5-[(acetyloxy)(13C)methyl](2,3,4,5-13C4)furan-2-carboxylic acid

• ChemBase ID: 159035
• Molecular Formular: C8H8O5
• Molecular Mass: 190.10204903
• Monoisotopic Mass: 190.05730238
• SMILES: [13c]1([13cH][13cH][13c](o1)[13CH2]OC(=O)C)[13C](=O)O
• Canonical SMILES: CC(=O)O[13CH2][13c]1[13cH][13cH][13c](o1)[13C](=O)O
• InChI: InChI=1S/C8H8O5/c1-5(9)12-4-6-2-3-7(13-6)8(10)11/h2-3H,4H2,1H3,(H,10,11)/i2+1,3+1,4+1,6+1,7+1,8+1
• InChIKey: VEHIMKWMEKVUMD-BOCFXHSMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(acetyloxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)furan-2-carboxylic acid
• IUPAC Traditional name: 5-[(acetyloxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)furan-2-carboxylic acid
• Synonyms: 5-(Acetoxymethyl)-2-furoic Acid-13C6; Acetyl Sumiki's Acid-13C6; 5-(Hydroxymethyl)-2-furoic Acid Acetate-13C6; 5-Acetoxymethyl-2-furancarboxylic Acid-13C6

Database IDs

• PubChem SID: 162253170
• PubChem CID: 71312777

CALCULATED PROPERTIES

• Acid pKa: 3.1123526
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.0743186
• LogD (pH = 7.4): -3.174781
• Log P: 0.28485215
• Molar Refractivity: 41.55 cm^3
• Polarizability: 16.011623 Å^3
• Polar Surface Area: 76.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A167522

Labelled 5-Acetoxymethyl-2-furancarboxylic Acid (A167520). Used in the preparation of 3-tetrahydrofurylcephem-3-carboxylates and analogs as antibiotics.

REFERENCES

• Jadulco, R., et al.: J. Nat. Prod., 64, 527 (2001)