(3S,4R,5R)-2-(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,4,5-triol

• ChemBase ID: 133314
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: C1[C@H]([C@H]([C@@H](C(O1)(CO)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)COC2(O)CO)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H22O11/c13-1-5-7(17)8(18)9(19)11(22-5)23-10-6(16)4(15)2-21-12(10,20)3-14/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12?/m1/s1
• InChIKey: SEWFWJUQVJHATO-PUVWEJBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-2-(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,4,5-triol; (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(3S,4R,5R)-2,4,5-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4R,5R)-2-(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,4,5-triol; (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(3S,4R,5R)-2,4,5-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• Synonyms: D-Turanose; 3-O-α-D-Glucopyranosyl-D-fructose; D-(+)-Turanose; 3-O-alpha-D-glucopyranosyl-D-fructose; 松二糖

Database IDs

• CAS Number: 547-25-1
• EC Number: 208-918-5
• MDL Number: MFCD00006606
• Beilstein Number: 93771
• Merck Index: 149821
• PubChem SID: 162227591; 24900072
• PubChem CID: 54301978

CALCULATED PROPERTIES

• Acid pKa: 10.275808
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.5288424
• LogD (pH = 7.4): -4.5294123
• Log P: -4.528835
• Molar Refractivity: 68.7741 cm^3
• Polarizability: 28.969793 Å^3
• Polar Surface Area: 189.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless
• Melting Point: 168-172 °C (dec.); 170 °C (dec.)(lit.); ca 170°C dec.
• Optical Rotation: [α]20/D +75°, c = 4 in H2O; [α]20/D +77±2°, 6 hr, c = 4% in H2O

Safety Information

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

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C12H22O11

DETAILS

Sigma Aldrich - T2754

Biochem/physiol Actions
Turanose is an analog of sucrose that is not metabolized by higher plants but is used as a carbon source by many bacteria, fungi, and other organisms. It is taken up into plant cells by sucrose transporters and is involved in intracellular sugar signaling.
包装
1 g in poly tube
5, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T2754.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 287377

Packaging
1 g in glass bottle

Sigma Aldrich - 93760

Biochem/physiol Actions
Turanose is an analog of sucrose that is not metabolized by higher plants but is used as a carbon source by many bacteria, fungi, and other organisms. It is taken up into plant cells by sucrose transporters and is involved in intracellular sugar signaling.