Benzyl acetate (T3D3214)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:56:28 UTC
Update Date2014-12-24 20:26:00 UTC
Accession NumberT3D3214
Identification
Common NameBenzyl acetate
ClassSmall Molecule
DescriptionBenzyl acetate is found in alcoholic beverages. Benzyl acetate occurs in jasmine, apple, cherry, guava fruit and peel, wine grape, white wine, tea, plum, cooked rice, Bourbon vanilla, naranjila fruit (Solanum quitoense), Chinese cabbage and quince. Benzyl acetate is a flavouring agent Benzyl acetate is an organic compound with the molecular formula C9H10O2. It is the ester formed by condensation of benzyl alcohol and acetic acid. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Benzyl acetate belongs to the family of Benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(acetoxymethyl)benzene
Acetato de bencilo
Acetic acid benzyl ester
Acetic acid phenylmethyl ester
Acetic acid, benzyl ester
Acetic acid, phenylmethyl ester
alpha-Acetoxytoluene
Benzyl acetate + glycine combination
Benzyl acetic acid
Benzyl ester of acetic acid
Benzyl ethanoate
Benzylester kyseliny octove
FEMA 2135
Nchem.167-comp5
Phenylmethyl acetate
Phenylmethyl ethanoate
Plastolin I
Chemical FormulaC9H10O2
Average Molecular Mass150.175 g/mol
Monoisotopic Mass150.068 g/mol
CAS Registry Number140-11-4
IUPAC Namebenzyl acetate
Traditional Namebenzyl acetate
SMILESCC(=O)OCC1=CC=CC=C1
InChI IdentifierInChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChI KeyInChIKey=QUKGYYKBILRGFE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyloxycarbonyls
Direct ParentBenzyloxycarbonyls
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceWater-white liquid (3).
Experimental Properties
PropertyValue
Melting Point-51.3°C
Boiling Point210°C (410°F)
Solubility3.1 mg/mL at 25°C
LogP1.96
Predicted Properties
PropertyValueSource
Water Solubility0.52 g/LALOGPS
logP2.07ALOGPS
logP1.65ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.03 m³·mol⁻¹ChemAxon
Polarizability16.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9500000000-cff0c394a1b0b3cc92072017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9500000000-841f27b9e65e2ce89c1a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-623c61f61fdb6da2b8d52017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-25dd8e6faa7ec0169f6b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9500000000-cff0c394a1b0b3cc92072018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9500000000-841f27b9e65e2ce89c1a2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9400000000-623c61f61fdb6da2b8d52018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-25dd8e6faa7ec0169f6b2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-17b9d18d5fb4783325ba2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9700000000-abe92e96f1d84e65be702020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-9000000000-c754ef385d6b93795a902020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-75c07172980b788be9a72020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4r-4900000000-530ce1ca47f4b6dd88eb2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-40a46bd1fe10e848be932021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-f95214ead4fcf995cc2f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900000000-fcba2e2d8766512672222021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9000000000-e01217d3d96977aead452021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4r-4900000000-a5cc39c53acb1a2179412021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-035e3c3e1d8e79d12dd52015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-1900000000-20dbebba6e1a1e7b6b1b2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9200000000-12ccb23d1b98b40680b92015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-498c774b4001661ce18f2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-3edd7ab114803f4c05f72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-9da2fbbe84ceded6d9712015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-4900000000-72df46e2c6c70289affb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9700000000-fe550ab4d8eed595fcca2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2e2f653a7e5f9110776f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-6d5d1d348079810363172021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-420694b18a259683f9c82021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-61af7471e21d1a9ee8682021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9400000000-2a4e82268df5cfb3e4792014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7) ; eye contact (7)
Mechanism of ToxicityBenzyl acetate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
MetabolismParaoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.
Toxicity ValuesLD50: 2490 mg/kg (Oral, Rat) (7) LD50: 830 mg/kg (Oral, Mouse) (7) LC50: 245 ppm over 8 hours (Inhalation, Cat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (5)
Uses/SourcesIt is used widely in perfumery and cosmetics for its aroma and in flavorings to impart apple and pear flavors (6).
Minimum Risk LevelNot Available
Health EffectsAcute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsVomiting, drowiness, diarrhea, convulsions and burning sensation may result from ingestion or inhalation. Moreover, inhalation may cause laboured breathing and sore throat. Redness of the eyes, dry skin, depending of the contact surface (8).
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31310
PubChem Compound ID8785
ChEMBL IDCHEMBL1233714
ChemSpider ID13850405
KEGG IDC15513
UniProt IDNot Available
OMIM ID
ChEBI ID52051
BioCyc IDCPD-103
CTD IDNot Available
Stitch IDBenzyl acetate
PDB IDJ0Z
ACToR ID152
Wikipedia LinkBenzyl_acetate
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
  2. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  3. Lewis RJ Sr. (ed) (1993). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co.
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  6. Wikipedia. Benzyl acetate. Last Updated 4 August 2009. [Link]
  7. ScienceLab.com (2008). Material Safety Data Sheet (MSDS) for Benzyl Acetate. [Link]
  8. International Occupational Safety and Health Information Centre (2005). Benzyl acetate. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. Acetylcholinesterase
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Dafforn A, Anderson M, Ash D, Campagna J, Daniel E, Horwood R, Kerr P, Rych G, Zappitelli F: The mode of binding of potential transition-state analogs to acetylcholinesterase. Biochim Biophys Acta. 1977 Oct 13;484(2):375-85. [20963 ]