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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-12 23:25:38 UTC
Update Date2020-04-22 23:29:45 UTC
HMDB IDHMDB0003543
Secondary Accession Numbers
  • HMDB03543
Metabolite Identification
Common NameButanal
DescriptionButanal, also known as butyral or butyl aldehyde, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. It is miscible with most organic solvents. Butanal is an extremely weak basic (essentially neutral) compound (based on its pKa). Butanal exists in all living organisms, ranging from bacteria to humans. Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid. Butanal is an apple, bready, and chocolate tasting compound. Outside of the human body, Butanal is found, on average, in the highest concentration within milk (cow) and carrots. Butanal has also been detected, but not quantified in, several different foods, such as hard wheats, borages, ostrich ferns, skunk currants, and fennels. This could make butanal a potential biomarker for the consumption of these foods. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand Tppts. Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:CH3CHCH2 + H2 + CO → CH3CH2CH2CHOTraditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. This compound is the aldehyde derivative of butane. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. It is a colourless flammable liquid with an unpleasant smell.
Structure
Data?1586372718
Synonyms
ValueSource
1-ButanalChEBI
Aldehyde butyriqueChEBI
Aldeide butirricaChEBI
ButalChEBI
ButaldehydeChEBI
Butan-1-alChEBI
ButanaldehydeChEBI
Butyl aldehydeChEBI
ButylaldehydeChEBI
ButyralChEBI
ButyraldehydChEBI
ButyraldehydeChEBI
Butyric aldehydeChEBI
ButyrylaldehydeChEBI
N-ButanalChEBI
N-Butyl aldehydeChEBI
N-ButyraldehydeChEBI
N-C3H7CHOChEBI
ButalydeHMDB
N-ButylaldehydeHMDB
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Namebutanal
Traditional Namebutoxide
CAS Registry Number123-72-8
SMILES
CCCC=O
InChI Identifier
InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
InChI KeyZTQSAGDEMFDKMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • 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-99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility71 mg/mL at 25 °CNot Available
LogP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility50.9 g/LALOGPS
logP1.1ALOGPS
logP0.76ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)17.97ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.95 m³·mol⁻¹ChemAxon
Polarizability8.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-98b59bf5bd3eda9e49faSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-68ac34ab9def2e36ccc6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2900000000-6dd687b5afd856171273Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1900000000-d64b8c5293749714544aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2900000000-33689f43c983a22378e7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-98b59bf5bd3eda9e49faSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-68ac34ab9def2e36ccc6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2900000000-6dd687b5afd856171273Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1900000000-d64b8c5293749714544aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2900000000-33689f43c983a22378e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-4fb49b6897fd6c8e92b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-e43f72b51db74df7e649Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-038773fb1932929717e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-f3c990a0bfba019420a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-002f-9000000000-c275231e3f5b37fbd589Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-68ac34ab9def2e36ccc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-2c1d033322fd9522a728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-ca73d37ef37b38522b6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-90b6f84d1349c54881ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-819efd4b2a60ead6a85cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-59b84d540828a6511e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f665ffadd808f7e9b0caSpectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9000000000-6e0649a0dc70c28fcae9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Feces
Tissue Locations
  • Blood
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003378
KNApSAcK IDNot Available
Chemspider ID256
KEGG Compound IDC01412
BioCyc IDBUTANAL
BiGG IDNot Available
Wikipedia LinkButanal
METLIN ID6947
PubChem Compound261
PDB IDNot Available
ChEBI ID15743
Food Biomarker OntologyNot Available
VMH IDBTAL
MarkerDB ID
References
Synthesis ReferenceWeizmann, Charles; Garrard, Stanley Frederick. Some condensations of butyl alcohol and butyraldehyde. Journal of the Chemical Society, Transactions (1920), 117 324-38.
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 ]
  2. Holley AE, Walker MK, Cheeseman KH, Slater TF: Measurement of n-alkanals and hydroxyalkenals in biological samples. Free Radic Biol Med. 1993 Sep;15(3):281-9. [PubMed:8406128 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8