6,8-difluoro-4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

• ChemBase ID: 156248
• Molecular Formular: C16H16F2O8
• Molecular Mass: 374.2902464
• Monoisotopic Mass: 374.08132391
• SMILES: Cc1cc(=O)oc2c1cc(c(c2F)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)F
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c(F)cc3c(c2F)oc(=O)cc3C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H16F2O8/c1-5-2-9(20)25-14-6(5)3-7(17)15(10(14)18)26-16-13(23)12(22)11(21)8(4-19)24-16/h2-3,8,11-13,16,19,21-23H,4H2,1H3/t8-,11+,12+,13-,16+/m1/s1
• InChIKey: JZLOUZMEHMDFKY-DSERSLQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,8-difluoro-4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 6,8-difluoro-4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: 6,8-Difluoro-4-methylumbelliferyl-β-D-galactopyranoside

Database IDs

• CAS Number: 215868-26-1
• MDL Number: MFCD01863002
• PubChem SID: 162250386
• PubChem CID: 20576689

CALCULATED PROPERTIES

• Acid pKa: 12.1998625
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.20347542
• LogD (pH = 7.4): -0.2034822
• Log P: -0.20347533
• Molar Refractivity: 80.3887 cm^3
• Polarizability: 31.517313 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Fluorescence: λex 366 nm; λem 448 nm in 50 mM phosphate buffer pH 8.0 (β-galactosidase)

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)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C16H16F2O8

DETAILS

Sigma Aldrich - 36931

Other Notes
Fluorogenic substrate for the continuous assay of β-galactosidases1