196322

Baicalein

A cell-permeable flavone that inhibits the activity of 12-lipoxygenase (IC₅₀= 120 nM) and reverse transcriptase.

• Synonym(s): Baicalein, 5,6,7-Trihydroxyflavone
• Empirical Formula (Hill Notation): C₁₅H₁₀O₅
• CAS Number: 491-67-8
• Molecular Weight: 270.24
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00017459
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 942
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: yellow
• solubility: DMSO: 20 mg/mL, acetone: soluble
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: O1c2c(c(c(c(c2)O)O)O)C(=O)C=C1c3ccccc3
• InChI: 1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
• InChI key: FXNFHKRTJBSTCS-UHFFFAOYSA-N

Description

General description

A cell-permeable flavone that inhibits the activity of 12-lipoxygenase (IC₅₀ = 120 nM) and reverse transcriptase. Protects cortical neurons from β-amyloid induced toxicity. Reduces leukotriene biosynthesis and inhibits the release of lysosomal enzymes. Also inhibits cellular Ca²⁺ uptake and mobilization, and adjuvant-induced arthritis. Reported to inhibit microsomal lipid peroxidation by forming an iron-baicalein complex. Inhibits topoisomerase II and induces cell death in hepatocellular carcinoma cell lines. Potentiates contractile responses to nerve stimulation. Inhibits protein tyrosine kinase and PMA-stimulated protein kinase C.

Biochem/physiol Actions

Primary Target
12-lipoxygenase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 120 nM against 12-lipoxygenase

Cell permeable: yes

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Leabeau, A., et al. 2001. Neuroreport12, 2199.
Gao, D., et al. 1996. Biochem. Mol. Biol. Int. 39, 215.
Matsuzaki, Y., et al. 1996. Jpn. J. Cancer Res. 87, 170.
Huang, H.C., et al. 1994. Eur. J. Pharmacol. 268, 73.
Butenko, I.G., et al. 1993. Agents Actions 39, C49.
Abe, K., et al. 1990. Chem. Pharm. Bull.38, 209.
Kimura, Y., et al. 1987. Biochim. Biophys. Acta922, 278.
Sekiya, K., and Okuda, H. 1982. Biochem. Biophys. Res. Commun.105, 1090.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Safety Information

• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable