Pyranine

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Pyranine
Skeletal formula of pyranine
Space-filling model of pyranine as a sodium salt
Names
IUPAC name
trisodium 8-hydroxypyrene-1,3,6-trisulfonate
Other names
8-hydroxypyrene-1,3,6-trisulfonic acid, Solvent Green 7, HPTS, sulfonated hydroxy pyrene trisodium salt
Identifiers
3D model (JSmol)
ECHA InfoCard 100.026.166
EC Number 228-783-6
Properties
C16H7Na3O10S3
Molar mass 524.37
Appearance yellow-green crystalline powder
Soluble
Hazards
Main hazards XI
R-phrases (outdated) 36/37/38
S-phrases (outdated) 26-36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates.[1][2] Pyranine is soluble in water and has applications as a coloring agent, biological stain, optical detecting reagent, and a pH indicator.[3][4] One example would be the measurement of intracellular pH.[5] Pyranine is also found in yellow highlighters, giving them their characteristic fluorescence and bright yellow-green colour. It is also found in some types of soap.[6]

Synthesis[edit]

It is synthesized from pyrenetetrasulfonic acid and a solution of sodium hydroxide in water under reflux.[7] The trisodium salt crystallizes as yellow needles when adding an aqueous solution of sodium chloride.

See also[edit]

External links[edit]

References[edit]

  1. ^ "chem industry entry".
  2. ^ "Comparative Toxicogenomics Database entry".
  3. ^ "chemical land 21 entry".
  4. ^ "Sci-Toys entry".
  5. ^ "Loading pyranine via purinergic receptors Bing by Siang Gan".
  6. ^ http://householdproducts.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=218
  7. ^ Tietze, Ernst; Bayer, Otto (1939). "Die Sulfosäuren des Pyrens und ihre Abkömmlinge". Justus Liebig's Annalen der Chemie. 540 (1): 189–210. doi:10.1002/jlac.19395400113. ISSN 0075-4617.