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Human Metabolome Database Version 3.5

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Showing metabocard for Hexanal (HMDB05994)

Record Information
Version 3.5
Creation Date 2007-04-12 13:50:25 -0600
Update Date 2013-05-29 13:42:31 -0600
HMDB ID HMDB05994
Secondary Accession Numbers None
Metabolite Identification
Common Name Hexanal
Description Hexanal 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 Link_out, 17487452 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Caproaldehyde
  2. Caproic aldehyde
  3. Capronaldehyde
  4. Hexaldehyde
  5. Hexanaldehyde
  6. Hexylaldehyde
  7. N-Caproaldehyde
  8. N-Hexanal
  9. N-Hexylaldehyde
Chemical Formula C6H12O
Average Molecular Weight 100.1589
Monoisotopic Molecular Weight 100.088815006
IUPAC Name hexanal
Traditional IUPAC Name hexanal
CAS Registry Number 66-25-1
SMILES CCCCCC=O
InChI Identifier InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
InChI Key JARKCYVAAOWBJS-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Carbonyl Compounds
Sub Class Aldehydes
Other Descriptors
  • Fatty aldehydes(Lipidmaps)
  • Organic Compounds
  • an <i>n</i>-alkanal(Cyc)
Substituents
  • N/A
Direct Parent Medium-chain Aldehydes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -56 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5.64 mg/mL at 30 °C Not Available
LogP 1.78 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 4.49 g/L ALOGPS
LogP 2.37 ALOGPS
LogP 1.65 ChemAxon
LogS -1.35 ALOGPS
pKa (strongest acidic) 15.56 ChemAxon
pKa (strongest basic) -6.9 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 17.07 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 30.15 ChemAxon
Polarizability 12.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum EI-B (HITACHI RMU-6M)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 0.1 uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 24.5 uM Adult (>18 years old) Both Abnormal
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Breast cancer
Associated Disorders and Diseases
Disease References
Abnormal
  • Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. Pubmed: 7320160 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB008068
    KNApSAcK ID C00000357 Link_out
    Chemspider ID 5949 Link_out
    KEGG Compound ID C02373 Link_out
    BioCyc ID 4-METHYLPENTANAL Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB05994 Link_out
    Metagene Link HMDB05994 Link_out
    METLIN ID Not Available
    PubChem Compound 6184 Link_out
    PDB ID Not Available
    ChEBI ID 121338 Link_out
    References
    Synthesis Reference Hershberg, 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. Pubmed: 17934948 Link_out
    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. Pubmed: 17487452 Link_out
    Enzymes
    Name: Cholesterol side-chain cleavage enzyme, mitochondrial
    Reactions: Not Available
    Gene Name: CYP11A1
    Uniprot ID: P05108 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA