5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid

• ChemBase ID: 141119
• Molecular Formular: C6H4O5
• Molecular Mass: 156.09296
• Monoisotopic Mass: 156.00587323
• SMILES: c1c(=O)c(coc1C(=O)O)O
• Canonical SMILES: OC(=O)c1occ(c(=O)c1)O
• InChI: InChI=1S/C6H4O5/c7-3-1-5(6(9)10)11-2-4(3)8/h1-2,8H,(H,9,10)
• InChIKey: UUUICOMMFFTCHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid
• IUPAC Traditional name: 5-hydroxy-4-oxopyran-2-carboxylic acid
• Synonyms: 5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid; 2-Carboxy-5-hydroxy-4-pyrone; Comenic acid; 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic acid; 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic Acid; 5-Hydroxy-4-pyrone-2-carboxylic Acid; Comenic Acid; 2-羧基-5-羟基-4-吡喃酮; 考闷酸; 5-羟基-4-氧代-4H-吡喃-2-羧酸

Database IDs

• CAS Number: 499-78-5
• EC Number: 207-891-7
• MDL Number: MFCD03085981
• PubChem SID: 162235354; 24885670
• PubChem CID: 68139

CALCULATED PROPERTIES

• Acid pKa: 2.3809426
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.0050437
• LogD (pH = 7.4): -3.5509288
• Log P: -0.028018292
• Molar Refractivity: 35.2082 cm^3
• Polarizability: 12.713746 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 284-294 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C6H4O5

DETAILS

Sigma Aldrich - 681970

Application
Building block for an intramolecular olefin-α-pyrone cycloaddition providing the colchicine ring skeleton.1
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - C643500

Used in the regenerative anti-inflammatory composition.

REFERENCES

• Molenda, J., et al.: J. Med. Chem., 37, 93 (1994)
• Bransova, J., et al.: Anticancer Res., 17, 1175 (1994)
• Ozturk, G., et al.: Eur. J. Med. Chem., 37, 829 (1994)