Showing Compound Card for Hexanal (CDB000057)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:11 UTC
Updated at2020-12-07 19:07:01 UTC
CannabisDB IDCDB000057
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHexanal
DescriptionHexanal, 1-hexanal, n-hexanal, is also known as caproaldehyde or hexanaldehyde. It belongs to the class of organic compounds known as medium-chain aldehydes which have a chain length between 6 and 12 carbon atoms and therefore is considered a fatty aldehyde lipid molecule. Hexanal is a very hydrophobic molecule that is relatively neutral. It is a colorless clear liquid. It has a fresh green, fatty or grassy scent with a green, fatty, leafy or aldehydic taste. Hexanal exists in all eukaryotes, from yeast to humans. Hexanal is found in cannabis plants (PMID: 6991645 ). Different foods contain hexanal with the highest concentrations found in black walnuts, corns, and tea and with lower concentrations in common grapes, thornless blackberries, and tortilla. Hexanal has also been detected in palms, mentha (mint), wax gourds, grapes, and kiwis making hexanal a potential biomarker for the consumption of these foods. Hexanal has been used to increase post-harvest longevity and color of certain fruits ( Ref:DOI ). Hexanal was also detected in humans breastmilk samples. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal, together with higher levels of 2-hydroxyhexanal and 4-hydroxynonena, are associated with poorer patient prognosis (PMID: 17487452 ). Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group because its concentrations in uremic patients were found to exceed the normal general population concentrations (PMID: 22626821 ). Hexanal is a volatile compound that has been associated with the development of undesirable flavours and has been proposed as a potential marker of milk quality. Hexanal, a major breakdown product of linoleic acid (LA, n – 6, an polyunsaturated fatty acid, PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products such as baby formulae and was correlated with the hexanal concentration ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-HexanalChEBI
Aldehyde C-6ChEBI
C6 AldehydeChEBI
CaproaldehydeChEBI
Caproic aldehydeChEBI
HexaldehydeChEBI
Hexan-1-alChEBI
HexanaldehydeChEBI
Hexoic aldehydeChEBI
HexylaldehydeChEBI
N-C5H11CHOChEBI
N-CaproaldehydeChEBI
N-Caproic aldehydeChEBI
N-HexanalChEBI
N-HexylaldehydeChEBI
CapronaldehydeHMDB
HexanalMeSH
n-CapronaldehydeHMDB
Chemical FormulaC6H12O
Average Molecular Weight100.16
Monoisotopic Molecular Weight100.0888
IUPAC Namehexanal
Traditional Namehexanal
CAS Registry Number66-25-1
SMILES
CCCCCC=O
InChI Identifier
InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
InChI KeyJARKCYVAAOWBJS-UHFFFAOYSA-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
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-56 °CNot Available
Boiling Point130 - 131 °CWikipedia
Water Solubility5.64 mg/mL at 30 °CNot Available
logP1.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.37ALOGPS
logP1.65ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.15 m³·mol⁻¹ChemAxon
Polarizability12.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-72ae5d9e7cc61abeff7f2014-09-20View Spectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-65f52440a5d20229be6cSpectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-89f4d5edf8639a778ef4Spectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-98fd24ab2b6d3d9cf3cfSpectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-65f52440a5d20229be6cSpectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-89f4d5edf8639a778ef4Spectrum
GC-MSHexanal, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-98fd24ab2b6d3d9cf3cfSpectrum
Predicted GC-MSHexanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-9000000000-f6f6f2d2922256923f62Spectrum
Predicted GC-MSHexanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0089-9200000000-a864c6ae8f499374570f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00lr-9000000000-c35aa664e0abaa7ff7542012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-00lr-9100000000-32a2d24a74c86ead890b2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-65f52440a5d20229be6c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-13ae9f72ffb8573eac282012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-e06f68e7ce93f5ced9382012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4900000000-3680e8fedab54e7572cb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9400000000-d3150dfd70fdee4bfc782015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c161db43b692fc5585332015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-16f962506c93163431662015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-1fd34894f517ecf1f19a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-054aa18a9a05fa35cf012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-658fe53778817eb823012021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-b0e3f2f55178b8aacda12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c5c7ace495de00bff0082021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a5c-9000000000-d214e2877cddafdcb7572021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-f2f5a7e46a17ef9b2c6b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-7d79b3949754c58026242021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cholesterol side-chain cleavage enzyme, mitochondrialCYP11A115q23-q24P05108 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005994
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008068
KNApSAcK IDC00000357
Chemspider ID5949
KEGG Compound IDC02373
BioCyc IDHEXANAL
BiGG IDNot Available
Wikipedia LinkHexanal
METLIN IDNot Available
PubChem Compound6184
PDB IDNot Available
ChEBI ID88528
References
General References
  1. 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 ]
  2. 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 ]
  3. Zajdel A, Wilczok A, Slowinski J, Orchel J, Mazurek U: Aldehydic lipid peroxidation products in human brain astrocytomas. J Neurooncol. 2007 Sep;84(2):167-73. doi: 10.1007/s11060-007-9367-6. Epub 2007 May 9. [PubMed:17487452 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0