Tioniini

Tioniini
Tunnisteet
IUPAC-nimi 7-iminofenotiatsiini-3-amiini
CAS-numero 135-59-1
PubChem CID 65045 ja 65043
SMILES C1=CC2=C(C=C1N)SC3=CC(=N)C=CC3=N2 [1]
Ominaisuudet
Molekyylikaava C12H9N3S
Moolimassa 227,292 g/mol

Tioniini eli Lauthin violetti (C12H9N3S) on tiatsiinin rakenteen sisältävä orgaaninen yhdiste, jota käytetään väriaineena. Sillä voidaan värjätä muun muassa silkkiä tai villaa[2] ja lisäksi sitä käytetään redox-indikaattorina.

Valmistus

Charles Lauth syntetisoi tioniinia ensimmäisenä vuonna 1876. Lähtöaineina hän käytti p-fenyleenidiamiinia ja rikkivetyä ja hapetti muodostuneen tuotteen. Myöhemmin BASF:n tutkijat käyttivät samaa menetelmää tioniinin johdannaisen, metyleenisinisen valmistamiseen.[3]

Käyttö

Kiinteänä tioniini on väriltään vihreää. Se värjää kankaat, kuten silkin violetiksi.[2]

Tioniinia voidaan käyttää myös redox-indikaattorina. Yhdisteen väri muuttuu sinivioletista värittömäksi, kun se pelkistyy leuko-muodokseen.[4][5]

Tioniini fluoresoi virittyneessä tilassaan. Tätä voidaan käyttää hyväksi biologisissa tutkimuksissa. Tioniini voidaan virittää, jolloin se fluoresoi sinisenä. Virittyneessä tilassa yhdiste voi myös hapettaa useiden entsyymien koentsyymeinä toimivien NADH:n tai NADPH:n. Näiden hapettuessa tioniini palaa perustilaansa ja fluoresenssi heikkenee. Tätä voidaan käyttää hyväksi entsyymitutkimuksissa.[6][7]. Myös tioniini leuko-muoto fluoresoi ja fluoresenssi on jopa voimakkaampaa ja pitkäkestoisempaa kuin tioniinilla.[5]

Lähteet

  1. ↑ Thionine – Substance summary NCBI. Viitattu 3. toukokuuta 2010.
  2. ↑ a b Päivi Hintsanen: Värejä...L Coloria.net. Viitattu 3.5.2010.
  3. ↑ Synthesis of Thionine RIELE. Viitattu 3.5.2010. (englanniksi)[vanhentunut linkki]
  4. ↑ Complexometric, Oxidation, Redox and Adsorption Titration Indicators delloyd.50megs.com. Arkistoitu 25.8.2010. Viitattu 3.5.2010. (englanniksi)
  5. ↑ a b Soo-Keun Lee & Andrew Mills: Luminescence of Leuco-Thiazine Dyes. Journal of Fluorescence, 2003, 13. vsk, nro 5, s. 375–377. Springer. Artikkelin verkkoversio. Viitattu 6.10.2023. (englanniksi)
  6. ↑ Ashok Mulchandani,Kim R. Rogers: Enzyme and microbial biosensors: techniques and protocols, s. 189–195. Humana Press, 1998. ISBN 978-0-89603-410-5 Kirja Googlen teoshaussa Viitattu 3.5.2010. (englanniksi)
  7. ↑ Tuan Vo-Dinh: Protein nanotechnology: protocols, instrumentation, and applications, s. 96–70. Humana Press, 2005. ISBN 978-1-58829-310-7 Kirja Googlen teoshaussa Viitattu 3.5.2010. (englanniksi)

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