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From pod to spice: How much do you know about the history of coumarin?
Coumarin is an aromatic organic compound with a unique sweet smell. First isolated from bean pods in 1820, coumarin's uses and biological functions were gradually revealed over time. This article will explore the history, synthesis and applications of coumarin in modern life.
The molecular structure of coumarin can be seen as two adjacent hydrogen atoms on the benzene ring being replaced by an unsaturated lactone ring, forming the coexistence of two six-membered structures.
The naming and history of coumarin
The name coumarin comes from the French word "coumarou", which refers to a type of lentil sprout; it also comes from the ancient Tupi word "kumarú", which means the lentil tree. Coumarin was first isolated from lentils in 1820 by Alfred Vogel of Munich, but he initially misidentified the compound as benzoic acid. Nicholas Jean Baptiste Gaston Guibourt of France independently discovered coumarin and officially named it in a subsequent paper.
Over time, coumarin synthesis technology continues to advance. In 1868, British chemist William Henry Parkin successfully synthesized coumarin for the first time, a breakthrough that made it an important ingredient in the flavor and perfume industry. Especially in 1882, coumarin was first used in Houbigant's Fougère Royale perfume, redefining the style of perfume.
Coumarin became part of the perfume world and continues to influence the creation and delivery of perfume.
Synthesis and biosynthesis of coumarin
There are various synthesis methods for coumarin, among which "Parkin reaction" is one of the most representative. It involves the reaction of coumaraldehyde and acetic anhydride, and another synthesis scheme is the Pageman condensation reaction. With the development of these synthetic methods, coumarin derivatives have been synthesized one after another, expanding its application scope.
In plants, coumarin biosynthesis begins with the cyclization process of p-hydroxycinnamic acid. This allows coumarin to be naturally produced in a variety of plants, including spices and medicinal plants.
Natural sources and functions of coumarin
Coumarin occurs naturally in many plants, such as vanilla grass, sweet woodruff and tonka beans. These plants contain coumarins in varying concentrations, and some of them are widely used in foods, perfumes and medicines.
Research shows that true cinnamon (Cinnamomum verum) has very low coumarin content, while Chinese cinnamon (C. cassia) contains higher coumarin, which is a key factor affecting their use and consumption.
Coumarin’s modern application and support
In modern times, coumarin is widely used in products such as food, perfume, stationery, soap and cigarettes. Although many countries ban it as a food additive, coumarin can still be used legally in other products.
In addition to its aromatic properties, coumarin also has anticoagulant properties, and pharmaceutical-related drugs such as warfarin are based on coumarin derivatives. However, attention should be paid to its toxic properties at high doses.
Toxicity and risk assessment of coumarin
Coumarin has certain toxicity to the liver and kidneys, especially in animal tests, its half-lethal dose showed its potential danger. Although evidence of acute toxicity in humans is limited, some health agencies recommend avoiding foods with long-term high doses of coumarin.
According to the evaluation of the German Federal Risk Assessment Research Agency, 1 kilogram of cinnamon powder contains approximately 2.1 to 4.4 grams of coumarin, which means that the risk of excessive consumption cannot be underestimated.
When faced with coumarin, a familiar yet unfamiliar compound, have you thought more deeply about its history and modern uses?
