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Showing Compound Isoamyl salicylate (FDB019939)

Record Information
Version1.0
Creation date2010-04-08 22:14:41 UTC
Update date2019-11-26 03:18:08 UTC
Primary IDFDB019939
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 teas (Camellia sinensis), fruits, alcoholic beverages, herbal tea, and green 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.
CAS Number87-20-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
3-Methylbutyl 2-hydroxybenzoatedb_source
3-Methylbutyl o-hydroxybenzoatebiospider
Benzoic acid, o-hydroxy, 3-methylbutyl esterbiospider
FEMA 2084db_source
Isoamyl o-hydroxybenzoatebiospider
Isopentyl o-hydroxybenzoatebiospider
Predicted 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
Chemical FormulaC12H16O3
IUPAC name3-methylbutyl 2-hydroxybenzoate
InChI IdentifierInChI=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
Isomeric SMILESCC(C)CCOC(=O)C1=CC=CC=C1O
Average Molecular Weight208.2536
Monoisotopic Molecular Weight208.109944378
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.21%; H 7.74%; O 23.05%DFC
Melting PointNot Available
Boiling PointBp15.2 151-152°DFC
Experimental Water Solubility0.145 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 1.1DFC
Refractive Indexn20D 1.5065DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-e932949ffff596a0e7a8Spectrum
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9600000000-5a35db6cf062e262bd0fSpectrum
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-e62a29f19910b38602dcSpectrum
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9800000000-e932949ffff596a0e7a8Spectrum
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00dl-9600000000-5a35db6cf062e262bd0fSpectrum
GC-MSIsoamyl salicylate, non-derivatized, GC-MS Spectrumsplash10-00di-9700000000-e62a29f19910b38602dcSpectrum
Predicted GC-MSIsoamyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-8900000000-221dcc93cd4e631a6b26Spectrum
Predicted GC-MSIsoamyl salicylate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7910000000-ca285106374821c7dff0Spectrum
Predicted GC-MSIsoamyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsoamyl salicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-5490000000-1a44be2d7c5cbd1859f42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9410000000-7a0e217d95aa026bd9c32016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-9100000000-7898e32ef213461a0f5a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4390000000-48cde09d2017c68690002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-9820000000-4948a94706f178549d112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-48773c923f8afdbfa8cd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9070000000-c97178794593493ca4ca2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9110000000-b5a678739c9679b6c0f32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c24304b5660720a960ed2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0920000000-972274e34fe69d12098e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-bf7823578da1a19f182d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-35f8c7a337f718d6149d2021-09-25View Spectrum
NMRNot Available
ChemSpider ID6612
ChEMBL IDCHEMBL2260718
KEGG Compound IDNot Available
Pubchem Compound ID6874
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40225
CRC / DFC (Dictionary of Food Compounds) IDBLP36-T:MGW68-V
EAFUS ID1845
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1006771
SuperScent ID6874
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wintergreen
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
soapy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
orchid
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference