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Propanal (M2MDB001684)

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
DescriptionPropanal 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
MOLSDFPDBSMILESInChI
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
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
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 g/LALOGPS
logP0.31ALOGPS
logP0.32ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)17.32ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.35 m³·mol⁻¹ChemAxon
Polarizability6.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + NADP + Propanal >2 Hydrogen ion + NADPH + Propionic acid
Propanal + Pyruvic acid <> 4-Hydroxy-2-oxohexanoic acid
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-057i-9000000000-8f67579ff6f9ff36070fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-057i-9000000000-8f67579ff6f9ff36070fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-dd28a1a5691e42b98944View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-6e3379842f4da69e8e2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-6e3379842f4da69e8e2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-214db2e33bae0f659690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-cd36cdb80b20021fec3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-ea4dc2c9ba22fa57f265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-84b5273da6b73dbe78deView in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-666a0ffacd21addbc612View 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
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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

Protein Details
1. Aldehyde dehydrogenase B
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
Protein Details
2. 4-hydroxy-2-oxovalerate aldolase
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

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
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
Protein Details
3. Outer membrane protein F
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
Protein Details
4. Outer membrane protein C
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