Vicine

Vicine Vicine (CAS No. 152-93-2) is a naturally occurring alkaloid glycoside primarily found in fava beans ( Vicia faba ). It is chemically identified as 2,6-diamino-5-(β-D-glucopyranosyloxy)-4(1H)-pyrimidinone and has the molecular formula C₁₀H₁₆N₄O₇ with a molecular weight of 304.26 g/mol . Chemical and Physical Properties CAS Number : 152-93-2 EINECS : 205-809-4 Molecular Formula : C₁₀H₁₆N₄O₇ Molecular Weight : 304.26 g/mol Boiling Point : 445.09°C Melting Point : 242–244°C Density : 2.18 g/cm³ Appearance : White crystalline powder (typically stored neat at room temperature or -20°C for long-term stability). Structure and Sources Vicine consists of a divicine (pyrimidine aglycone) moiety linked to a β-D-glucopyranose sugar. It is biosynthesized in plants like Vicia faba and acts as a defense compound against herbivores. Biological Significance and Toxicity Favism : Vicine is toxic to individuals with glucose-6-phosphate dehydrogenase (G6PD) deficiency , causing oxidative stress and hemolytic anemia (favism). Mechanism : Hydrolysis by intestinal β-glucosidases releases divicine, which generates reactive oxygen species (ROS), damaging red blood cells. Applications Biochemical Research : Studied for its role in oxidative stress pathways and interactions with enzymes like xanthine oxidase. Reference Standard : Used as a certified primary reference material (purity >95% by HPLC) in analytical testing, particularly in phytochemical studies. Storage and Handling Storage : Store at 2–8°C for long-term stability. Short-term storage at room temperature is acceptable. Solubility : Soluble in water and DMSO. Safety Considerations Toxicity : Handle with caution due to its potential to induce hemolysis in susceptible individuals. Regulatory Status : Labeled with hazard warnings (e.g., "Warning") for occupational exposure. In summary, vicine is a biologically active glycoside with significant implications in nutrition, toxicology, and biochemistry. Its dual role as a plant defense compound and a research tool underscores its importance in both agricultural and medical sciences. Citations: https://pubs.acs.org/doi/10.1021/jf00118a041 https://pubs.acs.org/doi/10.1021/jf60194a016 https://centaur.reading.ac.uk/88530/8/1-s2.0-S0924224419301992-main.pdf https://www.nature.com/articles/s41598-024-83488-z https://pmc.ncbi.nlm.nih.gov/articles/PMC10934171/ https://pmc.ncbi.nlm.nih.gov/articles/PMC5006014/ https://en.wikipedia.org/wiki/Vicine