3',6'-bis({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase ID: 155180
• Molecular Formular: C32H32O15
• Molecular Mass: 656.58748
• Monoisotopic Mass: 656.17412032
• SMILES: c1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)Oc2c(C43OC(=O)c3c4cccc3)ccc(c2)O[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C32H32O15/c33-11-21-23(35)25(37)27(39)30(45-21)42-13-5-7-17-19(9-13)44-20-10-14(43-31-28(40)26(38)24(36)22(12-34)46-31)6-8-18(20)32(17)16-4-2-1-3-15(16)29(41)47-32/h1-10,21-28,30-31,33-40H,11-12H2/t21-,22-,23+,24+,25+,26+,27-,28-,30-,31-/m1/s1
• InChIKey: ZTOBILYWTYHOJB-WBCGDKOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-bis({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 3',6'-bis({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})spiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: FDG; Fluorescein di(β-D-galactopyranoside)

Database IDs

• CAS Number: 17817-20-8
• MDL Number: MFCD00077344
• PubChem SID: 24894829; 24870596; 162249318
• PubChem CID: 122063

CALCULATED PROPERTIES

• LogD (pH = 7.4): -0.65580714
• Log P: -0.65579337
• Molar Refractivity: 155.5089 cm^3
• Polarizability: 61.840675 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false
• Acid pKa: 11.89911
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -0.65579355

PROPERTIES

Physical Property

• Melting Point: 200-203 °C (dec.)
• Fluorescence: λex 490 nm; λem 514 nm in 0.1 M Tris 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)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C32H32O15

DETAILS

Sigma Aldrich - F2756

Packaging
1, 5, 25 mg in glass bottle
Substrates
Fluorogenic substrate for β-galactosidase

Sigma Aldrich - 46941

Other Notes
Sensitive fluorogenic substrate for β-galactosidase. Kinetics of hydrolysis1