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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-04-15 15:38:49 UTC
HMDB IDHMDB0014814
Secondary Accession Numbers
  • HMDB14814
Metabolite Identification
Common NameBenzyl benzoate
DescriptionBenzyl benzoate, also known as benylate or benylic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzyl benzoate is a faint, sweet, and almond tasting compound. Outside of the human body, benzyl benzoate is found, on average, in the highest concentration within Ceylon cinnamon. Benzyl benzoate has also been detected, but not quantified in, several different foods, such as fennels, garden tomato, annual wild rice, amaranths, and horseradish tree. This could make benzyl benzoate a potential biomarker for the consumption of these foods. Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite Sarcoptes scabiei. It is characterized by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and is therefore useful in the treatment of scabies. It is also used to treat lice infestations of the head and body.
Structure
Data?1586965129
Synonyms
ValueSource
BenylateChEBI
BENZOIC ACID phenylmethylesterChEBI
Benzoic acid, benzyl esterChEBI
Benzoic acid, phenylmethyl esterChEBI
Phenylmethyl benzoateChEBI
Benylic acidGenerator
BENZOate phenylmethylesterGenerator
Benzoate, benzyl esterGenerator
Benzoate, phenylmethyl esterGenerator
Phenylmethyl benzoic acidGenerator
Benzyl benzoic acidGenerator
BenzanilHMDB
NovoscabinHMDB
BenzemulHMDB
Benzylbenzoaat smeersel fnaHMDB
AcarosanHMDB
AnsarHMDB
AcarilHMDB
AntiscabiosumHMDB
AscabiolHMDB
Chemical FormulaC14H12O2
Average Molecular Weight212.2439
Monoisotopic Molecular Weight212.083729628
IUPAC Namebenzyl benzoate
Traditional Namebenzyl benzoate
CAS Registry Number120-51-4
SMILES
O=C(OCC1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2
InChI KeySESFRYSPDFLNCH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Benzoate ester
  • Benzoyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point21 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.02 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.43ALOGPS
logP3.7ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.7 m³·mol⁻¹ChemAxon
Polarizability22.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9600000000-053d8df1e84bfa72c807Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-b0cd2b3fa8283d974d76Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9810000000-7d82df2148f364364d37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9810000000-e3b80444bd7ae9437590Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3930000000-fa4d81201ce0caa8539cSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-5910000000-c5210f9077b94a2f81e1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-b15752c1190b0242b115Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-e4f7251f775b85f6af09Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9610000000-37d8d16fbb06548d4614Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4920000000-a552e18b70960ed092beSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9720000000-f05c57dce7b414894a2eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9600000000-053d8df1e84bfa72c807Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-b0cd2b3fa8283d974d76Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9810000000-7d82df2148f364364d37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9810000000-e3b80444bd7ae9437590Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3930000000-fa4d81201ce0caa8539cSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-5910000000-c5210f9077b94a2f81e1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-b15752c1190b0242b115Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-e4f7251f775b85f6af09Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9610000000-37d8d16fbb06548d4614Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4920000000-a552e18b70960ed092beSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9720000000-f05c57dce7b414894a2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5f1ad29b0d2e8f8a42c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00676 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00676 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00676
Phenol Explorer Compound IDNot Available
FooDB IDFDB012844
KNApSAcK IDC00019221
Chemspider ID13856959
KEGG Compound IDC12537
BioCyc IDCPD-6443
BiGG IDNot Available
Wikipedia LinkBenzyl_Benzoate
METLIN IDNot Available
PubChem Compound2345
PDB IDBZM
ChEBI ID41237
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [PubMed:12667233 ]
  2. Bachewar NP, Thawani VR, Mali SN, Gharpure KJ, Shingade VP, Dakhale GN: Comparison of safety, efficacy, and cost effectiveness of benzyl benzoate, permethrin, and ivermectin in patients of scabies. Indian J Pharmacol. 2009 Feb;41(1):9-14. doi: 10.4103/0253-7613.48882. [PubMed:20177574 ]