56961-74-1

Usage

Ester derived from

phenylacetic acid and 1-phenylethanol

Uses

perfumery, fragrance applications, flavoring agent in food products

Odor

sweet, floral, slightly fruity

Potential properties

antifungal, antioxidant

Physical form

clear, colorless to pale yellow liquid

Solubility

low in water

Stability

typically stable under normal conditions

Safety

considered safe for use in various consumer products when used at low concentrations

InChI:InChI=1/C16H16O2/c1-13(15-10-6-3-7-11-15)18-16(17)12-14-8-4-2-5-9-14/h2-11,13H,12H2,1H3

Upstream product

• 98-85-1 1-Phenylethanol 
• 105512-18-3 1-phenylethyl 2-bromoacetate 
• 98-80-6 phenylboronic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-80-0 phenylacetyl chloride 
• 536-74-3 phenylacetylene 
• 103-82-2 phenylacetic acid 

Downstream Products

• 98-85-1 1-Phenylethanol 
• 7631-42-7 phenylacetic acid anion 

Relevant academic research and scientific papers

Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Sulfonated nanohydroxyapatite functionalized with 2-aminoethyl dihydrogen phosphate (HAP@AEPH2-SO3H) as a reusable solid acid for direct esterification of carboxylic acids with alcohols

Sulfonated nanohydroxyapatite functionalized with 2-aminoethyl dihydrogen phosphate (HAP@AEPH2-SO3H) efficiently catalyzed direct esterification of carboxylic acids and alcohols with high selectivity toward the formation of esters in good to excellent yields. Our results clearly show that HAP@AEPH2-SO3H can be easily recovered by simple filtration and reused for subsequent five runs without any significant impact on yields of products. The main advantage of this methodology is easy and ecofriendly catalyst preparation, easy catalyst separation, practical simplicity, safe reaction conditions, recyclable catalyst and high products yields.

Palladium-Catalyzed C(sp3)-C(sp2) Cross-Couplings of O -(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantioenriched N -Acylated β-Amino Alcohols

Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.

Zwitterionic salts as mild organocatalysts for transesterification

(Chemical Equation Presented) The exothermic reaction of 3,5-bis(trifluoromethyl)phenyl or 4-nitrophenyl isothiocyanate with 4-pyrrolidinopyridine (PPY) gave the corresponding arylaminothiocarbonylpyridinium salts in quantitative yields. These novel zwitterionic salts were effective as organocatalysts for the transesterification reaction of an equimolar mixture of methyl carboxylates and alcohols in hydrocarbons such as heptane and octane under azeotropic reflux conditions with the removal of methanol. In sharp contrast, PPY was inert as a catalyst under the same reaction conditions.

Combined epimerisation and acylation: Meerwein-ponndorf-verley-oppenauer catalysts in action

A practical racemisation-epimerisation method for chiral secondary alcohols has been developed. Meerwein-Ponndorf-Verley-Oppenauer catalysts such as neodymium(III) isopropoxide are able to racemise these alcohols with retention of other stereocentres in the molecule. This is particularly useful for the recycling of the undesired products of kinetic resolutions of alcohols. By combination of such a racemisation with an acylation using isopropenyl or ethoxyvinyl esters as acyl donors, a fast straightforward recycling of starting materials may be achieved. The combined epimerisation and acylation process is demonstrated for the steroid estradiol methyl ether.

Solubilizing agents for active or functional organic compounds

An active or functional organic compound is solubilized in a diaryl organic compound having a polar or polarizable functional group therein, as a solvent, cosolvent or additive, to form a composition thereof. Representative active or functional organic compounds include those present in personal care products, e.g., sunscreens containing UVA/UVB absorbing compounds, such as avobenzone, benzophenone-3, and 4-methylbenzylidene camphor. Such compositions also show increased SPF, UVA/UVB absorbance ratio, and critical wavelength performance properties.

Oxidation of Alkynes by Hydrogen Peroxide Catalyzed by Methylrhenium Trioxide

The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium tioxide.The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne.Internal alkynes yield α-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds.Rearrangement products were observed only for aliphatic alkynes.Terminal alkynes gave carboxylic acids and their derivatives and α-keto acids as the major products, but their yields varied with the solvent used.

Structure-Activity Relationships in the Esterase-catalysed Hydrolysis and Transesterification of Esters and Lactones

The Broensted exponents for the alkaline hydrolysis of alkyl esters are 1.3 and 0.4 for substitution in the acyl and alcohol portions, respectively, which is indicative of a transition state which resembles the anionic tetrahedral intermediate with a localised negative charge.By contrast, the rate of the pig liver esterase (PLE)-catalysed hydrolysis shows little dependence upon the electron-withdrawing power of substituents.The values of kcat are independent of the pKa of the leaving group alcohol suggesting rate-limiting deacylation.There is a small steric effect of α-substitution in both the alcohol and carboxylic acid residues for the enzyme-catalysed reactions but the enzyme rate enhancement factor remains high for most esters.There is no substantial ee observed for the hydrolysis of racemic esters although the kinetic data can be used for determining the regioselective hydrolysis of diesters.Unsubstituted lactones are poor substrates for PLE but derivatives with hydrophobic substituents show kcat/Km values similar to those for acyclic esters.Dihydrocoumarin undergoes transesterification catalysed by PLE, kcat increases with increasing alcohol concentration indicative of rate-limiting deacylation.There is enantioselectivity in the PLE-catalysed hydrolysis of some racemic lactones but little or none in the transesterification of racemic alcohols with dihydrocoumarin.

Generation of esters from carboxylic acids using Appel's salt (4,5-dichloro-1,2,3-dithiazolium chloride)

Esters can be generated directly in good yields under mild conditions from the corresponding carboxylic acid and alcohol using Appel's salt (4,5-dichloro-1,2,3-dithiazolium chloride) and 2,6-lutidine.