1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

• ChemBase ID: 126911
• Molecular Formular: C20H18O5
• Molecular Mass: 338.35392
• Monoisotopic Mass: 338.11542368
• SMILES: COc1cc(ccc1O)/C=C/C(=O)CC(=O)/C=C/c1ccc(cc1)O
• Canonical SMILES: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(cc2)O)ccc1O
• InChI: InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3
• InChIKey: HJTVQHVGMGKONQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• IUPAC Traditional name: 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• Synonyms: Curcumin II; Desmethoxycurcumin; Monodemethoxycurcumin; Desmethoxycurcumin; (E,E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; Demethoxycurcumin; 1-(4-Hydroxy-3-methoxyphenyl)-7-(p-hydroxyphenyl)-1,6-heptadiene-3,5-dione; (1E,6E)-1-(4-Hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; Demethoxy Curcumin

Database IDs

• CAS Number: 22608-11-3
• MDL Number: MFCD03427310
• PubChem SID: 162221237
• PubChem CID: 5469424
• Chemspider ID: 39463964
• Wikipedia Title: Desmethoxycurcumin

CALCULATED PROPERTIES

• Acid pKa: 8.837232
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.281997
• LogD (pH = 7.4): 4.2665524
• Log P: 4.282196
• Molar Refractivity: 97.3474 cm^3
• Polarizability: 36.34574 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 2
• Risk Statements: 50
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥98% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C20H18O5

DETAILS

Toronto Research Chemicals - D230815

The demethoxy derivative of Curcumin (C838500) that regulates anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. It attenuates the Wnt/β-catenin pathway through down-regulation of the transcriptional coactivator p300.

REFERENCES

• Ryu, M.J. et al.: Biochem. Biophys. Res. Comm., 377, 1304 (2008)
• Sandur, S.K. et al.: Carcinogenesis, 28, 1765 (2008)
• Huang, T. et al.: J. Agric. Food. Chem., 58, 10639 (2008)