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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.