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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:23 UTC
HMDB IDHMDB0014814
Secondary Accession Numbers
  • HMDB14814
Metabolite Identification
Common NameBenzyl Benzoate
DescriptionBenzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.
Structure
Thumb
Synonyms
ValueSource
BenylateChEBI
BENZOIC ACID phenylmethylesterChEBI
Benzoic acid, benzyl esterChEBI
Benzoic acid, phenylmethyl esterChEBI
Phenylmethyl benzoateChEBI
Benylic acidGenerator
Benzyl benzoic acidGenerator
BENZOate phenylmethylesterGenerator
Benzoate, benzyl esterGenerator
Benzoate, phenylmethyl esterGenerator
Phenylmethyl benzoic acidGenerator
BenzanilMeSH
NovoscabinMeSH
BenzemulMeSH
Benzylbenzoaat smeersel fnaMeSH
AcarosanMeSH
AnsarMeSH
AcarilMeSH
AntiscabiosumMeSH
AscabiolMeSH
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
DescriptionThis compound 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Agriculture:

    Pesticide:

  Pharmaceutical industry:

Physical Properties
StateLiquid
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9600000000-053d8df1e84bfa72c807View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-b0cd2b3fa8283d974d76View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9810000000-7d82df2148f364364d37View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9810000000-e3b80444bd7ae9437590View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3930000000-fa4d81201ce0caa8539cView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-5910000000-c5210f9077b94a2f81e1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-b15752c1190b0242b115View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7920000000-e4f7251f775b85f6af09View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9610000000-37d8d16fbb06548d4614View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4920000000-a552e18b70960ed092beView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9720000000-f05c57dce7b414894a2eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5f1ad29b0d2e8f8a42c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012844
KNApSAcK IDC00019221
Chemspider ID13856959
KEGG Compound IDC12537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl_Benzoate
METLIN IDNot Available
PubChem Compound2345
PDB IDBZM
ChEBI ID41237
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 ]