Thenoyltrifluoroacetone

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Thenoyltrifluoroacetone[1]
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Names
IUPAC name
4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione
Other names
2-thenoyltrifluoroacetone
Identifiers
326-91-0 YesY
ChemSpider 5399 YesY
DrugBank DB04795 YesY
Jmol 3D model Interactive image
PubChem 5601
  • InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2 YesY
    Key: TXBBUSUXYMIVOS-UHFFFAOYSA-N YesY
  • InChI=1/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
    Key: TXBBUSUXYMIVOS-UHFFFAOYAR
  • O=C(c1sccc1)CC(=O)C(F)(F)F
Properties
C8H5F3O2S
Molar mass 222.18 g mol−1
Appearance fine, slightly yellow crystals
Melting point 40 to 44 °C (104 to 111 °F; 313 to 317 K)
Boiling point 96 to 98 °C (205 to 208 °F; 369 to 371 K) 8 mmHg
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Thenoyltrifluoroacetone, C8H5F3O2S, is a chemical compound used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.

Perhaps the first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.[2] Tappel had the (erroneous) idea that inhibitors like antimycin and alkyl hydroxyquinoline-N-oxide might work by chelating iron in the hydrophobic milieu of respiratory membrane proteins, so he tested a series of hydrophobic chelating agents. TTFA was a potent inhibitor, but not because of its chelating ability. TTFA binds at the quinone reduction site in Complex II, preventing ubiquinone from binding. The first x-ray structure of Complex II showing how TTFA binds, 1ZP0, was published in 2005 .[3]

References

  1. Sigma-Aldrich product page
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  3. Lua error in package.lua at line 80: module 'strict' not found.


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