Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:31 UTC |
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HMDB ID | HMDB0000108 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethanol |
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Description | Ethanol is a clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in alcoholic beverages. Indeed, ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. Ethanol has a depressive effect on the central nervous system and because of its psychoactive effects, it is considered a drug. Ethanol has a complex mode of action and affects multiple systems in the brain, most notably it acts as an agonist to the GABA receptors. Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3-0.4 %. Ethanol is metabolized by the body as an energy-providing carbohydrate nutrient, as it metabolizes into acetyl CoA, an intermediate common with glucose metabolism, that can be used for energy in the citric acid cycle or for biosynthesis. Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into acetic acid by acetaldehyde dehydrogenase. The product of the first step of this breakdown, acetaldehyde, is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver,[77] multiple forms of cancer, and alcoholism. Industrially, ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, by fermenting sugars with yeast. Small amounts of ethanol are endogenously produced by gut microflora through anaerobic fermentation. However most ethanol detected in biofluids and tissues likely comes from consumption of alcoholic beverages. Absolute ethanol or anhydrous alcohol generally refers to purified ethanol, containing no more than one percent water. Absolute alcohol is not intended for human consumption. It often contains trace amounts of toxic benzene (used to remove water by azeotropic distillation). Consumption of this form of ethanol can be fatal over a short time period. Generally absolute or pure ethanol is used as a solvent for lab and industrial settings where water will disrupt a desired reaction. Pure ethanol is classed as 200 proof in the USA and Canada, equivalent to 175 degrees proof in the UK system. Ethanol is a general biomarker for the consumption of alcohol. Ethanol is also a metabolite of Hansenula and Saccharomyces (PMID: 14613880 ) (https://ac.els-cdn.com/S0079635206800470/1-s2.0-S0079635206800470-main.pdf?_tid=4d340044-3230-4141-88dd-deec4d2e35bd&acdnat=1550288012_0c4a20fe963843426147979d376cf624). |
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Structure | InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 |
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Synonyms | Value | Source |
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1-Hydroxyethane | ChEBI | [CH2Me(OH)] | ChEBI | [OEtH] | ChEBI | Alcohol | ChEBI | Alcohol etilico | ChEBI | Alcool ethylique | ChEBI | Alkohol | ChEBI | Aethanol | ChEBI | Aethylalkohol | ChEBI | C2H5OH | ChEBI | Dehydrated ethanol | ChEBI | Etanol | ChEBI | Ethyl alcohol | ChEBI | EtOH | ChEBI | Hydroxyethane | ChEBI | Methylcarbinol | ChEBI | Spiritus vini | ChEBI | Anhydrous ethanol | Kegg | Absolute alcohol | HMDB | Absolute ethanol | HMDB | Absolute ethyl alcohol | HMDB | Alcare hand degermer | HMDB | Alcohols | HMDB | Alcool etilico | HMDB | Algrain | HMDB | Alkoholu etylowego | HMDB | Anhydrol | HMDB | Anhydrous alcohol | HMDB | Cologne spirit | HMDB | Cologne spirits | HMDB | Dehydrated alcohol | HMDB | Denatured alcohol | HMDB | Denatured ethanol | HMDB | Desinfektol el | HMDB | Diluted alcohol | HMDB | Distilled spirits | HMDB | Ethanol 200 proof | HMDB | Ethanol solution | HMDB | Ethicap | HMDB | Ethyl alc | HMDB | Ethyl alcohol anhydrous | HMDB | Ethyl alcohol in alcoholic beverages | HMDB | Ethyl alcohol usp | HMDB | Ethyl hydrate | HMDB | Ethyl hydroxide | HMDB | Fermentation alcohol | HMDB | Grain alcohol | HMDB | Hinetoless | HMDB | Infinity pure | HMDB | Jaysol | HMDB | Jaysol S | HMDB | Lux | HMDB | Molasses alcohol | HMDB | Potato alcohol | HMDB | Punctilious ethyl alcohol | HMDB | Pyro | HMDB | Silent spirit | HMDB | Spirit | HMDB | Spirits OF wine | HMDB | Spirt | HMDB | Synasol | HMDB | Tecsol | HMDB | Tecsol C | HMDB | Thanol | HMDB | Undenatured ethanol | HMDB | Alcohol, absolute | HMDB | Alcohol, ethyl | HMDB | Alcohol, grain | HMDB |
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Chemical Formula | C2H6O |
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Average Molecular Weight | 46.0684 |
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Monoisotopic Molecular Weight | 46.041864814 |
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IUPAC Name | ethanol |
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Traditional Name | ethyl alcohol |
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CAS Registry Number | 64-17-5 |
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SMILES | CCO |
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InChI Identifier | InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 |
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InChI Key | LFQSCWFLJHTTHZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). |
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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 | Alcohols and polyols |
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Direct Parent | Primary alcohols |
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Alternative Parents | |
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Substituents | - Hydrocarbon derivative
- Primary alcohol
- 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 | |
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Disposition | Biological locationRoute of exposureSourceExogenousFood- Food (HMDB: HMDB0000108)
Animal originHerb and spiceVegetableFruitNutCereal and cereal productPulseGourdCoffee and coffee productSoyTeaDishBaking goodBeverageAquatic originConfectioneryMilk and milk productOther milk productFermented milkFermented milk productUnfermented milk- Milk (Other mammals) (FooDB: FOOD00690)
- Milk (Human) (FooDB: FOOD00666)
- Milk (Cow) (FooDB: FOOD00618)
- Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
- Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
- Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
- Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
Fat and oilCocoa and cocoa productBaby foodUnclassified food or beverageSnackEgg Synthetic Endogenous- Saccharomyces cerevisiae (HMDB: HMDB0000108)
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Process | |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | -114.1 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL | Not Available | LogP | -0.31 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 117.862 | 30932474 | DeepCCS | [M-H]- | 115.966 | 30932474 | DeepCCS | [M-2H]- | 151.286 | 30932474 | DeepCCS | [M+Na]+ | 125.566 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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Ethanol | CCO | 821.1 | Standard polar | 33892256 | Ethanol | CCO | 408.8 | Standard non polar | 33892256 | Ethanol | CCO | 428.3 | Semi standard non polar | 33892256 |
Derivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Ethanol EI-B (Non-derivatized) | splash10-001j-9000000000-a705823ce4aeba7f89e1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Ethanol EI-B (Non-derivatized) | splash10-001j-9000000000-a705823ce4aeba7f89e1 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethanol GC-MS (Non-derivatized) - 70eV, Positive | splash10-002b-9000000000-7fa80a491183c1cdd23e | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethanol GC-MS (1 TMS) - 70eV, Positive | splash10-0fmi-9200000000-587cc3c48ab7fbf9cd3a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethanol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethanol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethanol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-003s-9000000000-dabf5a61c5a7da9fbe13 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Ethanol EI-B (HITACHI RMU-7M) , Positive-QTOF | splash10-001j-9000000000-a705823ce4aeba7f89e1 | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 10V, Positive-QTOF | splash10-0002-9000000000-d75d9996bc68c673f090 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 20V, Positive-QTOF | splash10-0002-9000000000-893c2599624722912f25 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 40V, Positive-QTOF | splash10-004i-9000000000-8af4124822065023744f | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 10V, Negative-QTOF | splash10-0002-9000000000-22231ed69c5f28bfed79 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 20V, Negative-QTOF | splash10-0002-9000000000-d2881505c47bbef13f18 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 40V, Negative-QTOF | splash10-0002-9000000000-2ed988bb761ac20ba44a | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 10V, Positive-QTOF | splash10-0002-9000000000-5c5e98353b75870c1c55 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 20V, Positive-QTOF | splash10-0002-9000000000-326f4f38d260a85ea469 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 40V, Positive-QTOF | splash10-002b-9000000000-f850ab2a079485c4a276 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 10V, Negative-QTOF | splash10-0002-9000000000-b6602db69e5662ad67a9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 20V, Negative-QTOF | splash10-0002-9000000000-b6602db69e5662ad67a9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethanol 40V, Negative-QTOF | splash10-0002-9000000000-4d0d1c69f8440a7fda18 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Disease References | Kidney disease |
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- Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [PubMed:914932 ]
| Alcoholism |
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- Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed:2779169 ]
- Jones AW, Helander A: Changes in the concentrations of ethanol, methanol and metabolites of serotonin in two successive urinary voids from drinking drivers. Forensic Sci Int. 1998 May 11;93(2-3):127-34. [PubMed:9717263 ]
| Early preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
| Pregnancy |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
- Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Late-onset preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
| Cervical myelopathy |
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- Meshitsuka S, Morio Y, Nagashima H, Teshima R: 1H-NMR studies of cerebrospinal fluid: endogenous ethanol in patients with cervical myelopathy. Clin Chim Acta. 2001 Oct;312(1-2):25-30. [PubMed:11580906 ]
| Ulcerative colitis |
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- Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
- Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
| Irritable bowel syndrome |
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- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
| Nonalcoholic fatty liver disease |
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- Raman M, Ahmed I, Gillev
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