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Record Information
Version4.0
Creation Date2014-10-11 02:23:41 UTC
Update Date2017-09-27 08:44:18 UTC
HMDB IDHMDB0061942
Secondary Accession Numbers
  • HMDB61942
Metabolite Identification
Common Namecis-3-Hexenyl salicylate
Descriptioncis-3-Hexenyl salicylate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Structure
Thumb
Synonyms
ValueSource
3-Hexenyl salicylate, (e)-isomerMeSH
3-Hexenyl salicylateMeSH
Chemical FormulaC13H16O3
Average Molecular Weight220.2643
Monoisotopic Molecular Weight220.109944378
IUPAC Name(3Z)-hex-3-en-1-yl 2-hydroxybenzoate
Traditional Name(3Z)-hex-3-en-1-yl 2-hydroxybenzoate
CAS Registry NumberNot Available
SMILES
CC\C=C/CCOC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted 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

Biological Location:

  Biofluid and excreta:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00yi-9300000000-fd064cad5f590089b816View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-f1045e1c3e9d37526e91View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-5900000000-66ff71ab7da7411e7267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-5490000000-3969028aebe51d411964View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9310000000-a206aa1fa5f8b968bc42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdo-9200000000-b6c075772626ebbb6eeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3390000000-916271a409795bce3f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ko-9820000000-1964ec1ba183ba075130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-2743837cc64958ae3c42View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5371102
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Ketel WG: Sensitization to cis-3-hexenyl salicylate. Contact Dermatitis. 1983 Mar;9(2):154. [PubMed:6851526 ]
  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. [PubMed:8987857 ]
  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. [PubMed:15898496 ]
  4. Shaw DW: Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. 2006 Sep;17(3):152-5. [PubMed:16956469 ]
  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. [PubMed:18035471 ]
  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. [PubMed:19704435 ]
  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. [PubMed:22516741 ]
  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. [PubMed:24040645 ]
  9. John Behan, David Bradshaw, Jonathan Richards, Michael Munroe, 'Flavour compositions.' U.S. Patent US20060153959, issued July 13, 2006. [Link]