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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]
The major route, however, is the conversion of cinnamaldehyde into cinnamic acid by the enzyme aldehyde dehydrogenase. Next, the cinnamic acid is transformed into cinnamoyl CoA which is again converted to either cinnamoylglycine by N-acyl transferase or to benzoyl CoA through β-oxidation , the latter being the major route.
It is obtained from oil of cinnamon, or from balsams such as storax. [4] It is also found in shea butter. [citation needed] Cinnamic acid has a honey-like odor; [2] and its more volatile ethyl ester, ethyl cinnamate, is a flavor component in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.
Nitration of cinnamaldehyde via acidification of a nitrate salt with H 2 SO 4 also yields the ortho-nitro compound, however it also yields some of the para-nitro compound, which is generally undesired. 2-Nitrocinnamaldehyde can also be prepared by reacting 2-nitrobenzaldehyde with acetaldehyde in a condensation reaction. [2]
Investigation of trans-cinnamaldehyde showed that it significantly reduced the production of NO by macrophages (cells of the immune system), which is something that normally occurs during inflammation. The same study of methyl cinnamate did not show this effect. [7]
trans-coniferyl aldehyde. ... It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor to lignin. [1] [2]
The commercial material often contains low levels of 2,6-di-tert-butyl-4-methoxyphenol as a stabilizer. It is a derivative of cinnamaldehyde with a hexyl substituent. One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% trans isomer. [2]
It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol , a lignol that is a major precursor to lignin .
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