(2S,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid

• ChemBase ID: 106842
• Molecular Formular: C5H10O6
• Molecular Mass: 166.1293
• Monoisotopic Mass: 166.04773804
• SMILES: OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H](C(=O)O)O)O)O
• InChI: InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3-,4+/m1/s1
• InChIKey: QXKAIJAYHKCRRA-JJYYJPOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid
• IUPAC Traditional name: arabinonate
• Synonyms: D-Arabinonic Acid Calcium Salt; NSC 224305; Calcium D-Arabinonate; ARABINIC ACID

Database IDs

• CAS Number: 22373-09-7; 32609-14-6
• PubChem SID: 162087716
• PubChem CID: 122045

CALCULATED PROPERTIES

• Acid pKa: 3.3931398
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.873542
• LogD (pH = 7.4): -6.1840506
• Log P: -2.7794094
• Molar Refractivity: 32.3085 cm^3
• Polarizability: 13.306913 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C145000

Used in the synthesis of D-erythroascorbic acid from D-glucose.

REFERENCES

• Gan, L.X., et al.: Carbohydrate Res., 220, 117 (1991)