Fraxin

Names

[ CAS No. ]:
524-30-1

[ Name ]:
Fraxin

[Synonym ]:
7,8-Dihydroxy-6-methoxycoumarin-8-b-D-glucoside
7-Hydroxy-6-methoxy-2-oxo-2H-chromen-8-yl β-D-glucopyranoside
8-(Glucosyloxy)-6-methoxyumbelliferone
UNII-V7M270Y072
2H-1-Benzopyran-2-one, 8-(β-D-glucopyranosyloxy)-7-hydroxy-6-methoxy-
7-Hydroxy-6-méthoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-2H-chromén-2-one
7-Hydroxy-6-methoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2H-chromen-2-on
8-(β-D-Glucopyranosyloxy)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one
Fraxin
8-(b-D-Glucopyranosyloxy)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one
Fraxoside
Fraxetin-8-O-glucoside
Fraxetin-8-glucoside
Paviin
7-Hydroxy-6-methoxy-2-oxo-2H-chromen-8-yl-β-D-glucopyranoside
Fraxetol 8-glucoside
7-Hydroxy-6-methoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2H-chromen-2-one

Biological Activity

[Description]:

Fraxin isolated from Acer tegmentosum, F. ornus or A. hippocastanum, is a glucoside of fraxetin and reported to exert potent anti-oxidative stress action[1], anti-inflammatory and antimetastatic properties. Fraxin shows its antioxidative effect through inhibition of cyclo AMP phosphodiesterase enzyme[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Inflammation/Immunology

Natural Products >> Saccharides and Glycosides

[Target]

Cyclo AMP phosphodiesterase enzyme[2].

[In Vitro]

Fraxin (100 μM) is non-cytotoxic on Hep G2 cells. Fraxin at non-cytotoxic concentrations significantly decreases the t-BHP-induced ROS generation in a dose-dependent manner[1]. Fraxin (0.5 mM) shows free radical scavenging effect at high concentration and cell protective effect against H2O2-mediated oxidative stress[2].

[In Vivo]

Fraxin (50 mg/kg, p.o.) significantly blocks the CCl4-induced elevation of ALT and AST. Fraxin (10 and 50 mg/kg, p.o.) significantly reduces the GSSG levels (1.7±0.3 and 1.5±0.2 nM/g liver, respectively) compared with the GSSG levels of the CCl4-treated group[1].

[References]

[1]. Fraxin (50 mg/kg, p.o.) significantly blocks the CCl₄-induced elevation of ALT and AST. Fraxin (10 and 50 mg/kg, p.o.) significantly reduces the GSSG levels (1.7±0.3 and 1.5±0.2 nM/g liver, respectively) compared with the GSSG levels of the CCl₄-treated group^[1].

[2]. Whang WK, et al. Natural compounds,fraxin and chemicals structurally related to fraxin protect cells from oxidative stress. Exp Mol Med. 2005 Oct 31;37(5):436-46.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
722.2±60.0 °C at 760 mmHg

[ Melting Point ]:
205-208ºC

[ Molecular Formula ]:
C₁₆H₁₈O₁₀

[ Molecular Weight ]:
370.308

[ Flash Point ]:
267.1±26.4 °C

[ Exact Mass ]:
370.089996

[ PSA ]:
159.05000

[ LogP ]:
-1.93

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.664

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ3091000

Precursor & DownStream

Precursor

DownStream

Articles

Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm.

J. Med. Microbiol. 60(Pt 12) , 1827-34, (2011)

The objective of this study was to screen for novel quorum-sensing inhibitors (QSIs) from traditional Chinese medicines (TCMs) that inhibit bacterial biofilm formation. Six of 46 active components fou...

[Studies on chemical constituents from stem barks of Fraxinus paxiana].

Zhongguo Zhong Yao Za Zhi 33(16) , 1990-3, (2008)

To investigate the chemical constituents of Fraxinus paxiana.The chemical constituents were isolated and purified by chromatographic techniques and the structures of the compounds were identified with...

[Coumarins from branch of Fraxinus sieboldiana and their antioxidative activity].

Zhongguo Zhong Yao Za Zhi 33(14) , 1708-10, (2008)

To investigate the chemical constituents from the branch of Fraxinus sieboldiana, and evaluate their antioxidative activity.The chemical constituents were isolated and purified by chromatographic tech...