Ascorbic acid (Vitamin C) is a crucial nutrient and biomolecule for human [1]. This plays a major role in various biological pathways which are necessary fundamental for normal cellular function [2].
In organic chemistry, ascorbic acid is used as a starting material and also as a catalyst. In continuation of our research on catalysis, we have reported ascorbic acid-catalyzed reactions in synthesis [3]. The present study describes the synthesis of various organic compounds using ascorbic acid as the starting molecule.
Numerous derivatives of L-Ascorbic acid are synthesized. These include zinc-ascorbate, calcium L-ascorbate, D-araboascorbic acid, ascorbyl monophosphate, sodium-calcium ascorbyl phosphate, 6-O-palmitoyl-L-ascorbic acid, L-ascorbic acid sodium salt, 6-O-stearoyl-L-ascorbic acid, di-O-butyryl-L-ascorbic acid, di-O-palmitoyl-L-ascorbic acid, L-ascorbic acid 2-phosphate sesquimagnesium, glyceryl ascorbate, 3-O-ethyl-L-ascorbic acid, sodium isoascorbate and (+)-5,6-O-isopropylidene-L-ascorbic acid [1, 2]. Many of these derivatised molecules possess significant pharmacological activities. For example, this induces apoptosis in cancer cells [3]. A few purine and pyrimidine derivatives of didehydro-dideoxy-L-ascorbic acid have cytostatic properties [4, 5]. The 2-C-alkylated products of ascorbic acid have immunostimulant activity [6, 7]. The 2-O and 3-O-alkylated lipid-soluble molecules are used to protect the lipid peroxidation of the biomembrane structures [8]. The preparation of liposoluble ascorbic acid derivatives is identified [8]. The fatty acids esters are the crucial derivatives which are used as food additives [9].
The preparation of a series of 2,3-di-O-alkyl derivatives of 5,6-O-isopropylidene-L-ascorbic acid following phase transfer catalysis in water is known. These products are active against MCF-7 breast cancer cell line. The synthesis of diversely halogenated 3-deazapurine, 7-deazapurine, and alkylated 9-deazapurine products of L-ascorbic or imino-L-ascorbic acid is reported.
Synthesis of L-ascorbyl flurbiprofenate by lipase-mediated esterification of L-ascorbic acid with flurbiprofen in amyl alcohol is performed. The ascorbic acid prodrug of ibuprofen is the choice in some examples.
Ascorbic acid serves as a crucial micronutrient and antioxidant in the treatment of cancer and antiviral diseases. Pyrimidine and purine derivatives of ascorbic acid have antiviral and cytostatic activities. Most importantly, the chiral carbons of ascorbic acid are manipulated in the preparation of many compounds of predictable configuration. Due to the current trend of conducting reactions under environmentally friendly conditions, the preparation of compounds starting from ascorbic acid deserves much attention. Moreover, ascorbic acid catalyzes many useful reactions. Our study on dipole moments of medicinally active compounds have identified an explanation of their biological activities. The compounds obtained from ascorbic acid can be used for the examination of their dipole moments in order to focus on their biological aproperties. We expect more methods toward the synthesis of complex structures using ascorbic acid.
Acknowledgments
AD and BKB are grateful to Prince Mohammad Bin Fahd University for support.
References
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Aparna Das*and Bimal Krishna Banik*
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies,
