sodium [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl sulfate

• ChemBase ID: 154098
• Molecular Formular: C16H17NaO11S
• Molecular Mass: 440.35435
• Monoisotopic Mass: 440.03892665
• SMILES: Cc1cc(=O)oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)COS(=O)(=O)[O-])O)O)O.[Na+]
• Canonical SMILES: O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)COS(=O)(=O)[O-])Oc1ccc2c(c1)oc(=O)cc2C.[Na+]
• InChI: InChI=1S/C16H18O11S.Na/c1-7-4-12(17)26-10-5-8(2-3-9(7)10)25-16-15(20)14(19)13(18)11(27-16)6-24-28(21,22)23;/h2-5,11,13-16,18-20H,6H2,1H3,(H,21,22,23);/q;+1/p-1/t11-,13+,14+,15-,16-;/m1./s1
• InChIKey: KHTOBGQRIASILC-XNSOHGFJSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl sulfate
• IUPAC Traditional name: sodium [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-2-yl]methyl sulfate
• Synonyms: 4-Methylumbelliferyl β-D-galactopyranoside-6-sulfate sodium salt; 4-Methyl-7-[(6-O-sulfo-β-D-galactopyranosyl)oxy]-2H-1-benzopyran-2-one Monosodium Salt; 4-Methylumbelliferyl β-D-Galactopyranoside-6-sulfate Sodium Salt; 4-Methylumbelliferyl β-D-galactopyranoside-6-sulfate

Database IDs

• CAS Number: 126938-14-5; 206443-06-3
• MDL Number: MFCD01861961
• PubChem SID: 162248237
• PubChem CID: 71311791

CALCULATED PROPERTIES

• Acid pKa: -2.1001203
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.8102899
• LogD (pH = 7.4): -2.810299
• Log P: -2.355065
• Molar Refractivity: 88.826 cm^3
• Polarizability: 36.68598 Å^3
• Polar Surface Area: 171.88 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 158-160°C
• Fluorescence: λex 360 nm; λem 447 nm in 0.05 M phosphate buffer pH 7.8 (β-galactosidase)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: -20°C Freezer, Under Inert Atmosphere
• 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: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C16H17NaO11S

DETAILS

Sigma Aldrich - 68903

Application
suitable as a fluorogenic substrate for β-galactosidase; fluorogenic substrate for the diagnosis of Morquio disease type A1

Toronto Research Chemicals - M334481

Used for the determination of galactose-6-sulphate sulphatase activity. Used in the diagnosis of Mucopolysaccharidosis IV A.

REFERENCES

• van Diggelen, O.P., et al.: Clinica Chimica Acta, 187, 131 (1987)