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

• ChemBase ID: 156137
• Molecular Formular: C16H15F3O8
• Molecular Mass: 392.2807096
• Monoisotopic Mass: 392.0719021
• SMILES: c1cc2c(cc(=O)oc2cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C(F)(F)F
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C(F)(F)F)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H15F3O8/c17-16(18,19)8-4-11(21)26-9-3-6(1-2-7(8)9)25-15-14(24)13(23)12(22)10(5-20)27-15/h1-4,10,12-15,20,22-24H,5H2/t10-,12-,13+,14-,15-/m1/s1
• InChIKey: WXZJYRMHQCZVKG-TVKJYDDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(trifluoromethyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 4-(trifluoromethyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: 4-(Trifluoromethyl)umbelliferyl-β-D-glucopyranoside

Database IDs

• CAS Number: 116981-86-3
• MDL Number: MFCD00037683
• PubChem SID: 24889575; 162250275
• PubChem CID: 16218755

CALCULATED PROPERTIES

• Acid pKa: 12.20014
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.12445219
• LogD (pH = 7.4): -0.124458976
• Log P: -0.1244521
• Molar Refractivity: 80.8884 cm^3
• Polarizability: 31.478436 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble
• Melting Point: ≥220 °C(lit.)
• Fluorescence: λex 385 nm; λem 502 nm in 0.1 M acetate; pH 5.0; β-glucosidase

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPCE)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C16H15F3O8

DETAILS

Sigma Aldrich - 91880

Other Notes
Convenient substrate for the determination of β-glucosidase for diagnostic purposes1