(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

• ChemBase ID: 153880
• Molecular Formular: C5H8O5
• Molecular Mass: 148.11402
• Monoisotopic Mass: 148.03717336
• SMILES: C([C@@H]1[C@H]([C@@H](C(=O)O1)O)O)O
• Canonical SMILES: OC[C@H]1OC(=O)[C@H]([C@@H]1O)O
• InChI: InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m1/s1
• InChIKey: CUOKHACJLGPRHD-JJYYJPOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• IUPAC Traditional name: D-arabinono-1,4-lactone
• Synonyms: D-Arabinonic acid γ-lactone; D-Arabino-1,4-lactone

Database IDs

• CAS Number: 2782-09-4
• MDL Number: MFCD00153592
• PubChem SID: 162248019
• PubChem CID: 17723

CALCULATED PROPERTIES

• Acid pKa: 11.633838
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.1149385
• LogD (pH = 7.4): -2.1149635
• Log P: -2.1149383
• Molar Refractivity: 28.8163 cm^3
• Polarizability: 12.117866 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D 73.0±2.0°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C5H8O5

DETAILS

Sigma Aldrich - 79469

Application
D-Arabino-1,4-lactone is used as a substrate to identify, differentiate and characterize stereospecific arabino-1,4-lactone oxidase(s)/ arabinonolactone oxidase(s) (LdALO) involved in vitamin C biosynthesis. D-Arabino-1,4-lactone is used as a precursor for the biosynthesis of erythroascorbate.