4-amino-2',7'-difluoro-3',6'-dihydroxy-5-(methylamino)-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase ID: 154567
• Molecular Formular: C21H14F2N2O5
• Molecular Mass: 412.3430664
• Monoisotopic Mass: 412.087078
• SMILES: CNc1ccc2c(c1N)C(=O)OC12c2cc(c(cc2Oc2c1cc(c(c2)O)F)O)F
• Canonical SMILES: CNc1ccc2c(c1N)C(=O)OC12c2cc(F)c(cc2Oc2c1cc(F)c(c2)O)O
• InChI: InChI=1S/C21H14F2N2O5/c1-25-13-3-2-8-18(19(13)24)20(28)30-21(8)9-4-11(22)14(26)6-16(9)29-17-7-15(27)12(23)5-10(17)21/h2-7,25-27H,24H2,1H3
• InChIKey: DIJCILWNOLHJCG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-2',7'-difluoro-3',6'-dihydroxy-5-(methylamino)-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 4-amino-2',7'-difluoro-3',6'-dihydroxy-5-(methylamino)spiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: 4-Amino-5-methylamino-2′,7′-difluorescein; Diaminofluorescein-FM; DAF-FM

Database IDs

• CAS Number: 254109-20-1
• PubChem SID: 162248705
• PubChem CID: 10431792

CALCULATED PROPERTIES

• Acid pKa: 7.608721
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.4469314
• LogD (pH = 7.4): 3.2276785
• Log P: 3.4595988
• Molar Refractivity: 106.5471 cm^3
• Polarizability: 38.02147 Å^3
• Polar Surface Area: 114.04 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >1 mg/mL
• Apperance: white to beige powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C21H14F2N2O5

DETAILS

Sigma Aldrich - D1821

Caution
hygroscopic
Biochem/physiol Actions
DAF-FM is a highly sensitive, photo-stable fluorescent probe for the detection of nitric oxide (NO). DAF-2 is the original compound and is widely used, but DAF-FM is more sensitive to nitric oxide (NO) compared with DAF-2. DAF-FM is more photo-stable and less pH sensitive than DAF-2. DAF-FM is not quite as cell-permeable as the diacetate derivative, DAF-FM, but it does not need to be activated by cytosolic enzymes.