1,7-bis(3,4-dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione

• ChemBase ID: 154751
• Molecular Formular: C25H28O6
• Molecular Mass: 424.48622
• Monoisotopic Mass: 424.18858862
• SMILES: CC(C(=O)/C=C/c1cc(c(cc1)OC)OC)(C(=O)/C=C/c1cc(c(cc1)OC)OC)C
• Canonical SMILES: COc1cc(/C=C/C(=O)C(C(=O)/C=C/c2ccc(c(c2)OC)OC)(C)C)ccc1OC
• InChI: InChI=1S/C25H28O6/c1-25(2,23(26)13-9-17-7-11-19(28-3)21(15-17)30-5)24(27)14-10-18-8-12-20(29-4)22(16-18)31-6/h7-16H,1-6H3
• InChIKey: VMMZAMVBGQWOHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,7-bis(3,4-dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione
• IUPAC Traditional name: 1,7-bis(3,4-dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione
• Synonyms: (E,E)-1,7-Bis(3,4-dimethoxyphenyl)-4,4-dimethyl-1,6-heptadiene-3,5-dione; Tetramethylcurcumin; FLLL31

Database IDs

• CAS Number: 52328-97-9
• MDL Number: MFCD19443859
• PubChem SID: 162248889
• PubChem CID: 11487078

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 5.515313
• LogD (pH = 7.4): 5.515313
• Log P: 5.515313
• Molar Refractivity: 121.8507 cm^3
• Polarizability: 46.374866 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C25H28O6

DETAILS

Sigma Aldrich - F9057

Biochem/physiol Actions
FLLL31 selectively binds to Janus kinase 2 and the STAT3 Src homology-2 (SH2) domain, effective inhibitors of STAT3 phosphorylation. STAT3 plays a critical role in early embryogenesis, but is largely dispensable in normal adult cells and tissues. On the other hand the JAK2/STAT3 signaling pathway is persistently activated in great number of human solid and blood cancers. Such activation is commonly associated with a worse prognosis. FLLL31 is a curcumin derivative locked in diketone-tautomeric form, which supposedly improves binding to SH2 domain. The compound inhibits JAK2 kinase activity and prevents STAT3 phosphorylation. FLLK31 is a potent and selective inhibitor of the STAT3 signaling pathway.