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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 18:53:42 UTC
HMDB IDHMDB0001140
Secondary Accession Numbers
  • HMDB01140
Metabolite Identification
Common NameOctanal
DescriptionCaprylaldehyde, also known as 1-octylaldehyde or aldehyde c-8, 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. Thus, caprylaldehyde is considered to be a fatty aldehyde lipid molecule. Caprylaldehyde exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Caprylaldehyde has been detected in multiple biofluids, such as feces and saliva. Within the cell, caprylaldehyde is primarily located in the membrane (predicted from logP). Caprylaldehyde exists in all eukaryotes, ranging from yeast to humans. Caprylaldehyde is an aldehydic, citrus, and fat tasting compound that can be found in a number of food items such as loganberry, peanut, elliott's blueberry, and teff. This makes caprylaldehyde a potential biomarker for the consumption of these food products. Caprylaldehyde has been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
Synonyms
ValueSource
1-CaprylaldehydeChEBI
1-OctaldehydeChEBI
1-OctanalChEBI
1-OctylaldehydeChEBI
Aldehyde C-8ChEBI
C-8 AldehydeChEBI
CaprylaldehydChEBI
CaprylaldehydeChEBI
Caprylic aldehydeChEBI
KaprylaldehydChEBI
N-CaprylaldehydeChEBI
N-OctaldehydeChEBI
N-OctanalChEBI
N-Octyl aldehydeChEBI
N-OctylalChEBI
Octan-1-alChEBI
OctanaldehydeChEBI
Octanoic aldehydeChEBI
OctylaldehydChEBI
OctylaldehydeChEBI
OktanalChEBI
OktylaldehydChEBI
Aldehyde C8HMDB
Antifoam-LFHMDB
OctaldehydeHMDB
Chemical FormulaC8H16O
Average Molecular Weight128.212
Monoisotopic Molecular Weight128.120115134
IUPAC Nameoctanal
Traditional Nameoctanal
CAS Registry Number124-13-0
SMILES
CCCCCCCC=O
InChI Identifier
InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3
InChI KeyNUJGJRNETVAIRJ-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 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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-23 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.56 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP3.19ALOGPS
logP2.54ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability16.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-fe177a98511039e9f7a6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-5116ccc02f51ccb0e86aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-b395bc62397f2d3ead7dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000x-9000000000-70ec440a61fb95915131View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-f67b980d2d2a991b2179View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9300000000-2f4aa9d5b7cd47e5d002View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-4970000000-957d3c05049cd98e4df4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-fe177a98511039e9f7a6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-5116ccc02f51ccb0e86aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-b395bc62397f2d3ead7dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000x-9000000000-70ec440a61fb95915131View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-f67b980d2d2a991b2179View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9300000000-2f4aa9d5b7cd47e5d002View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-4970000000-957d3c05049cd98e4df4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9000000000-e3eb771931f18e535c7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-afbedb8b18342773ec25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-5116ccc02f51ccb0e86aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-052f-9000000000-e20fdcbb6710ee07f303View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-000x-9000000000-70ec440a61fb95915131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-e4de633fb7345cb25ac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-9600000000-ffa4810bd6f0997adbe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-0663d075e83465e0b94aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-54dee15774147b509eeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-0c41e22b27b06ecc562dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7cb58e4c39970a374f81View in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-23d54ae7b45c372a7325View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-58522.863 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0-24412.691 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003339
KNApSAcK IDC00030880
Chemspider ID441
KEGG Compound IDC01545
BioCyc IDCPD-371
BiGG IDNot Available
Wikipedia LinkOctanal
METLIN ID6033
PubChem Compound454
PDB IDOYA
ChEBI ID17935
References
Synthesis ReferenceYokoyama, Toshiharu; Matsuyama, Naoko; Maki, Takao. Preparation of aldehydes. Jpn. Kokai Tokkyo Koho (1992), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Orhan H, van Holland B, Krab B, Moeken J, Vermeulen NP, Hollander P, Meerman JH: Evaluation of a multi-parameter biomarker set for oxidative damage in man: increased urinary excretion of lipid, protein and DNA oxidation products after one hour of exercise. Free Radic Res. 2004 Dec;38(12):1269-79. [PubMed:15763951 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
Molecular weight:
54672.24