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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:44 UTC
Update Date2023-02-21 17:27:58 UTC
HMDB IDHMDB0040225
Secondary Accession Numbers
  • HMDB40225
Metabolite Identification
Common NameIsoamyl salicylate
DescriptionIsoamyl 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. Isoamyl salicylate is a bitter, floral, and herbal tasting compound. Isoamyl salicylate has been detected, but not quantified in, several different foods, such as black tea, teas (Camellia sinensis), alcoholic beverages, fruits, and red tea. This could make isoamyl salicylate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoamyl salicylate.
Structure
Data?1677000478
Synonyms
ValueSource
Isoamyl salicylic acidGenerator
2-Hydroxybenzoic acid, 3-methylbutyl esterHMDB
3-Methylbutyl O-hydroxybenzoateHMDB
3-Methylbutyl salicylateHMDB
Benzoic acid, 2-hydroxy-, 3-methylbutyl esterHMDB
Benzoic acid, O-hydroxy, 3-methylbutyl esterHMDB
Isoamyl O-hydroxybenzoateHMDB
Isopentyl O-hydroxybenzoateHMDB
Isopentyl salicylateHMDB
Isopentyl-2-hydroxyphenyl methanoateHMDB
OrchideeHMDB
Salicylic acid, isopentyl esterHMDB
SanfoinHMDB
TrefleHMDB
TrefolHMDB
TressaneHMDB
3-Methylbutyl 2-hydroxybenzoic acidGenerator
Isoamyl salicylateMeSH
Chemical FormulaC12H16O3
Average Molecular Weight208.2536
Monoisotopic Molecular Weight208.109944378
IUPAC Name3-methylbutyl 2-hydroxybenzoate
Traditional Name3-methylbutyl 2-hydroxybenzoate
CAS Registry Number87-20-7
SMILES
CC(C)CCOC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=1S/C12H16O3/c1-9(2)7-8-15-12(14)10-5-3-4-6-11(10)13/h3-6,9,13H,7-8H2,1-2H3
InChI KeyPMGCQNGBLMMXEW-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
  • 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point277.00 to 278.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.14 mg/mL at 25 °CNot Available
LogP4.370The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP3.44ALOGPS
logP3.93ChemAxon
logS-2.7ALOGPS
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 Count5ChemAxon
Refractivity58.49 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings1ChemAxon
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]+148.01931661259
DarkChem[M-H]-143.69631661259
DeepCCS[M+H]+147.90330932474
DeepCCS[M-H]-145.34230932474
DeepCCS[M-2H]-181.30130932474
DeepCCS[M+Na]+156.71230932474
AllCCS[M+H]+146.932859911
AllCCS[M+H-H2O]+143.032859911
AllCCS[M+NH4]+150.532859911
AllCCS[M+Na]+151.532859911
AllCCS[M-H]-150.032859911
AllCCS[M+Na-2H]-150.632859911
AllCCS[M+HCOO]-151.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isoamyl salicylateCC(C)CCOC(=O)C1=CC=CC=C1O2167.8Standard polar33892256
Isoamyl salicylateCC(C)CCOC(=O)C1=CC=CC=C1O1541.1Standard non polar33892256
Isoamyl salicylateCC(C)CCOC(=O)C1=CC=CC=C1O1598.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoamyl salicylate,1TMS,isomer #1CC(C)CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C1701.8Semi standard non polar33892256
Isoamyl salicylate,1TBDMS,isomer #1CC(C)CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C1926.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00dl-9800000000-e932949ffff596a0e7a82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00dl-9600000000-5a35db6cf062e262bd0f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00di-9700000000-e62a29f19910b38602dc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00dl-9800000000-e932949ffff596a0e7a82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00dl-9600000000-5a35db6cf062e262bd0f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)splash10-00di-9700000000-e62a29f19910b38602dc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl salicylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-8900000000-221dcc93cd4e631a6b262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl salicylate GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7910000000-ca285106374821c7dff02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Positive-QTOFsplash10-0ab9-5490000000-1a44be2d7c5cbd1859f42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Positive-QTOFsplash10-00di-9410000000-7a0e217d95aa026bd9c32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Positive-QTOFsplash10-0kml-9100000000-7898e32ef213461a0f5a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Negative-QTOFsplash10-0a4i-4390000000-48cde09d2017c68690002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Negative-QTOFsplash10-052o-9820000000-4948a94706f178549d112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Negative-QTOFsplash10-0006-9100000000-48773c923f8afdbfa8cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Negative-QTOFsplash10-052f-9070000000-c97178794593493ca4ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Negative-QTOFsplash10-0006-9110000000-b5a678739c9679b6c0f32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Negative-QTOFsplash10-0006-9000000000-c24304b5660720a960ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Positive-QTOFsplash10-00fr-0920000000-972274e34fe69d12098e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Positive-QTOFsplash10-00di-4900000000-bf7823578da1a19f182d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Positive-QTOFsplash10-0a4i-9300000000-35f8c7a337f718d6149d2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB019939
KNApSAcK IDNot Available
Chemspider ID6612
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6874
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006772
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.. .