Aldehydes cinnamaldehyde

A substituted a,/3-unsaturated aldehyde, cinnamaldehyde, has been observed to undergo the same type of two-step 1,3-cycloaddition reaction with a cyclohexanone enamine as acrolein does, forming in this case a stereo-isomeric mixture of substituted bicycloaminoketones in excellent yield (29a,31a,31b). 

As with other aromatic aldehydes, cinnamaldehyde is readily oxidized by air to its corresponding carboxylic acid. The latter must be separated just before the use of the aldehyde. 

In practice the low potentials permit a choice of approaches this is illustrated in Scheme 18 for a Wittig reaction in the presence of EGB wherein the desired product, 1,4-diphenylbutadiene, may be formed either from a reactive aldehyde (cinnamaldehyde) and an ylid from a benzylic phosphonium salt, or from a less reactive aldehyde and the ylid from a more acidic phosphonium salt The stereochemical course of the Wittig reaction is particularly sensitive to reaction conditions, especially cations which may be present. This point is partly made in Scheme 18 but deserves further elaboration. 

Cinammic aldehyde (cinnamaldehyde) is also a powerful skin sensitizer and the International Fragrance Association recommends its use with equal amounts of d-limonene as a quencher (see page 65). 

The inactivation of CYP2B4 by aldehydes such as citral (an a,P unsaturated terpenoid aldehyde), and other 2iromatic aldehydes (cinnamaldehyde, benzaldehyde, and 3-phenylpropionaldehyde) is accompanied by bleaching of the heme chro-mophore that is not prevented by catalase, superoxide dismutase, epoxide hydrolase, GSH, or ascorbic acid ". The corresponding values revealed that saturated aldehydes are generally... 

Fig. 3.72). Furthermore, if 30 mol % of chiral (l )-242 is used as the catalyst for this transformation, 243 is obtained in 75% yield with an 88% enantiomeric excess.Substimtion of electron-donating and electron-withdrawing groups on the benzaldehyde did not affect enantioselectivity. The nonaromatic aldehydes cinnamaldehyde and propanal also reacted with 241 to give the corresponding cti-2-oxazohnes with good selectivity, but in poor yield. 

Synonyms cas 104-54-1 cinnamic aldehyde cinnamaldehyde 3-phenyl propenal 3-phenylallyl alcohol... 

While enologists have been interested in the odorous constituents of grapes and wines for many years, Hennig and Villforth (1942) and Hennig (1943, 1950-1951) seem to have made the first systematic studies on the subject. They extracted wine with pentane and after hydrolysis identified the alcohols and acids. They reported the following aldehydes, ketones, and related compounds (formaldehyde, acetaldehyde, propion-aldehyde, cinnamaldehyde, vanillin, acetone, methyl ketone, acetyl-methylcarbinol, and acetal—caproaldehyde and higher members of the series, benzaldehyde, and furfural were not positively identified but probably also occur) alcohols (methyl, ethyl, isopropyl, isobutyl, isoamyl, and a-terpineol—n-propyl, n-heptyl, and sec-nonyl (2-nonanol)... 

In this experiment we wHl isolate the principal component of the oil of cinnamon, another naturally occurring aldehyde, cinnamaldehyde.The oil is first extracted from the dried parts of the Cinnamomum plant by steam distillation. Although this aromatic aldehyde is a component of an essential oil, it is not formed from mevalonic acid and is not a terpene. Cinnamaldehyde is also not an acetogenin nor is it related to usnic add.The origin of this fragrant material is shikimic acid, which is part of the plant s primary metabolism. 

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