C6H5CHCHCHO

C6H5CHCHCHO is the condensed notation for cinnamaldehyde, an organic compound with the formula C9H8O. It is the principal aldehyde found in cinnamon oil and is widely used as a flavoring and fragrance ingredient. The molecule features a conjugated enal system, with a phenyl group attached to a vinyl segment that is connected to an aldehyde, giving the structure Ph–CH=CH–CHO. Its IUPAC name is 3-phenylprop-2-enal, reflecting the this conjugated, α,β-unsaturated aldehyde framework.

Occurrence and biosynthesis: Cinnamaldehyde occurs naturally in the essential oils of cinnamon (Cinnamomum species) and other plants as part of the phenylpropanoid pathway. It can be formed biologically from cinnamyl alcohol or produced industrially by condensation reactions such as Knoevenagel condensation of benzaldehyde with acetaldehyde, often followed by dehydration.

Production and supply: Commercial cinnamaldehyde is typically obtained by chemical methods starting from benzaldehyde and acetaldehyde or by oxidation of cinnamyl alcohol derived from cinnamyl derivatives. It is also extracted in small amounts from cinnamon bark oil.

Properties: Cinnamaldehyde is a colorless to pale yellow oily liquid with a characteristic cinnamon odor. It is a reactive α,β-unsaturated aldehyde, undergoing reactions such as Michael additions and aldol-type processes, and it is soluble in many organic solvents while exhibiting limited water solubility.

Applications: It is used as a flavoring agent in foods and beverages and as a fragrance ingredient in perfumery. It serves as a synthetic intermediate for fragrances, dyes, and polymer-related applications. It can be hydrogenated to hydrocinnamaldehyde or reduced to cinnamyl alcohol; oxidation yields cinnamic acid.

Safety: Cinnamaldehyde is a skin and eye irritant and may cause sensitization in some individuals. It is flammable and should be stored away from heat and oxidizers in tightly closed containers.