Cinnamaldehyde

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Cinnamaldehyde
Skeletal formula of cinnamaldehyde
Ball-and-stick model of the cinnamaldehyde molecule
Names
IUPAC name
(2E)-3-phenylprop-2-enal
Other names
Cinnamic aldehyde; trans-cinnamaldehyde
Identifiers
104-55-2 YesY
ChEBI CHEBI:16731 YesY
ChEMBL ChEMBL293492 YesY
ChemSpider 553117 YesY
EC number 203-213-9
IUPHAR ligand 2423
Jmol-3D images Image
KEGG C00903 YesY
PubChem 637511
RTECS number GD6475000
UNII SR60A3XG0F YesY
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
1.6195
Hazards
R-phrases R36 R37 R38
S-phrases 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)
3400 mg/kg (rat, oral)
Related compounds
Related compounds
Cinnamic acid
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Cinnamaldehyde is the organic compound that gives cinnamon its flavor and odor.[1] This pale yellow, viscous liquid occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde.

Structure and synthesis[edit]

Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Dumas and Péligot[2] and synthesized in the laboratory by Chiozza in 1854.[3]

The natural product is trans-cinnamaldehyde. The molecule consists of a phenyl group 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.[4]

Synthesis[edit]

Several methods of laboratory synthesis exist, but cinnamaldehyde is most economically obtained from the steam distillation of the oil of cinnamon bark. The compound can be prepared from related compounds such as cinnamyl alcohol, (the alcohol form of cinnamaldehyde), but the first synthesis from unrelated compounds was the aldol condensation of benzaldehyde and acetaldehyde.

Metabolism[edit]

Cinnamaldehyde occurs widely, and closely related compounds give rise to lignin. All such compounds are biosynthesized starting from phenylalanine, which undergoes conversion.[5]

Cinnamoyl-CoA reductase is an enzyme responsible for the production of cinnamoyl-CoA from cinnamaldehyde.

Applications[edit]

As a flavorant[edit]

The most obvious application for cinnamaldehyde is as flavoring in chewing gum, ice cream, candy, and beverages; use levels range from 9 to 4900 parts per million (ppm) (that is, less than 0.5%). It is also used in some perfumes of natural, sweet, or fruity scents. Almond, apricot, butterscotch, and other aromas may partially employ the compound for their pleasant smells. Cinnamaldehyde can be used as a food adulterant; powdered beechnut husk aromatized with cinnamaldehyde can be marketed as powdered cinnamon.[6]

As an agrichemical[edit]

Cinnamaldehyde is also used as a fungicide.[7] Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. Cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals, such as cats and dogs.[7] It has recently been recognized as an effective insecticide for mosquito larvae.[8] A concentration of 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[9][10]

Miscellaneous uses[edit]

Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Its high refractive index of 1.6220 makes it a fairly safe and useful fluid for examining gemstone rough for inclusions.

Derivatives of cinnamaldehyde[edit]

Numerous derivatives of cinnamaldehyde are commercially useful. Dihydrocinnamyl alcohol, which occurs naturally but is produced by double hydrogenation of cinnamaldehyde, is used to confer the fragrances of hyacinth and lilac. Cinnamyl alcohol similarly occurs naturally and has the odor of lilac. Dihydrocinnamaldehyde is produced by the selective hydrogenation of the alkene subunit. α-Amyl- and α-hexylcinnamaldehyde are important commercial fragrances, but they are not prepared from cinnamaldehyde.[6]

Toxicology[edit]

Cinnamaldehyde is used in agriculture because of its low toxicity, but it's a skin irritant.

References[edit]

  1. ^ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V. Retrieved 2007-10-23. 
  2. ^ J.-B. Dumas, E. Peligot (1834). "Sur l’Huile de Cannelle, l’Acide Hippurique, et l’Acide Sébacique". Ann. Chim. Physique 57: 305–334. 
  3. ^ L. Chiozza (1856). "Sur la production artificielle de l´essence de cannelle". Comptes rendus 1: 222f. 
  4. ^ Kozo Inuzuka (1961). "π Electronic Structure of Cinnamaldehyde". Bulletin of the Chemical Society of Japan 34 (11): 1557–1560. 
  5. ^ Boerjan, W.; Ralph, J. and Baucher, M. (2003). "Lignin Biosynthesis". Annu. Rev. Plant Biol. 54 (1): 519–46. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002. 
  6. ^ a b Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_141
  7. ^ a b "Cinnamaldehyde Use". PAN Pesticides Database. Retrieved 2007-10-23. 
  8. ^ Cornelia Dick-Pfaff: Wohlriechender Mückentod, 19.07.2004
  9. ^ "Cinnamon Oil Kills Mosquitoes". www.sciencedaily.com. Retrieved 2008-08-05. 
  10. ^ Cheng SS, Liu JY, Tsai KH, Chen WJ, Chang ST (July 2004). "Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances". J. Agric. Food Chem. 52 (14): 4395–4400. doi:10.1021/jf0497152. PMID 15237942. 

External links[edit]