Trypan blue

Trypan blue
Names
IUPAC name
(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)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.715 Edit this at Wikidata
KEGG
UNII
  • 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+;;;; checkY
    Key: GLNADSQYFUSGOU-GPTZEZBUSA-J checkY
  • 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+;;;;
    Key: GLNADSQYFUSGOU-WLILTGDCBQ
  • Key: GLNADSQYFUSGOU-GPTZEZBUSA-J
  • [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
Properties
C34H24N6Na4O14S4
Molar mass 872.88
Appearance deep blue in aqueous solution[1]
Melting point > 300 °C (572 °F; 573 K)
10mg/ml [2]
Solubility 20 mg/mL in methyl Cellosolve, and 0.6 mg/mL in ethanol
Pharmacology
S01KX02 (WHO)
Hazards
Lethal dose or concentration (LD, LC):
6200 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trypan blue is an azo dye. It is a direct dye for cotton textiles.[3] 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.

  1. ^ PubChem. "CID 9562061 | C34H24N6Na4O14S4 - PubChem". Pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-19.
  2. ^ "Trypan Blue Powder Cell Viability Gold Standard Sigma-Aldrich". Merck.
  3. ^ Klaus Hunger; Peter Mischke; Wolfgang Rieper; Roderich Raue; Klaus Kunde; Aloys Engel (2005). "Azo Dyes". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.