O9890

5Z-7-Oxozeaenol

≥98% (HPLC), powder, TAK1 inhibitor

• Synonym(s): C 292, F 152, FR148083, L 783279, LL-Z1640-2
• Empirical Formula (Hill Notation): C₁₉H₂₂O₇
• CAS Number: 253863-19-3
• Molecular Weight: 362.37
• MDL number: MFCD12912700
• UNSPSC Code: 12352200
• PubChem Substance ID: 329818946
• NACRES: NA.77

Properties

• product name: 5Z-7-Oxozeaenol, ≥98% (HPLC)
• Assay: ≥98% (HPLC)
• form: powder
• color: white to off-white
• solubility: DMSO: >10 mg/mL
• storage temp.: 2-8°C
• SMILES string: COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1
• InChI: 1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1
• InChI key: NEQZWEXWOFPKOT-BYRRXHGESA-N

Description

Application

5Z-7-Oxozeaenol has been used:

• as transforming growth factor β-activated kinase 1 (TAK1) inhibitor to treat human colon cancer cells
• as TAK1-specific inhibitor to provide intraperitoneal injection to mice for aortic banding
• as TAK1 inhibitor to treat cells for luciferase reporter assay
• to test growth and differentiation factor 2 (GDF2)-mediated anoikis

Biochem/physiol Actions

5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC₅₀ = 80 nM), TAK1 (MEKK7), MKK7, and MEK1, which all contain a common cysteine residue in the ATP-binding site. 5Z-7-oxozeaenol has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.

The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the MAPKKKs and MAPKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable