Benzoic acid, 2-hydroxy-, (3Z)-3-hexenyl ester (CHEM013494)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:13:28 UTC
Update Date2016-11-09 01:14:47 UTC
Accession NumberCHEM013494
Identification
Common NameBenzoic acid, 2-hydroxy-, (3Z)-3-hexenyl ester
ClassSmall Molecule
Descriptioncis-3-Hexenyl salicylate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cis-3-Hexenyl salicylic acidGenerator
3-Hexenyl salicylate, (e)-isomerHMDB
3-Hexenyl salicylateHMDB
(3Z)-Hex-3-en-1-yl 2-hydroxybenzoic acidGenerator
Chemical FormulaC13H16O3
Average Molecular Mass220.264 g/mol
Monoisotopic Mass220.110 g/mol
CAS Registry Number65405-77-8
IUPAC Name(3Z)-hex-3-en-1-yl 2-hydroxybenzoate
Traditional Name(3Z)-hex-3-en-1-yl 2-hydroxybenzoate
SMILESCC\C=C/CCOC(=O)C1=CC=CC=C1O
InChI IdentifierInChI=1S/C13H16O3/c1-2-3-4-7-10-16-13(15)11-8-5-6-9-12(11)14/h3-6,8-9,14H,2,7,10H2,1H3/b4-3-
InChI KeyIEPWIPZLLIOZLU-ARJAWSKDSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP4.08ALOGPS
logP4.17ChemAxon
logS-2.8ALOGPS
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 Count6ChemAxon
Refractivity64.26 m³·mol⁻¹ChemAxon
Polarizability24.32 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00yi-9300000000-fd064cad5f590089b816Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00yi-9300000000-fd064cad5f590089b816Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-f1045e1c3e9d37526e91Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-5900000000-66ff71ab7da7411e7267Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3390000000-916271a409795bce3f74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ko-9820000000-1964ec1ba183ba075130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-2743837cc64958ae3c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014l-6290000000-19965aed4eb3c8f1e319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-9ba8c888cfe721064947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b73e8de79e5d1ff289ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-5490000000-3969028aebe51d411964Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9310000000-a206aa1fa5f8b968bc42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdo-9200000000-b6c075772626ebbb6eeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0930000000-9fa9ee9b460183a90355Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-318243c530965998a5f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-9300000000-2b251f0254dea9a92e77Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061942
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5371102
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. van Ketel WG: Sensitization to cis-3-hexenyl salicylate. Contact Dermatitis. 1983 Mar;9(2):154.
2. Moon JH, Watanabe N, Ijima Y, Yagi A, Sakata K: Cis- and trans-linalool 3,7-oxides and methyl salicylate glycosides and (Z)-3-hexenyl beta-D-glucopyranoside as aroma precursors from tea leaves for oolong tea. Biosci Biotechnol Biochem. 1996 Nov;60(11):1815-9.
3. James DG: Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects. J Chem Ecol. 2005 Mar;31(3):481-95.
4. Shaw DW: Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. 2006 Sep;17(3):152-5.
5. Lapczynski A, McGinty D, Jones L, Letizia CS, Api AM: Fragrance material review on cis-3-hexenyl salicylate. Food Chem Toxicol. 2007;45 Suppl 1:S402-5. Epub 2007 Sep 14.
6. Ballhorn DJ, Kautz S, Lion U, Heil M: Qualitative variability of lima bean's VOC bouquets and its putative ecological consequences. Plant Signal Behav. 2008 Nov;3(11):1005-7.
7. Hegde M, Oliveira JN, da Costa JG, Loza-Reyes E, Bleicher E, Santana AE, Caulfield JC, Mayon P, Dewhirst SY, Bruce TJ, Pickett JA, Birkett MA: Aphid antixenosis in cotton is activated by the natural plant defence elicitor cis-jasmone. Phytochemistry. 2012 Jun;78:81-8. doi: 10.1016/j.phytochem.2012.03.004. Epub 2012 Apr 18.
8. Umasankar Y, Ramasamy RP: Highly sensitive electrochemical detection of methyl salicylate using electroactive gold nanoparticles. Analyst. 2013 Nov 7;138(21):6623-31. doi: 10.1039/c3an01295f.
9. John Behan, David Bradshaw, Jonathan Richards, Michael Munroe, 'Flavour compositions.' U.S. Patent US20060153959, issued July 13, 2006.: http://www.google.ca/patents/US20060153959