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| | Thenoyltrifluoroacetone Basic information |
| | Thenoyltrifluoroacetone Chemical Properties |
| Melting point | 40-44 °C(lit.) | | Boiling point | 96-98 °C8 mm Hg(lit.) | | density | 1.4373 (estimate) | | Fp | 233 °F | | storage temp. | 2-8°C | | solubility | sparingly soluble in water, readily soluble in organic solvents. Distribution ratio between acidic water and benzene is about 40. In alkaline aqueous medium it exists in the enolate form, this being relatively more soluble in water. The equilibrium distribution ratio between benzene and alkaline aqueous medium (about pH 8) is about 1. In alkaline aqueous medium of pH > 9 TTA decomposes to trifluoroacetone and acetylthiophen. | | pka | 5.60±0.23(Predicted) | | form | Crystalline Powder, Crystals and/or Chunks | | color | Light yellow or beige to brown | | Odor | Odorless | | Water Solubility | INSOLUBLE | | BRN | 168645 | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | | InChIKey | TXBBUSUXYMIVOS-UHFFFAOYSA-N | | CAS DataBase Reference | 326-91-0(CAS DataBase Reference) | | NIST Chemistry Reference | 1,3-Butanedione, 4,4,4-trifluoro-1-(2-thienyl)-(326-91-0) | | EPA Substance Registry System | 1,3-Butanedione, 4,4,4-trifluoro-1-(2-thienyl)- (326-91-0) |
| | Thenoyltrifluoroacetone Usage And Synthesis |
| Description | TTFA?(326-91-0) blocks the respiratory chain complex II causing inhibition of mitochondrial respiration.? Respiratory chain complex II inhibition is caused via binding of TTFA to two ubiquinone binding sites, Qp and Qd.1?Inhibition of Complex II by TFA has been shown to cause a delay in overall cell cycle progression leading to oxidative stress.2,3?TTFA also was found to inhibit porcine liver carboxylesterase (IC50?= 0.54 μM).4 | | Chemical Properties | light yellow to beige to brown crystalline powder, | | Uses | Thenoyltrifluoroacetone is one of the most proved extracting agents in solventextraction analysis. It is equally suitable for the separation and selective enrichment of metal ions.
2-Thenoyltrifluoroacetone (TTFA) is an inhibitor of respiration in animals and bacteria. In animals, TTFA binds at the quinone reduction site of succinate:ubiquinone oxidoreductase (SQR; Complex II), preventing ubiquinone from binding. It inhibits NADH fumarate reductase in bacteria. TTFA also inhibits photosystem II in plants and NADH-ubiquinone oxidoreductase of the virus Vibrio cholerae, decreasing cholera toxin production. This compound is also a chelator of metals, including lanthanum, zirconium, hafnium, and neodymium. Reagent for the determination of actinides and lanthanides.
2-Thenoyltrifluoroacetone is used for the extractive spectrophotometric determination of ruthenium at ph 4.0 (acetate buffer).
Thenoyltrifluoroacetone has also been used as an alternative β-diketone for in-house assay development since NTA was not, until recently, commercially available.
| | Uses | 2-Thenoyltrifluoroacetone is an inhibitor of respiration in animals and bacteria. TTFA binds at the quinone reduction site of succinate ubiquinone oxidoreductase. | | Purification Methods | Crystallise the dione from hexane or *benzene. (Anaqueous solutions slowly decompose it). It has 1638(C=O), 1657(C=C)cm-1 . The oxime crystallises from H2O or aqueous EtOH. It is used for the determination of Actinides and Lanthanides. [Chaston et al. Aust J Chem 18 673 1956, Jeffrey et al. In Vogel’s Textbook of Qunatitative Chemical Analysis 5thedn J Wiley & Sons, p170 1989, Beilstein 17 III/IV 5989, 17/11 V 128.] | | References | 1) Sun?et al.?(2005),?Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II; Cell?121?1043
2) Byon?et al.?(2008),?Mitochondrial dysfunction by complex II inhibition delays overall cell cycle progression via reactive oxygen species production; J. Cell Biochem.?104?1747
3) Siebels and Dr?se (2013),?Q-site inhibitor induced ROS production of mitochondrial complex II is attenuated by TCA cycle dicarboxylates; Biochim. Biophys. Acta?1827?1156
4) Zhang and Fariss (2002),?Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity; Biochem. Pharmacol.?63?751 |
| | Thenoyltrifluoroacetone Preparation Products And Raw materials |
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