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Record Information
Version1.0
Creation Date2016-05-19 01:31:45 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003994
Identification
Common NameTrypan blue
ClassSmall Molecule
DescriptionAn organosulfonate salt that is the tetrasodium salt of 3,3'-bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
C.I. 23850ChEBI
C.I. direct blue 14ChEBI
C.I. direct blue 14, tetrasodium saltChEBI
Direct blue 14ChEBI
Niagara blue 3bChEBI
Sodium ditolyl-diazobis-8-amino-1-naphthol-3,6-disulfonateChEBI
Sodium ditolyldisazobis-8-amino-1-naphthol-3,6-disulfonateChEBI
Sodium ditolyldisazobis-8-amino-1-naphthol-3,6-disulphonateChEBI
Sodium ditolyl-diazobis-8-amino-1-naphthol-3,6-disulfonic acidGenerator
Sodium ditolyl-diazobis-8-amino-1-naphthol-3,6-disulphonateGenerator
Sodium ditolyl-diazobis-8-amino-1-naphthol-3,6-disulphonic acidGenerator
Sodium ditolyldisazobis-8-amino-1-naphthol-3,6-disulfonic acidGenerator
Sodium ditolyldisazobis-8-amino-1-naphthol-3,6-disulphonic acidGenerator
Chemical FormulaC34H24N6Na4O14S4
Average Molecular Mass960.790 g/mol
Monoisotopic Mass959.982 g/mol
CAS Registry Number72-57-1
IUPAC Nametetrasodium 5-amino-3-[(E)-2-{4'-[(E)-2-(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazen-1-yl]-3,3'-dimethyl-[1,1'-biphenyl]-4-yl}diazen-1-yl]-4-hydroxynaphthalene-2,7-disulfonate
Traditional Nametetrasodium 5-amino-3-[(E)-2-{4'-[(E)-2-(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazen-1-yl]-3,3'-dimethyl-[1,1'-biphenyl]-4-yl}diazen-1-yl]-4-hydroxynaphthalene-2,7-disulfonate
SMILES[Na+].[Na+].[Na+].[Na+].CC1=CC(=CC=C1\N=N\C1=C(O)C2=C(N)C=C(C=C2C=C1S([O-])(=O)=O)S([O-])(=O)=O)C1=CC=C(\N=N\C2=C(O)C3=C(C=C(C=C3N)S([O-])(=O)=O)C=C2S([O-])(=O)=O)C(C)=C1
InChI IdentifierInChI=1S/C34H28N6O14S4.4Na/c1-15-7-17(3-5-25(15)37-39-31-27(57(49,50)51)11-19-9-21(55(43,44)45)13-23(35)29(19)33(31)41)18-4-6-26(16(2)8-18)38-40-32-28(58(52,53)54)12-20-10-22(56(46,47)48)14-24(36)30(20)34(32)42;;;;/h3-14,41-42H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4/b39-37+,40-38+;;;;
InChI KeyGLNADSQYFUSGOU-GPTZEZBUSA-J
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3,3'-disubstituted benzidines. These are organic compounds containing a benzidine skeleton, which is substituted only at the 3- and 3'-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct Parent3,3'-disubstituted benzidines
Alternative Parents
Substituents
  • 3,3'-disubstituted benzidine
  • Naphthalene sulfonate
  • 2-naphthalene sulfonic acid or derivatives
  • Naphthalene sulfonic acid or derivatives
  • 2-naphthalene sulfonate
  • 1-naphthol
  • Naphthalene
  • Arylsulfonic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • Toluene
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Azo compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic alkali metal salt
  • Hydrocarbon derivative
  • Organic salt
  • Organic sodium salt
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP3.34ALOGPS
logP1.13ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)-4.2ChemAxon
pKa (Strongest Basic)2.38ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area370.74 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity214.18 m³·mol⁻¹ChemAxon
Polarizability85.16 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0bt9-0000000009-a1434a96adf7cfec9ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000009-a9e7bb56c06a63334216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000009-a9e7bb56c06a63334216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000000009-a9e7bb56c06a63334216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000009-a8c021f30a62513d73b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000009-a8c021f30a62513d73b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000000009-a8c021f30a62513d73b5View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09158
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 LinkTrypan_blue
Chemspider IDNot Available
ChEBI ID78897
PubChem Compound IDNot Available
Kegg Compound IDC19307
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23889365
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24238944
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24464534
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24512297
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24519684
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24643390
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24652322
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24867494
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25717323
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25815522
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25840295
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26379749
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26529666