methyl 2-oxo-2H-pyran-5-carboxylate

• ChemBase ID: 91002
• Molecular Formular: C7H6O4
• Molecular Mass: 154.12014
• Monoisotopic Mass: 154.02660867
• SMILES: o1cc(C(=O)OC)ccc1=O
• Canonical SMILES: COC(=O)c1ccc(=O)oc1
• InChI: InChI=1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3
• InChIKey: HHWWWZQYHPFCBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-oxo-2H-pyran-5-carboxylate
• IUPAC Traditional name: methyl 6-oxopyran-3-carboxylate
• Synonyms: Methyl coumalate; Methyl 2-oxo-2H-pyran-5-carboxylate 97%; Coumalic acid methyl ester; methyl 2-oxo-2H-pyran-5-carboxylate; 2-Oxo-2H-pyran-5-carboxylic Acid Methyl Ester; 5-(Carbomethoxy)-2-pyrone; 5-(Methoxycarbonyl)-2-pyrone; NSC 137387; NSC 34627; Methyl Coumalate; Methyl 2-pyrone-5-carboxylate; Methyl 2-oxo-2H-pyran-5-carboxylate; Methyl coumalate; 2-吡喃酮-5-甲酸甲酯; 2-氧-2H-吡喃-5-羧酸甲酯; 香豆灵酸甲酯

Database IDs

• CAS Number: 6018-41-3
• EC Number: 227-871-1
• MDL Number: MFCD00010120
• Beilstein Number: 126301
• Merck Index: 142557
• PubChem SID: 24855810; 162077706
• PubChem CID: 80113

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.56030375
• LogD (pH = 7.4): 0.56030375
• Log P: 0.56030375
• Molar Refractivity: 36.8638 cm^3
• Polarizability: 14.041528 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 65 - 67°C; 65-67 °C(lit.); 65-67°C; 68-72°C
• Boiling Point: 178-180 °C/60 mmHg(lit.); 178-180°C/60mm; 178-180°C/60mm
• Hydrophobicity(logP): -0.0030

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%; 98%
• Empirical Formula (Hill Notation): C7H6O4

DETAILS

Sigma Aldrich - 261432

Packaging
1, 10 g in glass bottle

Toronto Research Chemicals - M294530

α, β-Unsaturated ketone Methyl Coumalate showed cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2.

REFERENCES

• Sakagami, H., et al.: Anticancer Res., 16, 2635 (1996)
• Lee, K., et al.: Science, 196, 533 (1996)
• Ducki, S., et al.: Bioorg. Med. Chem. Lett., 8, 1051 (1996)
• Glaab, V., et al.: Mutat. Res., 497, 185 (1996)
• Murakami, A., et al.: Carcinogenesis, 23, 795