• Journal of the Korea Academia-Industrial cooperation Society
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• v.20 no.12
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• pp.555-562
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• 2019

This study was undertaken to develop a stable self-microemulsifying drug delivery system (SMEDDS) for trans-cinnamaldehyde, a known antibacterial and antifungal agent. A simultaneous analytical method was established for quantification of trans-cinnamaldehyde and its degradant, cinnamic acid. Various surfactants were applied to assess their effect on the aqueous solubility of trans-cinnamaldehyde, and pseudo-ternary phase diagrams were plotted. Of the various formulations tested, the liquid SMEDDS composed of trans-cinnamaldehyde (oil), Cremophor EL (surfactant) and Transcutol P (cosurfactant) at a volume ratio of 10/70/20, produced the smallest emulsion droplet size (around 23 nm). The stability test determined the superior stability of the trans-cinnamaldehyde SMEDDS with constant trans-cinnamaldehyde content and z-average diameter of emulsion, under accelerated and heat stressed condition. Thus, we believe that this novel trans-cinnamaldehyde SMEDDS formulation has the potential to be applied for the development of trans-cinnamaldehyde medicines in the pharmaceutical industry.

• Food Science of Animal Resources
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• v.33 no.1
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• pp.16-23
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• 2013

This study was carried out to investigate the effect of trans-cinnamaldehyde and high pressure treatment on milk. Cinnamon oil milk was manufactured by high speed homogenization (3,000 rpm) and high pressure homogenization (500 and 2,000 bar) processing UHT milk and trans-cinnamaldehyde of various concentrations (0 to 0.1% (w/v)). Cinnamon oil milk was inoculated with Escherichia coli (6.4 Log CFU/mL) and kept at $7^{\circ}C$ for 10 d to observe the antibacterial effect. The cinnamon oil milk containing 0.05% (w/v) trans-cinnamaldehyde initially began to show an antibacterial effect and Escherichia coli completely died in cinnamon oil milk added 0.1% (w/v) trans-cinnamaldehyde on the 6th day of storage. The result of the TBA value showed that the addition of 0.1% (w/v) trans-cinnamaldehyde was also effective to protect lipid oxidation. In the physical properties of cinnamon oil milk, particle sizes were enlarged in all samples during storage periods and the total color difference of cinnamon oil milk was slightly increased as level of high pressure. The surface tension of cinnamon oil milk treated 2,000 bar was remarkably higher than other samples. It seems that trans-cinnamaldehyde showed antibacterial activity and antioxidation effect at 0.05 and 0.1% (w/v) of concentration. Remarkably, high pressure treatment did not influence its microbial property but slightly affected the physical properties of cinnamon oil milk.

• YAKHAK HOEJI
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• v.45 no.5
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• pp.431-436
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• 2001

Antifungal activities of trans-cinnamaldehyde (CA) derivatives including commercial CA derivatives as well as synthesized CA derivatives against various human pathogenic fungi were investigated. Among the derivatives tested, -chlorocinnamaldehyde, $\alpha$-bromocinnamaldehyde and 7-phenyl-2,4,6-heptatrienal were more potent than CA in antifungal activity, $\alpha$-Bromocinnamaldehyde was the most effective in inhibiting the growth of representative fungi of dermatomycosis with minimum inhibitory cocentration(MIC) of 0.61~9.76$\mu\textrm{g}$/ml . In the structure-activity relationship, introduction of the chlorine and bromine group into the C-2 of CA resulted in the decrease of MIC. Derivative with more double bonds exhibited the increase of antifungal activity against various pathogenic fungi.

• Journal of Photoscience
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• v.10 no.2
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• pp.181-184
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• 2003

Photochemical reactions of some organic molecules on titanium dioxide were investigated in methanol. A methanolic solution of trans-cinnamic acid and titanium dioxide was irradiated with 300 nm UV lamps for 24 h to afford methyl cinnamate. In the case of trans-cinnamamide, the major product was found to be 3-phenylpropionamide, i.e., a saturation product of ethylenic double bond. However, irradiation of urocanic acid, caffeic acid, ethyl cinnamate, trans-chalcone, trans-cinnamonitrile, trans-stilbene or trans, trans-1,4-diphenyl-1,3-butadiene on titanium dioxide under the same conditions did not give any noticeable products. Meanwhile, when irradiated some aromatic aldehydes, such as trans-cinnamaldehyde, l-naphthaldehyde, and 2-naphthaldehyde in methanol, vicinal diols and alcohols derived from the diols were produced. On the other hand, irradiation of 9-anthraldehyde and titanium dioxide in methanol afforded only alcohols, in which diol was not observed.

• Bulletin of the Korean Chemical Society
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• v.18 no.8
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• pp.806-810
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• 1997

A series of new hydridocarbonyl osmium(Ⅱ) complexes, OsHCl(CO)(PPh3)(L-L)[L-L=Ph2P(CH2)nPPh2 (n=1 (1), 2 (2), 3 (3), cis-Ph2PCH=CHPPh2 (4), and Fe(η5-C5H4PPh2)2 (5)] has been synthesized from OsHCl(CO)(PPh3)3 and chelating diphosphines. These complexes have been characterized by IR, 1H NMR and elemental analysis. The catalytic activities of these complexes both for the transfer hydrogenation of trans-cinnamaldehyde with 2-propanol as the hydrogen donor, and for the selective hydrogenation of trans-cinnamaldehyde with H2, have been examined. Complexes (1)-(5) were shown to have higher selectivities for the transfer hydrogenation of the C=O bond of aldehyde than for the transfer hydrogenation of the C=C bond of aldehyde. The selectivities for the transfer hydrogenation with 2-propanol as well as for the hydrogenation with H2 have been found to decrease in the order 3 > 5 > 2 > 4 > 1. Complex (3) has shown to possess almost 90% of the selectivity to cinnamyl alcohol for transfer hydrogenation. It is also found that there is a correlation between the ν(CO) of each complex and the hydrogenation, of the C=O bond of trans-cinnamaldehyde. Overall, the selectivities with the complexes (1)-(5) are greater for the transfer hydrogenation with 2-propanol than for the hydrogenation with H2.

• Journal of Microbiology and Biotechnology
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• v.14 no.6
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• pp.1176-1181
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• 2004

The cytotoxic activities of Cinnamomum cassia (Blume) bark-derived materials toward six human HeLa epithelioid cervix, A549 lung, SK-OV-3 ovarian, SK-MEL-2 melanoma, XF-498 central nerve system, and HCT-15 colon tumor cell lines were evaluated by using sulforhodamine B assay and compared to those of the anticancer agents, cisplatin and mitomycin C. The biologically active constituent of the Cinnamomum bark was characterized as trans­cinnamaldehyde by spectroscopic analysis. The cytotoxic activity of cinnamaldehyde against HeLa, SK-MEL-2, and HCT -15 cell lines was comparable to that of cisplatin and mitomycin C. The compound showed lower activity against A549, SK-OV-3, and XF-498 cell lines than the anticancer agents. Eugenol exhibited moderate activity against SK-OV­3, XF-498, and HCT-15 tumor cells, and trans-cinnamic acid, cinnamyl alcohol, $\alpha-pinene,\;and\;\beta-pinene$ showed little or no activity against model tumor cells. Cinnamaldehyde was not mutagenic against four strains (TA 98, TA 100, TA 1535, and TA 1537) of Salmonella typhimurium (Castel and Chalm). These results indicate at least one pharmacological action of C. cassia.

• The Korean Journal of Mycology
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• v.25 no.4 s.83
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• pp.348-353
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• 1997

Ether extract of Cinnamomi Cortex showing antifungal activity was purified and characterized. The active component from the extract was identified to be trans-cinnamaldehyde, which was effective in inhibiting the growth of the representative fungi of dermatomycosis with minimum inhibitory concentration of $39{\sim}78\;{\mu}g/ml$. The antifungal spectrum of trans-cinnamaldehyde was broader than that of commercial antifungal agent, Ketoconazole.

• Archives of Pharmacal Research
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• v.15 no.3
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• pp.239-241
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• 1992

The methanol extract of Cinnamoni Cortex showed antibacterial action against cariogenic bacterium, Streptococcus mutans OMZ 176. The active principle of the extract was identified to be trans-cinnamaldehyde, which was bactericidal in the minimal inhibitory concentration (MIC) of $100\;\mu$g/ml against the strain. From the results of antibacterial activity of cinnamaldehyde and its derivatives, the acrolein group in the cinnamaldehyde was elucidated to be an essential element for the activity.

• YAKHAK HOEJI
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• v.37 no.3
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• pp.247-253
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• 1993

Eight new derivatives of allylamine which are related to naftifine and expected to have antifungal activity were synthesized. Schiff base 2a-2d and 2'e-2'h were obtained by conventional methods using trans-cinnamylamine or trans-cinnamaldehyde. The reduction of azomethine linkage with NaBH$_{4}$ yielded secondary amine 3a-3h, which were then methylated by means of HCHO and excess NaBH$_{4}$ or HCOOH to give 4a-4h.

• Food Science and Biotechnology
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• v.16 no.2
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• pp.218-222
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• 2007

The anticoagulant properties of Cinnamomum cassia bark-derived materials were evaluated against platelet aggregation induced by arachidonic acid (AA), collagen, platelet activating factor (PAF), or thrombin, and these effects were then compared to those of three commercially available compounds (cinnamic acid, cinnamyl alcohol, and aspirin). The active constituent obtained from C. cassia barks was isolated by silica gel column chromatography and high pressure liquid chromatography (HPLC), and was characterized as trans-cinnamaldehyde by MS, $^1H-NMR$, $^{13}C-NMR$, and IR spectroscopy. With regard to 50% inhibitory concentration ($IC_{50}$) values, cinnamaldehyde was found to effectively inhibit platelet aggregation induced by AA ($IC_{50},\;43.2\;{\mu}M$) and collagen ($IC_{50},\;3.1\;{\mu}M$). By way of comparison, cinnamaldehyde proved to be a significantly more potent platelet inhibitor against platelet aggregation induced by collagen than aspirin. The effect exerted by cinnamaldehyde against platelet aggregation induced by AA was 1.2 times less than that of aspirin. These results indicate that cinnamaldehyde may prove useful as a lead compound for the inhibition of platelet aggregation induced by AA and collagen.