Phenyl-acetic acid cinnamate

Benzoic acid — Thio-benzoic acid — Sulpho-benzoic acid — Phthalic acid—Ethyl-potassium phthalate—Phenyl-acetic acid—Cinnamic acid—Benzyl-malonic acid.56-58... 

Phenyl acetic acid. Hydro cinnamic acid. Cinnamic acid or Phenyl acrylic acid Phenyl propiolic acid. Phenyl vinyl acetic acid. 

The side-chain carboxy acids which we have studied are phenyl acetic, phenyl propionic or hydrocinnamic, phenyl acrylic or cinnamic and phenyl propiolic. Phenol derivatives of all of these are known. Hydroxy phenyl acetic acid is not important. 

A different approach consists of a two-steps stereoselective synthesis of Combretastatin A-4, based on the Perkin condensation of 3,4,5-trimethoxy phenyl acetic acid and 3-hydroxy-4-methoxy benzaldehyde, followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline [11] (Schema 4). 

There are several ways in which phenols have been categorized. Harbome and Simmonds categorized polyphenols based on the number of carbon atoms, which includes simple phenols (Ce) phenolic acids and related compounds (Ce—Ci) acetophenones and phenyl acetic acids (Cg—C2) cinnamic acids, cinamyl aldehydes, and alcohols (Cg—C3) coumarins, isocoumarins, and chromones (Cg—C3) flavonoids (C15) biflavonyls (C30) stilbenes (Cg—C2—Cg) benzophenones and xanthones (Cg—C2—Cg) quinones (Cg, Cio, Cm) betacyanins (Cjg) and lignans, lignins, tannins, and phlobaphenes (which are dimmers, oligomers, or polymers) [19]. Polyphenols have also been categorized by some researchers based on their... 

Methyl cinnamate ( CiqH,QO2 ) Phenyl acetic acid... 

Cinnamic alcohol, C Hj. CH CH. CH OH, or y-phenyl-allyl alcohol, is found in the form of esters, principally of either acetic or cinnamic acid in storax, balsam of Peru, and in hyacinth and other essential oils. 

Benzaldehyde, ortho-Nitro Cinnamic Acid, ortho-Nitro Phenyl Propiolic Acid.—Later he started with benzaldehyde and obtained first benzal chloride which by condensation with sodium acetate yielded cinnamic acid salt. 

From the cinnamic acids or phenyl propanoids described above, / -oxidation and truncation of side chains yields a variety of benzoic or simple phenolic acids [28], Rao et al., [22] identified gallic acid (18), gentisic acid (19), protocatechuic acid (20), />-hydroxybenzoic acid (21), oc-resorcyclic acid (22), vanillic acid (23) and salicylic acid (24) in C. arietinum and showed that overall, leaf content of all phenolic compounds was much greater than in roots and stem. They postulated that the production of these compounds may enhance the activity of indole acetic acid oxidase or may express antimicrobial properties when leached into the soil. However, Singh et al. [24] showed that the production of both 18 and 24 by C. arietinum was induced when treated by the culture filtrate of Sclerotium rolfsii along with the phenyl propanoids 14, 15 and 17 mentioned above. 

Phenyl-3-(phenylthio)propionic acid 21 Cinnamic acid (10 g), thiophenol (8 g), and glacial acetic acid (10 g) saturated with hydrogen bromide are heated in a pressure flask for 9 h at 100°, then diluted with much water. Unchanged thiophenol is removed by distillation in steam. The oil that separates is removed it crystallizes when cooled and seeded and, after recrystallization from light petroleum, has m.p. 85-86° (yield about 75 %). 

Synonyms Acetic acid, cinnamyl ester Cinnamic acetate 3-Phenylallyl acetate y-Phenylallyl acetate 2-Phenyl-2-propen-1-ol acetate... 

Phenethyl benzoate Phenethyl butyrate Phenethyl cinnamate Phenethyl formate Phenethyl isobutyrate Phenethyl isovalerate Phenethyl 2-methylbutyrate Phenethyl phenylacetate Phenethyl propionate Phenethyl salicylate Phenethyl senecioate Phenethyl tiglate Phenoxyacetic acid Phenoxyethyl isobutyrate Phenylacetaldehyde Phenylacetaldehyde 2,3-butylene glycol acetal Phenylacetaldehyde diisobutyl acetal Phenylacetaldehyde dimethyl acetal Phenylacetaldehyde glyceryl cyclic acetals Phenyl acetate... 

Fig. 1. A generalized scheme showing the kinds of secondary products that arise from the aromatic amino acids in higher plants. Several similarities are found in fungi and bacteria some fungi produce alkaloids ftom tryptophan and lignin-like materials from phenylalanine. Plant pathogenic fungi produce cinnamate and para and meta hydroxy phenyl-acetate from phenylalanine. Certain bacteria produce antibiotics and fluorescent pigments from metabolites in the shikimate pathway. Microorganisms are not known to produce coumarin, substituted coumarins, flavonoids and isoflavonoids.

Methyl, ethyl, n-propyl, isopropyl, n-hutyl, benzyl, cyclohexyl esters of formic, acetic, oxalic, succinic, tartaric, citric, benzoic, salicylic (and other substituted benzoic acids), phthalic and cinnamic acids phenyl esters of acetic, benzoic and salicylic acids. 

Phenyl-propyl alcohol, CgH. CHj. CH.2. CHj. OH, is the next highest homologue of phenyl-ethyl alcohol, and is also known as hydro-cinnamyl alcohol. Like the last described bodies it has been known for many years, its first preparation being described in the Aivnalen (188, 202). It occurs as a cinnamic acid ester in storax, and as an acetic ester in cassia oil. It is prepared synthetically by the reduction of cinnamyl alcohol with sodium amalgam and water, or by the reduction of cinnamic or benzyl acetic esters with sodium and absolute alcohol. It has the following characters —... 

Phenyl cinnamate and other phenolic esters have been prepared by heating the acid and phenol in the presence of phosphorus oxychloride,1 and by heating the acid anhydride and phenol together in the presence of a dehydrating agent such as fused zinc chloride or anhydrous sodium acetate.2 Phenyl cinnamate has also been prepared by the careful distillation of phenyl fumarate.3... 

A modified Perkin procedure is illustrated in the synthesis of a-phenyl-cinnamic acid in which benzaldehyde is condensed with phenylacetic acid in the presence of acetic anhydride and triethylamine. Presumably equilibria are set up which result in the formation of either a mixed anhydride, phenylacetic acetic anhydride or the symmetrical phenylacetic anhydride. 

---