Methyl phenylacetate

Description

Methyl phenylacetate belongs to an ester compound form between the methanol and phenylacetate. It chemical formula is C6H5CH2COOCH3. It is generally found in brandy, capsicum, honey, pepper, some wine, coca and coca products. It is mainly used as a flavouring agent, and is also supplemented into perfumes to enhance honey scents. It can also be used as the precursor for the manufacture of synthetic perfumes. In addition, as an acylating agent, it can participate in the enantioselective acylation reaction of beta-lactam intermediate catalyzed by the penicillin G amidase.

Chemical properties

Methyl phenylacetate is a clear colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. It has a strong odor similar to honey. The odor is so strong that recommended smelling is of a solution with 10% or less methyl phenyl acetate. This compound also naturally occurs in brandy, capsicum, coffee, honey, pepper and some wine.

Occurrence

Reported found in cocoa, coffee, strawberry, pineapple, pepper, hop oil, cognac, peanut, honey, starfruit, Bourbon vanilla, mountain papaya, roasted chicory root and rooibus tea (Aspalathus linearis).

The Uses of Methyl phenylacetate

Methyl phenylacetate is utilized for partition coefficient measurement experiments. It is mainly used in the flavor industry and in perfumes to impart honey scents. Further, it acts as a precursor to prepare synthetic perfumes. It acts as an acylating agent and involved in the enantioselective acylation of beta-lactam intermediate using penicillin G amidase.

Preparation

Methyl phenylacetate is synthesized from phenylacetonitrile by hydrolysis and esterification. Put methanol into a dry glass-lined reaction pot, stir and cool to below 30°C, add sulfuric acid dropwise, heat up to 90°C after adding, and start adding phenylacetonitrile dropwise, control the temperature at about 95°C, and finish adding in 1.5h. After reacting at 95-100 °C for 6 h, it was cooled to below 40 °C and diluted with water equivalent to about 0.6 times the reaction solution. The acid water was separated by standing, and a saturated sodium carbonate solution was added for neutralization and washing, and the aqueous layer was discarded. It is dehydrated with anhydrous calcium chloride and fractionated under reduced pressure to obtain methyl phenylacetate with a yield of 80%.

What are the applications of Application

Methyl Phenylacetate is used as a reagent in the synthesis of various organic reactions, one of which is the synthesis of Vulpinic Acid; a lichen metabolite with anti-inflammatory properties. It is also used in the formulation of edible flavors, for the preparation of honey, chocolate, tobacco and other flavors; it can also be used in daily chemical flavors for the preparation of rose, oriental flavors and other flavors. IFRA has no restrictions.

Definition

ChEBI: Methyl benzeneacetate is a member of benzenes. It is a flavoring ingredient. Odoriferous constituent of many plants. It is generally found in brandy, capsicum, honey, pepper, some wine, coca and coca products.

Aroma threshold values

Detection: 25 ppb

Taste threshold values

Taste characteristics at 30 ppm: floral, fruity, honey, spice, waxy and sweet

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4919, 1971 DOI: 10.1021/ja00748a051
Tetrahedron Letters, 30, p. 2945, 1989 DOI: 10.1016/S0040-4039(00)99165-2

General Description

Methyl phenylacetate has been identified in the volatile fraction of beewax absolute oil, dried fruiting bodies of Boletus auripes, Chinese fermented black soybeans and peated malt.

Biochem/physiol Actions

Methyl phenylacetate undergoes decomposition on photolysis in methanol. Methyl phenylacetate acts as acylating agent and causes the enantioselective acylation of beta-lactam intermediate using penicillin G amidase. Methyl phenylacetate is the starting material in manufacture of synthetic perfumes.

Safety Profile

Moderately toxic by ingestion and skin contact. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.