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 C6H6CH=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. The bark of cinnamon tree contains high concentrations of cinnamaldehyde. [3]

Contents

Structure and synthesis

Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Jean-Baptiste Dumas and Eugène-Melchior Péligot [4] and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. [5]

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. [6]

Biosynthesis

Pathway for the biosynthesis of trans-cinnamaldehyde. Cinnamaldehyde biosynthesis pathway.png
Pathway for the biosynthesis of trans-cinnamaldehyde.

Cinnamaldehyde is biosynthesized from phenylalanine. [7] Deamination of L-phenylalanine into cinnamic acid is catalyzed by phenylalanine ammonia lyase (PAL). [8] [9] PAL catalyzes this reaction by a non-oxidative deamination. This deamination relies on the MIO prosthetic group of PAL. [10] 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. [8] 4CL uses ATP to catalyze the formation of cinnamoyl-CoA. [11] 4CL effects this reaction in two steps. [12] 4CL forms a hydroxycinnamate–AMP anhydride, followed by a nucleophile attack on the carbonyl of the acyl adenylate. [13] Finally, Cinnamoyl-CoA is reduced by NADPH catalyzed by CCR (cinnamoyl-CoA reductase) to form cinnamaldehyde. [8] [14]

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. [15] Cinnamaldehyde can also be obtained from the steam distillation of the oil of cinnamon bark.

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. [16] Some breakfast cereals contain as much as 187 ppm cinnamaldehyde. [17]

As an agrichemical

Cinnamaldehyde has been tested as a safe and effective insecticide against mosquito larvae. [18] A concentration of 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours. [19] Trans-cinnamaldehyde works as a potent fumigant and practical repellant for adult mosquitos. [20] It also has antibacterial and antifungal properties. [21] [22]

Miscellaneous uses

Cinnamaldehyde is a corrosion inhibitor for steel and other alloys. It is believed to form a protective film on the metal surface. [23]

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. [24] 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. [16] Hydrogenation of cinnamaldehyde, if directed to the alkene, gives hydrocinnamaldehyde.

Toxicology

Cinnamaldehyde is used in agriculture because of its low toxicity, but it is a skin irritant. [25] Cinnamaldehyde may cause allergic contact stomatitis in sensitised individuals, however allergy to the compound is believed to be uncommon. [26]

Cinnamaldehyde can contain traces of styrene, which arises during storage or transport. Styrene especially forms in high humidity and high temperatures. [27]


DNA repair

Cinnamaldehyde is a dietary antimutagen that effectively inhibits both induced and spontaneous mutations. [28] 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. [28] [29] In mice, X-ray–induced chromosome aberrations were reduced when cinnamaldehyde was given orally to the mice after X-ray irradiation, [30] perhaps due to cinnamaldehyde-stimulated DNA repair.

Related Research Articles

<span class="mw-page-title-main">Phenylalanine</span> Type of α-amino acid

Phenylalanine is an essential α-amino acid with the formula C
9H
11NO
2. It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the biological pigment melanin. It is encoded by the messenger RNA codons UUU and UUC.

<span class="mw-page-title-main">Vanillin</span> Chemical compound

Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

<span class="mw-page-title-main">Eugenol</span> Chemical compound

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.

<span class="mw-page-title-main">Umbelliferone</span> Chemical compound

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Apigenin</span> Chemical compound

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

<i>p</i>-Coumaric acid Chemical compound

p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.

<span class="mw-page-title-main">Phenylpropanoid</span> Any organic aromatic compound with a structure based on a phenylpropane skeleton

The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<span class="mw-page-title-main">Cinnamyl alcohol</span> Chemical compound

Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the hydrolysis of storax.

<span class="mw-page-title-main">Pinosylvin</span> Chemical compound

Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.

<span class="mw-page-title-main">Phenylalanine ammonia-lyase</span>

The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and trans-cinnamic acid.:

In enzymology, a 4-coumarate—CoA ligase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Rosavin</span> Chemical compound

Rosavin are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L.,. R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.

<span class="mw-page-title-main">Xanthohumol</span> Chemical compound

Xanthohumol is a natural product found in the female inflorescences of Humulus lupulus, also known as hops. This compound is also found in beer and belongs to a class of compounds that contribute to the bitterness and flavor of hops. Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes.

<span class="mw-page-title-main">Angelicin</span> Chemical compound

Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as Bituminaria bituminosa. It has a skin permeability coefficient (LogKp) of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in this database. The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarin.

The biosynthesis of phenylpropanoids involves a number of enzymes.

<span class="mw-page-title-main">Cinnamyl acetate</span> Chemical compound

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

<span class="mw-page-title-main">Cinnamonitrile</span> Chemical compound

(E)-Cinnamonitrile is an organic compound approved for use as a fragrance in products such as air fresheners. It has a spicy cinnamon aroma.

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. ↑ PubChem. "Cinnamaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-10-18.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Ligninbiosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID   14503002.
  8. 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ Richmond, H. Preparation of Cinnamaldehyde. US Patent Application 2529186, November 7, 1950.
  16. 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.
  17. ↑ 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.
  18. ↑ Dick-Pfaff, Cornelia (July 19, 2004). "Wohlriechender Mückentod" (in German).
  19. ↑ 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): 4395–4400. Bibcode:2004JAFC...52.4395C. doi:10.1021/jf0497152. PMID   15237942.
  20. ↑ 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.
  21. ↑ 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.
  22. ↑ 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.
  23. ↑ 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.
  24. ↑ 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.
  25. ↑ 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.
  26. ↑ 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.
  27. ↑ "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.
  28. 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.
  29. ↑ 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.
  30. ↑ 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.
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