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

• ChemBase ID: 154065
• Molecular Formular: C12H24O12
• Molecular Mass: 360.31176
• Monoisotopic Mass: 360.12677621
• SMILES: C1[C@H]([C@H]([C@@H]([C@@](O1)(CO)O)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)CO[C@@]([C@H]2O)(O)CO)[C@@H]([C@H]([C@@H]1O)O)O.O
• InChI: InChI=1S/C12H22O11.H2O/c13-1-5-6(16)7(17)8(18)11(22-5)23-9-4(15)2-21-12(20,3-14)10(9)19;/h4-11,13-20H,1-3H2;1H2/t4-,5-,6-,7+,8-,9-,10+,11-,12+;/m1./s1
• InChIKey: NNDCKRNDWLPICC-MDKWJHPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-2-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol hydrate
• IUPAC Traditional name: (2S,3S,4R,5R)-2-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol hydrate
• Synonyms: Maltulose monohydrate; 4-O-α-D-Glucopyranosyl-D-fructose

Database IDs

• CAS Number: 207511-09-9
• EC Number: 241-578-6
• MDL Number: MFCD00217057
• PubChem SID: 162248204
• PubChem CID: 2734156

CALCULATED PROPERTIES

• Acid pKa: 10.285819
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.528842
• LogD (pH = 7.4): -4.529399
• 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

• Melting Point: 137 °C (dec.)(lit.)

Safety Information

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

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C12H22O11 · H2O

DETAILS

Sigma Aldrich - 50796

Biochem/physiol Actions
A sugar molecule found in honey1,2,3
Application
Maltulose, an α(1,4) linked disaccharide of D-glucose and D-fructose, is used as a reference in analytical procedures to determine the extent of nonenzmatic browning induced by processes such as heating. Maltulose is used to identify, differentiate and characterize α-α-glucosidase(s).