Chemistry:Cinnamaldehyde

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Cinnamaldehyde is an organic compound with the formula C
9H
8O or C
6H
5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor.[1] It is a phenylpropanoid that is naturally synthesized by the shikimate pathway.[2] This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. It is an essential oil.

Structure and synthesis

Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Jean-Baptiste Dumas and Eugène-Melchior Péligot[3] and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854.[4] Synonyms for Cinnamaldehyde include 3-Phenyl-2-propenal, Cinnamic aldehyde, trans-Cinnamaldehyde, Cinnamal, Cinnamyl aldehyde, Cassia aldehyde, 3-Phenylacrolein, and β-Phenylacrolein.[5][6]

The natural product is trans-cinnamaldehyde. The molecule consists of a benzene ring attached to an unsaturated aldehyde. Cinnamaldehyde is an α,β-unsaturated carbonyl compound. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.[7]

The molecule can be identified by characteristic spectroscopic signals. Infrared spectra show strong absorption bands near 1685 cm-1 (C=O stretch) and 1620 cm-1 (C=C stretch). In the proton nuclear magnetic resonance (1H NMR) spectrum, the aldehydic proton resonates around 9.6 ppm, while aromatic and vinyl protons appear between 6.3 and 7.6 ppm.[8][9]

Biosynthesis

Pathway for the biosynthesis of trans-cinnamaldehyde.

Cinnamaldehyde is biosynthesized from phenylalanine.[10] Deamination of L-phenylalanine into cinnamic acid is catalyzed by phenylalanine ammonia lyase (PAL).[11][12] PAL catalyzes this reaction by a non-oxidative deamination. This deamination relies on the MIO prosthetic group of PAL.[13] PAL gives rise to trans-cinnamic acid. In the second step, 4-coumarate–CoA ligase (4CL) converts cinnamic acid to cinnamoyl-CoA by an acid–thiol ligation.[11] 4CL uses ATP to catalyze the formation of cinnamoyl-CoA.[14] 4CL effects this reaction in two steps.[15] 4CL forms a hydroxycinnamate–AMP anhydride, followed by a nucleophile attack on the carbonyl of the acyl adenylate.[16] Finally, Cinnamoyl-CoA is reduced by NADPH catalyzed by CCR (cinnamoyl-CoA reductase) to form cinnamaldehyde.[11][17]

Preparation

Several methods of laboratory synthesis exist. The compound can be prepared from related compounds such as cinnamyl alcohol. An early synthesis involved the aldol condensation of benzaldehyde and acetaldehyde.[18] Cinnamaldehyde can also be obtained from the steam distillation of the oil of cinnamon bark.

Cinnamaldehyde is stable under dry, cool, and dark storage conditions but slowly oxidizes in air and light to form cinnamic acid and related degradation products. It is slightly soluble in water but miscible with organic solvents such as ethanol, ether, and chloroform.[19][20]

Applications

As a flavorant

The most obvious application for cinnamaldehyde is as flavoring in chewing gum, ice cream, candy, e-liquid and beverages; use levels range from 9 to 4,900 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.[21] Some breakfast cereals contain as much as 187 ppm cinnamaldehyde.[22]

As an agrichemical

Cinnamaldehyde has been tested as a safe and effective insecticide against mosquito larvae.[23] A concentration of 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours.[24][25] Trans-cinnamaldehyde works as a potent fumigant and practical repellant for adult mosquitos.[26] It also has antibacterial and antifungal properties.[27][28]

Miscellaneous uses

Cinnamaldehyde is a corrosion inhibitor for steel and other alloys. It is believed to form a protective film on the metal surface.[29]

In addition to flavor and fragrance applications, cinnamaldehyde is used in small amounts as a natural preservative in cosmetic and personal care formulations. It exhibits mild antimicrobial and antioxidant activity that helps extend product shelf life.[30][31]

Derivatives

Numerous derivatives of cinnamaldehyde are commercially useful. Dihydrocinnamyl alcohol (3-phenylpropanol) occurs naturally but is produced by double hydrogenation of cinnamaldehyde. It has 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.[32] Dihydrocinnamaldehyde is produced by the selective hydrogenation of the alkene subunit. α-Amylcinnamaldehyde and α-hexylcinnamaldehyde are important commercial fragrances, but they are not prepared from cinnamaldehyde.[21] Hydrogenation of cinnamaldehyde, if directed to the alkene, gives hydrocinnamaldehyde. Aldol condensation of cinnamaldehyde with acetone forms dicinnamalacetone, which is used as an indicator. Cinnamonitrile can be produced by an elimination reaction of various oximes derived from cinnamaldehyde.[33] It is used in fragrance products.[34]

Toxicology

Cinnamaldehyde is used in agriculture because of its low toxicity, but it is a skin irritant.[35] Cinnamaldehyde may cause allergic contact stomatitis in sensitised individuals, however allergy to the compound is believed to be uncommon.[36]

Cinnamaldehyde can contain traces of styrene, which arises during storage or transport. Styrene especially forms in high humidity and high temperatures.[37]

DNA repair

Cinnamaldehyde is a dietary antimutagen that effectively inhibits both induced and spontaneous mutations.[38] Experimental evidence indicates that cinnamaldehyde induces a type of DNA damage in the bacterium Escherichia coli and in human cells that elicits recombinational DNA repair that then reduces spontaneous mutations.[38][39] In mice, X-ray–induced chromosome aberrations were reduced when cinnamaldehyde was given orally to the mice after X-ray irradiation,[40] perhaps due to cinnamaldehyde-stimulated DNA repair.

Biological effects

Cinnamaldehyde is a bioactive electrophile that activates the transient receptor potential ankyrin 1 (TRPA1) ion channel, a chemosensory receptor expressed in sensory neurons and in the gastrointestinal tract. TRPA1 detects pungent or irritant compounds such as those found in cinnamon, mustard oil, and clove, producing the characteristic warming or burning sensation associated with these spices.[41] In the gastrointestinal tract, TRPA1 activation by cinnamaldehyde influences the release of serotonin from enterochromaffin cells, linking chemical irritation with gut motility and sensory signaling.[42] Because of this interaction, dietary cinnamaldehyde and other TRPA1 agonists are being studied for their potential to modulate gut–brain communication, relieve symptoms of irritable bowel syndrome (IBS), and alter visceral pain perception in humans.[43]

References

  1. ↑ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V.. http://www.tis-gdv.de/tis_e/ware/gewuerze/zimt/zimt.htm. 
  2. ↑ Gutzeit, Herwig (2014). Plant Natural Products: Synthesis, Biological Functions and Practical Applications. Wiley. pp. 19–21. ISBN 978-3-527-33230-4. 
  3. ↑ Dumas, J.; Péligot, E. (1834). "Recherches de Chimie organique. — Sur l'Huile de Cannelle, l'Acide hippurique et l'Acide sébacique" (in fr). Annales de Chimie et de Physique 57: 305–334. http://gallica.bnf.fr/ark:/12148/bpt6k6568974z/f311.image.r. 
  4. ↑ Chiozza, L. (1856). "Sur la production artificielle de l'essence de cannelle" (in fr). Comptes Rendus 42: 222–227. http://gallica.bnf.fr/ark:/12148/bpt6k2999t/f226.item.r=.zoom. 
  5. ↑ "Cinnamaldehyde" (in en). https://www.chemspider.com/Chemical-Structure.553117.html. 
  6. ↑ Todorova, Nikolina; Mateeva, Alexandrina; Savova, Alexandra; Kondeva-Burdina, Magdalena (31 October 2025). "Current insights on cardiovascular and neurodegenerative relations of direct oral anticoagulants and their biotransformation". Pharmacia 72: Figure 3. doi:10.3897/pharmacia.72.e165858. https://doi.org/10.3897/pharmacia.72.e165858.figure3. 
  7. ↑ 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. 
  8. ↑ "SDBS-2003: cinnamaldehyde". https://sdbs.db.aist.go.jp/CompoundLanding.aspx?sdbsno=2003. 
  9. ↑ Watanabe, Mari; Matsuzaki, Kazuya; Sato, Osamu; Telada, Souichi; Takatsuji, Toshiyuki (March 2022). "Development of a novel gauge filled with resin for X-ray CT". e-Journal of Nondestructive Testing 27 (3). doi:10.58286/26637. ISSN 1435-4934. 
  10. ↑ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Ligninbiosynthesis". Annual Review of Plant Biology 54 (1): 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002. Bibcode: 2003AnRPB..54..519B. 
  11. ↑ 11.0 11.1 11.2 Bang, Hyun-bae; Lee, Yoon-hyeok; Kim, Sun-chang; Sung, Chang-keun; Jeong, Ki-jun (2016-01-19). "Metabolic engineering of Escherichia coli for the production of cinnamaldehyde" (in En). Microbial Cell Factories 15 (1): 16. doi:10.1186/s12934-016-0415-9. ISSN 1475-2859. PMID 26785776. 
  12. ↑ Koukol, J.; Conn, E. E. (1961-10-01). "The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare". The Journal of Biological Chemistry 236 (10): 2692–2698. doi:10.1016/S0021-9258(19)61721-7. ISSN 0021-9258. PMID 14458851. 
  13. ↑ Kong, Jian-Qiang (2015-07-20). "Phenylalanine ammonia-lyase, a key component used for phenylpropanoids production by metabolic engineering" (in en). RSC Advances 5 (77): 62587–62603. doi:10.1039/C5RA08196C. ISSN 2046-2069. Bibcode: 2015RSCAd...562587K. 
  14. ↑ Beuerle, Till; Pichersky, Eran (2002-03-15). "Enzymatic Synthesis and Purification of Aromatic Coenzyme A Esters". Analytical Biochemistry 302 (2): 305–312. doi:10.1006/abio.2001.5574. PMID 11878812. 
  15. ↑ Allina, Sandra M.; Pri-Hadash, Aviva; Theilmann, David A.; Ellis, Brian E.; Douglas, Carl J. (1998-02-01). "4-Coumarate:Coenzyme A Ligase in Hybrid Poplar". Plant Physiology 116 (2): 743–754. doi:10.1104/pp.116.2.743. ISSN 0032-0889. PMID 9489021. 
  16. ↑ Li, Zhi; Nair, Satish K. (2015-11-03). "Structural Basis for Specificity and Flexibility in a Plant 4-Coumarate:CoA Ligase". Structure 23 (11): 2032–2042. doi:10.1016/j.str.2015.08.012. ISSN 1878-4186. PMID 26412334. 
  17. ↑ Wengenmayer, Herta; Ebel, Jurgen; Grisebach, Hans (1976). "Enzymic Synthesis of Lignin Precursors. Purification and Properties of a Cinnamoyl-CoA:NADPH Reductase from Cell Suspension Cultures of Soybean (Glycine max)". European Journal of Biochemistry 65 (2): 529–536. doi:10.1111/j.1432-1033.1976.tb10370.x. ISSN 0014-2956. PMID 7454. 
  18. ↑ Richmond, H. Preparation of Cinnamaldehyde. US Patent Application 2529186, November 7, 1950.
  19. ↑ "NIST chemistry WebBook". Choice Reviews Online 41 (12): 41Sup–0257-41Sup-0257. 2004-08-01. doi:10.5860/choice.41sup-0257. ISSN 0009-4978. https://doi.org/10.5860/choice.41sup-0257. 
  20. ↑ PubChem. "Cinnamaldehyde" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/637511. 
  21. ↑ 21.0 21.1 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 978-3-527-30673-2. 
  22. ↑ Friedman, M.; Kozuekue, N.; Harden, L. A. (2000). "Cinnamaldehyde content in foods determined by gas chromatography-mass spectrometry". Journal of Agricultural and Food Chemistry 48 (11): 5702–5709. doi:10.1021/jf000585g. PMID 11087542. 
  23. ↑ Dick-Pfaff, Cornelia (July 19, 2004). "Wohlriechender Mückentod" (in de). http://www.wissenschaft.de/wissen/news/243037.html. 
  24. ↑ Cheng, Sen-Sung; Liu, Ju-Yun; Tsai, Kun-Hsien; Chen, Wei-June; Chang, Shang-Tzen (1 July 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): 4395–4400. doi:10.1021/jf0497152. PMID 15237942. Bibcode: 2004JAFC...52.4395C. 
  25. ↑ "Cinnamon Oil Kills Mosquitoes" (in en). 2004-07-16. https://www.sciencedaily.com/releases/2004/07/040716081706.htm. 
  26. ↑ Ma, W.-B.; Feng, J.-T.; Jiang, Z.-L.; 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. 
  27. ↑ Vasconcelos, N. G.; Croda, J.; Simionatto, S. (July 2018). "Antibacterial mechanisms of cinnamon and its constituents: A review". Microbial Pathogenesis 120: 198–203. doi:10.1016/j.micpath.2018.04.036. ISSN 1096-1208. PMID 29702210. 
  28. ↑ Shreaz, Sheikh; Wani, Waseem A.; Behbehani, Jawad M.; Raja, Vaseem; Irshad, Md; Karched, Maribasappa; Ali, Intzar; Siddiqi, Weqar A. et al. (July 2016). "Cinnamaldehyde and its derivatives, a novel class of antifungal agents". Fitoterapia 112: 116–131. doi:10.1016/j.fitote.2016.05.016. ISSN 1873-6971. PMID 27259370. 
  29. ↑ Cabello, Gema; Funkhouser, Gary P.; Cassidy, Juanita; Kiser, Chad E.; Lane, Jim; Cuesta, Angel (2013-05-01). "CO and trans-cinnamaldehyde as corrosion inhibitors of I825, L80-13Cr and N80 alloys in concentrated HCl solutions at high pressure and temperature" (in en). Electrochimica Acta 97: 1–9. doi:10.1016/j.electacta.2013.03.011. ISSN 0013-4686. https://www.sciencedirect.com/science/article/pii/S0013468613004076. 
  30. ↑ McGowan, D. R.; Bennett, G.; Crane, E. (August 2016). "Empowering patients through improving clarity of sun protection ratings on sunscreen". International Journal of Cosmetic Science 38 (4): 431. doi:10.1111/ics.12280. ISSN 0142-5463. PMID 26402652. 
  31. ↑ "Natural Flavouring Substances, Their Sources, and Added Artificial Flavouring Substances. Partial Agreement in the Social and Public Health Field". Food and Cosmetics Toxicology 13 (4): 459. January 1975. doi:10.1016/s0015-6264(75)80166-0. ISSN 0015-6264. 
  32. ↑ 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): 1224–1226. doi:10.1271/bbb.90025. PMID 19420690. 
  33. ↑ An, Xiao-De; Yu, Shouyun (2015-10-16). "Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source". Organic Letters 17 (20): 5064–5067. doi:10.1021/acs.orglett.5b02547. ISSN 1523-7060. PMID 26418564. https://doi.org/10.1021/acs.orglett.5b02547. 
  34. ↑ "Cinnamonitrile". https://www.whatsinproducts.com/chemicals/view/1/6123/004360-47-8. 
  35. ↑ 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. 
  36. ↑ Isaac-Renton, Megan; Li, Monica Kayi; Parsons, Laurie M. (May 2015). "Cinnamon spice and everything not nice: many features of intraoral allergy to cinnamic aldehyde". Dermatitis: Contact, Atopic, Occupational, Drug 26 (3): 116–121. doi:10.1097/DER.0000000000000112. ISSN 2162-5220. PMID 25984687. 
  37. ↑ "High daily intakes of cinnamon: Health risk cannot be ruled out". Federal Institute for Risk Assessment (BfR). 18 August 2006. https://www.bfr.bund.de/cm/349/high_daily_intakes_of_cinnamon_health_risk_cannot_be_ruled_out.pdf. 
  38. ↑ 38.0 38.1 Shaughnessy, D. T.; Schaaper, R. M.; Umbach, D. M.; Demarini, D. M. (2006). "Inhibition of spontaneous mutagenesis by vanillin and cinnamaldehyde in Escherichia coli: Dependence on recombinational repair". Mutation Research 602 (1–2): 54–64. doi:10.1016/j.mrfmmm.2006.08.006. PMID 16999979. Bibcode: 2006MRFMM.602...54S. 
  39. ↑ King, A. A.; Shaughnessy, D. T.; Mure, K.; Leszczynska, J.; Ward, W. O.; Umbach, D. M.; Xu, Z.; Ducharme, D. et al. (2007). "Antimutagenicity of cinnamaldehyde and vanillin in human cells: Global gene expression and possible role of DNA damage and repair". Mutation Research 616 (1–2): 60–69. doi:10.1016/j.mrfmmm.2006.11.022. PMID 17178418. Bibcode: 2007MRFMM.616...60K. 
  40. ↑ Sasaki, Y. F.; Ohta, T.; Imanishi, H.; Watanabe, M.; Matsumoto, K.; Kato, T.; Shirasu, Y. (1990). "Suppressing effects of vanillin, cinnamaldehyde, and anisaldehyde on chromosome aberrations induced by X-rays in mice". Mutation Research 243 (4): 299–302. doi:10.1016/0165-7992(90)90146-b. PMID 2325694. 
  41. ↑ Parker, Charles Thomas; Taylor, Dorothea; Garrity, George M (2010-03-24). Exemplar Abstract for Mycobacterium massiliense Adékambi et al. 2006, Mycobacteroides abscessus massiliense (Adékambi et al. 2006) Gupta et al. 2018, Mycobacterium abscessus massiliense (Adékambi et al. 2006) Tortoli et al. 2016 emend. Nouioui et al. 2018 and Mycobacterium abscessus bolletii (Adékambi et al. 2006) Leao et al. 2011 emend. Nouioui et al. 2018.. doi:10.1601/ex.10322. https://doi.org/10.1601/ex.10322. Retrieved 2025-11-12. 
  42. ↑ Tack, J.; Müller-Lissner, S.; Stanghellini, V.; Boeckxstaens, G.; Kamm, M. A.; Simren, M.; Galmiche, J.-P.; Fried, M. (August 2011). "Diagnosis and treatment of chronic constipation - a European perspective: Diagnosis and treatment of chronic constipation". Neurogastroenterology & Motility 23 (8): 697–710. doi:10.1111/j.1365-2982.2011.01709.x. PMID 21605282. 
  43. ↑ Jackson, Todd; Yang, Zhou; Su, Lin (October 2019). "Pain-related gaze biases and later functioning among adults with chronic pain: a longitudinal eye-tracking study". Pain 160 (10): 2221–2228. doi:10.1097/j.pain.0000000000001614. ISSN 0304-3959. PMID 31205233. 



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