The occurrence, metabolism and toxicity of cinnamic acid and related compounds

Abstract

Cinnamic acid is a compound of low toxicity, but its molecular structure and the known toxicity of similar molecules, such as styrene, have brought it to the toxicologist's attention. Commercially, its use is permitted as flavouring and it is ubiquitous in products containing cinnamon oil and to a lesser extent in all plants. The related aldehyde, alcohol and esters are all more toxic than cinnamic acid. Certain substituted cinnamates containing cyano and fluoro moieties are of particular interest because they inhibit mitochondrial pyruvate transport. The literature about this whole group of commercially important compounds is diverse and many key studies are in languages other than English. This review looks at the history and legal constraints, as well as the results of metabolism and toxicology studies.

Ethyl Cinnamate Derivatives as Promising High-Efficient Acaricides against <i>Psoroptes cuniculi</i>: Synthesis, Bioactivity and Structure–Activity Relationship

“…9) Cinnamic acid and its ester derivatives are widely distributed in plants including cereals, legumes, oilseeds, fruits, vegetables and tea or coffee beverages. 10) Due to their common occurrence in plants and their low toxicity, 11,12) cinnamic acid derivatives have attracted much attention of many pharmacologists. In the past decades, cinnamic acid derivatives including natural, semi-synthetic and synthetic compounds had been proven to have a variety of pharmacological activities, 13) such as anticancer, 14,15) antimicrobial, [16][17][18] antioxidative, 18) anti-inflammatory, 15,[19][20][21] anti-Mycobactrium tuberculosis, [22][23][24] antiviral, 25) anti-human immunodeficiency virus (HIV), [26][27][28] antidiabetic, 29) anticholesterolemic, 30) analgesic, 31) hepatoprotective, 32,33) immunoprotective, 34) inducing neural progenitor cell proliferation 35) and anxiolytic activity.…”

“…Our interest in the excellent antiparasitic activities [37][38][39][40][41] and the low toxicity 11,12) of cinnamic acid derivatives prompted us to explore their acaricidal activity and extend their pharmacologic activities. This investigation presented the preparation of a series of cinnamic acid ester derivatives and evaluation of their acaricidal activity against P. cuniculi as well as the discussion of their preliminary SAR.…”

Recycling antimalarial leads for cancer: Antiproliferative properties of N-cinnamoyl chloroquine analogues

“…cinnamic acids, which are found in different natural resources and widely used for diverse medicinal purposes, 3,4 have demonstrated to constitute scaffolds of great interest for the development of new antitumor agents. 5,6 In one hand, quinoline synthetic versatility promotes the development of large diversity of quinoline analogues.…”

Studies on the Interaction of Cinnamic Acid with Bovine Serum Albumin

“…4) It was also approved its use in cancer prevention and therapy because it has low toxicity in rats and rabbits. 1,5) Serum albumin, one of the most available and extensively studied of all proteins, is the most abundant protein in plasma, accounting for about 60% of its total protein content and providing about 80% of the blood osmotic pressure. It plays an important role in drug transport and storage in vertebrates.…”