Rrans-Cinnamic acid

Mizutani M, Ohta D, Sato R (1993) Purification and characterization of a cytochrome P450 (rran -cinnamic acid 4-hydroxylase) from etiolated mung bean seedlings. Plant Cell Physiol 34 481-488... 

In the absence of defects, the reactivity of organic solids is mainly determined by molecular packing. Reactions in which the crystal structure holds sway over intrinsic molecular reactivity are said to be topochemically controlled (Thomas, 1974). A classic example of a topochemically controlled organic reaction in the solid state is the photodimerization of rrans-cinnamic acids studied by Schmidt et al. (see Ginsburg,... 

Figure 8.11 Photoreactivity of rrans-cinnamic acid polymorphs.

Keywords rran -cinnamic acid, double salt formation, [2-i-2]photodimerization, truxillic acid, truxinic acid, cyclobutane... 

Under the action of phenylalanine ammonia lyase (EC 4.3.1.5) Phe is transformed to rrans- cinnamic acid. This plays an important role in plants as a precursor of numerous phenolic secondary products such as flav-onoids, lignin, etc. D-Phe is a component of grami-cidin S and tyrocidines. L-Phe tastes weakly bitter, D-Phe tastes sweet. 

For the red wines (82-84), which were injected directly into the HPLC without sample preparation, a ternary-gradient system using aqueous acetic acid (1% and 5% or 6%), and acidified acetonitrile (acetonitrile-acetic acid-water, 30 5 6) was used for cinnamic acid derivatives, catechins, flavonols, flavonol glycosides, and proanthocyanidins. Due to the large number of peaks, the gradient was extended to 150 min for the resolution of many peaks of important phenolics. This direct injection method was able to separate phenolic acids and esters, catechins, proanthocyanidins, flavonols, flavonol glycosides, and other compounds (such as tyrosol, and rrans-resveratrol) in wine in a single analysis. However, use of acetic acid did not permit the detector (PDA) to be used to record the UV spectra of phenolics below 240 nm (84). 

The established migration of the aryl group in the deamination reaction of phenylalanine ester has been ingeniously utilized in a synthesis of some tropane alkaloids. Thus, treatment of the 3a-tropanyl ester (19) of ( )-phenyl-alanine with nitrous acid affords a separable mixture of atropine (20), the 3a-tropanyl ester (21) of ( + )-3-hydroxy-3-phenylpropionate, apo-atropine (22), and 3a-tropanyl rrans-cinnamate (23). Although not obtained in a pure state the cis-isomer of (23), and littorine (24), were also shown to be present in the product mixture. ... 

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