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Record Information
Version1.0
Created at2007-04-12 19:50:25 UTC
Updated at2021-10-07 20:41:11 UTC
NP-MRD IDNP0001243
Secondary Accession NumbersNone
Natural Product 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 has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). 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
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
N-CapronaldehydeHMDB
HexanalMeSH
Chemical FormulaC6H12O
Average Mass100.1589 Da
Monoisotopic Mass100.08882 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)V.dorna832021-08-10View Spectrum
Species
Species of Origin
Species NameSourceReference
Anacardium occidentaleFooDB
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Alexander J. MacLeod, Glesni MacLeod, G. Subramanian. Volatile aroma constituents of celery. Phyt...
Apium graveolens var. rapaceumFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Avena sativa L.FooDB
Brassica hirtaKNApSAcK Database
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
    • Charles F. Forney and Michael A. Jordan. Induction of Volatile Compounds in Broccoli by Postharve...
Calamintha nepeta subsp. glandulosaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Capillipedium parviflorumKNApSAcK Database
Capsicum annuumFooDB
    • Edible Medicinal And Non-Medicinal Plants: Volume 6, Fruits. By T. K. Lim
Capsicum annuum var. annuumFooDB
Carica papayaKNApSAcK Database
Carica papaya L.FooDB
Carthamus tinctoriusFooDB
Cistus creticusKNApSAcK Database
Citrullus lanatusFooDB
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiifoliaFooDB
Citrus aurantiumKNApSAcK Database
Citrus grandisKNApSAcK Database
Citrus hystrixKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus maximaFooDB
Citrus paradisiKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cucumis sativus L.FooDB
    • Ancheng Zhou and Roger F. McFeeters. Volatile Compounds in Cucumbers Fermented in Low-Salt Condit...
Daucus carota ssp. sativusFooDB
Dianthus caryophyllus L.KNApSAcK Database
Dittrichia graveolensKNApSAcK Database
Eruca vesicaria subsp. SativaFooDB
Fagopyrum esculentumFooDB
Foeniculum vulgareKNApSAcK Database
Glycine maxFooDB
Helianthus annuus L.FooDB
Hibiscus sabbariffaFooDB
Houttuynia cordataKNApSAcK Database
Juglans nigra L.FooDB
Laminaria japonicaKNApSAcK Database
Laurus nobilis L.FooDB
Malus pumilaFooDB
Mandragora autumnalisKNApSAcK Database
Mangifera indicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Mentha aquaticaFooDB
Mentha spicataFooDB
Musa acuminataFooDB
Ocimum basilicumFooDB
Olea europaeaKNApSAcK Database
Origanum onitesFooDB
Origanum vulgareFooDB
Oryza sativaFooDB
Petroselinum crispumFooDB
Polygonum minusKNApSAcK Database
Prunus armeniaca L. (K604-19,K113-40,K33-81)KNApSAcK Database
Prunus aviumKNApSAcK Database
Prunus salcina Lindl. (Blackamber,Friar)KNApSAcK Database
Psidium guajavaKNApSAcK Database
Pyrus communisFooDB
    • Christian Chervin, Jim Speirs, Brian Loveys, Brian D Patterson. Influence of low oxygen storage o...
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Rhodiola rosea L.KNApSAcK Database
Rosmarinus officinalisKNApSAcK Database
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sesamum indicumFooDB
Sinapis albaFooDB
Solanum lycopersicum Mill.KNApSAcK Database
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumFooDB
Syzygium aromaticumFooDB
Tanacetum macrophyllumKNApSAcK Database
Thea sinensisKNApSAcK Database
Triticum aestivumFooDB
Vaccinium corymbosumFooDB
Vigna radiataFooDB
Vitis vinifera L.FooDB
    • D. D. Archbold, T. R. Hamilton-Kemp, M. M. Barth, and B. E. Langlois. Identifying Natural Volatil...
Xylopia parvifloraKNApSAcK Database
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Zingiber officinaleFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Blood)KNApSAcK Database
Homo sapiens (Exhaled breath)KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-56 °CNot Available
Boiling Point130.00 to 131.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5.64 mg/mL at 30 °CNot Available
LogP1.78Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility4.49 g/LALOGPS
logP10(2.37) g/LALOGPS
logP10(1.65) g/LChemAxon
logS10(-1.4) g/LALOGPS
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
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
Good Scents IDrw1011071
References
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 ]
  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 ]
  3. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. doi: 10.1017/s0022029902005782. [PubMed:12463694 ]
  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 ]
  5. De Preter V, Van Staeyen G, Esser D, Rutgeerts P, Verbeke K: Development of a screening method to determine the pattern of fermentation metabolites in faecal samples using on-line purge-and-trap gas chromatographic-mass spectrometric analysis. J Chromatogr A. 2009 Feb 27;1216(9):1476-83. doi: 10.1016/j.chroma.2008.12.095. Epub 2009 Jan 8. [PubMed:19167006 ]