Showing Compound Card for Butanal (CDB004962)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 18:54:58 UTC
Updated at2020-11-18 16:39:07 UTC
CannabisDB IDCDB004962
Secondary Accession NumbersNot Available
Cannabis Compound 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. Butanal is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight72.11
Monoisotopic Molecular Weight72.0575
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 Point74.8 °CWikipedia
Water Solubility71 mg/mL at 25 °CNot Available
logP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-9000000000-6e0649a0dc70c28fcae92015-03-01View Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-002f-9000000000-98b59bf5bd3eda9e49faSpectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-68ac34ab9def2e36ccc6Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-2900000000-6dd687b5afd856171273Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-d64b8c5293749714544aSpectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-2900000000-33689f43c983a22378e7Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-002f-9000000000-98b59bf5bd3eda9e49faSpectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-68ac34ab9def2e36ccc6Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-2900000000-6dd687b5afd856171273Spectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-d64b8c5293749714544aSpectrum
GC-MSButanal, non-derivatized, GC-MS Spectrumsplash10-0002-2900000000-33689f43c983a22378e7Spectrum
Predicted GC-MSButanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9000000000-4fb49b6897fd6c8e92b4Spectrum
Predicted GC-MSButanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ab9-9000000000-e43f72b51db74df7e6492012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-038773fb1932929717e02012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-f3c990a0bfba019420a92012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-002f-9000000000-c275231e3f5b37fbd5892012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-68ac34ab9def2e36ccc62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f9de404f1affa6abfa9a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-05fr-9000000000-cfe5c3be3e144243331c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0005-9000000000-1edcf9e61e3340fbf40d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052e-9000000000-bccfaaf4b9811638acfe2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-05fr-9000000000-c4d921bc1daac38823102021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-2c1d033322fd9522a7282015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-ca73d37ef37b38522b6e2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-90b6f84d1349c54881ce2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-819efd4b2a60ead6a85c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-59b84d540828a6511e532015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f665ffadd808f7e9b0ca2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-a41fb6d601c30ec7f8912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-cb39b818de83422d81fb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9000000000-6df66caca042bdf0c4092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-77e5dcf17bd83eca2c672021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-0a10c7980c8eb7716de62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-50a44f96027b04e2ca632021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Retinol dehydrogenase 13RDH1319q13.42Q8NBN7 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003543
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003378
KNApSAcK IDC00050431
Chemspider ID256
KEGG Compound IDC01412
BioCyc IDBUTANAL
BiGG IDNot Available
Wikipedia LinkButanal
METLIN ID6947
PubChem Compound261
PDB IDNot Available
ChEBI ID15743
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Retinol dehydrogenase 13
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