Procyanidin
[CAS# 4852-22-6]

Identification

• Classification: Biochemical >> Biochemical reagent >> Biological dye
• Name: Procyanidin
• Synonyms: 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
• Molecular Formula: C₃₀H₂₆O₁₃
• Molecular Weight: 594.52
• CAS Registry Number: 4852-22-6
• SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC4(C(C(C5=C(C=C(C=C5O4)O)O)O)O)C6=CC(=C(C=C6)O)O

Properties

• Density: 1.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.876, Calc.^*
• Boiling Point: 986.4±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 550.3±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Procyanidins are a class of naturally occurring polyphenolic compounds found predominantly in various fruits, vegetables, and plant-derived foods. The discovery of procyanidins can be traced back to studies in the late 20th century that sought to understand the health benefits associated with the consumption of flavonoid-rich foods. Procyanidins are oligomeric compounds composed of catechin and epicatechin units, and they are a significant subclass of flavan-3-ols, which play crucial roles in the plant's defense mechanisms against pests and diseases.

These compounds are widely distributed in the plant kingdom, particularly in foods such as apples, grapes, cocoa, and berries. Research has shown that procyanidins contribute to the astringent taste of certain fruits and have a role in the color and stability of red wine. The structure of procyanidins allows them to interact with proteins and other macromolecules, which may influence their biological activities.

Procyanidins have gained significant attention due to their potential health benefits. Numerous studies have suggested that they exhibit strong antioxidant properties, which can help mitigate oxidative stress in the body. This antioxidant capacity is linked to a reduced risk of chronic diseases such as cardiovascular diseases, diabetes, and certain types of cancer. Procyanidins are thought to exert their effects by scavenging free radicals, chelating metal ions, and modulating cellular signaling pathways.

In addition to their antioxidant properties, procyanidins are believed to have anti-inflammatory effects. Research has indicated that they can inhibit the expression of pro-inflammatory cytokines and enzymes, which may contribute to their protective effects against inflammation-related diseases. These properties have prompted investigations into the use of procyanidins as dietary supplements or functional food ingredients aimed at improving health outcomes.

Procyanidins also play a role in enhancing the absorption of other nutrients, particularly in the gut. Their ability to form complexes with minerals such as iron and zinc may improve the bioavailability of these essential nutrients, thereby supporting overall health.

The applications of procyanidins extend beyond health benefits; they are also utilized in the food industry as natural preservatives due to their antimicrobial properties. The ability of procyanidins to inhibit the growth of certain pathogens makes them valuable in extending the shelf life of various food products. Furthermore, their astringency and flavor-enhancing properties are harnessed in food formulations.

In the cosmetic industry, procyanidins are incorporated into skincare products for their antioxidant and anti-aging properties. Their potential to protect skin cells from oxidative damage makes them a sought-after ingredient in the formulation of creams and serums aimed at improving skin health.

Research on procyanidins continues to expand, with ongoing studies exploring their mechanisms of action, bioavailability, and potential therapeutic applications. As a result, procyanidins represent a promising area of study in the intersection of nutrition, health, and disease prevention.

References

2024. Hepatoprotective procyanidin derivatives. Journal of Agricultural and Food Chemistry, 72(15).
DOI: 10.1021/acs.jafc.4c01704

2025. Procyanidin delivery systems. Food Chemistry, 451.
DOI: 10.1016/j.foodchem.2024.141691