5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

• ChemBase ID: 154828
• Molecular Formular: C18H16O7
• Molecular Mass: 344.31544
• Monoisotopic Mass: 344.08960285
• SMILES: COc1ccc(cc1O)c1cc(=O)c2c(o1)cc(c(c2O)OC)OC
• Canonical SMILES: COc1cc2oc(cc(=O)c2c(c1OC)O)c1ccc(c(c1)O)OC
• InChI: InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
• InChIKey: KLAOKWJLUQKWIF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
• IUPAC Traditional name: eupatorin
• Synonyms: 3′,5-Dihydroxy-4′,6,7-trimethoxyflavone; 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one; 6-Methoxyluteolin 4′,7-dimethyl ether; NSC 106402; Eupatorin; Eupatorin; 3',5-Dihydroxy-4',6,7-trimethoxyflavone; 3',5-Dihydroxy-4',6,7-trimethoxyflavone; 3,5-二羟基-4,6,7-三甲氧基黄酮

Database IDs

• CAS Number: 855-96-9
• EC Number: 000-000-0
• MDL Number: MFCD00016929
• Beilstein Number: 1355109
• Merck Index: 143901
• PubChem SID: 162248966
• PubChem CID: 97214

CALCULATED PROPERTIES

• Acid pKa: 7.926436
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.5356312
• LogD (pH = 7.4): 2.424569
• Log P: 2.5372407
• Molar Refractivity: 90.3226 cm^3
• Polarizability: 34.0988 Å^3
• Polar Surface Area: 94.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: light tan powder; Yellow powder
• Melting Point: 190-192°C

Safety Information

• European Hazard Symbols: Toxic (T); Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 25; 36/37/38
• Safety Statements: 26-37; 45
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P301 + P310
• Storage Temperature: room temp

Product Information

• Purity: ≥97% (HPLC); 97%
• Empirical Formula (Hill Notation): C18H16O7

DETAILS

Sigma Aldrich - E4660

Biochem/physiol Actions
Eupatorin acts as an antiproliferative in cells expressing the CYP1A- family. It induces G2/M block follow by apoptosis in cells expressing the CYP1A- family. It also functions as an anti-inflammatory.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E4660.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.