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Record Information
Version5.0
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

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9600000000-053d8df1e84bfa72c8072017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-b0cd2b3fa8283d974d762017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9810000000-7d82df2148f364364d372017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9810000000-e3b80444bd7ae94375902017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3930000000-fa4d81201ce0caa8539c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-5910000000-c5210f9077b94a2f81e12017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-b15752c1190b0242b1152017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-e4f7251f775b85f6af092017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9610000000-37d8d16fbb06548d46142017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4920000000-a552e18b70960ed092be2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9720000000-f05c57dce7b414894a2e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9600000000-053d8df1e84bfa72c8072018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-b0cd2b3fa8283d974d762018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9810000000-7d82df2148f364364d372018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9810000000-e3b80444bd7ae94375902018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3930000000-fa4d81201ce0caa8539c2018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-5910000000-c5210f9077b94a2f81e12018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-b15752c1190b0242b1152018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-e4f7251f775b85f6af092018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9610000000-37d8d16fbb06548d46142018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4920000000-a552e18b70960ed092be2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9720000000-f05c57dce7b414894a2e2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5f1ad29b0d2e8f8a42c72017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-5f1ad29b0d2e8f8a42c72021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 14V, positivesplash10-0006-0910000000-6b126db6e8a8cd28cc922020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 19V, positivesplash10-01pp-1900000000-fc4ec954deb254aebe432020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 27V, positivesplash10-0gwb-3900000000-fa65eef00b7716b973cb2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 14V, positivesplash10-03di-2950000000-d7a69cff0ba48077d60a2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 19V, positivesplash10-0ik9-4920000000-7a2f3c483012572a195f2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 27V, positivesplash10-1009-7900000000-35c5b4005999dda19e872020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap 35V, positivesplash10-00di-0900000000-bb3de5861ac8095ebd912020-07-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a41042015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9bab2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec92015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a0652015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089f2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be12015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a41042015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9bab2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec92015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a0652015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089f2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be12015-05-27View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00676 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB 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 ]