| Cinnamaldehyde | |
|---|---|
 |
 |
| IUPAC name |
|
| Other names | Cinnamic aldehyde; cinnamaldehyde |
| Identifiers | |
| CAS number | [] |
| RTECS number | GD6475000 |
| SMILES |
|
| Properties | |
| Molecular formula | C9H8O |
| Molar mass | 132.16 g/mol |
| Appearance | Yellow oil |
| Density | 1.05 g/ml |
| Melting point |
-7.5 °C |
| Boiling point |
248 °C |
| Solubility in water | Slightly Soluble |
| Viscosity | ? cP at ?°C |
| Hazards | |
| MSDS | External MSDS |
| R-phrases | R36 R37 R38 |
| S-phrases | S26 S36 |
| NFPA 704 |
 2
2
0
|
| Flash point | 71 °C |
| Related compounds | |
| Related compounds | Cinnamic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
|
Cinnamic aldehyde or cinnamaldehyde (more precisely trans-cinnamaldehyde, the only naturally-occurring form) is the chemical compound that gives cinnamon its flavor and odor.[1]
Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde.
Contents |
History
Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Dumas and Péligot and synthesized in the laboratory by Chiozza in 1856.
Structure and physical properties
A yellow oily liquid more viscous than water, cinnamaldehyde smells strongly of cinnamon.
Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies[citation needed] suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde.
Both aromatic and an aldehyde, cinnamaldehyde has a mono-substituted benzene ring. A conjugated double bond (alkene) makes geometry of the compound planar. Cinnamaldehyde is technically trans-cinnamaldehyde because the terminal carbonyl is on the opposite side of the aromatic ring over the rigid double bond.
Cinnamaldehyde can be seen as a derivative of acrolein with a hydrogen atom replaced by a phenyl group. Its color is due to the π → π* transition, increased conjugation in comparison with acrolein shifts this band towards the red.[2]
Several methods of laboratory synthesis are now known, but cinnamaldehyde is most economically obtained from the steam distillation of the oil of cinnamon bark. The compound can be prepared from related compounds like cinnamyl alcohol, (the alcohol form of cinnamaldehyde), but the first synthesis from unrelated compounds was the aldol condensation of benzaldehyde and acetaldehyde.
Applications
The most obvious application for cinnamaldehyde is as a flavoring. 50 grams can be purchased for around US$20.00, and concentrations required for flavoring food items like chewing gum, ice cream, candy, and beverages range from 9 to 4900 ppm (that is, less than 0.5%).
Cinnamaldehyde is 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 is also used as a fungicide.[3] 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 like cats and dogs.[3] Cinnamaldehyde has recently been recognized as a very effective insecticide for mosquito larvae.[4] As little as 29 ppm (parts per million) of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[5][6]
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.
Cinnamaldehyde can be used as a food adulterant; powdered beechnut husk aromatized with cinnamaldehyde can be marketed as powdered cinnamon.
Cinnamaldehyde extracted from C. osmophloeum inhibits xanthine oxidase in mice, hence is a potential treatment for hyperuricemia and related medical conditions including gout.[7]
Toxicology
 |
This section requires expansion. |
References
 |
This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (October 2007) |
- ^ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V.. http://www.tis-gdv.de/tis_e/ware/gewuerze/zimt/zimt.htm. Retrieved on 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
- ^ a b "Cinnamaldehyde Use". PAN Pesticides Database. http://www.pesticideinfo.org/Detail_ChemUse.jsp?Rec_Id=PC33596. Retrieved on 2007-10-23.
- ^ Cornelia Dick-Pfaff: Wohlriechender Mückentod, 19.07.2004
- ^ "Cinnamon Oil Kills Mosquitoes". www.sciencedaily.com. http://www.sciencedaily.com/releases/2004/07/040716081706.htm. Retrieved on 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): 4395–400. doi:. PMID 15237942.
- ^ Wang SY, Yang CW, Liao JW, Zhen WW, Chu FH, Chang ST (August 2008). "Essential oil from leaves of Cinnamomum osmophloeum acts as a xanthine oxidase inhibitor and reduces the serum uric acid levels in oxonate-induced mice". Phytomedicine 15: 940. doi:. PMID 18693097.
See also
|
|||||
This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)
