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Hexanal (FDB008068)

Record Information
Version1.0
Creation date2010-04-08 22:07:54 UTC
Update date2020-09-17 15:30:02 UTC
Primary IDFDB008068
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 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 ( https://doi.org/10.1016/B978-0-12-809807-3.00009-3). 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 (https://doi.org/10.1016/j.foodchem.2007.08.042).
CAS Number66-25-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.49 g/LALOGPS
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
Chemical FormulaC6H12O
IUPAC namehexanal
InChI IdentifierInChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
InChI KeyJARKCYVAAOWBJS-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
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
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 71.95%; H 12.08%; O 15.97%DFC
Melting Point-56 oC
Boiling PointBp12 28°DFC
Experimental Water Solubility5.64 mg/mL at 30 oCDAVIS,PL (1968)
Experimental logP1.78HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4039DFC
Spectra
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
ChemSpider ID5949
ChEMBL IDCHEMBL280331
KEGG Compound IDC02373
Pubchem Compound ID6184
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05994
CRC / DFC (Dictionary of Food Compounds) IDDBQ01-O:DBQ01-O
EAFUS ID1619
Dr. Duke IDN-HEXANAL|HEXANAL|HEXAN-1-AL|CAPROALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00000357
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID66-25-1
GoodScent IDrw1011071
SuperScent IDNot Available
Wikipedia IDHexanal
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
grass
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tallow
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
aldehydic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leafy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweaty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.