5-[(acetyloxy)methyl]furan-2-carboxylic acid

• ChemBase ID: 159034
• Molecular Formular: C8H8O5
• Molecular Mass: 184.14612
• Monoisotopic Mass: 184.03717336
• SMILES: c1(ccc(o1)COC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)OCc1ccc(o1)C(=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)
• InChIKey: VEHIMKWMEKVUMD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(acetyloxy)methyl]furan-2-carboxylic acid
• IUPAC Traditional name: 5-[(acetyloxy)methyl]furan-2-carboxylic acid
• Synonyms: 5-(Acetoxymethyl)-2-furoic Acid; Acetyl Sumiki's Acid; 5-(Hydroxymethyl)-2-furoic Acid Acetate; 5-Acetoxymethyl-2-furancarboxylic Acid

Database IDs

• CAS Number: 90345-66-7
• PubChem SID: 162253169
• PubChem CID: 10330015

CALCULATED PROPERTIES

• Acid pKa: 3.1123564
• 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

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 107-109°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - 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)