| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2024-09-17 15:42:26 UTC |
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| NP-MRD ID | NP0000613 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common 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 an aldehyde with a chain length containing between 2 and 5 carbon atoms. 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. Acetaldehyde can also be converted to acetic acid by the enzyme aldehyde dehydrogenase (mitochondrial) and aldehyde dehydrogenase X (mitochondrial). The main method of production is the oxidation of ethylene by the Wacker process, which involves oxidation of ethylene using a homogeneous palladium/copper system: 2 CH2CH2 + O2 → 2 CH3CHO. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually. In humans, acetaldehyde is involved in disulfiram action pathway. Acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Outside of the human body, acetaldehyde is found, on average, in the highest concentration in a few different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine) and in a lower concentration in. Acetaldehyde has also been detected, but not quantified in several different foods, such as malabar plums, malus (crab apple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. In condensation reactions, acetaldehyde is prochiral. 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; also acetaldehyde has been linked to the inborn metabolic disorders including aldehyde dehydrogenase deficiency (III) sulfate is used to reoxidize the mercury back to the mercury. Acetaldehyde was first observed by the Swedish pharmacist/chemist Carl Wilhelm Scheele (1774); it was then investigated by the French chemists Antoine François, comte de Fourcroy and Louis Nicolas Vauquelin (1800), and the German chemists Johann Wolfgang Döbereiner (1821, 1822, 1832) and Justus von Liebig (1835). At room temperature, acetaldehyde (CH3CHO) is more stable than vinyl alcohol (CH2CHOH) by 42.7 KJ/mol: Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. The water industry generally recognizes 20–40 ppb as the taste/odor threshold for acetaldehyde. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. |
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| Structure | InChI=1S/C2H4O/c1-2-3/h2H,1H3 |
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| Synonyms | | Value | Source |
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| Acetaldehyd | ChEBI | | Acetaldehydes | ChEBI | | Acetic aldehyde | ChEBI | | Azetaldehyd | ChEBI | | Ethanal | ChEBI | | Ethyl aldehyde | ChEBI | | Aldehyde | HMDB |
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| Chemical Formula | C2H4O |
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| Average Mass | 44.0526 Da |
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| Monoisotopic Mass | 44.02621 Da |
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| IUPAC Name | acetaldehyde |
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| Traditional Name | acetaldehyde |
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| CAS Registry Number | 75-07-0 |
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| SMILES | CC=O |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-10 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | |
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| Predicted Properties | |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Burton A: Acetaldehyde links alcohol consumption to cancer. Lancet Oncol. 2005 Sep;6(9):643. [PubMed:16161263 ]
- 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 ]
- 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 ]
- Deitrich RA: Acetaldehyde: deja vu du jour. J Stud Alcohol. 2004 Sep;65(5):557-72. [PubMed:15536764 ]
- 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 ]
- 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 ]
- 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 ]
- Brooks PJ, Theruvathu JA: DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005 Apr;35(3):187-93. [PubMed:16054980 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Jamal M, Ameno K, Tanaka N, Ito A, Takakura A, Kumihashi M, Kinoshita H: Ethanol and Acetaldehyde After Intraperitoneal Administration to Aldh2-Knockout Mice-Reflection in Blood and Brain Levels. Neurochem Res. 2016 May;41(5):1029-34. doi: 10.1007/s11064-015-1788-6. Epub 2015 Dec 8. [PubMed:26646001 ]
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