Record Information
Version1.0
Creation date2010-04-08 22:06:16 UTC
Update date2020-09-17 15:35:56 UTC
Primary IDFDB004502
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHex-trans-2-en-1-al
Description2-Hexenal, also known as 2-hexenaldehyde, 3-propyl-acrolein or leaf aldehyde, 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. 2-Hexenal occurs in two isomeric forms (trans - and cis -2-hexenal), with the trans form being of greater importance. trans-2-Hexenal is an inflammable, colorless, light and air sensitive liquid. As an odorant, 2-hexnal has a sharp, vegetable-green smell with a slight sharpness that smells like acrolein. When diluted, however, it smells pleasantly green and apple-like. Indeed, 2-hexenal is one of the aldehydes that contribute to the taste of apples and is often referred to as green notes (the taste of green apples, such as Granny Smith). It has a sweet, berry, apple-like taste and a fresh, floral green odor. 2-Hexenal is one of the major volatile compounds in ripe tomatoes. It also contributes to the aroma of cherries. 2-Hexenal has been detected, but not quantified in, several different fruits, vegetables, spices and nuts, such as soybeans, cucumbers, blackcurrants, ginkgo nuts, green tea and common walnuts. 2-Hexenal is used as a food additive and in perfuming agents. Specifically, it is used in perfume compositions as part of fresh-green, natural topnote complexes, particularly in delicately floral or fruity fragrance types, and in general as a fresh top note. 2-Hexenal is a potentially toxic compound as it can be flammable, harmful to skin contact and irritates the eyes. 2-Hexenal is a known uremic toxin (PMID: 22626821). Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. As a uremic toxin, this compound can cause uremic syndrome. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart). Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present in individuals suffering from uremia. Uremia or uremic syndrome can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
CAS NumberNot Available
Structure
Thumb
Synonyms
Predicted 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
Chemical FormulaC6H10O
IUPAC name(2E)-hex-2-enal
InChI IdentifierInChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
InChI KeyMBDOYVRWFFCFHM-SNAWJCMRSA-N
Isomeric SMILES[H]\C(CCC)=C(\[H])C=O
Average Molecular Weight98.145
Monoisotopic Molecular Weight98.073164942
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHex-trans-2-en-1-al, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00or-9000000000-ef8fb4a16f9e47588e24Spectrum
Predicted GC-MSHex-trans-2-en-1-al, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-0002-9000000000-ea4667e9ee10cccddb242020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4j-9000000000-13fcd86dcfc328ec27a62020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-db77fc4d5edd7bdc39072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9000000000-8c4cc267531a0c711b322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-1018f15c3b2d6e22c2262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9232ec723afab464ccc22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-a839e50ee7ad7503877e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4a1d88a16ebce778de702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0540-9000000000-6923af674dd1206069572021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9000000000-3ea4a5ca74032209afaf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0573-9000000000-b0552bcc819f05df9c042021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-649f52184fb4997b20fb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-3e77d5cdc17bcd3c255e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0n2d-9000000000-022c1508f6a2751bcc392021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDHEX-TRANS-2-EN-1-AL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Bilberry0.00600 - 0.00600 mg/100 g0.00600 mg/100 gDUKE
Black tea127.450 - 2595.000 1361.225 DUKE
Common wheatExpected but not quantifiedNot AvailableDUKE
Corn6800.000 - 6800.000 mg/100 g6800.000 mg/100 gDUKE
Ginkgo nutsExpected but not quantifiedNot AvailableDUKE
Green tea127.450 - 2595.000 1361.225 DUKE
Herbal tea127.450 - 2595.000 1361.225 DUKE
Red tea127.450 - 2595.000 1361.225 DUKE
SpearmintExpected but not quantifiedNot AvailableDUKE
SunflowerExpected but not quantifiedNot AvailableDUKE
Showing 1 to 10 of 11 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).