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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:40 UTC
Update Date2022-03-07 02:53:00 UTC
HMDB IDHMDB0031496
Secondary Accession Numbers
  • HMDB31496
Metabolite Identification
Common Name2-Hexenal
Description2-Hexenal (CAS: 505-57-7), also known as 2-hexenaldehyde or 3-propylacrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, 2-hexenal is considered to be a fatty aldehyde lipid molecule. Outside of the human body, 2-hexenal is found, on average, in the highest concentration within a few different foods, such as corn, tea, and bilberries. 2-Hexenal has also been detected, but not quantified in, several different foods, such as common wheat, ginkgo nuts, spearmints, sunflowers, and watermelons. This could make 2-hexenal a potential biomarker for the consumption of these foods. (E)-2-Hexenal is found in allspice. It is used in perfumery and flavouring. (E)-2-Hexenal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1601268415
Synonyms
ValueSource
(e)-2-HexenalChEBI
(e)-Hex--2-enalChEBI
(e)-Hex-2-enalChEBI
2-trans-HexenalChEBI
3-PropylacroleinChEBI
beta-Propyl acroleinChEBI
beta-PropylacroleinChEBI
Leaf aldehydeChEBI
trans-2-HexenalChEBI
b-Propyl acroleinGenerator
Β-propyl acroleinGenerator
b-PropylacroleinGenerator
Β-propylacroleinGenerator
Hex-2-en-1-alHMDB
2-Hexenal, eHMDB
(2E)-2-HexenalHMDB
(2E)-HexenalHMDB
(e)-2-Hexen-1-alHMDB
2-Hexen-1-alHMDB
Hex-2-enalHMDB
trans-2-Hexen-1-alHMDB
2-HexenaldehydeHMDB
3-Propyl-acroleinHMDB
Hexen-2-alHMDB
Hexen-2-en-1-alHMDB
Hexylenic aldehydeHMDB
alpha,beta-HexylenaldehydeHMDB
Α,β-hexylenaldehydeHMDB
Green leaf aldehydeHMDB
2-HexenalMeSH
Chemical FormulaC6H10O
Average Molecular Weight98.145
Monoisotopic Molecular Weight98.073164942
IUPAC Name(2E)-hex-2-enal
Traditional Name(E)-2-hexenal
CAS Registry Number6728-26-3
SMILES
CCC\C=C\C=O
InChI Identifier
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
InChI KeyMBDOYVRWFFCFHM-SNAWJCMRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point47.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility5261 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.790 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.2 g/LALOGPS
logP1.8ALOGPS
logP1.65ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.24 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.85430932474
DeepCCS[M-H]-124.95930932474
DeepCCS[M-2H]-160.40730932474
DeepCCS[M+Na]+134.81530932474
AllCCS[M+H]+124.532859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.832859911
AllCCS[M-H]-129.032859911
AllCCS[M+Na-2H]-132.832859911
AllCCS[M+HCOO]-137.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-HexenalCCC\C=C\C=O1177.3Standard polar33892256
2-HexenalCCC\C=C\C=O821.5Standard non polar33892256
2-HexenalCCC\C=C\C=O839.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-9000000000-ef8fb4a16f9e47588e242018-04-09Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hexenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hexenal LC-ESI-QTOF 32V, positive-QTOFsplash10-0002-9000000000-ea4667e9ee10cccddb242020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hexenal LC-ESI-QFT , positive-QTOFsplash10-0a4j-9000000000-13fcd86dcfc328ec27a62020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 10V, Negative-QTOFsplash10-0002-9000000000-9232ec723afab464ccc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 20V, Negative-QTOFsplash10-0002-9000000000-a839e50ee7ad7503877e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 40V, Negative-QTOFsplash10-0006-9000000000-4a1d88a16ebce778de702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 10V, Negative-QTOFsplash10-0002-9000000000-649f52184fb4997b20fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 20V, Negative-QTOFsplash10-004i-9000000000-3e77d5cdc17bcd3c255e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 40V, Negative-QTOFsplash10-0n2d-9000000000-022c1508f6a2751bcc392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 10V, Positive-QTOFsplash10-0002-9000000000-db77fc4d5edd7bdc39072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 20V, Positive-QTOFsplash10-000t-9000000000-8c4cc267531a0c711b322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 40V, Positive-QTOFsplash10-0a4l-9000000000-1018f15c3b2d6e22c2262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 10V, Positive-QTOFsplash10-0540-9000000000-6923af674dd1206069572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 20V, Positive-QTOFsplash10-052r-9000000000-3ea4a5ca74032209afaf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hexenal 40V, Positive-QTOFsplash10-0573-9000000000-b0552bcc819f05df9c042021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.23 +/- 0.07 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.63 +/- 0.21 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004502
KNApSAcK IDC00000351
Chemspider ID4444608
KEGG Compound IDC08497
BioCyc IDTRANS-2-HEXENAL
BiGG IDNot Available
Wikipedia LinkCis-3-Hexenal
METLIN IDNot Available
PubChem Compound5281168
PDB IDNot Available
ChEBI ID28913
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029832
Good Scents IDrw1013831
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .