Acetaldehyde (T3D3471)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:58:34 UTC
Update Date2014-12-24 20:26:06 UTC
Accession NumberT3D3471
Identification
Common NameAcetaldehyde
ClassSmall Molecule
DescriptionAcetaldehyde is a colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. In the chemical industry, acetaldehyde is used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals. it is also an air pollutant resulting from combustion, such as automotive exhaust and tobacco smoke. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis. 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. Acetaldehyde is linked to most of the negative clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver, multiple forms of cancer, and alcoholism.
Compound Type
  • Aldehyde
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Acetic aldehyde
Aldehyde
Ethanal
Ethyl aldehyde
Chemical FormulaC2H4O
Average Molecular Mass44.053 g/mol
Monoisotopic Mass44.026 g/mol
CAS Registry Number75-07-0
IUPAC Nameacetaldehyde
Traditional Nameacetaldehyde
SMILESCC=O
InChI IdentifierInChI=1S/C2H4O/c1-2-3/h2H,1H3
InChI KeyInChIKey=IKHGUXGNUITLKF-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue Locations
  • Adrenal Medulla
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Stratum Corneum
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Ethanol DegradationSMP00449 Not Available
Pyruvate MetabolismSMP00060 map00620
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-123°C
Boiling Point21°C (69.8°F)
Solubility1000 mg/mL at 25°C [RIDDICK,JA et al. (1986)]
LogP-0.34
Predicted Properties
PropertyValueSource
Water Solubility225 g/LALOGPS
logP-0.01ALOGPS
logP-0.38ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)16.73ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.72 m³·mol⁻¹ChemAxon
Polarizability4.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-69e31ccd415894a689122016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-f1274d4b6066776ca8982012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001l-9000000000-c1e37abbf2ad6054dc102012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000t-9000000000-2289ead4f7210282cd872012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-cf54221d95714f5478c42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-8d8afe7422ae76f7ebb92015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-d68dec9f846cfe9acc722015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-4430d6a790eca4132aa42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-607a755de038203a6b682015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-63c9f623d8dc4b1e60a22015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc29402021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc29402021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-0d922cdfd7f6947230c02021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-452a5f79625d3401d4952021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-452a5f79625d3401d4952021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2758497e574a090105472021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9000000000-65d53ef91644a0bacd6c2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAcetaldehyde can form adducts with DNA, causing damage such as cross-links. (1)
MetabolismIn the liver, the enzyme acetaldehyde dehydrogenase converts acetaldehyde into the harmless compound acetic acid. (25)
Toxicity ValuesLD50: 661 mg/kg (Oral, Rat) (21) LD50: 212 mg/kg (Intravenous, Mouse) (21) LD50: 3540 mg/kg (Dermal, Rabbit) (21) LD50: 640 mg/kg (Subcutaneous, Rat) (22) LD50: 96 mg/kg (Intratracheal, Hamster) (21) LD50: 500 mg/kg (Intraperitoneal, Mouse) (26) LC50: 1500 ppm over 4 hours (Inhalation, Mouse) (21)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. Acetaldehyde associated with consumption of alcoholic beverages is carcinogenic to humans (Group 1). (24)
Uses/SourcesAcetaldehyde occurs naturally in ripe fruit, coffee, and bread, and is produced by plants as part of their normal metabolism. It is popularly known as a chemical that causes hangovers, as it is produced from the breakdown of ethanol. In the chemical industry, acetaldehyde is used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals. it is also an air pollutant resulting from combustion, such as automotive exhaust and tobacco smoke. (25)
Minimum Risk LevelNot Available
Health EffectsAcetaldehyde is a probable carcinogen. (25)
SymptomsSkin contact with acetaldehyde causes irritation. (25)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00990
PubChem Compound ID177
ChEMBL IDCHEMBL170365
ChemSpider ID172
KEGG IDC00084
UniProt IDNot Available
OMIM ID100650
ChEBI ID15343
BioCyc IDACETALD
CTD IDNot Available
Stitch IDAcetaldehyde
PDB IDACE
ACToR ID3
Wikipedia LinkAcetaldehyde
References
Synthesis ReferenceWertheim, E. Laboratory preparation of acetaldehyde. Journal of the American Chemical Society (1922), 44 2658-9.
MSDSLink
General References
  1. Brooks PJ, Theruvathu JA: DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005 Apr;35(3):187-93. [16054980 ]
  2. 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. [14574447 ]
  3. 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. [12769188 ]
  4. 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. [15542751 ]
  5. 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. [15777233 ]
  6. 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. [12492137 ]
  7. Boyden TW, Silvert MA, Pamenter RW: Acetaldehyde acutely impairs canine testicular testosterone secretion. Eur J Pharmacol. 1981 Apr 9;70(4):571-6. [7195339 ]
  8. 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. [15972793 ]
  9. Burton A: Acetaldehyde links alcohol consumption to cancer. Lancet Oncol. 2005 Sep;6(9):643. [16161263 ]
  10. 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. [12566241 ]
  11. 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. [14533100 ]
  12. Deitrich RA: Acetaldehyde: deja vu du jour. J Stud Alcohol. 2004 Sep;65(5):557-72. [15536764 ]
  13. 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. [16630710 ]
  14. 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. [12063798 ]
  15. 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. [11912075 ]
  16. 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. [11692094 ]
  17. 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. [15834228 ]
  18. 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. [11707631 ]
  19. 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. [16385226 ]
  20. 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. [11707639 ]
  21. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  22. ITII (1988). Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute.
  23. WHO (1995). Environmental Health Criteria 167: Acetaldehyde.
  24. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  25. Wikipedia. Acetaldehyde. Last Updated 17 July 2009. [Link]
  26. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

Target Details
1. Aldehyde dehydrogenase family 3 member B1
General Function:
Aldehyde dehydrogenase [nad(p)+] activity
Specific Function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular Weight:
51839.245 Da
References
  1. Marchitti SA, Brocker C, Orlicky DJ, Vasiliou V: Molecular characterization, expression analysis, and role of ALDH3B1 in the cellular protection against oxidative stress. Free Radic Biol Med. 2010 Nov 15;49(9):1432-43. doi: 10.1016/j.freeradbiomed.2010.08.004. Epub 2010 Aug 10. [20699116 ]