6-hydroxy-7-methoxy-2H-chromen-2-one

• ChemBase ID: 156122
• Molecular Formular: C10H8O4
• Molecular Mass: 192.16812
• Monoisotopic Mass: 192.04225874
• SMILES: COc1cc2c(ccc(=O)o2)cc1O
• Canonical SMILES: COc1cc2oc(=O)ccc2cc1O
• InChI: InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
• InChIKey: SYTYLPHCLSSCOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-7-methoxy-2H-chromen-2-one
• IUPAC Traditional name: 6-hydroxy-7-methoxychromen-2-one
• Synonyms: 7-Methoxyesculetin; Esculetin 7-methyl ether; Isoscopoletin; 6-Hydroxy-7-methoxycoumarin; Isoscopoletin

Database IDs

• CAS Number: 776-86-3
• EC Number: 212-282-4
• MDL Number: MFCD00016976
• Beilstein Number: 157280
• PubChem SID: 162250260; 24850702
• PubChem CID: 69894

CALCULATED PROPERTIES

• Acid pKa: 9.838875
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3221033
• LogD (pH = 7.4): 1.3205556
• Log P: 1.322123
• Molar Refractivity: 49.9927 cm^3
• Polarizability: 18.858894 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; methanol: soluble
• Apperance: Powder
• Fluorescence: λex 353 nm; λem 440 nm in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C10H8O4

DETAILS

Sigma Aldrich - 17795

Biochem/physiol Actions
Isoscopoletin is a coumarin that is produced in many plant species by the demethylation of scoparone. It inhibits proliferation of both control and multidrug resistant leukemia cell lines. It also inhibits proliferation of hepatitis B virus in cellular systems.