3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one

• ChemBase ID: 133565
• Molecular Formular: C15H12O5
• Molecular Mass: 272.25278
• Monoisotopic Mass: 272.06847348
• SMILES: Cc1cc(cc2c1c1cc(cc(c1c(=O)o2)O)OC)O
• Canonical SMILES: COc1cc(O)c2c(c1)c1c(C)cc(cc1oc2=O)O
• InChI: InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3
• InChIKey: LCSDQFNUYFTXMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one
• IUPAC Traditional name: 3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
• Synonyms: Alternariol monomethyl ether from Alternaria alternata (tenuis); 3,7(3,9 or 7,9)-Dihydroxy-9(7 or 3)-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; Alternariol Monomethyl Ether

Database IDs

• CAS Number: 26894-49-5
• MDL Number: MFCD00058532
• PubChem SID: 162227842
• PubChem CID: 5360741

CALCULATED PROPERTIES

• Acid pKa: 7.7084627
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.3212848
• LogD (pH = 7.4): 3.1504784
• Log P: 3.323947
• Molar Refractivity: 72.4053 cm^3
• Polarizability: 28.600874 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 61-26/27/28
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H360
• GHS Precautionary statements: P201-P260-P264-P280-P284-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

DETAILS

Toronto Research Chemicals - A575770

An alternaria mycotoxin and genotoxin, found in common edible crops. It inhibits the activity of various DNA-topoisomerases, increasing he rate of DNA strand breaks.

REFERENCES

• Asam, S., et al.: J. Agric. Food Chem., 57, 5152 (2009)
• Fehr, M., et al.: Mol. Nut. Food Res., 53, 441 (2009)
• Tiemann, U., et al.: Toxicol. Lett., 186, 139 (2009)