A coumarin glycoside
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Fraxin

Item No. 28217

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-(β-D-glucopyranosyloxy)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one
CAS Number
524-30-1
Synonyms
  • Fraxetol 8-glucoside
  • Fraxoside
Molecular Formula
C16H18O10
Formula Weight
370.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: Partially solublePBS (pH 7.2): 2 mg/ml
λmax
229, 344 nm
SMILES
OC[C@H]1O[C@@H](OC2=C(O)C(OC)=CC(C=C3)=C2OC3=O)[C@H](O)[C@@H](O)[C@@H]1O
InChi Code
InChI=1S/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)15(11(7)20)26-16-13(22)12(21)10(19)8(5-17)24-16/h2-4,8,10,12-13,16-17,19-22H,5H2,1H3/t8-,10-,12+,13-,16+/m1/s1
InChi Key
CRSFLLTWRCYNNX-QBNNUVSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $121

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    10 mg

    $215

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    25 mg

    $477

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    50 mg

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    Product Description

    Fraxin is a coumarin glycoside that has been found in Fraxinus and has anti-inflammatory activity.1 It inhibits formation of 5-hydroxyeicosatetraenoic acid (5-HETE) from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in rat polymorphonuclear leukocytes when used at concentrations ranging from 1 to 1,000 µM in vitro.2 Fraxin inhibits production of nitric oxide (NO) in LPS-stimulated RAW 264.7 cells (IC50 = 84.5 µM).3 It also decreases LPS-induced TNF-α, IL-6, IL-1β, NF-ĸB, and NLRP3 expression in the lung in mouse models of acute lung injury and endotoxic shock when administered at doses ranging from 10 to 40 mg/kg.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, H., Xiao, B., Hao, Z., et al. Simultaneous determination of fraxin and its metabolite, fraxetin, in rat plasma by liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1017-1018, 70-74 (2016).

    2. Kimura, Y., Okuda, H., Arichi, S., et al. Inhibition of the formation of 5-hydroxy-6,8,11,14-eicosatetraenoic acid from arachidonic acid in polymorphonuclear leukocytes by various coumarins. Biochim. Biophys. Acta 834(2), 224-229 (1985).

    3. Kwon, J.-H., Kim, S.-B., Park, K.-H., et al. Antioxidative and anti-inflammatory effects of phenolic compounds from the roots of Ulmus macrocarpa. Arch. Pharm. Res. 34(9), 1459-1466 (2011).

    4. Li, W., Li, W., Yu, J., et al. Fraxin inhibits lipopolysaccharide-induced inflammatory cytokines and protects against endotoxic shock in mice. Fundam. Clin. Pharmacol. (2019).

    5. Li, W., Li, W., Zang, L., et al. Fraxin ameliorates lipopolysaccharide-induced acute lung injury in mice by inhibiting the NF-κB and NLRP3 signalling pathways. Int. Immunopharmacol. 67, 1-12 (2019).