1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one

• ChemBase ID: 154822
• Molecular Formular: C16H14O4
• Molecular Mass: 270.27996
• Monoisotopic Mass: 270.08920893
• SMILES: COc1cc(cc(c1C(=O)/C=C/c1ccccc1)O)O
• Canonical SMILES: COc1cc(O)cc(c1C(=O)/C=C/c1ccccc1)O
• InChI: InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3
• InChIKey: NYSZJNUIVUBQMM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one; (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
• IUPAC Traditional name: cardamomin; cardamonin
• Synonyms: (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one; (8CI); Alpinetin chalcone; (E)-2′,4′-Dihydroxy-6′-methoxy-chalcone; Cardamonin; 2',4'-Dihydroxy-6'-methoxychalcone

Database IDs

• CAS Number: 19309-14-9
• MDL Number: MFCD00238554
• PubChem SID: 162248960
• PubChem CID: 641785

CALCULATED PROPERTIES

• Acid pKa: 7.1982746
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.7669728
• LogD (pH = 7.4): 3.3569512
• Log P: 3.7755234
• Molar Refractivity: 77.302 cm^3
• Polarizability: 29.05835 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: Orange powder; yellow powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 99.0
• Empirical Formula (Hill Notation): C16 H14 O4

DETAILS

Sigma Aldrich - C8249

Biochem/physiol Actions
Cardamonin is a calchone from Aplinia species (zingiberaceous plant species). Cardamonin inhibits pigmentation in melanocytes through suppression of Wnt/b-catenin signaling pathway. Cardamonin suppressed Wnt/b-catenin signaling by a mechanism involving proteasome-mediated degradation of b-catenin (GSK-3b-independent pathway). Research has shown that Cardamonin possesses anti-inflammatory activity via suppression of NF-kB nuclear translocation and Ik-Ba phosphorylation.