Tetrazolium chloride

Triphenyl tetrazolium chloride, TTC, or simply tetrazolium chloride (with the formula 2,3,5-triphenyl-2H-tetrazolium chloride) is a redox indicator commonly used in biochemical experiments especially to indicate cellular respiration (example: to check for the viability of seeds). It is a white crystalline salt, soluble in water, ethanol and acetone but insoluble in ether.[1][2]

Tetrazolium chloride
Names
Preferred IUPAC name
2,3,5-Triphenyl-2H-tetrazol-3-ium chloride
Other names
TTC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.520
EC Number
  • 206-071-6
KEGG
UNII
  • InChI=1S/CH2N4.ClH/c1-2-4-5-3-1;/h1H,(H,2,3,4,5);1H checkY
    Key: JXCNUCFTHLGXDQ-UHFFFAOYSA-N checkY
  • InChI=1/CH2N4.ClH/c1-2-4-5-3-1;/h1H,(H,2,3,4,5);1H
    Key: JXCNUCFTHLGXDQ-UHFFFAOYAY
  • [Cl-].c4ccc(c3nn(c1ccccc1)[n+](c2ccccc2)n3)cc4
Properties
C19H15ClN4
Molar mass 334.8 g/mol
Appearance white crystalline powder
Soluble
Solubility in water ~1 mg/ml
Solubility in PBS (pH 7.2) ~1 mg/ml
Solubility in ethanol ~1 mg/ml
Solubility in DMSO ~0.25 mg/ml
log P −2.4
Hazards
GHS labelling:
GHS02: Flammable
Danger
H228, H315, H319, H335
P210, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
0
0
Lethal dose or concentration (LD, LC):
5.6 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

TTC assay

In the TTC assay (also known as TTC test or tetrazolium test), TTC is used to differentiate between metabolically active and inactive tissues. The white compound is enzymatically reduced to red TPF (1,3,5-triphenylformazan) in living tissues due to the activity of various dehydrogenases (enzymes important in oxidation of organic compounds and thus cellular metabolism), while it remains in its unreacted state in areas of necrosis since these enzymes have either denatured or degraded.

TTC has been employed in autopsy pathology to identify myocardial infarctions. Healthy viable heart muscle will stain deep red from the cardiac lactate dehydrogenase, while areas of potential infarctions will be more pale.[3]

See also

References
  1. Witty M. (2012). Topographischer Nachweis der Keimfähigkeit der Getreidefrüchte durch Tetrazoliumsalze (Topographic Detection of Germination in Cereal Crops by Tetrazolium Salts) — A Translation of Lakon’s 1942 Paper on Tetrazolium Seed Testing. Seed Technology 34(2):275-282.
  2. Witty M. (2012). The process for 2, 3, 5 - triphenyl – tetrazolium chloride synthesis, an intellectual property seized immediately after world war II. Bulletin for the History of Chemistry 37(2):91-95.
  3. Fishbein, M. C.; Meerbaum, S.; Rit, J.; Lando, U.; Kanmatsuse, K.; Mercier, J. C.; Corday, E.; Ganz, W. (May 1981). "Early phase acute myocardial infarct size quantification: validation of the triphenyl tetrazolium chloride tissue enzyme staining technique". American Heart Journal. 101 (5): 593–600. doi:10.1016/0002-8703(81)90226-x. ISSN 0002-8703. PMID 6164281.
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