A flavonoid with diverse biological activities
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Isomer(s)
35229Genkwanin
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Oroxylin A

Item No. 27363

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,7-dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one
CAS Number
480-11-5
Synonyms
  • 6-Methoxybaicalein
Molecular Formula
C16H12O5
Formula Weight
284.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml
λmax
215, 273, 321 nm
SMILES
O=C1C2=C(O)C(OC)=C(O)C=C2OC(C3=CC=CC=C3)=C1
InChi Code
InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3
InChi Key
LKOJGSWUMISDOF-UHFFFAOYSA-N
Origin
Plant/Oroxylum indicum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    1 mg

    $61

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    5 mg

    $213

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    10 mg

    $303

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    25 mg

    $605

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    Cayman Chemical
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    Product Description

    Oroxylin A is a flavonoid that has been found in S. radix and has diverse biological activities.1,2,3 It inhibits decreases in cell viability and increases in nitric oxide (NO) production induced by polyinosinic-polycytidylic acid (poly(I:C)) in RAW 264.7 macrophages when used at concentrations ranging from 5 to 25 μM.2 Oroxylin A (10-50 μM) also inhibits poly(I:C)-induced increases in IL-1α, IL-1β, GM-CSF, IL-6, IL-10, monocyte chemoattractant protein-1 (MCP-1), and TNF-α production in RAW 264.7 cells. Oroxylin A (10 and 20 μM) inhibits hypoxia-induced migration and invasion of MCF-7, DU145, and HepG2 cells in wound healing and cell invasion assays, respectively.3 It is an inhibitor of the UDP-glucuronosyltransferase (UGT) isoform UGT1A1 (IC50 = 9.14 μM) and P-glycoprotein (IC50 = 78.3 μM).4,5 Oroxylin A increases the cytotoxicity of the P-glycoprotein substrate paraquat in MDR1-MDCKII cells and paclitaxel (Item No. 10461) in MX-1 and MX-1/T cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lu, L., Guo, Q., and Zhao, L. Overview of oroxylin A: A promising flavonoid compound. Phytother. Res. 30(11), 1765-1774 (2016).

    2. Lee, J.Y., and Park, W. Anti-inflammatory effects of oroxylin A on RAW 264.7 mouse macrophages induced with polyinosinic-polycytidylic acid. Exp. Ther. Med. 12(1), 151-156 (2016).

    3. Cheng, Y., Zhao, K., Li, G., et al. Oroxylin A inhibits hypoxia-induced invasion and migration of MCF-7 cells by suppressing the Notch pathway. Anticancer Drugs 25(7), 778-789 (2014).

    4. Liu, X.Y., Lv, X., Wang, P., et al. Inhibition of UGT1A1 by natural and synthetic flavonoids. Int. J. Biol. Macromol. 126, 653-661 (2019).

    5. Bai, J., Zhao, S., Fan, X., et al. Inhibitory effects of flavonoids on P-glycoprotein in vitro and in vivo: Food/herb-drug interactions and structure-activity relationships. Toxicol. Appl. Pharmacol. 369, 49-59 (2019).