Showing Compound Card for 2-Hexenal (CDB000687)

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Record Information
Version1.0
Created at2020-03-19 00:51:14 UTC
Updated at2020-12-07 19:07:40 UTC
CannabisDB IDCDB000687
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Hexenal
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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. Indeed a mix of 2-hexenal and 2-actenal has been used to attract and detect bed bugs (PMID: 28399295 ). 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 has also been reported to be found in Cannabis sativa (PMID: 6991645 , 26657499 ). 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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight98.15
Monoisotopic Molecular Weight98.0732
IUPAC Name(2E)-hex-2-enal
Traditional Name(E)-2-hexenal
CAS Registry Number73543-95-0
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
Role

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Hexenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00or-9000000000-ef8fb4a16f9e47588e24Spectrum
Predicted GC-MS2-Hexenal, 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
NADPH oxidase 4NOX411q14.2-q21Q9NPH5 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
NADPH oxidase 4NOX411q14.2-q21Q9NPH5 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031496
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Anderson JF, Ferrandino FJ, Vasil MP, Bedoukian RH, Maher M, Mckenzie K: Relatively Small Quantities of CO2, Ammonium Bicarbonate, and a Blend of (E)-2-Hexenal Plus (E)-2-Octenal Attract Bed Bugs (Hemiptera: Cimicidae). J Med Entomol. 2017 Mar 1;54(2):362-367. doi: 10.1093/jme/tjw189. [PubMed:28399295 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  4. 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 ]

Enzymes

Enzyme Details
1. NADPH oxidase 4
General function:
Involved in oxidoreductase activity
Specific function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 4 displays an increased activity. Isoform 5 and isoform 6 display reduced activity
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular weight:
66931.0