PHENYL ACETATE

Chemical properties

colourless liquid

Chemical properties

Phenylacetate, a product of phenylalanine metabolism. It is a small molecule normally present in the mammalian circulation in low concentrations. Phenylacetate has an offensive odor.

The Uses of PHENYL ACETATE

Phenyl Acetate is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea.

The Uses of PHENYL ACETATE

Phenyl acetate levels in urine are marker for the diagnosis of some forms of unipolar major depressive disorders. It undergoes Fries rearrangement to form a mixture of o- and p-hydroxyacetophenones which are useful intermediates in manufacture of pharmaceuticals. It is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea.

What are the applications of Application

Phenyl acetate is a useful synthesis reagent and intermediate

Definition

ChEBI: An acetate ester obtained by the formal condensation of phenol with acetic acid.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4567, 1988 DOI: 10.1016/S0040-4039(00)80548-1
Chemical and Pharmaceutical Bulletin, 30, p. 4242, 1982 DOI: 10.1248/cpb.30.4242
Synthetic Communications, 19, p. 1271, 1989 DOI: 10.1080/00397918908054534

General Description

A clear colorless liquid with a sweetish solvent odor. Specific gravity 1.073. Flash point 176°F. Boiling point 383-384°F. Difficult to ignite. Used as a laboratory reagent and in the production of some organic chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

An ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. A skin irritant. Combustible when exposed to heat, flame oroxidizers. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Phenyl acetate acid is freed from phenol and acetic acid by washing (either directly or as a solution in pentane) with aqueous 5% Na2CO3, then with saturated aqueous CaCl2, drying with CaSO4 or Na2SO4, and fractionally distilling under reduced pressure. [Beilstein 6 II 153, 6 III 595, 6 IV 611.]