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Pyranine

Chemical compound From Wikipedia, the free encyclopedia

Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates.[2][3] Pyranine is soluble in water and is used as a coloring agent, biological stain, optical detecting reagent, and pH indicator.[4] Pyranine is also used in yellow highlighters to provide their characteristic fluorescence and bright yellow-green colour. It is also found in some types of soap.[5]

Quick facts Names, Identifiers ...
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)
4107272
ChEBI
ChemSpider
ECHA InfoCard 100.026.166 Edit this at Wikidata
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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Synthesis

Pyranine is synthesized from pyrenetetrasulfonic acid and a solution of sodium hydroxide in water under reflux.[6] The trisodium salt crystallizes as yellow needles when adding an aqueous solution of sodium chloride.

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