Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:42 UTC |
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Update date | 2020-09-17 15:42:10 UTC |
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Primary ID | FDB000753 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ethanol |
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Description | Ethanol, also known as ethyl alcohol or alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds having a primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). 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 adverse clinical effects of alcohol. Ethanol has been shown to increase the risk of developing cirrhosis of the liver, 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). |
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CAS Number | 64-17-5 |
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Structure | |
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Synonyms | Synonym | 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 | 1-hydroxyethane | manual | Drinking alcohol | manual | Ethylic alcohol | manual | Ethylol | manual | FEMA 2419 | db_source | Pure alcohol | manual |
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Predicted Properties | |
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Chemical Formula | C2H6O |
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IUPAC name | ethanol |
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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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Isomeric SMILES | CCO |
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Average Molecular Weight | 46.0684 |
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Monoisotopic Molecular Weight | 46.041864814 |
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Classification |
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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 | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Indirect biological role: Industrial application: |
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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 52.14%; H 13.13%; O 34.73% | DFC |
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Melting Point | Fp -117.3° (-112.3°) | DFC |
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Boiling Point | Bp16 4° | 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 | -0.31 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 15.93 (25°) | 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 0.79 | DFC |
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Refractive Index | n20.5D 1.3610 | 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) | splash10-003s-9000000000-dabf5a61c5a7da9fbe13 | 2014-09-20 | View Spectrum | GC-MS | Ethanol, non-derivatized, GC-MS Spectrum | splash10-001j-9000000000-a705823ce4aeba7f89e1 | Spectrum | GC-MS | Ethanol, non-derivatized, GC-MS Spectrum | splash10-001j-9000000000-a705823ce4aeba7f89e1 | Spectrum | Predicted GC-MS | Ethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002b-9000000000-7fa80a491183c1cdd23e | Spectrum | Predicted GC-MS | Ethanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fmi-9200000000-587cc3c48ab7fbf9cd3a | Spectrum | Predicted GC-MS | Ethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ethanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ethanol, TBDMS_1_1, 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 - EI-B (HITACHI RMU-7M) , Positive | splash10-001j-9000000000-a705823ce4aeba7f89e1 | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-d75d9996bc68c673f090 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-893c2599624722912f25 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-8af4124822065023744f | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-22231ed69c5f28bfed79 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-d2881505c47bbef13f18 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9000000000-2ed988bb761ac20ba44a | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-5c5e98353b75870c1c55 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-326f4f38d260a85ea469 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002b-9000000000-f850ab2a079485c4a276 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-b6602db69e5662ad67a9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-b6602db69e5662ad67a9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9000000000-4d0d1c69f8440a7fda18 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 682 |
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ChEMBL ID | CHEMBL545 |
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KEGG Compound ID | C00469 |
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Pubchem Compound ID | 702 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16236 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00898 |
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HMDB ID | HMDB00108 |
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CRC / DFC (Dictionary of Food Compounds) ID | BGT97-X:BGT97-X |
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EAFUS ID | 1148 |
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Dr. Duke ID | ETHANOL|ETHYL-ALCOHOL |
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BIGG ID | 35062 |
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KNApSAcK ID | C00019560 |
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HET ID | EOH |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 64-17-5 |
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GoodScent ID | rw1000511 |
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SuperScent ID | Not Available |
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Wikipedia ID | Ethanol |
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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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allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | anesthetic | | | DUKE | anhydrotic | | | DUKE | anti atherosclerotic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti pruritic | 50177 | A drug used to treat or prevent skin disorders or for the routine care of skin. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | expectorant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | hepatotoxic | 50908 | A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. | DUKE | hypertensive | | | DUKE | hypnotic | | | DUKE | hypocalcemic | | | DUKE | hypotensive | | | DUKE | mucotropic | | | DUKE | neurolytic | | | 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 | rubefacient | | | DUKE | sclerosant | | | DUKE | surfactant | 35195 | A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces. | DUKE | teratogenic | 50905 | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. | DUKE | tremorilytic | | | DUKE | ulcerogenic | | | DUKE | neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | CHEBI |
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Enzymes | Name | Gene Name | UniProt ID |
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Serum paraoxonase/lactonase 3 | PON3 | Q15166 | Serum paraoxonase/arylesterase 1 | PON1 | P27169 | Serum paraoxonase/arylesterase 2 | PON2 | Q15165 | Lysosomal acid phosphatase | ACP2 | P11117 | Sulfotransferase family cytosolic 2B member 1 | SULT2B1 | O00204 | Alcohol dehydrogenase [NADP(+)] | AKR1A1 | P14550 | 3-mercaptopyruvate sulfurtransferase | MPST | P25325 | Beta-glucuronidase | GUSB | P08236 | Plasma alpha-L-fucosidase | FUCA2 | Q9BTY2 | Lecithin retinol acyltransferase | LRAT | O95237 | Nuclear receptor subfamily 1 group I member 3 | NR1I3 | Q14994 | Fatty acyl-CoA reductase 2 | FAR2 | Q96K12 | Acyl-CoA wax alcohol acyltransferase 2 | AWAT2 | Q6E213 | Testicular acid phosphatase | ACPT | Q9BZG2 | Carboxylesterase 5A | CES5A | Q6NT32 | Acid phosphatase-like protein 2 | ACPL2 | Q8TE99 | Synaptic vesicle membrane protein VAT-1 homolog-like | VAT1L | Q9HCJ6 | Quinone oxidoreductase PIG3 | TP53I3 | Q53FA7 | Synaptic vesicle membrane protein VAT-1 homolog | VAT1 | Q99536 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Ethanol Degradation | SMP00449 | Not Available |
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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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sweet |
- 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
| strong |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| alcoholic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| ethereal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| medical |
- 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 | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — 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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