Kumariini

Kumariini, known in English as coumarin, is an aromatic organic compound that belongs to the benzopyrone (coumarin) family. It has a characteristic sweet, vanilla-like odor and is used in perfumery and flavorings. Its chemical formula is C9H6O2, and it is a colorless crystalline solid that dissolves in organic solvents but is only sparingly soluble in water.

Natural occurrence and biosynthesis

Coumarin occurs naturally in several plant species, notably in tonka beans (Dipteryx odorata) and sweet clover (Melilotus officinalis). It is produced in plants through the phenylpropanoid pathway, beginning with phenylalanine and leading to o-hydroxycinnamic acid derivatives, which undergo lactonization to form the coumarin ring. The compound is often present in trace amounts in various herbs and spices and can contribute to the aroma of certain essential oils.

Uses

In industry, kumariini is used as a fragrance ingredient in cosmetics, soaps, and some flavor formulations. It also serves as a chemical intermediate in the synthesis of various pharmaceuticals and organic compounds. Historically, coumarin has been the basis for anticoagulant drugs such as warfarin and other 1,3-dihydro-2H-benzopyran-2-one derivatives, though these derivatives are not the same compound and are used for distinct medical purposes.

Safety and regulation

Coumarin can be hepatotoxic at high doses in humans and animals, and long exposure has raised safety concerns. Because of toxicity concerns, tonka beans, a natural source, are restricted or banned as culinary flavoring in several jurisdictions. In cosmetics and fragrances, coumarin content is regulated, and products may be required to limit or disclose its presence.

See also

Warfarin and other coumarin-derived anticoagulants; plant phenylpropanoid metabolism; fragrance ingredients.