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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-11 02:23:41 UTC
Update Date2019-07-23 07:17:29 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 o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. cis-3-Hexenyl salicylate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866249
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 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
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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+153.9230932474
DeepCCS[M-H]-151.56230932474
DeepCCS[M-2H]-185.8930932474
DeepCCS[M+Na]+161.27530932474
AllCCS[M+H]+151.132859911
AllCCS[M+H-H2O]+147.432859911
AllCCS[M+NH4]+154.632859911
AllCCS[M+Na]+155.632859911
AllCCS[M-H]-154.132859911
AllCCS[M+Na-2H]-154.632859911
AllCCS[M+HCOO]-155.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-3-Hexenyl salicylateCC\C=C/CCOC(=O)C1=CC=CC=C1O2371.5Standard polar33892256
cis-3-Hexenyl salicylateCC\C=C/CCOC(=O)C1=CC=CC=C1O1696.4Standard non polar33892256
cis-3-Hexenyl salicylateCC\C=C/CCOC(=O)C1=CC=CC=C1O1740.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-3-Hexenyl salicylate,1TMS,isomer #1CC/C=C\CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C1833.7Semi standard non polar33892256
cis-3-Hexenyl salicylate,1TBDMS,isomer #1CC/C=C\CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C2064.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl salicylate EI-B (Non-derivatized)splash10-00yi-9300000000-fd064cad5f590089b8162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl salicylate EI-B (Non-derivatized)splash10-00yi-9300000000-fd064cad5f590089b8162018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-f1045e1c3e9d37526e912017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (1 TMS) - 70eV, Positivesplash10-0006-5900000000-66ff71ab7da7411e72672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl 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 - cis-3-Hexenyl salicylate 10V, Positive-QTOFsplash10-00di-5490000000-3969028aebe51d4119642016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Positive-QTOFsplash10-0089-9310000000-a206aa1fa5f8b968bc422016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Positive-QTOFsplash10-0fdo-9200000000-b6c075772626ebbb6eea2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Negative-QTOFsplash10-014i-3390000000-916271a409795bce3f742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Negative-QTOFsplash10-00ko-9820000000-1964ec1ba183ba0751302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Negative-QTOFsplash10-0006-9100000000-2743837cc64958ae3c422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Positive-QTOFsplash10-00di-0930000000-9fa9ee9b460183a903552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Positive-QTOFsplash10-00di-3900000000-318243c530965998a5f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Positive-QTOFsplash10-0adi-9300000000-2b251f0254dea9a92e772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Negative-QTOFsplash10-014l-6290000000-19965aed4eb3c8f1e3192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Negative-QTOFsplash10-0006-9200000000-9ba8c888cfe7210649472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Negative-QTOFsplash10-0006-9000000000-b73e8de79e5d1ff289dd2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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]