1241892-06-7Relevant academic research and scientific papers
Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof
Sidoryk, Katarzyna,Filip, Katarzyna,Cmoch, Piotr,?aszcz, Marta,Cybulski, Marcin
, p. 135 - 148 (2018)
The synthesis and molecular structure details of R- 3,4-dihydroxyphenyl lactic acid (danshensu) and related compounds, i.e. S isomer and the key intermediates have been described. Danshensu is an important water soluble phenolic acid of Salvia miltiorrhiza herb (danshen or red sag) with numerous applications in traditional Chinese medicine (TCM). Our synthetic approach was based on the Knoevenagel condensation of the protected 3,4-dihydroxybenzaldehyd and Meldrum acid derivative, followed by asymmetric Sharples dihydroxylation, reductive mono dehydroxylation and final deprotection. All compounds were characterized by various spectroscopic techniques: 1H-, 13C- magnetic resonance (NMR); Fourier-transformed infrared (FTIR); Raman, HR mass spectroscopy. For the determination of compound optical purities original HPLC methods were developed which allowed for the efficient resolution of danshensu R and S enantiomers as well as its intermediate enantiomers, using commercially available chiral stationary phases. Furthermore, in order to better understand danshensu specificity as a potential API in drug formulation, the physicochemical properties of the compounds were studied by thermal analysis, including differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).
Enantioselective synthesis and antioxidant activity of 3-(3,4- dihydroxyphenyl)-glyceric acid - Basic monomeric moiety of a biologically active polyether from Symphytum asperum and S. caucasicum
Merlani, Maia,Barbakadze, Vakhtang,Amiranashvili, Lela,Gogilashvili, Lali,Yannakopoulou, Elina,Papadopoulos, Kyriakos,Chankvetadze, Bezhan
experimental part, p. 717 - 725 (2010/11/16)
The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (+)-(2R,3S)-2,3-dihydroxy-3-(3
