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

1. Biochemical Research: Studied for its role in oxidative stress pathways and interactions with enzymes like xanthine oxidase.
2. 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:

1. https://pubs.acs.org/doi/10.1021/jf00118a041
2. https://pubs.acs.org/doi/10.1021/jf60194a016
3. https://centaur.reading.ac.uk/88530/8/1-s2.0-S0924224419301992-main.pdf
4. https://www.nature.com/articles/s41598-024-83488-z
5. https://pmc.ncbi.nlm.nih.gov/articles/PMC10934171/
6. https://pmc.ncbi.nlm.nih.gov/articles/PMC5006014/
7. https://en.wikipedia.org/wiki/Vicine