Oroxylin A
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574127

CAS#: 480-11-5

Description: Oroxylin A is a flavonoid that inhibits decreases in cell viability and increases in nitric oxide (NO) production induced by polyinosinic-polycytidylic acid (poly(I:C)) macrophages. Oroxylin A 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. Oroxylin A inhibits hypoxia-induced migration and invasion of MCF-7, DU145, and HepG2 cells in wound healing and cell invasion assays, respectively. It is an inhibitor of the UDP-glucuronosyltransferase (UGT) isoform UGT1A1and P-glycoprotein. Oroxylin A increases the cytotoxicity of the P-glycoprotein substrate paraquat in MDR1-MDCKII cells and paclitaxel.


Chemical Structure

img
Oroxylin A
CAS# 480-11-5

Theoretical Analysis

MedKoo Cat#: 574127
Name: Oroxylin A
CAS#: 480-11-5
Chemical Formula: C16H12O5
Exact Mass: 284.07
Molecular Weight: 284.267
Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
25mg USD -2 2 Weeks
5g USD -2 2 Weeks
50mg USD 350 2 Weeks
100mg USD 550 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1750 2 Weeks
1g USD 2650 2 Weeks
2g USD 4650 2 Weeks
Bulk inquiry

Synonym: Oroxylin A

IUPAC/Chemical Name: 5,7-dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one

InChi Key: LKOJGSWUMISDOF-UHFFFAOYSA-N

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

SMILES Code: O=C1C2=C(O)C(OC)=C(O)C=C2OC(C3=CC=CC=C3)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Oroxylin A is a natural active flavonoid with strong anticancer effects.
In vitro activity: The data showed that oroxylin A remarkably reduced the generation of lactate and glucose uptake under hypoxia in HepG2 cells. Moreover, oroxylin A inhibited HIF-1α expression and its stability. The downstream targets (PDK1, LDHA, and HK II), as well as their mRNA levels were also suppressed by oroxylin A under hypoxia. The silencing or the overexpression of HIF-1α assays suggested that HIF-1α is required for metabolic effect of oroxylin A in HepG2 cells during hypoxia. Reference: Mol Carcinog. 2016 Aug;55(8):1275-89. https://pubmed.ncbi.nlm.nih.gov/26259145/
In vivo activity: Here, an AIH model of mouse was induced by Concanavalin A (Con A). It found that serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels were decreased in mice with the treatment of OA (oroxylin A). ELISA analysis of cytokines and chemokines suggested that OA reduced the expression of IL-6, IL-17A, CCL2, CXCL1 and CXCL10, but promoted the expression of IL-10 and TGF-β in mice. The proportion of Treg/Th17 detected by flow cytometry revealed that OA promoted the differentiation of Treg and inhibited the differentiation of Th17 both in the liver and spleen. Reference: Exp Anim. 2023 Mar 13. https://pubmed.ncbi.nlm.nih.gov/36927981/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 105.53
DMSO 39.6 139.42
DMSO:PBS (pH 7.2) (1:4) 0.2 0.70

Preparing Stock Solutions

The following data is based on the product molecular weight 284.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Dai Q, Yin Q, Wei L, Zhou Y, Qiao C, Guo Y, Wang X, Ma S, Lu N. Oroxylin A regulates glucose metabolism in response to hypoxic stress with the involvement of Hypoxia-inducible factor-1 in human hepatoma HepG2 cells. Mol Carcinog. 2016 Aug;55(8):1275-89. doi: 10.1002/mc.22369. Epub 2015 Aug 10. PMID: 26259145. 2. Wei L, Zhou Y, Qiao C, Ni T, Li Z, You Q, Guo Q, Lu N. Oroxylin A inhibits glycolysis-dependent proliferation of human breast cancer via promoting SIRT3-mediated SOD2 transcription and HIF1α destabilization. Cell Death Dis. 2015 Apr 9;6(4):e1714. doi: 10.1038/cddis.2015.86. PMID: 25855962; PMCID: PMC4650553. 3. Yang J, Li J, Wang J, Wu J, Yin L, Dou H, Hou Y. Oroxylin A relieves intrauterine adhesion in mice through inhibiting macrophage pyroptosis via SIRT3-SOD2-ROS pathway. Int Immunopharmacol. 2023 Mar 17;118:110023. doi: 10.1016/j.intimp.2023.110023. Epub ahead of print. PMID: 36934562. 4. Zhu J, Chen H, Cui J, Zhang X, Liu G. Oroxylin A inhibited autoimmune hepatitis-induced liver injury and shifted Treg/Th17 balance to Treg differentiation. Exp Anim. 2023 Mar 13. doi: 10.1538/expanim.22-0171. Epub ahead of print. PMID: 36927981.
In vitro protocol: 1. Dai Q, Yin Q, Wei L, Zhou Y, Qiao C, Guo Y, Wang X, Ma S, Lu N. Oroxylin A regulates glucose metabolism in response to hypoxic stress with the involvement of Hypoxia-inducible factor-1 in human hepatoma HepG2 cells. Mol Carcinog. 2016 Aug;55(8):1275-89. doi: 10.1002/mc.22369. Epub 2015 Aug 10. PMID: 26259145. 2. Wei L, Zhou Y, Qiao C, Ni T, Li Z, You Q, Guo Q, Lu N. Oroxylin A inhibits glycolysis-dependent proliferation of human breast cancer via promoting SIRT3-mediated SOD2 transcription and HIF1α destabilization. Cell Death Dis. 2015 Apr 9;6(4):e1714. doi: 10.1038/cddis.2015.86. PMID: 25855962; PMCID: PMC4650553.
In vivo protocol: 1. Yang J, Li J, Wang J, Wu J, Yin L, Dou H, Hou Y. Oroxylin A relieves intrauterine adhesion in mice through inhibiting macrophage pyroptosis via SIRT3-SOD2-ROS pathway. Int Immunopharmacol. 2023 Mar 17;118:110023. doi: 10.1016/j.intimp.2023.110023. Epub ahead of print. PMID: 36934562. 2. Zhu J, Chen H, Cui J, Zhang X, Liu G. Oroxylin A inhibited autoimmune hepatitis-induced liver injury and shifted Treg/Th17 balance to Treg differentiation. Exp Anim. 2023 Mar 13. doi: 10.1538/expanim.22-0171. Epub ahead of print. PMID: 36927981.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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).