Cinnamaldehyde is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula or . Occurring naturally as predominantly the ''trans'' (''E'') isomer, it gives

cinnamon Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, b ...

its

flavor Flavour or flavor is either the sensory perception of taste or smell, or a flavoring in food that produces such perception. Flavour or flavor may also refer to: Science * Flavors (programming language), an early object-oriented extension to L ...

and

odor An odor (American English) or odour ( Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive ...

. It is a

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

that is naturally synthesized by the

shikimate pathway The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine) ...

. This pale yellow,

viscous Viscosity is a measure of a fluid's rate-dependent resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for example, syrup h ...

liquid occurs in the

bark Bark may refer to: Common meanings * Bark (botany), an outer layer of a woody plant such as a tree or stick * Bark (sound), a vocalization of some animals (which is commonly the dog) Arts and entertainment * ''Bark'' (Jefferson Airplane album), ...

of cinnamon

tree In botany, a tree is a perennial plant with an elongated stem, or trunk, usually supporting branches and leaves. In some usages, the definition of a tree may be narrower, e.g., including only woody plants with secondary growth, only ...

s and other species of the

genus Genus (; : genera ) is a taxonomic rank above species and below family (taxonomy), family as used in the biological classification of extant taxon, living and fossil organisms as well as Virus classification#ICTV classification, viruses. In bino ...

Cinnamomum ''Cinnamomum'' is a genus of evergreen aromatic trees and shrubs belonging to the laurel family, Lauraceae. The species of ''Cinnamomum'' have aromatic oils in their leaves and bark. The genus contains approximately 234 species, distributed in ...

''. It is an

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.

Structure and synthesis

Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by

Jean-Baptiste Dumas Jean Baptiste André Dumas (; 14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuri ...

and

Eugène-Melchior Péligot Eugène-Melchior Péligot (24 March 1811 – 15 April 1890), also known as Eugène Péligot, was a French chemist who isolated the first sample of uranium metal in 1841. Péligot proved that the black powder of Martin Heinrich Klaproth was not ...

and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. The natural product is ''

trans Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Sociology * Trans, a sociological term which may refer to: ** Transgender, people who identify themselves with a gender that di ...

''-cinnamaldehyde. The molecule consists of a benzene ring attached to an unsaturated aldehyde. Cinnamaldehyde is an

α,β-unsaturated carbonyl compound α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ−R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds, the carb ...

. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.

Biosynthesis

Cinnamaldehyde is biosynthesized from

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...

Deamination Deamination is the removal of an amino group from a molecule. Enzymes that catalysis, catalyse this reaction are called deaminases. In the human body, deamination takes place primarily in the liver; however, it can also occur in the kidney. In s ...

of L-phenylalanine into

cinnamic acid Cinnamic acid is an organic compound with the formula phenyl, C6H5-CH=CH-Carboxylic acid, COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxy ...

is catalyzed by

phenylalanine ammonia lyase The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and ''trans''-cinnamic acid.: :L-phenylalanine = ''trans''-cinnamate + NH3 Phenylalanine ammonia lyase (PAL) is the first and committe ...

(PAL). PAL catalyzes this reaction by a non-oxidative deamination. This deamination relies on the MIO prosthetic group of PAL. PAL gives rise to ''trans-''cinnamic acid. In the second step, 4-coumarate–CoA ligase (4CL) converts cinnamic acid to cinnamoyl-CoA by an acid–

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...

ligation. 4CL uses ATP to catalyze the formation of cinnamoyl-CoA. 4CL effects this reaction in two steps. 4CL forms a hydroxycinnamate–AMP anhydride, followed by a nucleophile attack on the carbonyl of the acyl adenylate. Finally, Cinnamoyl-CoA is reduced by NADPH catalyzed by CCR (cinnamoyl-CoA reductase) to form cinnamaldehyde.

Preparation

Several methods of laboratory synthesis exist. The compound can be prepared from related compounds such as

cinnamyl alcohol Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the ...

. An early synthesis involved the

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond-li ...

and

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

. Cinnamaldehyde can also be obtained from the

steam distillation Steam distillation is a separation process that consists of distilling water together with other volatile and non-volatile components. The steam from the boiling water carries the vapor of the volatiles to a condenser; both are cooled and retu ...

of the oil of cinnamon bark.

Applications

As a flavorant

The most obvious application for cinnamaldehyde is as

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of ...

chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its tex ...

ice cream Ice cream is a frozen dessert typically made from milk or cream that has been flavoured with a sweetener, either sugar or an alternative, and a spice, such as Chocolate, cocoa or vanilla, or with fruit, such as strawberries or peaches. Food ...

candy Candy, alternatively called sweets or lollies, is a Confectionery, confection that features sugar as a principal ingredient. The category, also called ''sugar confectionery'', encompasses any sweet confection, including chocolate, chewing gum ...

e-liquid An electronic cigarette is a handheld battery-powered vaporizer that simulates smoking, but without tobacco combustion. E-cigarette components include a mouthpiece (drip tip), a cartridge (liquid storage area), a heating element/ atomizer, a m ...

and

beverage A drink or beverage is a liquid intended for human consumption. In addition to their basic function of satisfying thirst, drinks play important roles in human culture. Common types of drinks include plain drinking water, milk, juice, smoothie ...

s; use levels range from 9 to 4,900 parts per million ( ppm) (that is, less than 0.5%). It is also used in some

perfume Perfume (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...

s of natural,

sweet Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, ...

, or

fruit In botany, a fruit is the seed-bearing structure in flowering plants (angiosperms) that is formed from the ovary after flowering. Fruits are the means by which angiosperms disseminate their seeds. Edible fruits in particular have long propaga ...

scent An odor (American English) or odour (English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is a smell or a scent caused by one or more volatilized ...

Almond The almond (''Prunus amygdalus'', Synonym (taxonomy)#Botany, syn. ''Prunus dulcis'') is a species of tree from the genus ''Prunus''. Along with the peach, it is classified in the subgenus ''Amygdalus'', distinguished from the other subgenera ...

apricot An apricot (, ) is a fruit, or the tree that bears the fruit, of several species in the genus ''Prunus''. Usually an apricot is from the species '' P. armeniaca'', but the fruits of the other species in ''Prunus'' sect. ''Armeniaca'' are also ...

butterscotch Butterscotch is a type of confection whose primary ingredients are brown sugar and butter. Some recipes include corn syrup, cream, vanilla, and salt. The earliest known recipes, in mid-19th century Yorkshire, used treacle (molasses) in plac ...

, and other

aroma An odor (American English) or odour (Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive v ...

s may partially employ the compound for their pleasant smells. Cinnamaldehyde can be used as a food adulterant; powdered

beech Beech (genus ''Fagus'') is a genus of deciduous trees in the family Fagaceae, native to subtropical (accessory forest element) and temperate (as dominant element of Mesophyte, mesophytic forests) Eurasia and North America. There are 14 accepted ...

nut

husk Husk (or hull) in botany is the outer shell or coating of a seed. In the United States, the term husk often refers to the leafy outer covering of an Ear (botany), ear of maize (corn) as it grows on the plant. Literally, a husk or hull includes t ...

aromatized with cinnamaldehyde can be marketed as powdered

. Some breakfast cereals contain as much as 187 ppm cinnamaldehyde.

As an agrichemical

Cinnamaldehyde has been tested as a safe and effective insecticide against

mosquito Mosquitoes, the Culicidae, are a Family (biology), family of small Diptera, flies consisting of 3,600 species. The word ''mosquito'' (formed by ''Musca (fly), mosca'' and diminutive ''-ito'') is Spanish and Portuguese for ''little fly''. Mos ...

larva A larva (; : larvae ) is a distinct juvenile form many animals undergo before metamorphosis into their next life stage. Animals with indirect development such as insects, some arachnids, amphibians, or cnidarians typically have a larval phase ...

e. A concentration of 29 ppm of cinnamaldehyde kills half of ''

Aedes aegypti ''Aedes aegypti'' ( or from Greek 'hateful' and from Latin, meaning 'of Egypt'), sometimes called the Egyptian mosquito, dengue mosquito or yellow fever mosquito, is a mosquito that spreads diseases like dengue fever, yellow fever, malar ...

'' mosquito larvae in 24 hours. * Trans-cinnamaldehyde works as a potent

fumigant Fumigation is a method of pest control or the removal of harmful microorganisms by completely filling an area with gaseous pesticides, or fumigants, to suffocate or poison the pests within. It is used to control pests in buildings (structural ...

and practical repellant for adult

s. It also has

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...

and

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as ...

properties.

Miscellaneous uses

Cinnamaldehyde is a

corrosion inhibitor A corrosion inhibitor or anti-corrosive is a chemical compound added to a liquid or gas to decrease the corrosion rate of a metal that comes into contact with the fluid. The effectiveness of a corrosion inhibitor depends on fluid composition and ...

for

steel Steel is an alloy of iron and carbon that demonstrates improved mechanical properties compared to the pure form of iron. Due to steel's high Young's modulus, elastic modulus, Yield (engineering), yield strength, Fracture, fracture strength a ...

and other

alloy An alloy is a mixture of chemical elements of which in most cases at least one is a metal, metallic element, although it is also sometimes used for mixtures of elements; herein only metallic alloys are described. Metallic alloys often have prop ...

s. It is believed to form a protective film on the metal surface.

Derivatives

Numerous derivatives of cinnamaldehyde are commercially useful. Dihydrocinnamyl alcohol (3-phenylpropanol) occurs naturally but is produced by double

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of cinnamaldehyde. It has the fragrances of hyacinth and lilac.

Cinnamyl alcohol Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the ...

similarly occurs naturally and has the odor of lilac but can be also produced starting from cinnamaldehyde. Dihydrocinnamaldehyde is produced by the selective hydrogenation of the alkene subunit. α-Amylcinnamaldehyde and α-hexylcinnamaldehyde are important commercial fragrances, but they are not prepared from cinnamaldehyde. Hydrogenation of cinnamaldehyde, if directed to the alkene, gives

hydrocinnamaldehyde Hydrocinnamaldehyde is the organic compound with the formula C6H5CH2CH2CHO. It is produced by the hydrogenation of cinnamaldehyde Cinnamaldehyde is an organic compound with the formula or . Occurring naturally as predominantly the ''trans'' ('' ...

. Aldol condensation of cinnamaldehyde with

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

forms

dicinnamalacetone Dicinnamalacetone is a Conjugated system, conjugated organic compound. It is used as an indicator for the presence of hydrogen halides in solvents, and its preparation is used as an example of the aldol condensation in organic chemistry teaching l ...

, which is used as an indicator.

Toxicology

Cinnamaldehyde is used in agriculture because of its low toxicity, but it is a skin irritant. Cinnamaldehyde may cause allergic contact stomatitis in sensitised individuals, however allergy to the compound is believed to be uncommon. Cinnamaldehyde can contain traces of

styrene Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easi ...

, which arises during storage or transport. Styrene especially forms in high humidity and high temperatures.

DNA repair

Cinnamaldehyde is a dietary antimutagen that effectively inhibits both induced and spontaneous

mutation In biology, a mutation is an alteration in the nucleic acid sequence of the genome of an organism, virus, or extrachromosomal DNA. Viral genomes contain either DNA or RNA. Mutations result from errors during DNA or viral replication, ...

s. Experimental evidence indicates that cinnamaldehyde induces a type of

DNA damage DNA repair is a collection of processes by which a cell identifies and corrects damage to the DNA molecules that encode its genome. A weakened capacity for DNA repair is a risk factor for the development of cancer. DNA is constantly modified ...

in the bacterium ''

Escherichia coli ''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus '' Escherichia'' that is commonly fo ...

'' and in human cells that elicits recombinational DNA repair that then reduces spontaneous mutations. In mice,

X-ray An X-ray (also known in many languages as Röntgen radiation) is a form of high-energy electromagnetic radiation with a wavelength shorter than those of ultraviolet rays and longer than those of gamma rays. Roughly, X-rays have a wavelength ran ...

–induced chromosome aberrations were reduced when cinnamaldehyde was given orally to the mice after X-ray irradiation, perhaps due to cinnamaldehyde-stimulated

DNA repair DNA repair is a collection of processes by which a cell (biology), cell identifies and corrects damage to the DNA molecules that encode its genome. A weakened capacity for DNA repair is a risk factor for the development of cancer. DNA is cons ...

References

External links

GMD MS Spectrum
{{Transient receptor potential channel modulators Alkene derivatives Conjugated aldehydes Flavors Fungicides Plant toxin insecticides Phenylpropanoids Corrosion inhibitors Xanthine oxidase inhibitors Cinnamon Substances discovered in the 19th century