Record Information
Version2.0
Creation Date2012-05-31 13:03:00 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00990
Identification
Name:Acetaldehyde
Description:Acetaldehyde is a colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. Small amounts of acetaldehyde are produced naturally through gut microbial fermentation. Acetaldehyde is produced through the action of alcohol dehydrogenase on ethanol and is somewhate more toxic than ethanol.
Structure
Thumb
Synonyms:
  • Acetaldehyde
  • Acetic aldehyde
  • Aldehyde
  • Ethanal
  • Ethyl aldehyde
Chemical Formula:C2H4O
Weight:Average: 44.0526
Monoisotopic: 44.02621475
InChI Key:IKHGUXGNUITLKF-UHFFFAOYSA-N
InChI:InChI=1S/C2H4O/c1-2-3/h2H,1H3
CAS number:75-07-0
IUPAC Name:acetaldehyde
Traditional IUPAC Name:acetaldehyde
SMILES:CC=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentShort-chain aldehydes
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:-123 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [RIDDICK,JA et al. (1986)]PhysProp
LogP:-0.34 [TSCATS]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility225.0 mg/mLALOGPS
logP-0.01ALOGPS
logP-0.38ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)14.5ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.72 m3·mol-1ChemAxon
Polarizability4.48 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 Pw001890Pw001890 greyscalePw001890 simple
2-Oxopent-4-enoate metabolism 2PW002035 Pw002035Pw002035 greyscalePw002035 simple
Collection of Reactions without pathwaysPW001891 Pw001891Pw001891 greyscalePw001891 simple
Phenylalanine metabolismPW000921 Pw000921Pw000921 greyscalePw000921 simple
ethanolaminePW002094 Pw002094Pw002094 greyscalePw002094 simple
preQ0 metabolismPW001893 Pw001893Pw001893 greyscalePw001893 simple
purine deoxyribonucleosides degradationPW002077 Pw002077Pw002077 greyscalePw002077 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-9000000000-69e31ccd415894a68912View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-f1274d4b6066776ca898View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001l-9000000000-c1e37abbf2ad6054dc10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000t-9000000000-2289ead4f7210282cd87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-cf54221d95714f5478c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-8d8afe7422ae76f7ebb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-d68dec9f846cfe9acc72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-4430d6a790eca4132aa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-607a755de038203a6b68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-63c9f623d8dc4b1e60a2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-002f-9000000000-65d53ef91644a0bacd6cView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
References
References:
  • Boyden TW, Silvert MA, Pamenter RW: Acetaldehyde acutely impairs canine testicular testosterone secretion. Eur J Pharmacol. 1981 Apr 9;70(4):571-6. Pubmed: 7195339
  • Brooks PJ, Theruvathu JA: DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005 Apr;35(3):187-93. Pubmed: 16054980
  • Burton A: Acetaldehyde links alcohol consumption to cancer. Lancet Oncol. 2005 Sep;6(9):643. Pubmed: 16161263
  • Deitrich RA: Acetaldehyde: deja vu du jour. J Stud Alcohol. 2004 Sep;65(5):557-72. Pubmed: 15536764
  • Forn-Frias C, Sanchis-Segura C: [The possible role of acetaldehyde in the brain damage caused by the chronic consumption of alcohol] Rev Neurol. 2003 Sep 1-15;37(5):485-93. Pubmed: 14533100
  • Hard ML, Iqbal U, Brien JF, Koren G: Binding of acetaldehyde to human and Guinea pig placentae in vitro. Placenta. 2003 Feb-Mar;24(2-3):149-54. Pubmed: 12566241
  • Higuchi S, Matsushita S, Masaki T, Yokoyama A, Kimura M, Suzuki G, Mochizuki H: Influence of genetic variations of ethanol-metabolizing enzymes on phenotypes of alcohol-related disorders. Ann N Y Acad Sci. 2004 Oct;1025:472-80. Pubmed: 15542751
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Latvala J, Melkko J, Parkkila S, Jarvi K, Makkonen K, Niemela O: Assays for acetaldehyde-derived adducts in blood proteins based on antibodies against acetaldehyde/lipoprotein condensates. Alcohol Clin Exp Res. 2001 Nov;25(11):1648-53. Pubmed: 11707639
  • Mascia MP, Maiya R, Borghese CM, Lobo IA, Hara K, Yamakura T, Gong DH, Beckstead MJ: Does acetaldehyde mediate ethanol action in the central nervous system? Alcohol Clin Exp Res. 2001 Nov;25(11):1570-5. Pubmed: 11707631
  • Matsuse H, Shimoda T, Fukushima C, Mitsuta K, Kawano T, Tomari S, Saeki S, Kondoh Y, Machida I, Obase Y, Asai S, Kohno S: Screening for acetaldehyde dehydrogenase 2 genotype in alcohol-induced asthma by using the ethanol patch test. J Allergy Clin Immunol. 2001 Nov;108(5):715-9. Pubmed: 11692094
  • Morozov IuE, Salomatin EM, Okhotin VE: [Brain acetaldehyde and ethanol: method of determination and diagnostic significance in ethanol poisoning] Sud Med Ekspert. 2002 Mar-Apr;45(2):35-40. Pubmed: 12063798
  • Nakamura K, Iwahashi K, Furukawa A, Ameno K, Kinoshita H, Ijiri I, Sekine Y, Suzuki K, Iwata Y, Minabe Y, Mori N: Acetaldehyde adducts in the brain of alcoholics. Arch Toxicol. 2003 Oct;77(10):591-3. Epub 2003 Sep 17. Pubmed: 14574447
  • Nishimura FT, Fukunaga T, Kajiura H, Umeno K, Takakura H, Ono T, Nishijo H: Effects of aldehyde dehydrogenase-2 genotype on cardiovascular and endocrine responses to alcohol in young Japanese subjects. Auton Neurosci. 2002 Nov 29;102(1-2):60-70. Pubmed: 12492137
  • Oba T, Maeno Y, Ishida K: Differential contribution of clinical amounts of acetaldehyde to skeletal and cardiac muscle dysfunction in alcoholic myopathy. Curr Pharm Des. 2005;11(6):791-80. Pubmed: 15777233
  • Takeuchi M, Saito T: Cytotoxicity of acetaldehyde-derived advanced glycation end-products (AA-AGE) in alcoholic-induced neuronal degeneration. Alcohol Clin Exp Res. 2005 Dec;29(12 Suppl):220S-4S. Pubmed: 16385226
  • Takeuchi M, Watai T, Sasaki N, Choei H, Iwaki M, Ashizawa T, Inagaki Y, Yamagishi S, Kikuchi S, Riederer P, Saito T, Bucala R, Kameda Y: Neurotoxicity of acetaldehyde-derived advanced glycation end products for cultured cortical neurons. J Neuropathol Exp Neurol. 2003 May;62(5):486-96. Pubmed: 12769188
  • Theruvathu JA, Jaruga P, Nath RG, Dizdaroglu M, Brooks PJ: Polyamines stimulate the formation of mutagenic 1,N2-propanodeoxyguanosine adducts from acetaldehyde. Nucleic Acids Res. 2005 Jun 21;33(11):3513-20. Print 2005. Pubmed: 15972793
  • Tyulina OV, Prokopieva VD, Boldyrev AA, Johnson P: Erythrocyte and plasma protein modification in alcoholism: a possible role of acetaldehyde. Biochim Biophys Acta. 2006 May;1762(5):558-63. Epub 2006 Apr 3. Pubmed: 16630710
  • Tyulina OV, Prokopieva VD, Dodd RD, Hawkins JR, Clay SW, Wilson DO, Boldyrev AA, Johnson P: In vitro effects of ethanol, acetaldehyde and fatty acid ethyl esters on human erythrocytes. Alcohol Alcohol. 2002 Mar-Apr;37(2):179-86. Pubmed: 11912075
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yokoyama T, Saito K, Lwin H, Yoshiike N, Yamamoto A, Matsushita Y, Date C, Tanaka H: Epidemiological evidence that acetaldehyde plays a significant role in the development of decreased serum folate concentration and elevated mean corpuscular volume in alcohol drinkers. Alcohol Clin Exp Res. 2005 Apr;29(4):622-30. Pubmed: 15834228
Synthesis Reference:Wertheim, E. Laboratory preparation of acetaldehyde. Journal of the American Chemical Society (1922), 44 2658-9.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15343
HMDB IDHMDB00990
Pubchem Compound ID177
Kegg IDC00084
ChemSpider ID172
WikipediaAcetaldehyde
BioCyc IDACETALD
EcoCyc IDACETALD
Ligand ExpoMCB

Enzymes

General function:
Involved in catalytic activity
Specific function:
2-deoxy-D-ribose 5-phosphate = D- glyceraldehyde 3-phosphate + acetaldehyde
Gene Name:
deoC
Uniprot ID:
P0A6L0
Molecular weight:
27733
Reactions
2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
glyA
Uniprot ID:
P0A825
Molecular weight:
45316
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine.
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme has three activities:ADH, ACDH, and PFL- deactivase. In aerobic conditions it acts as a hydrogen peroxide scavenger. The PFL deactivase activity catalyzes the quenching of the pyruvate-formate-lyase catalyst in an iron, NAD, and CoA dependent reaction
Gene Name:
adhE
Uniprot ID:
P0A9Q7
Molecular weight:
96126
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.
General function:
Involved in catalytic activity
Specific function:
Ethanolamine = acetaldehyde + NH(3)
Gene Name:
eutB
Uniprot ID:
P0AEJ6
Molecular weight:
49403
Reactions
Ethanolamine = acetaldehyde + NH(3).
General function:
Involved in ethanolamine ammonia-lyase activity
Specific function:
Ethanolamine = acetaldehyde + NH(3)
Gene Name:
eutC
Uniprot ID:
P19636
Molecular weight:
31781
Reactions
Ethanolamine = acetaldehyde + NH(3).
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the breakdown of putrescine. Was previously shown to have a weak but measurable ALDH enzyme activity that prefers NADP over NAD as coenzyme
Gene Name:
puuC
Uniprot ID:
P23883
Molecular weight:
53418
Reactions
Gamma-glutamyl-gamma-aminobutyraldehyde + NAD(+) + H(2)O = gamma-glutamyl-gamma-aminobutyrate + NADH.
An aldehyde + NAD(P)(+) + H(2)O = a carboxylate + NAD(P)H.
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
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 zinc ion binding
Specific function:
Preferred specificity is towards 1-propanol
Gene Name:
adhP
Uniprot ID:
P39451
Molecular weight:
35379
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
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.
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
Gene Name:
queD
Uniprot ID:
P65870
Molecular weight:
13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.
General function:
Involved in lyase activity
Specific function:
Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
Gene Name:
ltaE
Uniprot ID:
P75823
Molecular weight:
36494
Reactions
L-threonine = glycine + acetaldehyde.
L-allo-threonine = glycine + acetaldehyde.
General function:
Involved in acetaldehyde dehydrogenase (acetylating) activity
Specific function:
Catalyzes the conversion of acetaldehyde to acetyl-CoA, using NAD(+) and coenzyme A. Is the final enzyme in the meta- cleavage pathway for the degradation of 3-phenylpropanoate. Functions as a chaperone protein for folding of mhpE
Gene Name:
mhpF
Uniprot ID:
P77580
Molecular weight:
33442
Reactions
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Not Available
Specific function:
Not Available
Gene Name:
eutE
Uniprot ID:
P77445
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
yiaY
Uniprot ID:
P37686
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
eutA
Uniprot ID:
P76551
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
eutG
Uniprot ID:
P76553
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents). Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents).
Gene Name:
alkB
Uniprot ID:
P05050
Molecular weight:
Not Available
Reactions
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).

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