Synthesis and characterization of solid 2-methoxycinnamylidenepyruvic acid

Abstract

The 2-methoxycinnamylidenepyruvic acid (2-MeO-HCP) was synthesized and characterized for nuclear magnetic resonance (¹H and 13C NMR), mass spectrometry (MS), Infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). The application of DSC for purity determination is well documented in literature and is used in the analysis of pure organic compounds. The molecular geometry and vibrational frequencies of 2-MeO-HCP have been calculated.

Synthesis, characterization and thermal behaviour of solid 2-methoxycinnamylidenepyruvate of light trivalent lanthanides

“…Sodium 2-methoxycinnamylidenepyruvate (Na-2-MeO-CP) and its corresponding acid were both synthesized following a procedure described in the literature, 9 with the following modifications: an aqueous solution of sodium pyruvate (8.71 g per 10 mL) was added under continuous stirring to 20 mL of a methanolic solution of 2-methoxycinnamaldehyde (13.23 g). Sixty three milliliters of an aqueous sodium hydroxide solution 5% (w/v) were slowly added, while the reacting system was stirred and cooled in an ice bath.…”

“…2 Several metal ion complexes of phenyl-substituted derivatives of cinnamylidenepyruvate, C 6 H 5 (CH) 4 C(O)COO -(CP), have been investigated in aqueous solutions 3 and in the solid state. [4][5][6][7][8][9] These works reported the thermodynamic stability (β 1 ) and spectroscopic parameters (ε 1max , λ 1max ) in aqueous solutions associated with 1:1 complex species. They also report the synthesis and investigation of the compounds in the solid state by means of thermogravimetry (TG), differential thermal analysis (DTA), differential scanning calorimetry (DSC), X-ray powder diffractometry and other methods of analysis.…”

Rare-earth metal compounds with a novel ligand 2-methoxycinnamylidenepyruvate: A thermal and spectroscopic approach

“…The 2-methoxycinnamaldehyde, (CH 3 O-C 6 H 4 -(CH) 2 -CHO) 96% pure predominantly trans, was obtained from Aldrich and sodium pyruvate (H 3 C-CO-COONa) 99% pure from Sigma. Sodium 2-methoxycinnamylidenepyruvate (Na-2-MeO-CP) and its corresponding acid were both synthesized following the procedure described in the literature [10], with some modifications which include an aqueous solution of sodium pyruvate (8.71 g per 10 mL) added under continuous stirring to 20 mL of methanolic solution of 2-methoxycinnamaldehyde (13.23 g). Sixty-three milliliters of an aqueous sodium hydroxide solution 5% (m/v) was slowly added while the reacting system was stirred and cooled in an ice bath.…”

“…In this study, the organic ligand 2methoxycinnamylidenepyruvate (2-MeO-HCP), obtained from aldolic condensation of cinnamic acid and pyruvate, was used to synthesize the compounds in solid state with heavy trivalent lanthanides. The synthesis and characterization of 2-MeO-HCP and other compounds have been reported in previous studies [10][11][12] which aimed at fundamentally performing the synthesis and investigation of the compounds in solid state by the establishment of stoichiometry, thermal behavior and thermal decomposition, FT-IR spectroscopy and the classical analysis method of titration with EDTA. In this paper, the compounds of lanthanides 2-methoxycinnamylidenepyruvate were studied using the techniques mentioned, as well as employing complementary techniques like X-ray powder diffraction to provide qualitative information on the cristallinity of the compounds and mass spectrometry coupled to a thermogravimetric system (TG/MS) to support the gases analysis performed by TG/FT-IR on the gases evolved from the samples undergone thermal decomposition process.…”