Cinnamyl aldehydes

Fio. 37. Van t Hoff plots for various compounds. Eluites (1) cinnamyl aldehyde, (2) es-tragole, (3) cinnamyl alcohol, (4) cinnamyl acetate. (5) methyleugenol, and (6) s role. The data were obtained on pyrocarbon, 400 x 2.17 mm i.d., with acetonitrile as mobile phase. Reprinted with permission from Colin ei al. (142). 

Chlorophyll, 295 Chlorotil s, 135, 140 m-Chlorotoluene, 182,183 Chloitoluron, 292 Chlorzoxoneacetaminophen, 264 4 -Cholettenone, 74 Cholestanyl silica, 158 Cholesterol, 283, 295 Cholinesterase, 293 Chromatographic enzyme reactor, 291 Chrysene, 69, 105, 107 Cinnamic acid, 293 Cinnamyl acetate, 198 Cinnamyl alcohol, 198 Cinnamyl aldehyde, 198 dausius-Mosotti fimction, 208 Qindamycin, 297 Clonazqmm, 195 Clusters of hetaeron, 250 Coating of polar adsoibent by polar solvent, 86... 

Since cinnamyl aldehyde is the main component of cassia oil (approximately 90%) and Sri Lanka cinnamon bark oil (approximately 75%) [49], it is industrially more important to generate cinnamyl alcohol, which is less abundantly available from nature but is important as cinnamon flavour, by biotransformation of natural cinnamyl aldehyde than vice versa. Recently, a whole-cell reduction of cinnamyl aldehyde with a conversion yield of 98% at very high precursor concentrations of up to 166 g L was described [136]. Escherichia coli DSM 14459 expressing a NADPH-dependent R alcohol dehydrogenase from Lactobacillus kefir and a glucose dehydrogenase from Thermoplasma acidophilum for intracellular cofactor regeneration was applied as the biocatalyst (Scheme 23.8). 

The alcohol is obtained by reaction of CH3MgBr with cinnamyl aldehyde in THF at 0° (95% yield). 

As a further reflection of their high nucleophilicity, silyl ketene acetals, such as 65, proved to be reactive not only toward aromatic, heteroaromatic, and cinnamyl aldehydes but also, very importantly, even to aliphatic aldehydes. (For experimental details see Chapter 14.1.9). Furthermore, the catalyst loading can be reduced to 1 mol%, without erosion of enantioselectivity [64]. 

The partial oxidation of cinnamyl alcohol (Ph-CH—CH-CH2OH) to cinnamalde-hyde was conducted in the presence of a surfactant (sodium dodecylbenzene sulfonate) because reactant and product were insoluble in water [45,50]. Oxidation on Bi-Pt/AljOj catalysts was performed at basic pH obtained by addition of Li2C03, and by controlling the air supply to avoid over-oxidation of the metal. The maximum selectivity for cinnamaldehyde, 98.5 % at 95.5 % conversion, was obtained for a Bi/Pts ratio of 0.5. The high selectivity for cinnamyl aldehyde was attributed to the negligible hydration of the aldehyde because of the conjugation of C—O, C=C, and aromatic nucleus (see Section 9.2.2.1). Under similar conditions the selectivity for oxidation of 1-dodecanol [50] to dodecanal was poor. 

CINNAMYL ALDEHYDE (104-55-2) Combustible liquid (flash point 231 F/111 °C). A strong reducing agent. Contact with oxidizers, sodium hydroxide can cause fire and explosion. Incompatible with strong acids, strong bases, alkaline earth and alkali metals elevated temperatures will increase reaction. Attacks iron, aluminum, plastics, and coatings. 

Cinnamaldehyde (sin-uh-MAL-duh-hide) is also known as cinnamic aldehyde 3-phenyl-2-propenal cinnamyl aldehyde phenylalacrolein cinnamal and trans-cinnamaldehyde. It is a yellowish oily, liquid with a sweet taste and a cinnamish odor responsible for the characteristic taste and odor of cinnamon spice. It occurs naturally in the bark of the cinnamon tree, Cinnamomum zeylanicum, which is native to Sri Lanka and India, and has been cultivated in other parts of the world, such as Brazil, Jamaica, and Mauritius. Cinnamaldehyde is also found in other members of the the Cinnamomum species, including cassia and camphor. 

Synonyms cas 104-55-2 benzylideneacetaldehyde cassia aldehyde cinnamal cinnamyl aldehyde ... 

Cinnamyl alcohol, o-methyl-. See Methylcinnamyl alcohol Cinnamyl alcohol, o-pentyl, acetate. See o-Amylcinnamyl acetate Cinnamyl aldehyde. SeeCinnamal Cinnamyl-2-aminobenzoate Cinnamyl-o-aminobenzoate. See Cinnamyl anthranilate Cinnamyl anthranilate CAS 87-29-6 FEMA 2295... 

Synonyms 3-phenyl-2-propenal cinnamic aldehyde 2-propenal-3-phenyl cinnamal phenylacrolein cassia aldehyde 3-phenylpro-penal cinnamyl aldehyde 3-phenylacrolein benzylideneacetaldehyde 3-phenyl-2-propenaldehyde zimtaldehyde 3-phenylacryalde-hyde phenyl-2-propenal Zimtaldehyde light 3-phenyl-2-propen-i-al cinnamal... 

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