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Butanal (FDB003378)

Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2020-09-17 15:39:14 UTC
Primary IDFDB003378
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number123-72-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
Chemical FormulaC4H8O
IUPAC namebutanal
InChI IdentifierInChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
InChI KeyZTQSAGDEMFDKMZ-UHFFFAOYSA-N
Isomeric SMILESCCCC=O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 66.63%; H 11.18%; O 22.19%DFC
Melting PointFp -99°DFC
Boiling PointBp 75°DFC
Experimental Water Solubility71 mg/mL at 25 oCUNION CARBIDE (1974)
Experimental logP0.88HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd25 0.8DFC
Refractive Indexn20D 1.3790DFC
Spectra
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
ChemSpider ID256
ChEMBL IDCHEMBL1478334
KEGG Compound IDC01412
Pubchem Compound ID261
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03543
CRC / DFC (Dictionary of Food Compounds) IDCXB54-W:CXB54-W
EAFUS ID436
Dr. Duke IDN-BUTYRALDEHYDE|BUTYRALDEHYDE|BUTANAL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID123-72-8
GoodScent IDrw1007681
SuperScent ID261
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
narcotic35482 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.DUKE
Enzymes
NameGene NameUniProt ID
Retinol dehydrogenase 13RDH13Q8NBN7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vegetable
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
herbaceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
creamy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fatty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
chocolate
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
citrus
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
woody
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
meaty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
wine_like
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
earthy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
apple
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fruity
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
pear
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
nutty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cocoa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
malty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bready
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).