(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

• ChemBase ID: 126172
• Molecular Formular: C19H16O4
• Molecular Mass: 308.32794
• Monoisotopic Mass: 308.10485899
• SMILES: c1cc(ccc1/C=C/C(=O)CC(=O)/C=C/c1ccc(cc1)O)O
• Canonical SMILES: O=C(CC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
• InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2
• InChIKey: PREBVFJICNPEKM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; 1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• IUPAC Traditional name: bisdemethoxycurcumin; 1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• Synonyms: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; Bisdemethoxycurcumin; (1E,6E)-1,7-Bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; Curcumin III; bis(4-hydroxycinnamoyl)methanI; didemethoxycurcumiI; bisdemethoxycurcumiI; Bis(p-hydroxycinnamoyl)methanI; NSC687839; Bis-desmethoxycurcumin; (E,E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; Bisdesmethoxycurcumin; Didemethoxycurcumin

Database IDs

• CAS Number: 24939-16-0; 33171-05-0
• MDL Number: MFCD03419284
• Beilstein Number: 3149384
• PubChem SID: 162220513
• PubChem CID: 5315472
• Chemspider ID: 4474770
• Wikipedia Title: Bis-desmethoxycurcumin

CALCULATED PROPERTIES

• Acid pKa: 8.690004
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.439588
• LogD (pH = 7.4): 4.4179583
• Log P: 4.439867
• Molar Refractivity: 90.8842 cm^3
• Polarizability: 33.825954 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: solid
• Melting Point: 91–3℃
• Density: 1.285

Safety Information

• German water hazard class: 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥98% (HPLC); 97%
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C19H16O4

DETAILS

Sigma Aldrich - B6938

Biochem/physiol Actions
Bisdemethoxycurcumin (BDMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. BDMC shares similar anti-inflammatory properties with demethoxycurcumin. It inhibits LPS-induced nitric oxide (NO) production and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. BDMC also displays unique properties in that it enhances Abeta clearance by upregulating expression MGAT3 and TLR genes. BDMC potently inhibits AKR1B10.