689043

Caffeic acid is a type of hydroxycinnamic acid, specifically a derivative of cinnamic acid with hydroxy groups substituted at the 3 and 4 positions on the phenyl ring. It can exist in both cis and trans forms, with the trans form being more common. This compound plays multiple roles in biological systems and has various inhibitory functions, including as an inhibitor of enzymes such as arachidonate 15-lipoxygenase, glutathione transferase, arachidonate 5-lipoxygenase, and histone deacetylase. As a member of the hydroxycinnamic acids and catechols, caffeic acid is a significant plant metabolite. Caffeic acid is found naturally in various organisms, including Pavetta indica and Eupatorium cannabinum. It possesses a range of bioactive properties, such as antioxidant, anti-inflammatory, and antineoplastic activities. When ingested, it acts as an antioxidant, reducing oxidative stress and thereby minimizing DNA damage caused by free radicals. Caffeic acid targets and inhibits specific oncoproteins like GASC1, which is involved in tumor cell development, and plays a role in the demethylation of histone proteins, impacting cancer cell proliferation. As an organic compound, caffeic acid is characterized by its phenolic and acrylic functional groups. It appears as a yellow solid and is ubiquitous in plants, serving as an intermediate in the biosynthesis of lignin. Lignin is a primary component of woody plant biomass, underscoring the widespread occurrence of caffeic acid in plant life. Caffeic acid is present in a variety of common plants and foods. It can be found in the bark of Eucalyptus globulus, the barley grain Hordeum vulgare, the herb Dipsacus asperoides, the freshwater fern Salvinia molesta, and the mushroom Phellinus linteus. In terms of dietary sources, caffeic acid is present in beverages like brewed coffee and red wine, and it's found at high levels in herbs like thyme, sage, and spearmint, as well as in spices such as Ceylon cinnamon and star anise. Additionally, it's found in sunflower seeds, apple sauce, apricots, prunes, black chokeberry, and in high amounts in the South American herb yerba mate. It also occurs in lower levels in grains like barley and rye. Overall, caffeic acid's presence in a diverse array of plant-based sources, coupled with its significant biological activities, makes it a compound of interest in nutrition, medicine, and pharmacology.

GHS Hazard Statements

• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

• H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

Chemical and Physical Properties

Source: PubChem