2-hydroxy(1,2,3,4-13C4)butanedioic acid

• ChemBase ID: 172506
• Molecular Formular: C4H6O5
• Molecular Mass: 138.05805935
• Monoisotopic Mass: 138.03494264
• SMILES: [13CH2]([13CH](O)[13C](=O)O)[13C](=O)O
• Canonical SMILES: O[13C](=O)[13CH2][13CH]([13C](=O)O)O
• InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1,2+1,3+1,4+1
• InChIKey: BJEPYKJPYRNKOW-JCDJMFQYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy(1,2,3,4-^1^3C₄)butanedioic acid
• IUPAC Traditional name: 2-hydroxy(1,2,3,4-^1^3C₄)butanedioic acid
• Synonyms: 2-Hydroxybutanedioic Acid-13C4; Malic Acid-13C4; (+/-)-Malic Acid-13C4; 2-Hydroxyethane-1,2-dicarboxylic Acid-13C4; 2-Hydroxysuccinic Acid-13C4; DL-Malic Acid-13C4; Deoxytetraric Acid-13C4; E 296-13C4; FDA 2018-13C4; Hydroxysuccinic Acid-13C4; Musashi-no-Ringosan-13C4; NSC 25941-13C4; Pomalus Acid-13C4; R,S(+/-)-Malic Acid-13C4; α-Hydroxysuccinic Acid-13C4; DL-Malic Acid-13C4

Database IDs

• PubChem SID: 164228416
• PubChem CID: 71749880

CALCULATED PROPERTIES

• Acid pKa: 3.198357
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.9168313
• LogD (pH = 7.4): -6.814561
• Log P: -1.1136414
• Molar Refractivity: 24.8752 cm^3
• Polarizability: 10.123206 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M159512

Labelled Malic Acid. The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds in

REFERENCES

• Rindi, G., et al.: Biochem. J., 80, 214 (1961)
• Wolfgang, M., et al.: J. Biol. Chem., 281, 37265 (1961)
• Navarro, D., et al.: Metab. Brain Dis., 23, 115 (1961)