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

• ChemBase ID: 125734
• Molecular Formular: C14H10O5
• Molecular Mass: 258.2262
• Monoisotopic Mass: 258.05282342
• SMILES: Cc1cc(cc2c1c1cc(cc(c1c(=O)o2)O)O)O
• Canonical SMILES: Oc1cc(C)c2c(c1)oc(=O)c1c2cc(O)cc1O
• InChI: InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
• InChIKey: CEBXXEKPIIDJHL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
• IUPAC Traditional name: alternariol
• Synonyms: Alternariol; NSC 638263; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; Alternariol from Alternaria sp.

Database IDs

• CAS Number: 641-38-3
• MDL Number: MFCD00133068
• PubChem SID: 24890529; 162220084
• PubChem CID: 5359485
• CHEBI ID: 64983
• CHEMBL: 519982
• Chemspider ID: 4514301
• KEGG ID: C16838
• Unique Ingredient Identifier: KN9L4260JW
• Wikipedia Title: Alternariol

CALCULATED PROPERTIES

• Acid pKa: 7.63033
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.1748657
• LogD (pH = 7.4): 2.9663825
• Log P: 3.178053
• Molar Refractivity: 67.923 cm^3
• Polarizability: 26.691673 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: HP8757000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 28-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• 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 3462 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ~96%

DETAILS

Toronto Research Chemicals - A575760

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)