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Record Information
Version3.6
Creation Date2007-04-12 19:50:25 UTC
Update Date2016-05-13 21:51:34 UTC
HMDB IDHMDB05994
Secondary Accession NumbersNone
Metabolite Identification
Common NameHexanal
DescriptionHexanal is an alkyl aldehyde found in human biofluids. Human milk samples collected from women contains hexanal. 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 are associated with poorer patient prognosis. Hexanal is a volatile compound that has been associated with the development of undesirable flavours. The content of hexanal, which is a major breakdown product of linoleic acid (LA, n - 6 PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products. This effect is highly correlated with the headspace concentration of hexanal. (Food Chemistry. Volume 107, Issue 1, 1 March 2008, Pages 558-569, PMID: 17934948 , 17487452 ).
Structure
Thumb
Synonyms
ValueSource
HexaldehydeMetaCyc
CaproaldehydeHMDB
Caproic aldehydeHMDB
CapronaldehydeHMDB
HexanaldehydeHMDB
HexylaldehydeHMDB
N-CaproaldehydeHMDB
N-HexanalHMDB
N-HexylaldehydeHMDB
Chemical FormulaC6H12O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
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 KeyInChIKey=JARKCYVAAOWBJS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassAldehydes
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-56 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.64 mg/mL at 30 °CNot Available
LogP1.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility4.49 mg/mLALOGPS
logP2.37ALOGPS
logP1.65ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.15 m3·mol-1ChemAxon
Polarizability12.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0089-9200000000-a864c6ae8f499374570fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00lr-9000000000-c35aa664e0abaa7ff754View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-00lr-9100000000-32a2d24a74c86ead890bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-65f52440a5d20229be6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-13ae9f72ffb8573eac28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-e06f68e7ce93f5ced938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4900000000-3680e8fedab54e7572cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9400000000-d3150dfd70fdee4bfc78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c161db43b692fc558533View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-16f962506c9316343166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-1fd34894f517ecf1f19aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-054aa18a9a05fa35cf01View in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-72ae5d9e7cc61abeff7fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.22 +/- 0.11 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.1 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.52 +/- 0.33 uMAdult (>18 years old)Bothuremia details
Cerebrospinal Fluid (CSF)Detected and Quantified24.5 uMAdult (>18 years old)BothEncephalopathy details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008068
KNApSAcK IDC00000357
Chemspider ID5949
KEGG Compound IDC02373
BioCyc IDHEXANAL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05994
Metagene LinkHMDB05994
METLIN IDNot Available
PubChem Compound6184
PDB IDNot Available
ChEBI ID121338
References
Synthesis ReferenceHershberg, E. B. Aldehyde synthesis. Helvetica Chimica Acta (1934), 17 351-8. CODEN: HCACAV ISSN:0018-019X. CAN 28:28437 AN 1934:28437
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Aronson DB, Bosch S, Gray DA, Howard PH, Guiney PD: A comparative human health risk assessment of p-dichlorobenzene-based toilet rimblock products versus fragrance/surfactant-based alternatives. J Toxicol Environ Health B Crit Rev. 2007 Oct;10(7):467-526. [17934948 ]
  2. 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. Epub 2007 May 9. [17487452 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87