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Acetaldehyde (FDB008297)

Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2020-09-17 15:29:56 UTC
Primary IDFDB008297
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetaldehyde
DescriptionAcetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are aldehydes with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol; which is mediated by the enzyme alcohol dehydrogenase 1B. In addition, acetaldehyde can be converted into acetic acid; which is mediated by mitochondrial aldehyde dehydrogenases. Industrially, the main method of production of acetaldehyde is via the oxidation of ethylene via the Wacker process. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process for producing acetaldehyde exceeded 2 million tonnes annually. Acetaldehyde is found in a number of different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine), Acetaldehyde has also been detected, but not quantified in, several different foods, such as malabar plums, malus (crabapple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. As a food constituent, acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and Crohn's disease. Acetaldehyde has also been linked to several inborn metabolic disorders including aldehyde dehydrogenase deficiency (III). The level at which an average consumer can detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Plastics Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. Acetaldehyde is known to be the most abundant carcinogen in tobacco smoke; it is easily dissolved in saliva while smoking (PMID:17382522, PMID:21556207).
CAS Number75-07-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H4O
IUPAC nameacetaldehyde
InChI IdentifierInChI=1S/C2H4O/c1-2-3/h2H,1H3
InChI KeyIKHGUXGNUITLKF-UHFFFAOYSA-N
Isomeric SMILESCC=O
Average Molecular Weight44.0526
Monoisotopic Molecular Weight44.02621475
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Naturally occurring process:

Role

Indirect biological role:

Industrial application:

Environmental role:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 54.53%; H 9.15%; O 36.32%DFC
Melting PointMp -121°DFC
Boiling PointBp 21°DFC
Experimental Water Solubility1000 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP-0.34TSCATS
Experimental pKapKa1 13.57 (25°,hydrate)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.78DFC
Refractive Indexn20D 1.3316DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-9000000000-65d53ef91644a0bacd6c2014-09-20View Spectrum
Predicted GC-MSAcetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-69e31ccd415894a68912Spectrum
Predicted GC-MSAcetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-f1274d4b6066776ca8982012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001l-9000000000-c1e37abbf2ad6054dc102012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000t-9000000000-2289ead4f7210282cd872012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-cf54221d95714f5478c42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-8d8afe7422ae76f7ebb92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-d68dec9f846cfe9acc722015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-4430d6a790eca4132aa42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-607a755de038203a6b682015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-63c9f623d8dc4b1e60a22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc29402021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc29402021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-0d922cdfd7f6947230c02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-452a5f79625d3401d4952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-452a5f79625d3401d4952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2758497e574a090105472021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID172
ChEMBL IDCHEMBL170365
KEGG Compound IDC00084
Pubchem Compound ID177
Pubchem Substance IDNot Available
ChEBI ID15343
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00990
CRC / DFC (Dictionary of Food Compounds) IDDFR74-T:DFR74-T
EAFUS ID5
Dr. Duke IDACETALDEHYDE
BIGG ID33792
KNApSAcK IDC00007392
HET IDACE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID75-07-0
GoodScent IDrw1019471
SuperScent ID177
Wikipedia IDAcetaldehyde
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
addictiveDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
respiraparalyticDUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.CHEBI
Enzymes
NameGene NameUniProt ID
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
Ethanolamine-phosphate phospho-lyaseAGXT2L1Q8TBG4
Putative deoxyribose-phosphate aldolaseDERAQ9Y315
Pathways
NameSMPDB LinkKEGG Link
Ethanol DegradationSMP00449 Not Available
Pyruvate MetabolismSMP00060 map00620
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ether
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
whiskey
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
aldehydic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.