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Record Information
Version1.0
Creation Date2009-03-06 18:58:30 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000260
Identification
Common NameRoxarsone
ClassSmall Molecule
DescriptionRoxarsone is used to control enteric infections in chicken and to improve growth and feed efficiency. Roxarsone is a fda approved additive for chicken, turkey and swine feeds.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2-Nitro-1-hydroxybenzene-4-arsonic acidChEBI
3-NitroChEBI
3-Nitro-4-hydroxybenzenearsonic acidChEBI
3-Nitro-4-hydroxyphenylarsonic acidChEBI
4-Hydroxy-3-nitrobenzenearsonic acidChEBI
4-Hydroxy-3-nitrophenylarsonic acidChEBI
NSC-2101ChEBI
Ren-O-salChEBI
RoxarsonChEBI
RoxarsonumChEBI
2-Nitro-1-hydroxybenzene-4-arsonateGenerator
3-Nitro-4-hydroxybenzenearsonateGenerator
3-Nitro-4-hydroxyphenylarsonateGenerator
4-Hydroxy-3-nitrobenzenearsonateGenerator
4-Hydroxy-3-nitrophenylarsonateGenerator
(4-Hydroxy-3-nitrobenzene)arsonic acidHMDB
(4-Hydroxy-3-nitrophenyl)-arsonic acidHMDB
2-Nitrophenol-4-arsonic acidHMDB
3-Nitro-10HMDB
3-Nitro-20HMDB
3-Nitro-50HMDB
3-Nitro-80HMDB
3n4HPaHMDB
4-HYDROXY-3-nitro-benzenearsonIC ACIDHMDB
4-Hydroxy-3-nitrophenyl arsonic acidHMDB
Aklomix-3HMDB
As-(4-hydroxy-3-nitrophenyl)-arsonic acidHMDB
C6H6AsNO6HMDB
Nitro acid 100 per centHMDB
Nitrophenolarsonic acidHMDB
Nitrophenoloarsonic acidHMDB
NSC 2101HMDB
Ren O-salHMDB
RistatHMDB
Roxarsone(usan)HMDB
Roxarsone, ban, inn, usanHMDB
Acid, 3-nitro-4-hydroxyphenylarsonicHMDB
3 Nitro 10HMDB
3 Nitro 4 hydroxyphenylarsonic acidHMDB
3Nitro10HMDB
Chemical FormulaC6H6AsNO6
Average Molecular Mass263.037 g/mol
Monoisotopic Mass262.941 g/mol
CAS Registry Number121-19-7
IUPAC Name(4-hydroxy-3-nitrophenyl)arsonic acid
Traditional Name3-nitro
SMILESOC1=C(C=C(C=C1)[As](O)(O)=O)N(=O)=O
InChI IdentifierInChI=1S/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12)
InChI KeyXMVJITFPVVRMHC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Pentaorganoarsane
  • C-nitro compound
  • Organic nitro compound
  • Oxygen-containing organoarsenic compound
  • Organic oxoazanium
  • Organic metalloid salt
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organoarsenic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearancePale yellow solid.
Experimental Properties
PropertyValue
Melting Point300°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.86 g/LALOGPS
logP0.17ALOGPS
logP0.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area123.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.35 m³·mol⁻¹ChemAxon
Polarizability18.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0002-1790000000-f715c8649a77c00beb03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-00di-7495000000-960cbe4266d513123513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-7283a1d879b75c66222fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0090000000-39a3f59584592464e81fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0490000000-87933a723d1263ada5d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-965c468eb37bebb7ec67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-06c411aff1d24a3623e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5940000000-d34c64ce51c0e25129a2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7); dermal (7)
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 carcinogenicity 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. (3, 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 ValuesLD50: 81 mg/kg (Oral, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/Sources3-nitro-4-hydroxy-phenyl-arsonic acid is found in poultry feed.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (8) Chronic Oral: 0.0003 mg/kg/day (8) Chronic Inhalation: 0.01 mg/m3 (8)
Health EffectsHypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well (2).
SymptomsInitial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness (2).
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 IDDB11458
HMDB IDHMDB0033205
FooDB IDFDB011218
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRoxarsone
Chemspider ID4925
ChEBI ID35817
PubChem Compound ID5104
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=12724787
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12731831
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12731832
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18414637
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21388897
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.