MS) method for the simultaneous determination of madecassoside and its major metabolite madecassic acid in rat plasma, and compare the pharmacokinetics of the t...detailed