75068
9,10-Anthracenediyl-bis(methylene)dimalonic acid
BioReagent, suitable for fluorescence, ≥90% (HPCE)
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Synonym(s):
ABDA, Single Oxygen Probe
Empirical Formula (Hill Notation):
C22H18O8
CAS Number:
Molecular Weight:
410.37
Beilstein:
3503804
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
product line
BioReagent
Quality Level
Assay
≥90% (HPCE)
form
powder
solubility
DMSO: soluble
fluorescence
λex 380 nm; λem 407 nm in 0.1 M phosphate pH 7.0
suitability
suitable for fluorescence
SMILES string
OC(=O)C(Cc1c2ccccc2c(CC(C(O)=O)C(O)=O)c3ccccc13)C(O)=O
InChI
1S/C22H18O8/c23-19(24)17(20(25)26)9-15-11-5-1-2-6-12(11)16(10-18(21(27)28)22(29)30)14-8-4-3-7-13(14)15/h1-8,17-18H,9-10H2,(H,23,24)(H,25,26)(H,27,28)(H,29,30)
InChI key
DNUYOWCKBJFOGS-UHFFFAOYSA-N
General description
9,10-Anthracenediyl-bis(methylene)dimalonic acid or ABDA is a singlet oxygen probe. It is highly fluorescent and soluble in water and binds to lipopolysaccharides (LPS) found in the cell membrane. 9,10-Anthracenediyl-bis(methylene)dimalonic acid takes four negative charges upon fully deprotonation in neutral aqueous solutions, stabilizing the ion-pair complex and facilitating selective recognition of LPS over other common ionic species of clinical significance. In addition to the emission maximum at 407 nm, there are lower maxima at 431, 457, and 485 nm.
Application
9,10-Anthracenediyl-bis(methylene)dimalonic acid is widely used as a singlet oxygen detector probe. 9,10-Anthracenediyl-bis(methylene)dimalonic acid is suitable for assessing the photodynamic effect of curcumin Vibrio parahaemolyticus, which is a significant cause of bacterial diarrhea.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Analysis Note
In addition to the emission maximum at 407 nm, there are lower maxima at 431, 457 and 485 nm.
Other Notes
Reagent for the assay of singlett oxygen; it has better characteristics than 9,10-anthracenediyl-bis-dipropionic acid
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Proceedings of the National Academy of Sciences of the United States of America, 116(24), 12013-12018 (2019-05-30)
Pigments often inflict tissue-damaging and proaging toxicity on light illumination by generating free radicals and reactive oxygen species (ROS). However, the molecular mechanism by which organisms sense phototoxic pigments is unknown. Here, we discover that Transient Receptor Potential Ankyrin 1-A
Tiago Entradas et al.
Journal of photochemistry and photobiology. B, Biology, 204, 111787-111787 (2020-01-21)
The sensitivity for singlet oxygen (1O2) of two convenient 1O2 probes, 1,3-diphenylisobenzofuran (DPBF) and 9,10-Anthracenediyl-bis(methylene)dimalonic acid (ABDA), has been investigated in different aqueous environments. Both probes are commercially available at reasonable cost and can be used with standard UV-vis spectrometers.
Mikkel Bregnhøj et al.
Photochemistry and photobiology, 95(1), 202-210 (2018-07-05)
Uric acid and/or its monoanion has long been used as chemical-trapping agents to demonstrate the presence of singlet oxygen, O2 (a1 Δg ), in aqueous systems. "Oxidative bleaching" of uric acid, generally monitored through changes in the uric acid absorption
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Chemistry, an Asian journal, 15(3), 365-370 (2019-12-13)
5,15-Diazaporphyrins, which have a large absorption at wavelengths over 600 nm, were dissolved in water by complex formation with β-(1,3-1,6)-d-glucans. Aqueous solutions of these complexes were relatively stable compared with their trimethyl-β-cyclodextrin-complexed analogues. β-Glucan-complexed diazaporphyrins showed quenched fluorescence and had low
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