(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

• ChemBase ID: 89302
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: C1[C@@H]2[C@H]([C@@H]([C@@H]([C@H](O1)O2)O)O)O
• Canonical SMILES: O[C@H]1[C@H](O)[C@H]2CO[C@@H]([C@H]1O)O2
• InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
• InChIKey: TWNIBLMWSKIRAT-VFUOTHLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• IUPAC Traditional name: levoglucosan
• Synonyms: 1,6-Anhydro-beta-D-glucopyranose; Levoglucosan; (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; 1,6-Anhydro-β-D-glucose; 1,6-Anhydro-beta-D-glucopyranose; 左旋葡聚糖; 1,6-脱水-β-D-葡萄糖; 1,6-脱水β-D-吡喃葡萄糖

Database IDs

• CAS Number: 498-07-7
• EC Number: 207-855-0
• MDL Number: MFCD00063248
• Beilstein Number: 80998
• PubChem SID: 162076183; 24846629; 24859027
• PubChem CID: 2724705

CALCULATED PROPERTIES

• Acid pKa: 12.212605
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.7708358
• LogD (pH = 7.4): -1.7708423
• Log P: -1.7708356
• Molar Refractivity: 32.4133 cm^3
• Polarizability: 13.814454 Å^3
• Polar Surface Area: 79.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-183 °C; 180-184°C; 182-184 °C(lit.); 182-184°C
• Optical Rotation: [α]18/D -66°, c = 1 in H2O; [α]20/D -66±2°, c = 10% in H2O

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C6H10O5
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 316555

Frequently Asked Questions
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Packaging
1 g in glass bottle
250 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 316555.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 10390

Other Notes
Important carbohydrate derivative with interesting chemical reactivity arising from its rigid bicyclic framework. Derivatisations proceed selectively to give the 2,4-disubstituted levoglucosan, reviews1,2; 1,6:2,3-Dianhydro-β-D-mannopyranose3,4