(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one

• ChemBase ID: 73154
• Molecular Formular: C21H20O6
• Molecular Mass: 368.3799
• Monoisotopic Mass: 368.12598836
• SMILES: c1(c(ccc(c1)/C=C/C(=O)/C=C(/C=C/c1ccc(c(c1)OC)O)\O)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=C/C(=O)/C=C/c2ccc(c(c2)OC)O)/O)ccc1O
• InChI: InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-
• InChIKey: ZIUSSTSXXLLKKK-KOBPDPAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
• IUPAC Traditional name: golden seal; tumeric; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
• Synonyms: Diferuloylmethane; Natural Yellow 3; C.I. 75300; Curcumin; Curcumin; C.I. 753000; (E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; Turmeric yellow

Database IDs

• CAS Number: 458-37-7
• EC Number: 207-280-5
• PubChem SID: 162038074
• PubChem CID: 5281767

CALCULATED PROPERTIES

• Acid pKa: 8.789717
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.7588172
• LogD (pH = 7.4): 3.7416093
• Log P: 3.7590394
• Molar Refractivity: 106.1263 cm^3
• Polarizability: 39.174744 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Orange powder

Safety Information

• Storage Condition: 0°C; -20°C
• RTECS: MI5230000

Product Information

• Salt Data: Free Base

DETAILS

MP Biomedicals - 02190313

C.I. 75300
Natural Yellow 3
Crystalline

Selleck Chemicals - S1848

Biological Activity:
Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). The curcuminoids are polyphenols and are responsible for the yellow color of turmeric. Curcumin can exist in at least two tautomeric forms, keto and enol. The enol form is more energetically stable in the solid phase and in solution. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Curcumin