Cinnamaldehyde
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| Names | |
|---|---|
| IUPAC name
(2E)-3-phenylprop-2-enal | |
| Other names
Cinnamic aldehyde; trans-cinnamaldehyde | |
| Identifiers | |
104-55-2  | |
| ChEBI | CHEBI:16731 |
| ChEMBL | ChEMBL293492 |
| ChemSpider | 553117 |
| EC Number | 203-213-9 |
| 2423 | |
| Jmol interactive 3D | Image |
| KEGG | C00903 |
| PubChem | 637511 |
| RTECS number | GD6475000 |
| UNII | SR60A3XG0F |
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| 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 |
| Refractive index (nD) |
1.6195 |
| Hazards | |
| R-phrases | R36 R37 R38 |
| S-phrases | S26 S36 |
| NFPA 704 | |
| 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 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 98% cinnamaldehyde.
Structure and synthesis
Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Dumas and Péligot[2] and synthesized in the laboratory by the Italian chemist Luigi Chiozza (1828-1889) in 1854.[3]
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.[4]
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.[5]
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.[6]
As an agrichemical
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 been tested as a safe and effective insecticide against mosquito larvae.[8] A concentration of 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[9] Trans-cinnamaldehyde works as a potent fumigant and practical repellant for adult mosquitos.[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, but can be also produced starting from cinnamaldehyde.[11] 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
Cinnamaldehyde is used in agriculture because of its low toxicity, but it is a skin irritant.[12]
References
- ↑ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V. Retrieved 2007-10-23.
- ↑ Dumas, J.; Péligot, E. (1834). "Recherches de Chimie organique. — Sur l'Huile de Cannelle, l' Acide hippurique et l' Acide sébacique" [Organic chemistry research – On cinnamon oil, the hippuric acid and sebacic acid]. Annales de chimie et de physique (in French) 57: 305–34.
- ↑ L. Chiozza (1856). "Sur la production artificielle de l´essence de cannelle" [On the artificial production of cinnamon oil]. Comptes rendus (in French) 42: 222–227.
- ↑ Inuzuka, Kozo (1961). "Π Electronic structure of cinnamaldehyde". Bulletin of the Chemical Society of Japan 34 (11): 1557–60. doi:10.1246/bcsj.34.1557.
- ↑ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Ligninbiosynthesis". Annual Review of Plant Biology 54: 519–46. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
- 1 2 Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 3-527-30673-0.
- 1 2 "Cinnamaldehyde Use". PAN Pesticides Database. Retrieved 2007-10-23.
- ↑ Dick-Pfaff, Cornelia (July 19, 2004). "Wohlriechender Mückentod" (in German).
- ↑ Cheng, Sen-Sung; Liu, Ju-Yun; Tsai, Kun-Hsien; Chen, Wei-June; Chang, Shang-Tzen (2004). "Chemical Composition and Mosquito Larvicidal Activity of Essential Oils from Leaves of Different Cinnamomum osmophloeum Provenances". Journal of Agricultural and Food Chemistry 52 (14): 4395–400. doi:10.1021/jf0497152. PMID 15237942. Lay summary – Science Daily (July 16, 2004).
- ↑ Ma WB, Feng JT, Jiang ZL, Zhang X (2014). "Fumigant Activity of 6 Selected Essential Oil Compounds and Combined Effect of Methyl Salicylate And Trans-Cinnamaldehyde Against Culex pipiens pallens". Journal of the American Mosquito Control Association 30 (3): 199–203. doi:10.2987/14-6412R.1. PMID 25843095.
- ↑ Zucca P, Littarru M, Rescigno A, Sanjust E (2009). "Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol". Bioscience, Biotechnology, and Biochemistry 73 (5): 1224–6. doi:10.1271/bbb.90025. PMID 19420690.
- ↑ Olsen, R. V.; Andersen, H. H.; Møller, H. G.; Eskelund, P. W.; Arendt-Nielsen, L (2014). "Somatosensory and vasomotor manifestations of individual and combined stimulation of TRPM8 and TRPA1 using topical L-menthol and trans-cinnamaldehyde in healthy volunteers". European Journal of Pain 18 (9): 1333–42. doi:10.1002/j.1532-2149.2014.494.x. PMID 24664788.
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