Madecassic Acid

CAS: 18449-41-7

Ref. TR-M107500

Product Information

• Name: Madecassic Acid
• Synonyms: (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-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,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-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, (2Alpha,3Beta,5Xi,6Beta,9Xi)-2,3,6,23-Tetrahydroxyurs-12-En-28-Oic Acid, (2Alpha,3Beta,6Beta)-2,3,6,23-Tetrahydroxyurs-12-En-28-Oic Acid, (2α,3β,4α,6β)-2,3,6,23-Tetrahydroxyurs-12-en-28-oic acid, 2,3,6,23-Tetrahydroxyurs-12-En-28-Oic Acid, 2α,3β,6β,23-Tetrahydroxy-urs-12-en-28-oic acid, 6β-Hydroxyasiatic acid, Brahmic acid, Cid 12073158, Madecassic acid, Nsc 88135, Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2alpha,3beta,4alpha,6beta)-, Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2α,3β,4α,6β)-, Urs-12-en-28-oic acid, 2α,3β,6β,23-tetrahydroxy-

Description

Applications 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.
References Wonh, J.H. et al.: Planta Med., 76, 251 (2010); Kwon, M.C. et al.: J. Biotechnol., 157, 100 (2012); Loiseau, A. et al.: Cosm. Toil., 115, 63 (2000);

• Brand: TRC

Chemical properties

• Molecular weight: 504.70
• Formula: C₃₀H₄₈O₆
• Purity: 97%
• Color/Form: Neat
• InChI: InChI=1S/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
• InChI key: InChIKey=PRAUVHZJPXOEIF-UQPQHHFRSA-N
• SMILES: C[C@@H]1C2C3=CCC4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)C5[C@H](O)C[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC[C@H]1C