Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof
PBN-AR
Instytucja
Sieć Badawcza Łukasiewicz - Instytut Farmaceutyczny
Informacje podstawowe
Główny język publikacji
angielski
Czasopismo
JOURNAL OF MOLECULAR STRUCTURE (20pkt w roku publikacji)
ISSN
0022-2860
EISSN
Wydawca
ELSEVIER SCIENCE BV
DOI
URL
Rok publikacji
2018
Numer zeszytu
Strony od-do
135-148
Numer tomu
1153
Identyfikator DOI
Liczba arkuszy
Słowa kluczowe
angielski
Phenolic acids
Asymmetric synthesis
Chiral column chromatography
Spectroscopy
Streszczenia
Język
angielski
Treść
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).
Cechy publikacji
oryginalny artykuł naukowy
Inne
System-identifier
PX-5b852393d5de77493b94f347
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