Chemistry:Pyranine

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
CAS Number	6358-69-6 Y
3D model (JSmol)	Interactive image
EC Number	228-783-6
PubChem CID	4136521
UNII	I2W85YOX9L Y
InChI 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
SMILES 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
Chemical formula	C16H7Na3O10S3
Molar mass	524.37 g·mol−1
Appearance	Yellow-green crystalline powder
Solubility in water	Soluble
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	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

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

Synthesis

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

See also

• Fluorescein
• Fluorescence

External links

• CTD's Pyranine page from the Comparative Toxicogenomics Database