(2R)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid

• ChemBase ID: 154072
• Molecular Formular: C6H8O7
• Molecular Mass: 192.12352
• Monoisotopic Mass: 192.0270026
• SMILES: [C@H]1([C@H](C(=O)O[C@@H]1[C@H](C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H]1OC(=O)[C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C6H8O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11/h1-4,7-9H,(H,10,11)/t1-,2-,3-,4+/m1/s1
• InChIKey: XECPAIJNBXCOBO-AJSXGEPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
• IUPAC Traditional name: (R)-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl](hydroxy)acetic acid
• Synonyms: L-Idaric acid 1,4-lactone; L-Idaro-1,4-lactone

Database IDs

• CAS Number: 80876-59-1
• PubChem SID: 162248211
• PubChem CID: 11873519

CALCULATED PROPERTIES

• Acid pKa: 3.0635793
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.8292956
• LogD (pH = 7.4): -5.891565
• Log P: -2.4249988
• Molar Refractivity: 34.6462 cm^3
• Polarizability: 14.693422 Å^3
• Polar Surface Area: 124.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C6H8O7

DETAILS

Sigma Aldrich - 07494

Biochem/physiol Actions
L-Idaro-1,4-lactone is an inhibitor of α-L-idosiduronase, an enzyme that hydrolyzes iduronosidic linkages in the desulfated glycosaminoglycan dermatan. 1