(3S,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

• ChemBase ID: 136972
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C([C@H]([C@H]([C@@H](C(=O)CO)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H](C(=O)CO)O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1
• InChIKey: BJHIKXHVCXFQLS-UYFOZJQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
• IUPAC Traditional name: keto-D-fructose
• Synonyms: (3S,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one; Laevulosum (Fructosum); D-Levulose; Fruit sugar; D-(-)-Fructose; Phenylethylene; U - Styrene; D(-)-Fructose; 左旋糖（果糖）; D-左旋糖; 果糖; D-(-)-果糖; 乙烯基苯; 苯乙烯

Database IDs

• CAS Number: 53188-23-1; 57-48-7; 100-42-5
• EC Number: 200-333-3
• MDL Number: MFCD00148910
• Beilstein Number: 1239004
• PubChem SID: 24894831; 24894847; 24849688; 24894986; 24871366; 24894826; 24871367; 24894716; 162231239
• PubChem CID: 5984

CALCULATED PROPERTIES

• Acid pKa: 9.481385
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2670772
• LogD (pH = 7.4): -3.2706153
• Log P: -3.267032
• Molar Refractivity: 37.5618 cm^3
• Polarizability: 15.251392 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble1 M, clear, colorless
• Melting Point: 119-122 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -89.5°, c = 2 in H2O; [α]20/D -92±2°, 1 hr, c = 10% in H2O; [α]20/D -93.5 to -91.0°, c = 10% in H2O; [α]25/D -89.0°, c = 5 in H2O
• Absorption Wavelength: λ: 260 nm Amax: 0.04; λ: 280 nm Amax: 0.04
• pH: 5.0-7.0 (25 °C, 0.1 M in H2O)

Safety Information

• RTECS: LS7120000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%; ≥98.0% (HPLC); ≥99%; ≥99.0% (HPLC); 95+%; 98%
• Grade: for biotechnological purposes; for microbiology; Ph Eur; SAJ special grade
• Suitability: in accordance for appearance of solution; meets USP testing specifications; suitable for cell culture; suitable for insect cell culture
• Ignition Residue: <0.1%; ≤0.1% (as SO4)
• Impurities: <0.0005% Phosphorus (P); <0.05% glucose (enzymatic); <0.1% Insoluble matter; ≤0.05% Glucose (enzymatic); ≤0.5% water (Karl Fischer); 5-hydroxymethylfurfurol and related substances, complies; acidity or alcalinity, complies; foreign sugar, complies; insoluble matter, passes filter test; residual solvents, complies
• Cation Traces: Al: <0.0005%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Ba:, in accordance; Bi: ≤5 mg/kg; Ca: <0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: <0.0005%; Cu: ≤5 mg/kg; Fe: <0.0005%; Fe: ≤5 mg/kg; K: <0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: <0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: <0.005%; Na: ≤50 mg/kg; NH4+: <0.05%; Ni: ≤5 mg/kg; Pb: <0.001%; Pb: ≤0.5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: <0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): <0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): <0.05%; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV)
• Quality Level: PREMIUM
• Quality: meets analytical specification of Ph. Eur., BP
• λ: 0.1 M in H2O
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioReagent; BioUltra; BioXtra
• Pharmacopeia Traceability: traceable to PhEur F0550000; traceable to USP 1286504
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - 47739

Application
D-Fructose is an important monosaccharide used in a wide range of applications. D-fructose is used in carbohydrate research, in organic and bioorganic synthesis; as a model compound; as a reference material, as an enzyme substrate and as a nutrient.

Sigma Aldrich - F0127

Packaging
1 kg in poly bottle
10 mg in autosmp vl
100, 500 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 140929

Packaging
500 g in poly bottle