Rhodol

Key facts

CAS number

3086-44-0

Purity

>95%

Form

Solid

form

Molecular weight

331.3 Da

Molecular formula

C₂₀H₁₃NO₄

PubChem

12314937

Nature

Synthetic

Solubility

Soluble in DMSO

Biochemical name

3'-Amino-6'-hydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one

Biological description

Highly fluorescent dye useful for labeling oligonucleotide, antibody and protein studies and for the preparation of peptide and esterase substrates.

Rhodol is a structural hybrid of fluorescein and rhodamine. It retains the pH-sensitive properties conferred by a phenolic hydroxyl group, but the amine substituent reduces the pKa values. Rhodol exhibits a high extinction coefficient (~70,000 cm-1M-1) and high quantum yield (~0.8-0.9) in aqueous solution, with absorption maxima at approximately 490 nm and emission maxima between 520 and 545 nm. As with fluorescein-based dyes, the fluorescence excitation profiles of rhodol-based dyes are pH dependent, which can be useful for ratiometric pH determinations intracellularly.

Canonical smiles

C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C=C4)N)OC5=C3C=CC(=C5)O

InChi

InChI=1S/C20H13NO4/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,22H,21H2

InChiKey

OKFGUUIODGPPLE-UHFFFAOYSA-N

IUPAC Name

3'-amino-6'-hydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one

Excitation/Emission

Ex: 490nm, Em: 521nm