Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:01 UTC |
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Update date | 2020-09-17 15:29:56 UTC |
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Primary ID | FDB008297 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Acetaldehyde |
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Description | Acetaldehyde, 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). |
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CAS Number | 75-07-0 |
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Structure | |
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Synonyms | Synonym | Source |
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Acetaldehyd | ChEBI | Acetaldehydes | ChEBI | Acetic aldehyde | ChEBI | Azetaldehyd | ChEBI | Ethanal | ChEBI | Ethyl aldehyde | ChEBI | Aldehyde | HMDB | Acetaldeyde | biospider | Aceteldehyde | biospider | Acetic ethanol | biospider | Acetylaldehyde | biospider | Ethaldehyde | biospider | Ethylaldehyde | biospider | FEMA 2003 | db_source |
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Predicted Properties | |
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Chemical Formula | C2H4O |
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IUPAC name | acetaldehyde |
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InChI Identifier | InChI=1S/C2H4O/c1-2-3/h2H,1H3 |
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InChI Key | IKHGUXGNUITLKF-UHFFFAOYSA-N |
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Isomeric SMILES | CC=O |
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Average Molecular Weight | 44.0526 |
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Monoisotopic Molecular Weight | 44.02621475 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Short-chain aldehydes |
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Alternative Parents | |
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Substituents | - Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Industrial process: Naturally occurring process: |
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Role | Indirect biological role: Industrial application: Environmental role: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 54.53%; H 9.15%; O 36.32% | DFC |
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Melting Point | Mp -121° | DFC |
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Boiling Point | Bp 21° | DFC |
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Experimental Water Solubility | 1000 mg/mL at 25 oC | RIDDICK,JA et al. (1986) |
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Experimental logP | -0.34 | TSCATS |
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Experimental pKa | pKa1 13.57 (25°,hydrate) | DFC |
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Isoelectric point | Not Available | |
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Charge | 0 | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d204 0.78 | DFC |
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Refractive Index | n20D 1.3316 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-002f-9000000000-65d53ef91644a0bacd6c | 2014-09-20 | View Spectrum | Predicted GC-MS | Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-69e31ccd415894a68912 | Spectrum | Predicted GC-MS | Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0002-9000000000-f1274d4b6066776ca898 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001l-9000000000-c1e37abbf2ad6054dc10 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000t-9000000000-2289ead4f7210282cd87 | 2012-07-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-cf54221d95714f5478c4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-8d8afe7422ae76f7ebb9 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004j-9000000000-d68dec9f846cfe9acc72 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-4430d6a790eca4132aa4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-607a755de038203a6b68 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-63c9f623d8dc4b1e60a2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-00ba25458eb6c0cc2940 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-00ba25458eb6c0cc2940 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-9000000000-0d922cdfd7f6947230c0 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-452a5f79625d3401d495 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-452a5f79625d3401d495 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-2758497e574a09010547 | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | 172 |
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ChEMBL ID | CHEMBL170365 |
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KEGG Compound ID | C00084 |
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Pubchem Compound ID | 177 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15343 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00990 |
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CRC / DFC (Dictionary of Food Compounds) ID | DFR74-T:DFR74-T |
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EAFUS ID | 5 |
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Dr. Duke ID | ACETALDEHYDE |
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BIGG ID | 33792 |
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KNApSAcK ID | C00007392 |
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HET ID | ACE |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 75-07-0 |
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GoodScent ID | rw1019471 |
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SuperScent ID | 177 |
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Wikipedia ID | Acetaldehyde |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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addictive | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | perfumery | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | respiraparalytic | | | DUKE | tyrosinase inhibitor | 59997 | 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 | carcinogenic | 50903 | 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 |
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Enzymes | Name | Gene Name | UniProt ID |
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Alcohol dehydrogenase [NADP(+)] | AKR1A1 | P14550 | Ethanolamine-phosphate phospho-lyase | AGXT2L1 | Q8TBG4 | Putative deoxyribose-phosphate aldolase | DERA | Q9Y315 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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pungent |
- 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
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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- 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 |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| ethereal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| aldehydic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruity |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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