Cinnamaldehyde

Last updated
Cinnamaldehyde
Zimtaldehyd - cinnamaldehyde.svg
Cinnamaldehyde-from-xtal-3D-bs-17.png
Cinnamaldehyde.jpg
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-enal
Other names
  • Cihinnamaldehyde
  • Cinnamal
  • Cinnamic aldehyde
  • trans-Cinnamaldehyde
Identifiers
3D model (JSmol)
1071571
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.111.079 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-213-9
KEGG
PubChem CID
RTECS number
  • GD6475000
UNII
  • InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ Yes check.svgY
    Key: KJPRLNWUNMBNBZ-QPJJXVBHSA-N Yes check.svgY
  • InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
    Key: KJPRLNWUNMBNBZ-QPJJXVBHBH
  • c1ccc(cc1)/C=C/C=O
Properties
C9H8O
Molar mass 132.16 g/mol
AppearanceYellow 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
−7.48×10−5 cm3/mol
1.6195
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319, H335
P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 71 °C (160 °F; 344 K)
Lethal dose or concentration (LD, LC):
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Cinnamaldehyde is an organic compound with the formula C9H8O or C6H5CH=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.

Contents

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 biosynthesis pathway.png
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. Retrieved 2007-10-23.
  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" [Organic chemistry research – On cinnamon oil, hippuric acid and sebacic acid]. Annales de Chimie et de Physique (in French). 57: 305–334.
  4. ↑ Chiozza, L. (1856). "Sur la production artificielle de l'essence de cannelle" [On the artificial production of cinnamon oil]. Comptes Rendus (in French). 42: 222–227.
  5. ↑ "Cinnamaldehyde". www.chemspider.com. Retrieved 2025-11-12.
  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 165858. Figure 3. doi: 10.3897/pharmacia.72.e165858 .
  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". Spectral Database for Organic Compounds. Retrieved 2025-11-12.
  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. Bibcode:2003AnRPB..54..519B. doi:10.1146/annurev.arplant.54.031902.134938. PMID   14503002.
  11. 1 2 3 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". Microbial Cell Factories. 15 (1): 16. doi: 10.1186/s12934-016-0415-9 . ISSN   1475-2859. PMC   4719340 . 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". RSC Advances. 5 (77): 62587–62603. Bibcode:2015RSCAd...562587K. doi:10.1039/C5RA08196C. ISSN   2046-2069.
  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. PMC   35134 . 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.
  20. ↑ PubChem. "Cinnamaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-11-12.
  21. 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   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 German).
  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. Bibcode:2004JAFC...52.4395C. doi:10.1021/jf0497152. PMID   15237942.
  25. ↑ "Cinnamon Oil Kills Mosquitoes". ScienceDaily. 2004-07-16.
  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. S2CID   36621630.
  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.; Hun, Lee Ting (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" . Electrochimica Acta. 97: 1–9. doi:10.1016/j.electacta.2013.03.011. hdl: 2164/2891 . ISSN   0013-4686.
  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.
  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. S2CID   28741979.
  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.
  34. ↑ "Cinnamonitrile". www.whatsinproducts.com. Retrieved 2025-07-05.
  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. S2CID   34286049.
  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" (PDF). Federal Institute for Risk Assessment (BfR). 18 August 2006. Archived (PDF) from the original on 7 March 2022. Retrieved 20 May 2022.
  38. 1 2 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. Bibcode:2006MRFMM.602...54S. doi:10.1016/j.mrfmmm.2006.08.006. PMC   2099251 . PMID   16999979.
  39. ↑ King, A. A.; Shaughnessy, D. T.; Mure, K.; Leszczynska, J.; Ward, W. O.; Umbach, D. M.; Xu, Z.; Ducharme, D.; Taylor, J. A.; Demarini, D. M.; Klein, C. B. (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. Bibcode:2007MRFMM.616...60K. doi:10.1016/j.mrfmmm.2006.11.022. PMC   1955325 . PMID   17178418.
  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". The NamesforLife Abstracts. 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. PMC   3170709 . 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.
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