Trypan blue

{{short description|Blue-colored dye}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470618341

| Name = Trypan blue

| ImageFile = TrypanBlueSalt.png

| ImageSize = 350

| IUPACName = (3Z,3'Z)-3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)di(1Z)hydrazin-2-yl-1-ylidene]bis(5-amino-4-oxo-3,4-dihydronaphthalene-2,7-disulfonic acid)

| SystematicName =

| OtherNames =

|Section1={{Chembox Identifiers

| Abbreviations =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10482308

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 78897

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1640

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = I2ZWO3LS3M

| InChI = 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+;;;;

| InChIKey = GLNADSQYFUSGOU-WLILTGDCBQ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+;;;;

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GLNADSQYFUSGOU-GPTZEZBUSA-J

| InChIKey1 = GLNADSQYFUSGOU-GPTZEZBUSA-J

| CASNo = 72-57-1

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo_Comment = (tetrasodium salt)

| EINECS =

| PubChem = 5904246

| SMILES = [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)c6cc1cc(cc(N)c1c(O)c6/N=N/c2ccc(cc2C)c5ccc(/N=N/c4c(cc3cc(cc(N)c3c4O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c5)S([O-])(=O)=O

| RTECS =

| MeSHName =

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C19307

}}

|Section2={{Chembox Properties

| C=34 | H=24 | N=6 | O=14 | S=4|Na=4

| MolarMass = 960.81

| Appearance = deep blue in aqueous solution{{cite web|author=PubChem |url=https://pubchem.ncbi.nlm.nih.gov/compound/9562061#section=Color |title=CID 9562061 {{!}} C34H24N6Na4O14S4 - PubChem |publisher=Pubchem.ncbi.nlm.nih.gov |date= |accessdate=2022-04-19}}

| Density =

| MeltingPt = >

| MeltingPtC = 300

| MeltingPt_notes =

| BoilingPt =

| BoilingPt_notes =

| Solubility = 10mg/ml {{cite web|title=Trypan Blue Powder Cell Viability Gold Standard Sigma-Aldrich|url=https://www.sigmaaldrich.com/AU/en/product/sigma/t6146|website=Merck}}

| SolubleOther = 20 mg/mL in methyl Cellosolve, and 0.6 mg/mL in ethanol

| Solvent =

| LogP =

| VaporPressure =

| HenryConstant =

| AtmosphericOHRateConstant =

| pKa =

| pKb = }}

|Section3={{Chembox Structure

| CrystalStruct =

| Coordination =

| MolShape = }}

|Section5={{Chembox Thermochemistry

| DeltaHf =

| DeltaHc =

| Entropy =

| HeatCapacity = }}

|Section6={{Chembox Pharmacology

| ATCCode_prefix = S01

| ATCCode_suffix = KX02

| ATC_Supplemental =

| AdminRoutes =

| Bioavail =

| Metabolism =

| HalfLife =

| ProteinBound =

| Excretion =

| Legal_status =

| Legal_US =

| Legal_UK =

| Legal_AU =

| Legal_CA =

| Pregnancy_category =

| Pregnancy_AU = }}

|Section4={{Chembox Explosive

| ShockSens =

| FrictionSens =

| DetonationV =

| REFactor = }}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| FlashPt =

| AutoignitionPt =

| ExploLimits =

| LD50 = 6200 mg/kg (oral, rat)

| PEL = }}

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherFunction =

| OtherFunction_label =

| OtherCompounds =

}}

}}

Trypan blue is an azo dye. It is a direct dye for cotton textiles.{{cite encyclopedia|author1=Klaus Hunger|author2=Peter Mischke|author3=Wolfgang Rieper|author4=Roderich Raue|author5=Klaus Kunde|author6=Aloys Engel|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a03_245|isbn=978-3527306732|chapter=Azo Dyes}} In biosciences, it is used as a vital stain to selectively colour dead tissues or cells blue.

Live cells or tissues with intact cell membranes are not coloured. Since cells are very selective in the compounds that pass through the membrane, in a viable cell trypan blue is not absorbed; however, it traverses the membrane in a dead cell. Hence, dead cells appear as a distinctive blue colour under a microscope. Since live cells are excluded from staining, this staining method is also described as a dye exclusion method.