153120-93-5

Basic information

• Product Name: Benzoic acid, 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-, methyl ester
• CAS NO: 153120-93-5
• Molecular Formula: C21H15NO5
• Molecular Weight: 361.354
• Mol File: 153120-93-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-, methyl ester(153120-93-5)
• EPA Substance Registry System: Benzoic acid, 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-, methyl ester(153120-93-5)

Safety Data

• Hazardous Substances Data: 153120-93-5(Hazardous Substances Data)

Upstream product

• 3326-35-0 3',6'-dihydroxy-5-nitrospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one 
• 67-56-1 methanol 
• 3326-34-9 fluoresceinamine 

Downstream Products

• 70672-06-9 methyl 2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoate 
• 181213-36-5 9-[1-(2-methoxycarbonyl-4-amino)phenyl]-6-methoxy-3H-xanthen-3-one 

Relevant articles and documents

Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines

The stable, water-soluble, and nonfluorescent FA-OMe can sense nitric oxide (NO) and form the intensely fluorescent product dA-FA-OMe via reductive deamination of the aromatic primary amine. The reaction is accompanied by a notable increase of the fluorescent quantum yield from 1.5 to 88.8%. The deamination mechanism of FA-OMe with NO was proposed in this study. The turn-on fluorescence signals were performed by suppression of photoinduced electron transfer (PeT), which was demonstrated by density functional theory (DFT) calculations of the components forming FA-OMe and dA-FA-OMe. Furthermore, FA-OMe showed water solubility and good stability at physiological pHs. Moreover, the selectivity study indicated that FA-OMe had high specificity for NO over other reactive oxygen/nitrogen species. In an endogenously generated NO detection study, increasing the incubation time of FA-OMe with lipopolysaccharide (LPS) pretreated Raw 264.7 murine macrophages could cause an enhanced fluorescence intensity image. In addition, a diffusion/localization cell imaging study showed that FA-OMe could be trapped in Raw 264.7 cells. These cell imaging results demonstrated that FA-OMe could be used as a turn-on fluorescent sensor for the detection of endogenously generated NO.

Rational design principle for modulating fluorescence properties of fluorescein-based probes by photoinduced electron transfer

Fluorescence properties of fluorescein-based probes are shown to be finely controlled by the rate of photoinduced electron transfer from the benzoic acid moiety (electron donor) to the singlet excited state of the xanthene moiety (electron acceptor fluoro