Cinnamyl alcohol

Cinnamyl alcohol is an organic compound that belongs to the class of compounds known as aromatic alcohols. It is a naturally occurring substance found in the bark of cinnamon trees and other species of the genus Cinnamomum, as well as in the leaves of the tea plant and other plants. Cinnamyl alcohol has the chemical formula C₉H₁₀O and is known for its distinctive, sweet, hyacinth-like odor, which makes it a valuable ingredient in the flavor and fragrance industry.

Properties

Cinnamyl alcohol has a molecular weight of 134.18 g/mol and appears as a colorless to pale yellow liquid at room temperature. It is sparingly soluble in water but highly soluble in organic solvents such as ethanol and diethyl ether. The compound has a boiling point of 250°C and a melting point of 33°C. Its chemical structure consists of a benzene ring attached to an ethylene group, which in turn is connected to a hydroxyl group, making it an alcohol.

Synthesis

Cinnamyl alcohol can be synthesized through several methods, including the Catalytic hydrogenation of cinnamaldehyde, which involves the addition of hydrogen to cinnamaldehyde in the presence of a catalyst. Another method is the Fischer-Speier esterification, where cinnamic acid reacts with methanol or ethanol in the presence of an acid catalyst to produce cinnamyl ester, which is then reduced to cinnamyl alcohol.

Applications

Cinnamyl alcohol is widely used in the Perfumery and Cosmetics industry due to its pleasant aroma. It is a key ingredient in the formulation of fragrances, soaps, and lotions. Additionally, it is used as a flavoring agent in food products, imparting a sweet, balsamic flavor. In the Pharmaceutical industry, cinnamyl alcohol is utilized as a precursor in the synthesis of other compounds and as an antimicrobial agent in some formulations.

Safety and Toxicology

While cinnamyl alcohol is generally considered safe for use in cosmetics and food products, it can cause allergic reactions in some individuals, particularly when applied to the skin. It is identified as a potential allergen by the International Fragrance Association (IFRA) and is subject to restrictions on its concentration in cosmetic products. Inhalation or ingestion of large amounts can lead to irritation of the respiratory tract and gastrointestinal system, respectively.

Regulation

The use of cinnamyl alcohol in food and cosmetic products is regulated by various international agencies, including the Food and Drug Administration (FDA) in the United States and the European Food Safety Authority (EFSA) in the European Union. These organizations set limits on the concentration of cinnamyl alcohol in products to ensure consumer safety.

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  Cinnamyl alcohol chemical structure

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  Cinnamyl alcohol on petri dish