Record Information
Version2.0
Creation Date2012-07-30 14:55:11 -0600
Update Date2015-09-13 15:15:31 -0600
Secondary Accession Numbers
  • ECMDB21277
Identification
Name:Propanal
Description:Propanal or propionaldehyde is the aldehyde of the 3 carbon propyl group. It has a chemical formula of CH3CH2CHO, and is a structural isomer of propanone. At room temperature, it is a colourless liquid with a slightly irritating, fruity odour.; It is principally used as a precursor to trimethylolethane (CH3C(CH2OH)3) through a condensation reaction with formaldehyde; this triol is an important intermediate in the production of alkyd resins. Other applications include reduction to propanol and oxidation to propionic acid.
Structure
Thumb
Synonyms:
  • 1-Propanal
  • 1-Propanone
  • Aldehyde propionique
  • C2H5CHO
  • Methylacetaldehyde
  • N-Propanal
  • N-Propionaldehyde
  • Propaldehyde
  • Propanal
  • Propanalaldehyde
  • Propanaldehyde
  • Propional
  • Propionaldehyde
  • Propionic aldehyde
  • Proprionaldehyde
  • Propyl aldehyde
  • Propylaldehyde
  • Propylic aldehyde
Chemical Formula:C3H6O
Weight:Average: 58.0791
Monoisotopic: 58.041864814
InChI Key:NBBJYMSMWIIQGU-UHFFFAOYSA-N
InChI:InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3
CAS number:123-38-6
IUPAC Name:propanal
Traditional IUPAC Name:propionaldehyde
SMILES:CCC=O
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Liquid
Charge:0
Melting point:-80 °C
Experimental Properties:
PropertyValueSource
Water Solubility:306 mg/mL at 25 deg CPhysProp
LogP:0.59; 0.59 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility146.0 mg/mLALOGPS
logP0.31ALOGPS
logP0.32ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)15.09ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.35 m3·mol-1ChemAxon
Polarizability6.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-056r-9000000000-dd28a1a5691e42b98944View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-057i-9000000000-8f67579ff6f9ff36070fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-addcd7ef3249da0c3006View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-b7cab81070aff00497c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-e9e60e8897ba5a8e14eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-057i-9000000000-52017f5345efcb7c9e18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-971c212b11d2cbddac7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-86839cd4133b824334acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2bde2476aa46442e7250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-4a423491df240f1b6594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-bcb4e63c226b3b43a90dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9000000000-b8b5099c348f5e885f6eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-666a0ffacd21addbc612View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • Nakashima K, Hidaka Y, Yoshida T, Kuroda N, Akiyama S: High-performance liquid chromatographic determination of short-chain aliphatic aldehydes using 4-(N,N-dimethylaminosulphonyl)-7-hydrazino-2,1, 3-benzoxadiazole as a fluorescence reagent. J Chromatogr B Biomed Appl. 1994 Nov 18;661(2):205-10. Pubmed: 7894659
  • Sakura N, Nishimura S, Fujita N, Namera A, Yashiki M, Kojima T: Determination of acrolein in human urine by headspace gas chromatography and mass spectrometry. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):209-12. Pubmed: 9869381
  • Takamoto S, Sakura N, Yashiki M, Kojima T: Determination of acrolein by headspace solid-phase microextraction gas chromatography and mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):123-8. Pubmed: 11482731
Synthesis Reference:Wang, Yan-bin; Yao, Xiao-ming. Development of the process of making propanal from natural gas and light oil. Tianranqi Huagong (2003), 28(1), 8-10,14.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17153
HMDB IDHMDB03366
Pubchem Compound ID527
Kegg IDC00479
ChemSpider ID512
WikipediaPropanal
BioCyc IDCPD-665
EcoCyc IDCPD-665
Ligand ExpoPNL

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADP-dependent oxidation of diverse aldehydes such as chloroacetaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, mafosfamide, 4- hydroperoxycyclophosphamide. Its preferred substrates are acetaldehyde and chloroacetaldehyde
Gene Name:
aldB
Uniprot ID:
P37685
Molecular weight:
56306
General function:
Involved in 4-hydroxy-2-oxovalerate aldolase activity
Specific function:
Catalyzes the retro-aldol cleavage of 4-hydroxy-2- oxopentanoate to pyruvate and acetaldehyde. Is involved in the meta-cleavage pathway for the degradation of 3-phenylpropanoate
Gene Name:
mhpE
Uniprot ID:
P51020
Molecular weight:
36470
Reactions
4-hydroxy-2-oxopentanoate = acetaldehyde + pyruvate.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368