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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:49 UTC
Update Date2022-03-07 02:52:18 UTC
HMDB IDHMDB0029818
Secondary Accession Numbers
  • HMDB29818
Metabolite Identification
Common NameBenzyl salicylate
DescriptionBenzyl salicylate belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Benzyl salicylate is a sweet, balsam, and clean tasting compound. Benzyl salicylate has been detected, but not quantified in, cloves (Syzygium aromaticum) and herbs and spices. This could make benzyl salicylate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl salicylate.
Structure
Data?1582753469
Synonyms
ValueSource
Benzyl salicylic acidGenerator
2-Hydroxybenzoic acid, phenylmethyl esterHMDB
Benzoic acid, 2-hydroxy-, phenylmethyl esterHMDB
Benzyl 2-hydroxybenzoateHMDB
Benzyl O-hydroxybenzoateHMDB
Benzyle salicylateHMDB
FEMA 2151HMDB
Phenylmethyl 2-hydroxybenzoateHMDB
Salicyclic acid benzyl esterHMDB
Salicyclic acid, benzyl esterHMDB
Salicylic acid, benzyl esterHMDB
Benzyl 2-hydroxybenzoic acidGenerator
Benzyl salicylateMeSH
Chemical FormulaC14H12O3
Average Molecular Weight228.2433
Monoisotopic Molecular Weight228.07864425
IUPAC Namebenzyl 2-hydroxybenzoate
Traditional Namebenzyl salicylate
CAS Registry Number118-58-1
SMILES
OC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
InChI KeyZCTQGTTXIYCGGC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parento-Hydroxybenzoic acid esters
Alternative Parents
Substituents
  • O-hydroxybenzoic acid ester
  • Benzyloxycarbonyl
  • Salicylic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point23.4 °CNot Available
Boiling Point208.00 °C. @ 26.00 mm HgThe Good Scents Company Information System
Water Solubility24.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.209 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.66ALOGPS
logP4.05ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity64.68 m³·mol⁻¹ChemAxon
Polarizability23.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.72631661259
DarkChem[M-H]-151.08731661259
DeepCCS[M+H]+151.27430932474
DeepCCS[M-H]-148.87830932474
DeepCCS[M-2H]-182.11530932474
DeepCCS[M+Na]+157.2130932474
AllCCS[M+H]+151.332859911
AllCCS[M+H-H2O]+147.332859911
AllCCS[M+NH4]+155.132859911
AllCCS[M+Na]+156.232859911
AllCCS[M-H]-153.632859911
AllCCS[M+Na-2H]-153.332859911
AllCCS[M+HCOO]-153.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzyl salicylateOC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C12620.1Standard polar33892256
Benzyl salicylateOC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C11873.8Standard non polar33892256
Benzyl salicylateOC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C11870.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzyl salicylate,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C12014.1Semi standard non polar33892256
Benzyl salicylate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C12251.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzyl salicylate EI-B (Non-derivatized)splash10-002f-9020000000-f8a29c2088c5bdab3e782017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl salicylate EI-B (Non-derivatized)splash10-0006-9000000000-f1bb87f256bac665a7912017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl salicylate EI-B (Non-derivatized)splash10-002f-9020000000-f8a29c2088c5bdab3e782018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzyl salicylate EI-B (Non-derivatized)splash10-0006-9000000000-f1bb87f256bac665a7912018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl salicylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-ea978c8f999b7c82ef8c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl salicylate GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9500000000-2057479e73d11f4937072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 15V, Negative-QTOFsplash10-002r-0970000000-092256d864de5333c7eb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 30V, Negative-QTOFsplash10-000i-1920000000-941449ab5809b96738152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 90V, Positive-QTOFsplash10-0k92-9800000000-0b1d0cd1020bc374ef162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 75V, Positive-QTOFsplash10-0zfs-6900000000-93f829ad7e33b844cc332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 15V, Positive-QTOFsplash10-004i-0390000000-ad3de2dd08a0f74845ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 30V, Positive-QTOFsplash10-0ufr-0950000000-ea5bd45203af17e711b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 60V, Positive-QTOFsplash10-0udi-1900000000-48db7eadcf37ffb5cfc72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 45V, Positive-QTOFsplash10-0udi-0900000000-19830cc271e0ceb7a4a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 60V, Negative-QTOFsplash10-052b-9800000000-472c239f18c11d2aee7b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 45V, Negative-QTOFsplash10-000j-4900000000-75374eef08d94124efab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 75V, Negative-QTOFsplash10-052b-9600000000-0d8ef15260a308fa0fbd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzyl salicylate 90V, Negative-QTOFsplash10-052b-9600000000-6ba0f9d07240e619ec872021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 10V, Positive-QTOFsplash10-004l-7390000000-1b68eaf022948e495e482016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 20V, Positive-QTOFsplash10-0006-9310000000-4df2d5af50c2b56200452016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 40V, Positive-QTOFsplash10-0006-9100000000-75fd5efee16fab949e192016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 10V, Negative-QTOFsplash10-004i-2290000000-a8f183e8663a1f8f08c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 20V, Negative-QTOFsplash10-002o-9630000000-cc6aa4daf9fb043748832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 40V, Negative-QTOFsplash10-0006-9100000000-efd816c92b753927d1bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 10V, Negative-QTOFsplash10-004i-1090000000-3116bf111b9e643da9262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 20V, Negative-QTOFsplash10-054o-9300000000-6c39e1952ed1e9788d202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 40V, Negative-QTOFsplash10-0006-9000000000-f165937fc20d39fca3e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 10V, Positive-QTOFsplash10-00fr-2950000000-2744ebd279893cb34b042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 20V, Positive-QTOFsplash10-006x-9610000000-cbd65b232617f9d1e6d02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl salicylate 40V, Positive-QTOFsplash10-0a4l-9700000000-82cad6c952fb0506dda22021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001029
KNApSAcK IDC00035059
Chemspider ID8060
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl salicylate
METLIN IDNot Available
PubChem Compound8363
PDB IDNot Available
ChEBI ID563619
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001792
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .