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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 414438444 | verifiedrevid = 426193536
| ImageFile = Pyranine.svg | ImageFile = Pyranine.svg
| ImageSize = | ImageSize =
| ImageAlt = Skeletal formula of pyranine
| ImageFile2 =
| IUPACName = trisodium 8-hydroxypyrene-1,3,6-trisulfonate | IUPACName = Trisodium 8-hydroxypyrene-1,3,6-trisulfonate
| OtherNames = 8-hydroxypyrene-1,3,6-trisulfonic acid, Solvent Green 7, sulfonated hydroxy pyrene trisodium salt | OtherNames = 8-Hydroxypyrene-1,3,6-trisulfonic acid; Solvent Green 7; HPTS; Sulfonated hydroxy pyrene trisodium salt
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6358-69-6 | CASNo = 6358-69-6
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EINECS = 228-783-6
| PubChem = 4136521 | UNII = I2W85YOX9L
⚫ | EINECS = 228-783-6
⚫ | SMILES = C1=CC2=C3C (=C(C=C2S(=O)(=O))S(=O)(=O)) C=CC4=C (C=C(C1=C43)O) S(=O)(=O) ...
| MeSHName = | PubChem = 4136521
| StdInChI=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
| StdInChIKey = KXXXUIKPSVVSAW-UHFFFAOYSA-K
⚫ | SMILES = C1=CC2=C3C(=C(C=C2S(=O)(=O))S(=O)(=O))C=CC4=C(C=C(C1=C43)O)S(=O)(=O)...
| MeSHName =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=16 | H=7 | Na=3 | O=10 | S=3
| Formula = C<sub>16</sub>H<sub>7</sub>Na<sub>3</sub>O<sub>10</sub>S<sub>3</sub>
⚫ | Appearance = Yellow-green crystalline powder
| MolarMass = 524.37
| Density =
⚫ | Appearance = yellow-green crystalline powder
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility = Soluble
| Solubility = Soluble
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = XI | FlashPt =
| GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/32949 |website=echa.europa.eu |access-date=13 December 2021}}</ref>
| FlashPt =
| GHSPictograms = {{GHS07}}
| RPhrases = 36/37/38
| GHSSignalWord = Warning
| SPhrases = 26-36
| HPhrases = {{H-phrases|315|319|335}}
| Autoignition =
| PPhrases = {{P-phrases|}}
| AutoignitionPt =
}} }}
}} }}
'''Pyranine''' is a ], ]-sensitive ] from the group of chemicals known as arylsulfonates.<ref>{{cite web | url = http://www.chemindustry.com/chemicals/1196265.html| title= chem industry entry}}</ref><ref>{{cite web | url= http://ctd.mdibl.org/detail.go;?type=chem&acc=C005047 | title = Comparative Toxicogenomics Database entry}}</ref> Pyranine is soluble in water and has applications as a coloring agent, biological stain, optical detecting reagent, and a ].<ref>{{cite web|url=http://chemicalland21.com/lifescience/foco/PYRANINE.htm|title=chemical land 21 entry}}</ref><ref>{{cite web | url = http://sci-toys.com/scichem/jqp000/4136521.html | title= Sci-Toys entry}}</ref> One example would be the measurement of ].<ref>{{cite web | url = http://ajpcell.physiology.org/cgi/content/abstract/275/4/C1158| title = Loading pyranine via purinergic receptors Bing by Siang Gan}}</ref> Pyranine is also found in ]s<ref>http://www.neelikon.com/index.htm</ref> and ]s<ref>http://householdproducts.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=218</ref>. '''Pyranine''' is a ], ]-sensitive ] from the group of chemicals known as arylsulfonates.<ref>{{cite web| url = http://www.chemindustry.com/chemicals/1196265.html| title = chem industry entry| access-date = 2007-12-31| archive-date = 2007-10-26| archive-url = https://web.archive.org/web/20071026155704/http://www.chemindustry.com/chemicals/1196265.html| url-status = dead}}</ref><ref>{{cite web | url= http://ctdbase.org/detail.go?type=chem&acc=C005047 | title = Comparative Toxicogenomics Database entry}}</ref> Pyranine is soluble in water and is used as a coloring agent, biological stain, optical detecting reagent, and ].<ref>{{cite web|url=http://chemicalland21.com/lifescience/foco/PYRANINE.htm|title=chemical land 21 entry}}</ref><ref>{{cite web | url = http://sci-toys.com/scichem/jqp000/4136521.html | title= Sci-Toys entry}}</ref> Pyranine is also used in yellow ]s to provide their characteristic ] and bright yellow-green colour. It is also found in some types of ].<ref>{{cite web |url=https://www.whatsinproducts.com/chemicals/view/1/115 |title=D&C Green No. 8 (C.I. 59040) |website=whatsinproducts.com |accessdate=2023-05-04}} </ref>

== Synthesis ==
Pyranine is synthesized from pyrenetetrasulfonic acid and a solution of sodium hydroxide in water under reflux.<ref name="TietzeBayer1939">{{cite journal|last1=Tietze|first1=Ernst|last2=Bayer|first2=Otto|title=Die Sulfosäuren des Pyrens und ihre Abkömmlinge|journal=Justus Liebig's Annalen der Chemie|volume=540|issue=1|year=1939|pages=189–210|issn=0075-4617|doi=10.1002/jlac.19395400113}}</ref> The trisodium salt crystallizes as yellow needles when adding an aqueous solution of ].


== See also == == See also ==
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* ] * ]

⚫ == External links ==
⚫ * from the ]


== References == == References ==
{{reflist}} {{reflist}}

⚫ == External links ==
⚫ * from the ]


] ]
] ]
] ]
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{{organic-compound-stub}}

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Latest revision as of 16:56, 6 January 2025

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
CAS Number
3D model (JSmol)
ECHA InfoCard 100.026.166 Edit this at Wikidata
EC Number
  • 228-783-6
PubChem CID
UNII
CompTox Dashboard (EPA)
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-3Key: KXXXUIKPSVVSAW-UHFFFAOYSA-K
SMILES
  • C1=CC2=C3C(=C(C=C2S(=O)(=O))S(=O)(=O))C=CC4=C(C=C(C1=C43)O)S(=O)(=O)...
Properties
Chemical formula C16H7Na3O10S3
Molar mass 524.37 g·mol
Appearance Yellow-green crystalline powder
Solubility in water Soluble
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates. Pyranine is soluble in water and is used as a coloring agent, biological stain, optical detecting reagent, and pH indicator. 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.

Synthesis

Pyranine 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

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. "D&C Green No. 8 (C.I. 59040)". whatsinproducts.com. Retrieved 2023-05-04.
  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.

External links

Categories: