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Record Information
Version1.0
Creation Date2009-06-19 21:58:34 UTC
Update Date2016-11-09 01:08:27 UTC
Accession NumberCHEM001123
Identification
Common Namep-Azobenzenearsonate
ClassSmall Molecule
Descriptionp-Azobenzenearsonate is an organoarsenic compound. Arsenic is a chemical element that has the symbol As and atomic number 33. It is a poisonous metalloid that has many allotropic forms: yellow (molecular non-metallic) and several black and grey forms (metalloids) are a few that are seen. Three metalloidal forms of arsenic with different crystal structures are found free in nature (the minerals arsenopyrite and the much rarer arsenolamprite and pararsenolamprite), but it is more commonly found as a compound with other elements. (3)
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(4,4'-Azodiphenyl)bisarsonic acidChEBI
ABAChEBI
AzobenzenearsonateChEBI
AzophenylarsonateChEBI
p-ABAChEBI
p-AzobenzenearsonateChEBI
p-AzophenylarsonateChEBI
Para-azobenzenearsonateChEBI
(4,4'-Azodiphenyl)bisarsonateGenerator
Azobenzenearsonic acidGenerator
Azophenylarsonic acidGenerator
p-Azobenzenearsonic acidGenerator
p-Azophenylarsonic acidGenerator
Para-azobenzenearsonic acidGenerator
4,4'-AzodibenzenearsonateGenerator
Chemical FormulaC12H12As2N2O6
Average Molecular Mass430.079 g/mol
Monoisotopic Mass429.913 g/mol
CAS Registry Number7334-23-8
IUPAC Name{4-[(E)-2-(4-arsonophenyl)diazen-1-yl]phenyl}arsonic acid
Traditional Nameazophenylarsonate
SMILESO[As](O)(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(C=C1)[As](O)(O)=O
InChI IdentifierInChI=1S/C12H12As2N2O6/c17-13(18,19)9-1-5-11(6-2-9)15-16-12-7-3-10(4-8-12)14(20,21)22/h1-8H,(H2,17,18,19)(H2,20,21,22)/b16-15+
InChI KeyITRMROGJSNWFKO-FOCLMDBBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Monocyclic benzene moiety
  • Benzenoid
  • Pentaorganoarsane
  • Azo compound
  • Oxygen-containing organoarsenic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic metalloid salt
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organoarsenic compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP1.06ALOGPS
logP2.11ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)-0.39ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.35 m³·mol⁻¹ChemAxon
Polarizability33.02 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-0369561f9ac0a529f879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0000900000-ec2717f1f7abc98ecea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100900000-7b516016bd49f7643687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-1002900000-61a1700c023dff336cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0123900000-ca689918e1db54f86050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-1956300000-ff8c56a008fe9b83b5ddView in MoNA
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityArsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (2, 1)
MetabolismArsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (5)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (8)
Uses/SourcesThree metalloidal forms of arsenic with different crystal structures are found free in nature (the minerals arsenopyrite and the much rarer arsenolamprite and pararsenolamprite), but it is more commonly found as a compound with other elements.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (7) Chronic Oral: 0.0003 mg/kg/day (7) Chronic Inhalation: 0.01 mg/m3 (7)
Health EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (2, 5)
SymptomsExposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of
TreatmentArsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (5)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkP-Azobenzenearsonate
Chemspider IDNot Available
ChEBI ID53554
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=211841
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23008448
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3569407
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6386988
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6448896
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6454743
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7868912