(3S,4R,5R)-3,4,5,6-tetrahydroxy-1-(morpholin-4-yl)hexan-2-one

• ChemBase ID: 133332
• Molecular Formular: C10H19NO6
• Molecular Mass: 249.26096
• Monoisotopic Mass: 249.12123733
• SMILES: C1COCCN1CC(=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H](C(=O)CN1CCOCC1)O)O)O
• InChI: InChI=1S/C10H19NO6/c12-6-8(14)10(16)9(15)7(13)5-11-1-3-17-4-2-11/h8-10,12,14-16H,1-6H2/t8-,9-,10-/m1/s1
• InChIKey: JPANQHVKLYKLEB-OPRDCNLKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-3,4,5,6-tetrahydroxy-1-(morpholin-4-yl)hexan-2-one
• IUPAC Traditional name: (3S,4R,5R)-3,4,5,6-tetrahydroxy-1-(morpholin-4-yl)hexan-2-one
• Synonyms: 1-Deoxy-1-morpholino-D-fructose

Database IDs

• CAS Number: 6291-16-3
• MDL Number: MFCD00166980
• Beilstein Number: 19582
• PubChem SID: 24894004; 162227609
• PubChem CID: 2728940

CALCULATED PROPERTIES

• Acid pKa: 10.737605
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.8118417
• LogD (pH = 7.4): -2.7774448
• Log P: -2.7767859
• Molar Refractivity: 58.3631 cm^3
• Polarizability: 23.371235 Å^3
• Polar Surface Area: 110.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 147-150 °C
• Optical Rotation: [α]20/D -51±2°, 48 hr, c = 2% in pyridine

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C10H19NO6

DETAILS

Sigma Aldrich - D6149

Application
1-Deoxy-1-morpholino-D-fructose (DMF), an analog of the 1-desoxy-1-amino-fructose radical found in glycated proteins, is used in the development of glycation assays.

Sigma Aldrich - 31125

Other Notes
Calibrant in the estimation of serum fructosamine1,2