Phenylacetat

1.49

1.49

1.49

1.073 @ 20 °C/4 °C

Relative density (water = 1): 1.07

1.073-1.079

COLORLESS, MOBILE LIQUID

WATER WHITE LIQUID

PRACTICALLY INSOL IN WATER; SOL IN GLACIAL ACETIC ACID; MISCIBLE WITH ALCOHOL, CHLOROFORM, ETHER

Miscible with oxygenated and chlorinated solvents.

Solubility in water: none

insoluble in water; miscible in alcohol

miscible (in ethanol)

176 °F (NFPA, 2010)

176 °F

80 °C

196 °C

196.00 to 198.00 °C. @ 760.00 mm Hg

196 °C

195-196 °C

This chemical does not meet GHS hazard criteria for 27.6% (89 of 322) of reports.

Warning

H302 (65.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 322 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Acetic acid, phenyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Acetic acid, phenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, phenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Cease Manufacture Update: 28-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/1922

Phenyl acetate: Does not have an individual approval but may be used under an appropriate group standard

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Combustible. Above 80 °C explosive vapour/air mixtures may be formed.

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.

1 - Materials that, under emergency conditions, can cause significant irritation.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use water spray, foam, powder, carbon dioxide.

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rest.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a log Kow value(2) and a regression-derived equation(3), indicates that phenyl acetate is expected to have high to moderate mobility in soil(SRC). In alkaline soils, hydrolysis of phenyl acetate is expected to be an important fate process with a half-life of 6 days at pH 8(6). Based on limited data, biodegradation of phenyl acetate is expected with a measured first-order rate constant of 0.060/hr(7). Volatilization of phenyl acetate from moist soil surfaces is expected to be important(SRC) given an estimated Henry's Law constant of 6.5X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Phenyl acetate is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.398 mm Hg(5,SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a log Kow value(2) and a regression-derived equation(3), indicates that phenyl acetate is not expected to adsorb to suspended solids and sediment in water(SRC). In alkaline water, hydrolysis of phenyl acetate is expected to be an important fate process with a half-life of 6 days at pH 8(6). Based on limited data, biodegradation of phenyl acetate is expected with a measured first-order rate constant of 0.060/hr(7). Phenyl acetate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 6.5X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 19 hours and 9 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 8(3,SRC), from a log Kow value(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenyl acetate, which has an estimated vapor pressure of 0.398 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase phenyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 8 days(3,SRC).

Redness.

Redness. Pain.

The Koc of phenyl acetate is estimated as approximately 150(SRC), using a log Kow value of 1.49(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that phenyl acetate is expected to have moderate to high mobility in soil(SRC).

An estimated BCF of 8 was calculated for phenyl acetate(SRC), using a log Kow value of 1.49(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for phenyl acetate is estimated as 6.5X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phenyl acetate is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 19 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 9 days(2,SRC). Phenyl acetate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). Phenyl acetate is not expected to volatilize from dry soil surfaces based on an extrapolated vapor pressure of 0.398 mm Hg(3).

The effects of phenylacetate (PA) on fetal brain growth were examined in pregnant rats receiving a 20% casein diet with 1.0, 1.5, 2.0, or 2.5% phenylacetate. Control rats were fed the 20% casein diet ad libitum or restricted to daily consumption of 9 and 6 g. In experimental groups of rats total food intake during pregnancy decreased. ... By plotting the fetal brain weight (Y, mg) against maternal food intake (X, g/21 days) in control groups /an/ hyperbolic regression equation was obtained. ... Similar plots for excess phenylacetate rats fell below this line, indicating that prenatal fetal brain growth was impaired by an excess in phenylacetate per se specifically, as well as by decreased food intake nonspecifically. Administering the excess phenylacetate diets resulted in decreases in total RNA, total protein and RNA/DNA ration in the fetal brain, whereas total DNA was unchanged, showing the impairment of protein synthesis, not proliferation. No remarkable changes in concentration and pattern of free amino acids in maternal plasma in excess phenylacetate groups were observed. ...

... The aim of this study was to determine the teratogenicity of phenylalanine and phenylalanine metabolites. The system of whole embryo culture was employed and D9 (neurulating) mouse embryos were exposed to phenylalanine, phenylethylamine (PEA), phenylpyruvate (PPA), phenylacetate (PAA), 2-OHphenylacetate (2-OH), and phenyllacetate (PLA) at concentrations from 0.01 mM to 10 mM for 24 hr. Embryos were examined for morphological abnormalities and protein content. Phenylalanine at 1 and 6 mM concentrations was not teratogenic, however, 10 mM produced NTD's in 82% of the embryos. Phenylethylamine was the most toxic factor at concentrations of 1 and 10 mM were embryo lethal whereas NTD's were observed at 0.1 mM in 70% of the embryos. 2-OHphenylacetate was the next most toxic metabolite at 1 and 10 mM producing NTD's in 10 and 100% of the conceptuses respectively. phenyllactate and phenylacetate produced no NTD's at 1 mM, 60% at 5 mM, and 100% at 10 mM. Phenylacetate produced approximately 50% NTD'S at both 1 mM and 10 mM. Phenyllactate, phenylacetate, 2-OHphenylacetate, and phenylpyruvate produced a significant reduction in embryonic protein, and phenylethylamine and 2-OHphenylacetate reduced yolk sac protein values. The results indicate that phenylalanine and its metabolites have differential effects on neurulating mouse embryos and would suggest that a combination of phenylalanine and one or more of its metabolites, or synergism between metabolites, play a role in the phenyl-ketonuric embryopathy.

PHENYL ACETATE /WAS METABOLIZED TO/ PHENOL, IN MAN; IN PIG; IN RABBIT; AND IN PEA.

The substrate specificity of carboxylesterases (CEs) in various respiratory tract tissues from F344/N-rats, New-Zealand-white-rabbits, and Syrian-hamsters was studied using ion chromatography to quantify hydrolysis rates. Thirteen esters were tested: pentyl-acetate, phenyl-acetate and beta-butyrolactone were used for interspecies comparison. Liver S9 had the most catalytic activity in rats whereas in rabbits and hamsters the values for trachea and nasal S9 were as active or more active than liver for all substrates tested except pentyl-acetate. Lung S9 showed reduced esterase activity relative to the other tissues. ... Straight chain alcohol esters were the most rapidly hydrolyzed and tertiary esters had the slowest hydrolysis rate. ...

The substrate specificity for carboxylic acid esters was determined for phosphoric triester hydrolases and serine esterases. Serum was obtained from 452 individuals, including non diseased person and patients with hyperlipemia. Correlations between enzyme activities, reversible inhibition by EDTA and progressive inhibition by organophosphate compounds and carbamates were made. The hydrolysis of paraoxon (POX), phenylacetate (PA), and beta-naphthylacetate (BNA) was studied. Results indicated that two paraoxonases hydrolyze paraoxon, one sensitive and the other insensitive to EDTA. The EDTA sensitive paraoxonase also hydrolyzed beta-naphthylacetate. The EDTA insensitive hydrolysis of beta-naphthylacetate and phenylacetate was assigned to a serine esterase. The EDTA sensitive hydrolysis of phenylacetate was likely due to more than one enzyme, which may be an arylesterase and a carboxylesterase.

Esterases in human liver microsomes hydrolyzed ... phenylacetate (Vmax 57 +/- 8 mumol/min/g tissue), whereas esterases found in the human liver cytosol hydrolyzed ... phenylacetate (Vmax 37 +/- 2.9 mumol/min/g tissue). ... Human plasma esterase hydrolyzed ... phenylacetate (Vmax 250 +/- 17 mumol/min/mL). ... Phenylacetate hydrolysis involved arylesterase in plasma, both arylesterase and carboxylesterase in liver microsomes and carboxylesterase in liver cytosol. ...

For more Metabolism/Metabolites (Complete) data for PHENYL ACETATE (6 total), please visit the HSDB record page.

Used as a solvent, laboratory reagent, and in organic synthesis; [Hawley]

Solvent, organic sythesis, laboratory reagent

High-boiling aprotic solvent

Used as a chemical intermediate for the synthesis of o-hydroxyacetophenone; p-hydroxyacetophenone; synephrine

PREPD FROM PHENOL & ACETYL CHLORIDE.

By heating triphenyl phosphate with potassium acetate and alcohol.

Phenol + acetic acid (esterification)

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Adhesive Manufacturing

Acetic acid, phenyl ester: ACTIVE