Cinnamaldehyde

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Cinnamaldehyde
Zimtaldehyd - cinnamaldehyde.svg Cinnamaldehyde.png
Identifiers
CAS number 104-55-2 YesY
PubChem 637511
ChemSpider 553117 YesY
UNII SR60A3XG0F YesY
EC number 203-213-9
KEGG C00903 YesY
ChEBI CHEBI:16731 YesY
ChEMBL CHEMBL293492 YesY
IUPHAR ligand 2423
RTECS number GD6475000
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water Slightly Soluble
Solubility soluble in ether, chloroform
insoluble in petroleum ether
miscible with alcohol, oils
Refractive index (nD) 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)
LD50 3400 mg/kg (rat, oral)
Related compounds
Related compounds Cinnamic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/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 a very effective insecticide for mosquito larvae.[8] As little as 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[9][10]

As an antimicrobial[edit]

Another use for cinnamaldehyde is as an antimicrobial. Researchers from the University of Illinois at Chicago (who were funded by the Wm. Wrigley Jr. Company) have found that cinnamic aldehyde, when used in Big Red, prevented oral bacterial growth by more than 50%.[11] It is especially effective against bacteria living at the back of the tongue, reducing anaerobic bacteria populations by about 43%.

As an anticancer agent[edit]

Recent research documents anticancer activity of cinnamaldehyde/cinnamic aldehyde observed in cell culture and animal models of the disease. Proliferation, invasion, and tumor growth were inhibited in a murine A375 model of human melanoma, though only at high doses not achievable through dietary intake.[12]

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 is a skin irritant.

The level of coumarin detected in 'cinnamon' extracts and powders has concerned the German Federal Institute for Risk Assessment (BfR).[13]

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). Bulletin of the Chemical Society of Japan 34 (11): 1557–1560 http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=bcsj1926&cdvol=34&noissue=11&startpage=1557 |url= missing title (help). 
  5. ^ Boerjan, W.; Ralph, J. and Baucher, M. (2003). "Lignin Biosynthesis". Annu. Rev. Plant Biol. 54: 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. 
  11. ^ "Popular Chewing Gum Eliminates Bacteria That Cause Bad Breath". Science Daily. Retrieved 2009-09-22. 
  12. ^ Cabello CM, Bair WB, Lamore SD, Ley S, Bause AS, Azimian S, Wondrak GT (January 2009). "The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth". Free Radic. Biol. Med. 46 (2): 220–231. doi:10.1016/j.freeradbiomed.2008.10.025. PMC 2650023. PMID 19000754. 
  13. ^ High daily intakes of cinnamon: Health risk cannot be ruled out. BfR Health Assessment No. 044/2006, 18 August 2006, 15p Bundesinstitut für Riskoberwertung

External links[edit]