| Identification | Back Directory | [Name]
Madecassic acid | [CAS]
18449-41-7 | [Synonyms]
Madecasoside
MADECASSIC ACID
MADECASSIC ACID(P)
Hydroxy asiaticoside
6-Hydroxyasiatic acid
Madecassic Acid (97%)
Brahmic acid 18449-41-7
6BETA-HYDROXYASIATIC ACID
Madecassic acid, froM Centella asiatica
2α,3β,6β,23-Tetrahydroxyurs-12-en-28-oic acid
Madecassic acid, 98%, from Centella asiatica (L.) Urb.
Urs-12-en-28-oic acid,2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-
Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2α,3β,4α,6β)-
(2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxy-urs-12-en-28-oic acid
Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2.alpha.,3.beta.,4.alpha.,6.beta.)-
(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
(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 | [EINECS(EC#)]
240-851-7 | [Molecular Formula]
C30H48O6 | [MDL Number]
MFCD00895441 | [MOL File]
18449-41-7.mol | [Molecular Weight]
504.7 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [Description]
Madecassic acid is a triterpenoid that has been found in C. asiatica and has diverse biological activities.1,2,3 It inhibits LPS-induced production of nitric oxide (NO), prostaglandin E2 (PGE2; Item No. 14010), TNF-α, IL-1β, and IL-6 in RAW 264.7 macrophages when used at a concentration of 150 μg/ml.1 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; Item No. 13104).2 It decreases tumor growth in a CT26 murine colon cancer model in a dose-dependent manner.3 | [Chemical Properties]
White powder | [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. | [Uses]
wound healing | [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.
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