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Molecule of the Day: Cinnamaldehyde

Cinnamaldehyde (C9H8O) is a yellowish, oily liquid found in the bark of cinnamon trees, and is a major component of the corresponding essential oil. It has the distinct scent of cinnamon, and is used in many foods as a flavouring agent, such as confectioneries and sweets. 

Cinnamaldehyde has been shown to have antimicrobial effects, and has been used to produce antimicrobial paper in conjunction with carvacrol. It is also a fungicide, insecticide, and a repellent for many animals.

It is also a key precursor and parent compound to many aroma compounds used in perfumery, such as alpha-alkyl cinnamaldehydes (shown below), and dihydrocinnamaldehyde.

Cinnamaldehyde is biosynthesised from phenylalanine through several steps:

In the laboratory, it can also be synthesised from benzaldehyde (Day 2) and acetaldehyde (ethanal) via an acid- or base-catalysed aldol condensation reaction, which produces water as a side product:

However, it is more economically efficient to produce it via extraction from cinnamon bark, which is thus the major industrial method for cinnamaldehyde production.

Originally posted by the-beauty-of-the-seasons

Requested by anonymous