StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Verbindung

Phenylacetat

Phenyl acetate

HCID 31229
Neue NotizNeue ReaktionAnfrage stellen
Druckvorschau

Daten werden ergänzt – lade die Seite später neu, um den aktuellen Stand zu sehen

GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
122-79-2
Standard-SMILES
CC(=O)Oc1ccccc1
InChIKey
IPBVNPXQWQGGJP-UHFFFAOYSA-N
Summenformel
C8H8O2
Durchschnittliche Molmasse
136,15 g/mol
Monoisotopische Masse
136,05242949

Überblick

Phenol acetate appears as a clear colorless liquid with a sweetish solvent odor. Difficult to ignite. Used as a laboratory reagent and in the production of some organic chemicals.

Namen und Bezeichner

Bevorzugter Name
Phenyl acetate
IUPAC
phenyl acetate
Lokaler Name
Phenylacetat
Englischer Name
PHENYL ACETATE
Summenformel
C8H8O2
Molmasse
136.15

Namen und Synonyme

PHENYL ACETATE122-79-2Acetic acid, phenyl esterPhenol acetateAcetylphenolAcetyl phenolAcetoxybenzeneAcetic acid,phenyl esterFenylester kyseliny octove(Acetyloxy)benzeneFEMA NO. 3958NSC-27795
Weitere Namen anzeigen
2-phenylacetateFEMA 3958NSC 27795BenzoateAcetatePhenylacetate 99%Phenyl acetate,97%Phenyl Acetate >
355G9R500YCHEBI:8082DTXSID3051626RefChem:6122DTXCID4030178204-575-0Acetic acid phenyl esterAcetates

Datenbank-Bezeichner

CAS
122-79-2
PubChem CID
31229
DTXSID
DTXSID3051626
ChEMBL
CHEMBL289559
ChEBI
CHEBI:8082
UNII
355G9R500Y
EC Number
204-575-0
Nikkaji
J32.787E

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,5
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
10
Formalladung
0
Komplexität
114

Experimentelle und physikochemische Eigenschaften

SolventsSolvents -> Esters (<C12)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 4 Einträge

1.49

1.49

1.49

1.49

OdorPHENOLIC ODOR
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 Einträge

1.073 @ 20 °C/4 °C

Relative density (water = 1): 1.07

1.073-1.079

Flavoring AgentsEU Flavoring substances
Color/Form · 2 Einträge

COLORLESS, MOBILE LIQUID

WATER WHITE LIQUID

Solubility · 5 Einträge

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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 5 Einträge

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)

REACH registered substance: Phenyl acetate (EC: 204-575-0)

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

Other Safety InformationIMAP assessments - Acetic acid, phenyl ester: Human health tier I assessment
DOT LabelCombustible Liquid
Fire Hazards · 2 Einträge

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

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

Fire PotentialCOMBUSTIBLE WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 5 Einträge

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.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Zugehörige Reaktionen

55
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 86531
HRID 86531als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 186907
HRID 186907als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 190788
HRID 190788als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 197472
HRID 197472als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 268510
HRID 268510als Produktuspto-grants-1976_03
Reaktionsgleichung von HRID 283433
HRID 283433als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 329315
HRID 329315als Produktuspto-grants-1977_04
Reaktionsgleichung von HRID 376070
HRID 376070als Eduktuspto-grants-1996_01
Seite 1 von 7

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen

Miscible with oxygenated and chlorinated solvents.

Solubility in water: none

insoluble in water; miscible in alcohol

miscible (in ethanol)

Flash Point · 3 Einträge

176 °F (NFPA, 2010)

176 °F

80 °C

Boiling Point · 4 Einträge

196 °C

196.00 to 198.00 °C. @ 760.00 mm Hg

196 °C

195-196 °C

Melting Point-30 °C

Physikochemische Eigenschaften

Schmelzpunkt
195 · 195-196℃
Siedepunkt
196 °C · 196 °C(lit.)
Dichte
1.073 g/mL · 1.073 g/mL at 25 °C(lit.)
Dampfdichte
4.7 · 4.7
Brechungsindex
20 · n20/D 1.501(lit.)
FEMA
3958 · 3958 | PHENYL ACETATE
Flammpunkt
170 °F · 170 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
4 g/l · 4g/l practically insoluble
Aggregatzustand
Liquid
Farbe
Clear colorless to slightly brown
Geruch (Odor)
10 % · at 10.00 % in dipropylene glycol. phenolic medicinal animal resinous castoreum woody smoky burnt
Geruchsart
phenolic
Wasserlöslichkeit
Soluble in water (4 g/L at 20°C).
Merck
14 · 14,7267
JECFA Number
734 · 734
BRN
636458 · 636458
Henry's Law Constant
1.3 · 1.3×100 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
6.9 · 6.9(20℃)
Stabilität
Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents. Combustible.
InChI
1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
InChIKey
IPBVNPXQWQGGJP-UHFFFAOYSA-N
SMILES
CC(=O)Oc1ccccc1
LogP
1.65 · 1.65
CAS Datenbank
122 · 122-79-2(CAS DataBase Reference)
EPA chemische Informationen
Acetic acid, phenyl ester (122-79-2)
Health Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Hazards SummaryA mild skin and eye irritant; [ICSC] Safe when used as a flavoring agent; [JECFA] An irritant; [MSDSonline] See ORGANIC SOLVENTS.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile · 1 Eintrag

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.

Air and Water ReactionsSlightly soluble in water.
NFPA Hazard Classification · 3 Einträge

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.

Hazard Classes and CategoriesAcute Tox. 4 (65.8%)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 Einträge

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.

First AidExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Fire Fighting ProceduresALCOHOL FOAM.
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 1 Eintrag

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.

Spillage Disposal · 1 Eintrag

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.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames. Above 80 °C use a closed system and ventilation.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.

Toxikologische Informationen

Environmental Fate · 3 Einträge

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Signs and Symptoms · 2 Einträge

Redness.

Redness. Pain.

Effluent ConcentrationsA process water sample from an in situ coal gasification process in Gillette, WY contained phenyl acetate at 4 ppb(1).
Soil Adsorption/Mobility · 1 Eintrag

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).

Natural Pollution Sources/PHENYL ACETATE IS A/ COMPD IN NATURAL COCOA AROMA. /FROM TABLE/
Artificial Pollution SourcesPhenyl acetate's production and use as a solvent(1), chemical intermediate(2), and as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation13% of the theoretical BOD was reached in 30 hours with a lag period ranging from 0 to 5 hours; a first-order rate constant of 0.060/hr was calculated from this process(1).
Environmental Bioconcentration · 1 Eintrag

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).

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity Excerpts · 2 Einträge

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.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
NA 1993 / PGIII
hs_code
29153900
RTECS-Nr.
AJ2800000
risk_code
22
Toxizität
LD50 orally in rats: 1.63 ml/kg, H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969)
hazard_code
Xn,Xi
hazard_note
Irritant
safety_code
36
hazard_class
CBL
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
122-79-2(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 Oral
Uses · 4 Einträge

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

U.S. Production2023: 5,000,000 - <10,000,000 lb
Consumer UsesAdhesion/cohesion promoter
Industry UsesAdhesion/cohesion promoter
Methods of Manufacturing · 3 Einträge

PREPD FROM PHENOL & ACETYL CHLORIDE.

By heating triphenyl phosphate with potassium acetate and alcohol.

Phenol + acetic acid (esterification)

Use Classification · 3 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 Einträge

Adhesive Manufacturing

Acetic acid, phenyl ester: ACTIVE

Anwendungen · 1 Eintrag

VerwendenPhenyl 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.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

4-Benzyloxy-3-nitroacetophenone4'-Hydroxyacetophenon1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONEp-Phenylendi(acetat)2,4,6-Tribromphenylacetat

Ergänzende Hinweise

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