Diazenedicarboxamide (T3D3209)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-30 17:56:25 UTC
Update Date2014-12-24 20:26:00 UTC
Accession NumberT3D3209
Identification
Common NameDiazenedicarboxamide
ClassSmall Molecule
DescriptionBleaching agent for flour. Diazenedicarboxamide belongs to the family of Azo Compounds. These are derivatives ofA diazene(diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPhA azobenzeneA or diphenyldiazene.
Compound Type
  • Amine
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,1'-Azobiscarbamide
1,1'-Azobis[formamide]
1,1'-Azodiformamide
AZM 2S
Azobis CA 110B
Azobis CA 51C
Azobiscarbonamide
Azobiscarboxamide
Azobisformamide
Azocel
Azodicarbamide
Azodicarboamide
Azodicarbonamide
Azodicarboxamide
Azodicarboxylic acid diamide
Azodiformamide
Azoform A
Azoformamide
Azoplastone
Celogen AZ
Evipor
Genitron EPC
Paramid K1
Vinyfor
Chemical FormulaC2H4N4O2
Average Molecular Mass116.079 g/mol
Monoisotopic Mass116.033 g/mol
CAS Registry Number123-77-3
IUPAC Name(E)-N-[(C-hydroxycarbonimidoyl)imino]carbamimidic acid
Traditional Nameazodicarbonamide
SMILESOC(=N)\N=N\C(O)=N
InChI IdentifierInChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+
InChI KeyInChIKey=XOZUGNYVDXMRKW-AATRIKPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as azo compounds. These are derivatives of diazene(diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAzo compounds
Direct ParentAzo compounds
Alternative Parents
Substituents
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearancePale yellow crystalline (3).
Experimental Properties
PropertyValue
Melting Point225°C
Boiling PointNot Available
Solubility0.035 mg/mL at 20°C
LogP-1.7
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP-1ALOGPS
logP-0.51ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)1.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.36 m³·mol⁻¹ChemAxon
Polarizability9.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-d9507c6601ed8a1597f52017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-d9507c6601ed8a1597f52018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-c307f8e6893df84fd2ce2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4900000000-232f2521a6984367eb012017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9600000000-911e5d6523695f11747d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-05b9dcc86a3c5daa28252016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-1ccba6e08aa707e5f9d62016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9400000000-94d273da4c163d9188ca2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-9000000000-f5939e858def38d57aa32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-25ff1dc3f963a249f5d82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9200000000-723f50b9a3b4f67ac2c02021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f2a1ebbed095f8bd69882021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-7900000000-04389a0e6ed5af1cd5ba2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e0c6e70e64689ecbab862021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c04342d4a4666f27eb472021-09-24View Spectrum
Toxicity Profile
Route of ExposureDermal (8) ; eye contact (8) ; inhalation (8) ; oral (8)
Mechanism of ToxicityAzodicarbonamide prevents the progression of human CD4+ T lymphocytes into the G1 phase of the cell cycle, inhibits their blastogenesis, down-regulates their membrane expression of CD25 and CD69, and decreases their transcription of cytokine genes (2).
MetabolismAzodicarbonamide is readily converted to biurea, the only breakdown product identified, and it is likely that systemic exposure is principally to this derivative rather than to the parent compound. Biurea is then eliminated rapidly from all tissues with the majority of the elimination via the urine (7, 1).
Toxicity ValuesLD50: >2,000 mg/kg (Dermal, Rabbit) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is used in food industry as a food additive, a flour bleaching agent and improving agent. The principal use of Azodicarbonamide is in the production of foamed plastics (6).
Minimum Risk LevelNot Available
Health EffectsPoisoning can cause pulmonary sensitization and dermatitis in people (7).
SymptomsSymptoms and signs include shortness of breath, chest tightness, wheezing, cough, rhinitis, conjunctivitis, and rash (7).
TreatmentAfter inhalation exposure, first aid treatment includes fresh air and rest. After skin exposure, remove contaminated clothes, then rinse and wash skin with water and soap. After eye exposure, rinse with plenty of water for several minutes (remove contact lenses if easily possible). After ingestion, rinse mouth, give plenty of water to drink, and rest. In all causes medical attention should be sought. (8)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29616
PubChem Compound ID5462814
ChEMBL IDNot Available
ChemSpider ID4575589
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID140828
BioCyc IDNot Available
CTD IDNot Available
Stitch IDAzodicarbonamide
PDB IDNot Available
ACToR ID3637
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3209.pdf
General References
  1. Mewhinney JA, Ayres PH, Bechtold WE, Dutcher JS, Cheng YS, Bond JA, Medinsky MA, Henderson RF, Birnbaum LS: The fate of inhaled azodicarbonamide in rats. Fundam Appl Toxicol. 1987 Apr;8(3):372-81. [3569707 ]
  2. Tassignon J, Vandevelde M, Goldman M: Azodicarbonamide as a new T cell immunosuppressant: synergy with cyclosporin A. Clin Immunol. 2001 Jul;100(1):24-30. [11414742 ]
  3. De Luca V, Voineskos S, Wong G, Kennedy JL: Genetic interaction between alpha4 and beta2 subunits of high affinity nicotinic receptor: analysis in schizophrenia. Exp Brain Res. 2006 Sep;174(2):292-6. Epub 2006 Apr 25. [16636791 ]
  4. Ashford, RD (1994). Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd.
  5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  6. Wikipedia. Azodicarbonamide. Last Updated 6 August 2009. [Link]
  7. International Programme on Chemical Safety (IPCS) INCHEM (1999). International Programme on Chemical Safety's Concise International Chemical Assessment Documents, Number 16: Azodicarbonamide. [Link]
  8. International Programme on Chemical Safety (IPCS) INCHEM (1997). International Chemical Safety Card on Azodicarbonamide. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available