4-oxo-4H-pyran-2,6-dicarboxylic acid

• ChemBase ID: 126491
• Molecular Formular: C7H4O6
• Molecular Mass: 184.10306
• Monoisotopic Mass: 184.00078785
• SMILES: O=c1cc(oc(C(=O)O)c1)C(=O)O
• Canonical SMILES: OC(=O)c1oc(cc(=O)c1)C(=O)O
• InChI: InChI=1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)
• InChIKey: PBAYDYUZOSNJGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4H-pyran-2,6-dicarboxylic acid
• IUPAC Systematic name: 4-Oxo-4H-pyran-2,6-dicarboxylic acid
• IUPAC Traditional name: 4-oxo-4H-pyran-2,6-dicarboxylic acid; compound XI*
• Synonyms: 4-Oxo-4H-pyran-2,6-dicarboxylic acid; Chelidonic acid; 4-Oxo-4H-pyran-2,6-dicarboxylic acid; gamma-Pyrone-2,6-dicarboxylic acid; Jerva acid; Jervaic acid; Jervasic acid; γ-Pyrone-2,6-dicarboxylic acid; Chelidonic acid; 4-氧代-4H-吡喃-2,6-二甲酸; 白屈菜酸

Database IDs

• CAS Number: 99-32-1
• EC Number: 202-749-0
• MDL Number: MFCD00006577
• Beilstein Number: 163607
• PubChem SID: 162220824; 24863888; 24853471
• PubChem CID: 7431
• Chemspider ID: 7153
• Wikipedia Title: Chelidonic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.8497183
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -6.1579156
• LogD (pH = 7.4): -7.1843815
• Log P: -0.15356745
• Molar Refractivity: 40.5461 cm^3
• Polarizability: 14.548089 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 257°C (decomp.); 265 °C (dec.)(lit.)

Safety Information

• RTECS: UP7350000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (T); 95+%; 98%
• Grade: purum
• Ignition Residue: ≤0.5%
• Biological Source: Occurs in numerous plants e.g. Veratrum album, Chelidonium majus . Detected chromatographically in 688 out of 1143 investigated plants (Ramstad)
• Application(s): Antianaphylactic
• Quality: anhydrous
• Empirical Formula (Hill Notation): C7H4O6

DETAILS

Sigma Aldrich - 382272

Packaging
5, 25 g in glass bottle

REFERENCES

• Sadtler Standard C-13 NMR Spectra, 11425, (cmr)
• Sadtler Standard Proton NMR Spectra, 47967, (pmr)
• Org. Synth., Coll. Vol., 2, 1943, 126, (synth)
• Ramstad, E., Pharm. Acta Helv., 1953, 28, 45, (occur)
• Bohm, B.A., Arch. Biochem. Biophys., 1966, 115, 181, (biosynth)
• Garkusha, G.A. et al., Zh. Org. Khim., 1967, 3, 1699
• Bough, W.A. et al., Phytochemistry, 1972, 11, 209, (isol, struct)
• Gagan, J.M.F. et al., Educ. Chem., 1976, 13, 140, (synth, isol)
• El-Kerdawy, M.M. et al., Indian J. Chem., Sect. B, 1979, 18, 168, (diamide)
• Ashok, D. et al., Indian J. Chem., Sect. B, 1988, 27, 862, (isol)
• Horvath, G. et al., Synth. Commun., 1999, 29, 3719-3731, (synth)
• Shen, Z.-W. et al., Phytochemistry, 2001, 57, 33-42, (biosynth)