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
3D model (Jmol)	Interactive image
ECHA InfoCard	100.026.166
EC Number	228-783-6
PubChem	4136521
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
Appearance	yellow-green crystalline powder
Solubility in water	Soluble
Hazards
Main hazards	XI
R-phrases	36/37/38
S-phrases	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

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

• Fluorescein
• Fluorescence

External links

• CTD's Pyranine page from the Comparative Toxicogenomics Database

References

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.