(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 130789
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C([C@@H]1[C@H]([C@@H]([C@@H](C(O1)O)O)O)O)O
• Canonical SMILES: OC[C@H]1OC(O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1
• InChIKey: WQZGKKKJIJFFOK-QTVWNMPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: β-glucose
• Synonyms: D-(+)-Mannose; D-Mannopyranose; D-吡喃甘露糖; D-(+)-甘露糖

Database IDs

• CAS Number: 3458-28-4
• EC Number: 222-392-4
• MDL Number: MFCD00064122
• Beilstein Number: 1564373
• Merck Index: 145747
• PubChem SID: 24882739; 24897068; 24896601; 162225067; 24882738
• PubChem CID: 18950

CALCULATED PROPERTIES

• Acid pKa: 11.298101
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.93254
• LogD (pH = 7.4): -2.932594
• Log P: -2.9325392
• Molar Refractivity: 35.9234 cm^3
• Polarizability: 15.155883 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble1 M, clear, colorless; H2O: soluble50 mg/mL; Soluble in water
• Apperance: powder
• Melting Point: 127-133°C; 133-140 °C(lit.)
• Density: 1.54
• Optical Rotation: [α]20/D +13.8±0.5°, 24 hr, c = 10% in H2O; [α]20/D +14.8°, c = 4 in H2O; +13.8 (c=10 in water, 24h)
• Absorption Wavelength: λ: 260 nm Amax: 0.1; λ: 280 nm Amax: 0.1

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, HPLC); ≥99.5% (sum of enantiomers, HPLC); 99%
• Grade: for microbiology
• Suitability: suitable for cell culture
• Ignition Residue: <0.1%; ≤0.1%; ≤0.1% (as SO4)
• Impurities: <0.005% Phosphorus (P); <0.1% Insoluble matter; ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; insoluble matter, passes filter test
• Cation Traces: Al: <0.001%; Al: ≤0.001%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: <0.005%; Ca: ≤0.005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: <0.0005%; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: <0.0005%; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: <0.005%; K: ≤0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: <0.0005%; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: <0.005%; Na: ≤0.05%; Na: ≤50 mg/kg; NH4+: <0.05%; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: <0.001%; Pb: ≤0.001%; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: <0.001%; Zn: ≤0.001%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): <0.05%; chloride (Cl-): ≤0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): <0.05%; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from wood
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV); ≤0.2% loss on drying, 20 °C (HV)
• λ: 1 M in H2O
• Product Line: BioUltra; BioXtra
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - M2069

Other Notes
From birch or beech wood
Quality
Predominantly α-isomer

Sigma Aldrich - M6020

Application
Mannose is an aldohexose carbohydrate. This product may be used to study the effects of exogenous mannose on in vitro processes such as glycosylation.

Sigma Aldrich - 63579

Application
D-(+)-Mannose, a C-2 epimer of D-glucose, is used in the formation of glycan structure and glycosylation.

REFERENCES

• Chiral building block. For use in a 15-step synthesis of the macrocycle (+)-aspicilin, in which 3 of the 4 asymmetric centers come from mannose, see: Helv. Chim. Acta, 72, 1753 (1989).