Cinnamaldehyde
| Cinnamaldehyde | |
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(2E)-3-phenylprop-2-enal |
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Other names
Cinnamic aldehyde; trans-cinnamaldehyde |
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| Identifiers | |
| CAS number | 104-55-2  |
| PubChem | 637511 |
| ChemSpider | 553117 |
| UNII | SR60A3XG0F |
| EC number | 203-213-9 |
| KEGG | C00903 |
| ChEBI | CHEBI:16731 |
| ChEMBL | CHEMBL293492 |
| IUPHAR ligand | 2423 |
| RTECS number | GD6475000 |
| Jmol-3D images | Image 1 |
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| 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, 266 K, 19 °F |
| Boiling point |
248 °C, 521 K, 478 °F |
| Solubility in water | Slightly Soluble |
| Solubility | soluble in ether, chloroform insoluble in petroleum ether miscible with alcohol, oils |
| Refractive index (nD) | 1.6195 |
| Hazards | |
| MSDS | External MSDS |
| R-phrases | R36 R37 R38 |
| S-phrases | S26 S36 |
| NFPA 704 |
 2
2
0
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| Flash point | 71 °C |
| LD50 | 3400 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds | Cinnamic acid |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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
Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Dumas and Péligot[citation needed] and synthesized in the laboratory by Chiozza in 1854.[citation needed]
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.[2]
Synthesis
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
Cinnamaldehyde occurs widely, and closely related compounds give rise to lignin. All such compounds are biosynthesized starting from phenylalanine, which undergoes conversion.[3]
Cinnamoyl-CoA reductase is an enzyme responsible for the production of cinnamoyl-CoA from cinnamaldehyde.
Applications
As a flavorant
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.[4]
As an agrichemical
Cinnamaldehyde is also used as a fungicide.[5] 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.[5] It has recently been recognized as a very effective insecticide for mosquito larvae.[6] As little as 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[7][8]
As an antimicrobial
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%.[9] It is especially effective against bacteria living at the back of the tongue, reducing anaerobic bacteria populations by about 43%.
As an anticancer agent
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.[10]
Miscellaneous uses
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
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.[4]
Toxicology
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).[11]
References
- ^ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V. Retrieved 2007-10-23.
- ^ Kozo Inuzuka, Bulletin of the Chemical Society of Japan Vol.34, [No.11(1961)pp.1557-1560] http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=bcsj1926&cdvol=34&noissue=11&startpage=1557
- ^ Boerjan, W.; Ralph, J. and Baucher, M., "Lignin Biosynthesis", Annu. Rev. Plant Biol. 2003. 54:519–46, 2003, 54, pages 519–546,doi:10.1146/annurev.arplant.54.031902.134938
- ^ 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
- ^ a b "Cinnamaldehyde Use". PAN Pesticides Database. Retrieved 2007-10-23.
- ^ Cornelia Dick-Pfaff: Wohlriechender Mückentod, 19.07.2004
- ^ "Cinnamon Oil Kills Mosquitoes". www.sciencedaily.com. Retrieved 2008-08-05.
- ^ 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.
- ^ "Popular Chewing Gum Eliminates Bacteria That Cause Bad Breath". Science Daily. Retrieved 2009-09-22.
- ^ 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.
- ^ High daily intakes of cinnamon: Health risk cannot be ruled out. BfR Health Assessment No. 044/2006, 18 August 2006, 15p Bundesinstitut für Riskoberwertung
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