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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:49 UTC
Update Date2020-02-26 21:44:29 UTC
HMDB IDHMDB0029818
Secondary Accession Numbers
  • HMDB29818
Metabolite Identification
Common NameBenzyl salicylate
DescriptionBenzyl salicylate, also known as fema 2151, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Trace impurities may have a significant influence on the odour. Benzyl salicylate is a sweet, balsam, and clean tasting compound. Outside of the human body, Benzyl salicylate has been detected, but not quantified in, cloves and herbs and spices. This could make benzyl salicylate a potential biomarker for the consumption of these foods. It occurs naturally in a variety of plants and plant extracts and is widely used in blends of fragrance materials. It is used as a solvent for crystalline synthetic musks and as a component and fixative in floral perfumes such as carnation, jasmine, lilac, and wallflower. Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics as a fragrance additive or UV light absorber. There is some evidence that people may become sensitized to this material and as a result, there is a restriction standard concerning the use of this material in fragrances by the International Fragrance Association. It appears as an almost colorless liquid with a mild odor described as "very faint, sweet-floral, slightly balsamic" by those who can smell it, but many people either can't smell it at all or describe its smell as "musky".
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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point23.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9020000000-f8a29c2088c5bdab3e78Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f1bb87f256bac665a791Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9020000000-f8a29c2088c5bdab3e78Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f1bb87f256bac665a791Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-ea978c8f999b7c82ef8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9500000000-2057479e73d11f493707Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-7390000000-1b68eaf022948e495e48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9310000000-4df2d5af50c2b5620045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-75fd5efee16fab949e19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2290000000-a8f183e8663a1f8f08c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-9630000000-cc6aa4daf9fb04374883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-efd816c92b753927d1bbSpectrum
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
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.. .