Cinnamaldehyde

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Cinnamaldehyde is an organic compound with the formula C₆H₅CH=CHCHO. It is a pale yellow viscous liquid that is the major component of cinnamon bark oil and other species of the genus Cinnamomum. This aromatic aldehyde gives cinnamon its flavor and odor.

Chemical Structure and Properties

Cinnamaldehyde consists of a benzene ring attached to an unsaturated aldehyde. The structure can be described as a phenylpropanoid, a class of organic compounds derived from the amino acid phenylalanine. The double bond in the side chain is in the trans (E) configuration.

• Molecular formula: C₉H₈O
• Molar mass: 132.16 g/mol
• Density: 1.05 g/cm³
• Boiling point: 248 °C (478 °F)
• Melting point: -7.5 °C (18.5 °F)

Natural Occurrence

Cinnamaldehyde is found predominantly in the bark of Cinnamomum verum (true cinnamon) and Cinnamomum cassia (cassia). It constitutes about 90% of the essential oil from these barks.

Synthesis

Cinnamaldehyde can be synthesized by the aldol condensation of benzaldehyde and acetaldehyde. This reaction is catalyzed by a base, typically sodium hydroxide.

Uses

Cinnamaldehyde is used in the flavoring and perfume industries due to its pleasant odor. It is also used as a fungicide and an antimicrobial agent. In agriculture, it is used as a pesticide and insecticide.

Flavoring Agent

Cinnamaldehyde is a common flavoring agent in foods and beverages, imparting a sweet and spicy flavor. It is used in products such as chewing gum, ice cream, and baked goods.

Perfume Industry

In the perfume industry, cinnamaldehyde is valued for its warm, spicy scent. It is used in various fragrances and personal care products.

Antimicrobial and Antifungal Properties

Cinnamaldehyde exhibits antimicrobial and antifungal properties, making it useful in preserving food and in medicinal applications. It is effective against a range of bacteria and fungi, including Escherichia coli and Candida albicans.

Safety and Toxicity

Cinnamaldehyde is generally recognized as safe (GRAS) by the Food and Drug Administration (FDA) when used in food. However, it can cause skin irritation and allergic reactions in some individuals. Proper handling and usage guidelines should be followed to avoid adverse effects.

See Also

• Cinnamon
• Essential oil
• Phenylpropanoid
• Aldol condensation

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