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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:15 UTC
Update Date2022-03-07 02:53:12 UTC
HMDB IDHMDB0032018
Secondary Accession Numbers
  • HMDB32018
Metabolite Identification
Common NamePhenyl salicylate
DescriptionPhenyl salicylate, also known as salol or musol, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Phenyl salicylate is a mild, sweet, and balsam tasting compound. Phenyl salicylate is a potentially toxic compound. Phenyl salicylate is used as a food additive ("EAFUS: Everything Added to Food in the United States. "). It is hydrolyzed to salicylic acid . It is used for the treatment of inflammation in the lower urinary tract.
Structure
Data?1563862207
Synonyms
ValueSource
2-Hydroxy-benzoic acid phenyl esterChEBI
2-PhenoxycarbonylphenolChEBI
Phenol salicylateChEBI
Phenyl-2-hydroxybenzoateChEBI
Salicylic acid phenyl esterChEBI
SalolChEBI
2-Hydroxy-benzoate phenyl esterGenerator
Phenol salicylic acidGenerator
Phenyl-2-hydroxybenzoic acidGenerator
Salicylate phenyl esterGenerator
Phenyl salicylic acidGenerator
2-Hydroxybenzoic acid phenyl esterHMDB
2-Hydroxybenzoic acid, phenyl esterHMDB
Benzoic acid, 2-hydroxy-, phenyl esterHMDB
Fenylester kyseliny salicyloveHMDB
MusolHMDB
Phenyl 2-hydroxybenzoateHMDB
Salicylic acid, phenyl esterHMDB
SalphenylHMDB
Seesorb 201HMDB
Seesorb K 201HMDB
Chemical FormulaC13H10O3
Average Molecular Weight214.2167
Monoisotopic Molecular Weight214.062994186
IUPAC Namephenyl 2-hydroxybenzoate
Traditional Namesalol
CAS Registry Number118-55-8
SMILES
OC1=CC=CC=C1C(=O)OC1=CC=CC=C1
InChI Identifier
InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
InChI KeyZQBAKBUEJOMQEX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • O-hydroxybenzoic acid ester
  • Benzoate ester
  • Salicylic acid or derivatives
  • Phenol ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point43 °CNot Available
Boiling Point172.00 to 173.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility0.15 mg/mL at 25 °CNot Available
LogP3.292 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP3.58ALOGPS
logP3.98ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.84 m³·mol⁻¹ChemAxon
Polarizability21.96 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]+148.25231661259
DarkChem[M-H]-148.47631661259
DeepCCS[M+H]+147.34730932474
DeepCCS[M-H]-144.95130932474
DeepCCS[M-2H]-179.09130932474
DeepCCS[M+Na]+153.57230932474
AllCCS[M+H]+147.432859911
AllCCS[M+H-H2O]+143.232859911
AllCCS[M+NH4]+151.332859911
AllCCS[M+Na]+152.432859911
AllCCS[M-H]-148.132859911
AllCCS[M+Na-2H]-147.832859911
AllCCS[M+HCOO]-147.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phenyl salicylateOC1=CC=CC=C1C(=O)OC1=CC=CC=C12506.3Standard polar33892256
Phenyl salicylateOC1=CC=CC=C1C(=O)OC1=CC=CC=C11722.4Standard non polar33892256
Phenyl salicylateOC1=CC=CC=C1C(=O)OC1=CC=CC=C11740.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenyl salicylate,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C11877.1Semi standard non polar33892256
Phenyl salicylate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C12141.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phenyl salicylate EI-B (Non-derivatized)splash10-00di-4900000000-fcc0d5e766dfb52cf2d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenyl salicylate EI-B (Non-derivatized)splash10-00di-4900000000-fcc0d5e766dfb52cf2d92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenyl salicylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9600000000-6e2ea24d5a7e7f20d7f92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenyl salicylate GC-MS (1 TMS) - 70eV, Positivesplash10-0fdo-6900000000-cc00b25f130b78905e8b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4910000000-5d4e08b10364ff3dc5252014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 60V, Negative-QTOFsplash10-0006-9200000000-a3457c55a7386db72a9b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 45V, Negative-QTOFsplash10-0006-9530000000-72aee7a7f7845b821eae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 15V, Negative-QTOFsplash10-03di-4090000000-21c500395dd98dddc80d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 30V, Negative-QTOFsplash10-03dl-6290000000-d4c4e6d7630398541f452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 90V, Negative-QTOFsplash10-0006-9000000000-a5ab86abdfdc5564d26a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenyl salicylate 75V, Negative-QTOFsplash10-0006-9000000000-dc0f72c8fa3ee9d425f92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 10V, Positive-QTOFsplash10-014i-0390000000-99da4cb99d88023844ad2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 20V, Positive-QTOFsplash10-00xr-2950000000-37c2025a458ede4ba4d22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 40V, Positive-QTOFsplash10-0uk9-9300000000-c7779524725bb16e6bb02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 10V, Negative-QTOFsplash10-03di-1090000000-e53ec6eaf869f0bc1d302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 20V, Negative-QTOFsplash10-03di-3190000000-157a064fd6d6fdb02acc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 40V, Negative-QTOFsplash10-0006-9200000000-6dc8ce8b6b3c630a30032015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 10V, Positive-QTOFsplash10-00di-1940000000-a7fd807b1dc9734a072c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 20V, Positive-QTOFsplash10-006x-9600000000-1b4f0741eb754f8ea91f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 40V, Positive-QTOFsplash10-0g4l-9400000000-b43dcb62d448c78be1c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 10V, Negative-QTOFsplash10-03dl-5090000000-21734187732a02b38c6e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 20V, Negative-QTOFsplash10-0006-9000000000-26441e7a9da764f1fb512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenyl salicylate 40V, Negative-QTOFsplash10-000f-9600000000-eab0f08f6c15cdd728172021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDDB11071
Phenol Explorer Compound IDNot Available
FooDB IDFDB008716
KNApSAcK IDNot Available
Chemspider ID8058
KEGG Compound IDC14163
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenyl_salicylate
METLIN IDNot Available
PubChem Compound8361
PDB IDNot Available
ChEBI ID34918
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1040381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Phenyl salicylate → 3,4,5-trihydroxy-6-[2-(phenoxycarbonyl)phenoxy]oxane-2-carboxylic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Phenyl salicylate → Phenoldetails