ACETALDEHYDE

Relevant Data

Food Additives Approved by WHO:

Flavouring Substances Approved by European Union:

  • Acetaldehyde [show]

General Information

MaintermACETALDEHYDE
Doc TypeASP
CAS Reg.No.(or other ID)75-07-0
Regnum 177.2410
182.60

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID177
IUPAC Nameacetaldehyde
InChIInChI=1S/C2H4O/c1-2-3/h2H,1H3
InChI KeyIKHGUXGNUITLKF-UHFFFAOYSA-N
Canonical SMILESCC=O
Molecular FormulaC2H4O
Wikipediaacetaldehyde

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight44.053
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity10.3
CACTVS Substructure Key Fingerprint A A A D c Y B A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A A A C g g A I C A A A A A A A I A A g Q g A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area17.1
Monoisotopic Mass44.026
Exact Mass44.026
XLogP3None
XLogP3-AA-0.3
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count3
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9833
Human Intestinal AbsorptionHIA+0.9942
Caco-2 PermeabilityCaco2+0.7557
P-glycoprotein SubstrateNon-substrate0.8268
P-glycoprotein InhibitorNon-inhibitor0.9712
Non-inhibitor0.9820
Renal Organic Cation TransporterNon-inhibitor0.9246
Distribution
Subcellular localizationMitochondria0.4845
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7858
CYP450 2D6 SubstrateNon-substrate0.9309
CYP450 3A4 SubstrateNon-substrate0.8027
CYP450 1A2 InhibitorNon-inhibitor0.8641
CYP450 2C9 InhibitorNon-inhibitor0.9741
CYP450 2D6 InhibitorNon-inhibitor0.9791
CYP450 2C19 InhibitorNon-inhibitor0.9800
CYP450 3A4 InhibitorNon-inhibitor0.9876
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9511
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9511
Non-inhibitor0.9805
AMES ToxicityNon AMES toxic0.6375
CarcinogensCarcinogens 0.6803
Fish ToxicityLow FHMT0.6158
Tetrahymena Pyriformis ToxicityHigh TPT0.8581
Honey Bee ToxicityHigh HBT0.7938
BiodegradationReady biodegradable0.7562
Acute Oral ToxicityIII0.8284
Carcinogenicity (Three-class)Non-required0.6767

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility0.8143LogS
Caco-2 Permeability1.5492LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8556LD50, mol/kg
Fish Toxicity1.6543pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3413pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure
Mechanism of ToxicityAcetaldehyde can form adducts with DNA, causing damage such as cross-links.
MetabolismIn the liver, the enzyme acetaldehyde dehydrogenase converts acetaldehyde into the harmless compound acetic acid.
Toxicity ValuesLD50: 661 mg/kg (Oral, Rat) LD50: 212 mg/kg (Intravenous, Mouse) LD50: 3540 mg/kg (Dermal, Rabbit) LD50: 640 mg/kg (Subcutaneous, Rat) LD50: 96 mg/kg (Intratracheal, Hamster) LD50: 500 mg/kg (Intraperitoneal, Mouse) LC50: 1500 ppm over 4 hours (Inhalation, Mouse)
Lethal Dose
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. Acetaldehyde associated with consumption of alcoholic beverages is carcinogenic to humans (Group 1).
Minimum Risk Level
Health EffectsAcetaldehyde is a probable carcinogen. (L1307)
Treatment
Reference
  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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesAldehydes
Direct ParentShort-chain aldehydes
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganic oxide - Hydrocarbon derivative - Short-chain aldehyde - Aliphatic acyclic compound
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.

From ClassyFire

Targets

Target Details

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 ]

From T3DB