Madecassic acid CAS 18449-41-7
Introduction：Basic information about Madecassic acid CAS 18449-41-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Madecassic acid Basic information
| Product Name: | Madecassic acid |
| Synonyms: | (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);6BETA-HYDROXYASIATIC ACID;2α,3β,6β,23-Tetrahydroxyurs-12-en-28-oic acid |
| CAS: | 18449-41-7 |
| MF: | C30H48O6 |
| MW: | 504.71 |
| EINECS: | 240-851-7 |
| Product Categories: | Inhibitors;Cofactor;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Miscellaneous Natural Products;The group of Asiaticoside |
| Mol File: | 18449-41-7.mol |
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 |
| Major Application | food and beverages |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChIKey | PRAUVHZJPXOEIF-MRQYELSVNA-N |
| SMILES | O[C@H]1[C@@H]2[C@@]([C@@H]3[C@]([C@@]4(CC[C@@]5([C@@H]([C@H]([C@@H](CC5)C)C)C4=CC3)C(=O)O)C)(C1)C)(C[C@H]([C@@H]([C@]2(CO)C)O)O)C |
| LogP | 4.321 (est) |
Safety Information
| Hazard Codes | Xi |
| Safety Statements | 24/25 |
| WGK Germany | WGK 3 |
| HS Code | 29389090 |
| Storage Class | 11 - Combustible Solids |
| 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). |
| References | [1] JONG-HEON WON. Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells.[J]. Planta medica, 2010: 251-257. DOI: 10.1055/s-0029-1186142 [2] Y. HSU. Anti-Diabetic Effects of Madecassic Acid and Rotundic Acid[J]. Nutrients, 2015, 7 1: 10065-10075. DOI: 10.3390/nu7125512 [3] HUA ZHANG. Madecassic acid inhibits the mouse colon cancer growth by inducing apoptosis and immunomodulation.[J]. Journal of Buon, 2014, 19 2: 372-376. |
Madecassic acid Preparation Products And Raw materials
| Raw materials | Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, methyl ester, (2α,3β,4α,6β)- |
