Pyranine

Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates.[2][3] Pyranine is soluble in water and has applications as a coloring agent, biological stain, optical detecting reagent, and a pH indicator.[4][5] One example would be the measurement of intracellular pH.[6] 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.[7]

Pyranine
Skeletal formula of pyranine
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
UNII
  • InChI=1S/C16H10O10S3.3Na/c17-11-5-12(27(18,19)20)8-3-4-10-14(29(24,25)26)6-13(28(21,22)23)9-2-1-7(11)15(8)16(9)10;;;/h1-6,17H,(H,18,19,20)(H,21,22,23)(H,24,25,26);;;/q;3*+1/p-3
    Key: KXXXUIKPSVVSAW-UHFFFAOYSA-K
  • C1=CC2=C3C(=C(C=C2S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC4=C(C=C(C1=C43)O)S(=O)(=O)[O-].[Na+].[Na+].[Na+]
Properties
C16H7Na3O10S3
Molar mass 524.37 g·mol−1
Appearance Yellow-green crystalline powder
Soluble
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
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

Synthesis

It is synthesized from pyrenetetrasulfonic acid and a solution of sodium hydroxide in water under reflux.[8] The trisodium salt crystallizes as yellow needles when adding an aqueous solution of sodium chloride.

See also

References
  1. "C&L Inventory". echa.europa.eu. Retrieved 13 December 2021.
  2. "chem industry entry". Archived from the original on 2007-10-26. Retrieved 2007-12-31.
  3. "Comparative Toxicogenomics Database entry".
  4. "chemical land 21 entry".
  5. "Sci-Toys entry".
  6. "Loading pyranine via purinergic receptors Bing by Siang Gan".
  7. "D&C Green No. 8 (C.I. 59040)". whatsinproducts.com. Retrieved 2023-05-04.
  8. 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.
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