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Madecassic acid

Names

[ CAS No. ]:
18449-41-7

[ Name ]:
Madecassic acid

[Synonym ]:
Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2α,3β,5ξ,6β,9ξ,18ξ)-
Brahmanic acid
(2α,3β,5ξ,6β,9ξ,18ξ)-2,3,6,23-Tetrahydroxyurs-12-en-28-oic acid
6-Hydroxyasiatic acid
6BETA-HYDROXYASIATIC ACID
madecaic acid
(2α,3β,6β)-2,3,6,23-Tetrahydroxyurs-12-en-28-oic acid
madesica acid
MADESIC ACID
Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2α,3β,6β)-
Madecassicacid
Brahmsaeure
(1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-Trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylic acid
Hydroxy asiaticoside
Brahmic acid

Biological Activity

[Description]:

Madecassic acid is isolated from Centella asiatica (Umbelliferae). Madecassic acid has anti-inflammatory properties caused by iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-κB activation in RAW 264.7 macrophage cells[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related
Signaling Pathways >> Immunology/Inflammation >> NO Synthase
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

COX-2

TNF-α

IL-1β

IL-6


[References]

[1]. Won JH, et al. Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaBpathway in LPS-induced RAW 264.7 macrophage cells. Planta Med. 2010 Feb;76(3):251-7.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
641.7±55.0 °C at 760 mmHg

[ Melting Point ]:
270ºC (dec.)

[ Molecular Formula ]:
C30H48O6

[ Molecular Weight ]:
504.698

[ Flash Point ]:
355.9±28.0 °C

[ Exact Mass ]:
504.345093

[ PSA ]:
118.22000

[ LogP ]:
4.99

[ Vapour Pressure ]:
0.0±4.3 mmHg at 25°C

[ Index of Refraction ]:
1.591

[ Storage condition ]:
2-8°C

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

Synthetic Route

Precursor & DownStream

Precursor

DownStream


Related Compounds