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

• ChemBase ID: 127577
• Molecular Formular: C6H8O6
• Molecular Mass: 176.12412
• Monoisotopic Mass: 176.03208798
• SMILES: O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O
• Canonical SMILES: O=C[C@@H]([C@H]1OC(=O)[C@H]([C@H]1O)O)O
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h1-5,8-10H/t2-,3+,4-,5+/m0/s1
• InChIKey: UYUXSRADSPPKRZ-SKNVOMKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetaldehyde
• IUPAC Traditional name: glucuronolactone
• Synonyms: D-(+)-Glucurono-6,3-lactone; D-Glucurono-6,3-lactone; D-Glucurone; Glucuronolactone; D-(+)-Glucuronic acid γ-lactone; D(+)-Glucuronic acid γ-lactone; Glucuronic acid lactone; Glucurone; Glucurolactone; D-Glucurono-3,6-lactone; D-glucurono-gamma-lactone; Glucuronolactone; D-(+)-葡萄糖醛酸-3,6-内酯; D-葡糖醛酸-6,3-内酯; D-葡糖醛酸内酯; 葡糖醛酸内酯; 葡醛内酯

Database IDs

• CAS Number: 32449-92-6
• EC Number: 251-053-3
• MDL Number: MFCD00135622
• Beilstein Number: 83595
• PubChem SID: 162221896; 24872830; 24888207
• PubChem CID: 92283
• Chemspider ID: 83317
• Wikipedia Title: Glucuronolactone

CALCULATED PROPERTIES

• Acid pKa: 11.332507
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.5836155
• LogD (pH = 7.4): -2.5836656
• Log P: -2.5836148
• Molar Refractivity: 33.7208 cm^3
• Polarizability: 14.112011 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 26.9 g/100 mL in water
• Melting Point: ~175 °C (dec.); 172-175 °C(lit.); 176–178 °C
• Density: 1.76 g/cm^3 (30 °C)
• Optical Rotation: [α]20/D +18.5±1°, 24 hr, c = 10% in H2O; [α]24/D +18.8°, c = 8 in H2O

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); ≥99%
• Grade: purum
• Empirical Formula (Hill Notation): C6H8O6

DETAILS

Sigma Aldrich - 851450

Packaging
1 kg in poly bottle
100 g in poly bottle
Application
Employed in the synthesis of optically active glucopyranoses1 and long-chain alkyl glucofuranosides.2
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 851450.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.