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Chemical Compound Review:

Cinnamal (E)-3-phenylprop-2-enal

Synonyms: CNMA, Zimtaldehyde, Cinnemaldehyde, Phenylacrolein, cinnamaldehyde, ...

Hooth, M.J. et al., Riter, L.S. et al., Chang, K.S. et al., Smith, C.K. et al., Peters, M.M. et al., et al.

Hooth, Sills, Burka, Haseman, Witt, Orzech, Fuciarelli, Graves, Johnson, Bucher, Svedman, Bruze, Johansen, Andersen, Goossens, Frosch, Lepoittevin, Rastogi, White, Menné, Lee, Diba, Statham,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of LS-378

trans-Cinnamaldehyde and trans-cinnamic alcohol have been commonly reported to cause allergic contact dermatitis (ACD) in humans [1].
The antimutagenic activity of trans-cinnamaldehyde (C6H5CH = CHCHO) on chemically induced mutagenesis has been shown in E. coli [2].
Contact allergy to cinnamal in a patient with oral lichen planus [3].
The data are discussed in terms of their relevance to the safety evaluation of trans-cinnamaldehyde, particularly the validity or otherwise of extrapolation of toxicity data from high to low dose [4].
Contact urticaria from cinnamal leading to anaphylaxis [5].

High impact information on LS-378

Following activity-guided fractionation, trans-cinnamaldehyde and 2-methoxycinnamaldehyde were identified as the NF-KB inhibitors from C cassia with IC50 values of 43 MM and 31 pM, respectively [6].
Membrane introduction mass spectrometry (MIMS) coupled to a miniature mass spectrometer equipped with a cylindrical ion trap (CIT) analyzer was used to monitor the flavor components, 3-phenyl-2-propenal and methyl salicylate, found in cinnamon and wintergreen candies, respectively, directly from human breath [7].
Toxicology and carcinogenesis studies of microencapsulated trans-cinnamaldehyde in rats and mice [8].
Squamous cell papillomas and carcinomas of the forestomach were observed in male and female mice but the incidences were within the NTP historical control range and were not considered to be related to trans-cinnamaldehyde exposure [8].
It has been shown that deodorants containing cinnamic aldehyde (cinnamal) can elicit axillary dermatitis in patients sensitized to this substance [9].

Chemical compound and disease context of LS-378

AIM: The effect of trans-cinnamaldehyde (CNMA) on the release of norepinephrine (NE) from nerve terminal was investigated using rat pheochromocytoma 12 (PC-12) cells [10].

Biological context of LS-378

These characteristic changes in AITC- or CA-treated cells were associated with the significant increase in frequencies of cells containing almost 3n to 4n chromosomes [11].

Anatomical context of LS-378

Inhibition of fungal cell wall synthesizing enzymes by trans-cinnamaldehyde [12].

Associations of LS-378 with other chemical compounds

In skin bioassay tests, (E)-cinnamaldehyde at 0.051 mg cm(-2) and DEET at 0.025 mg cm(-2) provided 87 and 95% protection at 30 min after application [13].
(E)-Cinnamaldehyde was significantly more effective than cinnamyl alcohol in both bioassays [13].

Gene context of LS-378

RESULTS: The biologically active constituents of C. cassia extract against lens aldose reductase were characterized as trans -cinnamaldehyde by spectral analysis [14].

Analytical, diagnostic and therapeutic context of LS-378

An isocratic high-performance liquid chromatography method has been developed for the quantification of the skin sensitisers trans-cinnamaldehyde and trans-cinnamic alcohol, and their cinnamic metabolites [15].

References

Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Smith, C.K., Moore, C.A., Elahi, E.N., Smart, A.T., Hotchkiss, S.A. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
Effects of the antimutagen cinnamaldehyde on reversion and survival of selected Salmonella tester strains. de Silva, H.V., Shankel, D.M. Mutat. Res. (1987) [Pubmed]
Contact allergy to cinnamal in a patient with oral lichen planus. Hoskyn, J., Guin, J.D. Contact Derm. (2005) [Pubmed]
Studies on trans-cinnamaldehyde. 1. The influence of dose size and sex on its disposition in the rat and mouse. Peters, M.M., Caldwell, J. Food Chem. Toxicol. (1994) [Pubmed]
Contact urticaria from cinnamal leading to anaphylaxis. Diba, V.C., Statham, B.N. Contact Derm. (2003) [Pubmed]
Cinnamaldehyde and 2-methoxycinnamaldehyde as NF-kappaB inhibitors from Cinnamomum cassia. Reddy, A.M., Seo, J.H., Ryu, S.Y., Kim, Y.S., Kim, Y.S., Min, K.R., Kim, Y. Planta Med. (2004) [Pubmed]
Direct analysis of volatile organic compounds in human breath using a miniaturized cylindrical ion trap mass spectrometer with a membrane inlet. Riter, L.S., Laughlin, B.C., Nikolaev, E., Cooks, R.G. Rapid Commun. Mass Spectrom. (2002) [Pubmed]
Toxicology and carcinogenesis studies of microencapsulated trans-cinnamaldehyde in rats and mice. Hooth, M.J., Sills, R.C., Burka, L.T., Haseman, J.K., Witt, K.L., Orzech, D.P., Fuciarelli, A.F., Graves, S.W., Johnson, J.D., Bucher, J.R. Food Chem. Toxicol. (2004) [Pubmed]
Deodorants: an experimental provocation study with hydroxycitronellal. Svedman, C., Bruze, M., Johansen, J.D., Andersen, K.E., Goossens, A., Frosch, P.J., Lepoittevin, J.P., Rastogi, S., White, I.R., Menné, T. Contact Derm. (2003) [Pubmed]
Stimulatory effect of trans-cinnamaldehyde on norepinephrine secretion in cultured pheochromocytoma (PC-12) cells. Tsai, C.C., Liu, I.M., Cheng, J.T. Acta Pharmacol. Sin. (2000) [Pubmed]
Transforming potency of flavoring agents in Chinese hamster cells. Kasamaki, A., Urasawa, S. The Journal of toxicological sciences. (1985) [Pubmed]
Inhibition of fungal cell wall synthesizing enzymes by trans-cinnamaldehyde. Bang, K.H., Lee, D.W., Park, H.M., Rhee, Y.H. Biosci. Biotechnol. Biochem. (2000) [Pubmed]
Repellency of Cinnamomum cassia bark compounds and cream containing cassia oil to Aedes aegypti (Diptera: Culicidae) under laboratory and indoor conditions. Chang, K.S., Tak, J.H., Kim, S.I., Lee, W.J., Ahn, Y.J. Pest Manag. Sci. (2006) [Pubmed]
Inhibitory activity of Cinnamomum cassia bark-derived component against rat lens aldose reductase. Lee, H.S. Journal of pharmacy & pharmaceutical sciences [electronic resource] : a publication of the Canadian Society for Pharmaceutical Sciences, Société canadienne des sciences pharmaceutiques. (2002) [Pubmed]
High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. Smith, C.K., Cheung, C., Elahi, E.N., Hotchkiss, S.A. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]

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