Thenoyltrifluoroacetone

Thenoyltrifluoroacetone^[1]
Names


Preferred IUPAC name 4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione
Other names 2-thenoyltrifluoroacetone
Identifiers
CAS Number	326-91-0^Y
3D model (JSmol)	Interactive image
Abbreviations	TTFA
ChEMBL	ChEMBL1236433
ChemSpider	5399^Y
DrugBank	DB04795^Y
ECHA InfoCard	100.005.743
EC Number	206-316-7
PubChem CID	5601
UNII	MYQ9MNW7NI^Y
CompTox Dashboard (EPA)	DTXSID1059812
InChI InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2^Y Key: TXBBUSUXYMIVOS-UHFFFAOYSA-N^Y InChI=1/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2 Key: TXBBUSUXYMIVOS-UHFFFAOYAR
SMILES O=C(c1sccc1)CC(=O)C(F)(F)F
Properties
Chemical formula	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
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Flash point	12 °C (54 °F; 285 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

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]

Thenoyltrifluoroacetone can be made in a Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.^[4]^[5]

References

^ Sigma-Aldrich product page
^ Tappel (July 1960). "Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds". Biochem. Pharmacol. 3 (4): 289–96. doi:10.1016/0006-2952(60)90094-0. PMID 13836892.
^ Sun, Fei; Huo, Xia; Zhai, Yujia; Wang, Aojin; Xu, Jianxing; Su, Dan; Bartlam, Mark; Rao, Zihe (2005). "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell. 121 (7): 1043–1047. doi:10.1016/j.cell.2005.05.025. PMID 15989954. S2CID 16697879.
^ Gergel, Max G. (March 1977). Excuse me sir, would you like to buy a kilo of isopropyl bromide?. Pierce Chemical. p. 130.
^ Taydakov, Ilya V; Kreshchenova, Yuliya M; Dolotova, Ekaterina P (27 December 2018). "A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety". Beilstein Journal of Organic Chemistry. 14: 3106–3111. doi:10.3762/bjoc.14.290. PMC 6317410. PMID 30643588.