Cinnamic acid, 4- , ethyl

Cinnamic acid ethyl ester Fr fixed oil° ° Cinnamic acid Fr fixed oil° ... 

T. B. Otero. Identification of cinnamic acid ethyl ester and 4-vinylphenol in off-flavour olive oils. Ann Chim Acta 1991 247(2) 295-297. 

Ethyl cinnamate Cinnamic acid, ethyl ester (8) 2-Propenoic acid, 3-phenyl-, ethyl ester (9) (103-36-6)... 

Cinnamic acid ethyl ester is a carbonyl compound, which like ben/.ophenone has the ability to accept an electron to form a rather stable anion radical. As tin t. /hunsaturated ester it may produce 1.2- and... 

Ethyl Cinnamate. C H5CH CHCOOC2H5. Required Cinnamic acid, 20 g. rectified spirit, 20 ml. 

Cinnamic acid can be readily esterified by the Fischer-Speier method without any risk of the addition of hydrogen chloride at the double bond. Proceed precisely as for the preparation of ethyl benzoate (p. 104), using 20 g. of cinnamic acid and 20 ml. of rectified spirit. When the crude product is poured into water, a sharp separation of the ester is not readily obtained, and hence the addition of about 10 ml. of carbon tetrachloride is particularly desirable. Finally distil off the carbon... 

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. 

Ethyl cinnamate may also be prepared by the esterification of cinnamic acid. The pure compound boils at 127°/6 mm. 

The couplings of vicinal protons in 1,2-disubstituted alkenes lie in the range 6-12 Hz for cis protons (dihedral angle 0°) and 12-17 Hz for trans protons (dihedral angle 180°), thus also following the Karplus-Conroy equation. Typical examples are the alkene proton AB systems of coumarin (16a, cis) and tra 5-cinnamic acid (16b), and of the cis-trans isomers 17a and b of ethyl isopente-nyl ether, in addition to those in problems 3, 4, 8, 11, 13 and 38. 

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 —... 

Ethyl Cinnamate.—The cinnamic ester of ethyl alcohol is a natural constituent of a few essential oils, including camphor oil and storax. It is formed synthetically by condensing cinnamic acid and ethyl alcohol by dry hydrochloric acid gas. It has a soft and sweet odour, and is particularly suitable for blending in soap perfumes. It is an oil at ordinary temperatures, melting at 12°, and boiling at 271°. Its specific gravity is 1 0546, and its refractive index 1 5590. 

Ethyl cinnamate[7] To 2.96 g (20.0 mmol) of cinnamic acid in 25 mL of anhydrous THF 3.24 g (20.0 mmol) of CDI was added. When C02 evolution had ceased, 5 mL of ethanol was added and the mixture was refluxed for 30 min. After concentration in a rotary evaporator the residue was taken up in 100 mL of diethylether and extracted three times each with 50 mL of water. After drying of the ethereal solution and concentration in vacuo the residue was distilled to give ethyl cinnamate (b.p. 145-147 °C/17 mm) in 80% yield. 

The procedure described is essentially that of Ballard and Dehn.1 Stilbene has also been prepared by reduction of desoxy-benzoin,20 benzaldehyde,23 and benzil 2o-2c by dehydrogenation of ethyl benzene,30 toluene,30- 33- 3, and bibenzyl 33-3alkaline reduction of phenylnitromethane,40 phenylnitroacetonitrile,40 and desoxybenzoin 43 by distillation of benzyl sulfone,50 benzyl sulfide,60-63 calcium cinnamate,5 cinnamic acid,5d phenyl cinna-mate,6e-6/ and diphenyl fumarate ie by dehydrohalogenation of a,a -dichlorobibenzyl60 and benzyl chloride 63 by dehalogenation of a,a,c/,a -tetrachlorobibenzyl70 and benzal chloride 73 by the coupling of cinnamic acid and phenyldiazonium chloride 8 by de-... 

A study of the regioselectivity of the 1,3-dipolar cycloaddition of aliphatic nitrile oxides with cinnamic acid esters has been published. AMI MO studies on the gas-phase 1,3-dipolar cycloaddition of 1,2,4-triazepine and formonitrile oxide show that the mechanism leading to the most stable adduct is concerted. An ab initio study of the regiochemistry of 1,3-dipolar cycloadditions of diazomethane and formonitrile oxide with ethene, propene, and methyl vinyl ether has been presented. The 1,3-dipolar cycloaddition of mesitonitrile oxide with 4,7-phenanthroline yields both mono-and bis-adducts. Alkynyl(phenyl)iodonium triflates undergo 2 - - 3-cycloaddition with ethyl diazoacetate, Ai-f-butyl-a-phenyl nitrone and f-butyl nitrile oxide to produce substituted pyrroles, dihydroisoxazoles, and isoxazoles respectively." 2/3-Vinyl-franwoctahydro-l,3-benzoxazine (43) undergoes 1,3-dipolar cycloaddition with nitrile oxides with high diastereoselectivity (90% de) (Scheme IS)." " ... 

A somewhat different route is used to prepare an analogue that bears additional oxygen. The sequence, in this case, starts by base-catalyzed formylation of the hydro-cinnamic acid derivative (40-1) with ethyl formate. Condensation of the product (40-2) with guanidine in this case leads to a pyrimidone (40-3), with the cyclization involving an ester-amide interchange between guanidine and the ester. Reaction of... 

Cinnamic acid, a-cyano-/3-methyl-, ethyl ester)... 

Ethyl /3-phenyl-/3-hydroxypropionate has been prepared by esterification of /3-phenyl-/3-hydroxypropionic acid obtained by the addition of hydrogen bromide to cinnamic acid and subsequent hydrolysis.1,2 The procedure given is based on that of Andrijewski 3 and of Blaise and Herman.4... 

Other preparations of 2-iminothiazolidin-4-ones which are discussed in the review by Brown139 utilize the reactions of thiourea with a-hydroxy acids,146 ethyl diazoacetate,73 glycidic esters,74,147 cinnamic acid,148 unsaturated diacids (fumaric, maleic, and citraconic) or their esters or imides,149-152 and propiolic esters.153,154 There has been considerable controversy in the literature surrounding the propiolic ester synthesis since many workers have proposed that the products are 1,3-thiazines (see Section IV, B, 1). The pertinent papers in this controversy have been summarized by Cain and Warrener.155 Nagase158 has recently settled the argument in favor of the 2-iminothiazolidin-4-... 

A pure culture of the organism was inoculated into a basal medium with the addition of 0.025% caffeic acid. After 7 days incubation at 25°C under conditions of reduced oxygen tension, the caffeic acid was completely metabolized. Metabolites of caffeic acid are identified as dihydrocaffeic acid and ethyl catechol, respectively. In the 1960s, it has been reported that a constitutive enzyme present in strains of Aerobacter decarboxylates caffeic acid to 4-vinylcatechol nonoxidatively [20], Several cinnamic acids have been tested and the decarboxylation product from /7-coumaric acid has been identified as 4-vinylphenol. Thus, the bacterial enzyme activity requires a relatively unhindered 4-hydroxy group on the aromatic ring and an acrylic acid side chain. 

Flowery Anisyl alcohol Benzyl acetate, phenylaceiate Cinnamic acid Cinnamyl acetate Citronellyl formate Crcsyl acetate Decanal Dimethyl benzyl carbinol Dimethyl benzyl carbinyl acetate Ethyl anthranilate Geranyl acetate Hydroxycitronellal dimethyl acetate Linalool Linalyl acetate Methyl benzoate Pcnethyl acetate 2-Phcnylpropionaldehyde 3-Phenylpropionaldehvde. 

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