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Cinnamic aldehyde

Cinnamaldehyde
Skeletal formula of cinnamaldehyde
Ball-and-stick model of the cinnamaldehyde molecule
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-enal
Other names
Cihinnamaldehyde
Cinnamic aldehyde
trans-Cinnamaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.922
EC Number 203-213-9
KEGG
PubChem CID
RTECS number GD6475000
UNII
Properties
C9H8O
Molar mass 132.16 g/mol
Appearance Yellow oil
Odor pungent, cinnamon-like
Density 1.0497 g/mL
Melting point −7.5 °C (18.5 °F; 265.6 K)
Boiling point 248 °C (478 °F; 521 K)
Slightly Soluble
Solubility soluble in ether, chloroform
insoluble in petroleum ether
miscible with alcohol, oils
-74.8·10−6 cm3/mol
1.6195
Hazards
R-phrases (outdated) R36 R37 R38
S-phrases (outdated) S26 S36
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 71 °C (160 °F; 344 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 3400 mg/kg (rat, oral)
Related compounds
Related compounds
 Cinnamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominately the trans (E) isomer, it gives cinnamon its flavor and odor. It is a flavonoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 50% cinnamaldehyde.

Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Dumas and Péligot and synthesized in the laboratory by the Italian chemist Luigi Chiozza (1828-1889) in 1854.

The natural product is trans-cinnamaldehyde. The molecule consists of a benzene ring attached to an unsaturated aldehyde. As such, the molecule can be viewed as a derivative of acrolein. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.

The biosynthesis of cinnamaldehyde begins with deamination of L-phenylalalanine into cinnamic acid by the action of phenylalanine ammonia lyase (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 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.

Cinnamoyl-CoA is reduced by NADPH catalyzed by CCR (cinnamoyl-CoA reductase) to form cinnamaldehyde.


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Wikipedia

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