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Identification |
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YMDB ID | YMDB00883 |
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Name | Ethanol |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | Ethanol (EtOH), also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene. In chemistry, ethanol is both an essential solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines. Ethanol can be prepared either by industrial fermentation from yeast or by conversion by from ethylene. Ethanol is the primary alcohol found in alcoholic beverages. It is also used in scents, flavorings, colorings, and medicines. Alcoholic beverages such as wine, beer, or distilled spirits all use yeast at some stage of their production. Alcoholic beverages vary considerably in ethanol content and in foodstuffs they are produced from. Most alcoholic beverages can be broadly classified as fermented beverages, beverages made by the action of yeast on sugary foodstuffs, or distilled beverages, beverages whose preparation involves concentrating the ethanol in fermented beverages by distillation. The ethanol content of a beverage is usually measured in terms of the volume fraction of ethanol in the beverage, expressed either as a percentage (~5% for beers, ~12% for wines) or in alcoholic proof units (40-80 proof for many spirits). Fermented beverages can be broadly classified by the grains, fruits or vegetables they are fermented from. Beers are made from cereal grains or other starchy materials, wines and ciders from fruit juices, and meads from honey. Distilled beverages are made by distilling fermented beverages. Broad categories of distilled beverages include whiskeys, distilled from fermented cereal grains; brandies, distilled from fermented fruit juices; and rum, distilled from fermented molasses or sugarcane juice. Vodka and similar neutral grain spirits can be distilled from any fermented material (grain or potatoes are most common); these spirits are so thoroughly distilled that no tastes from the particular starting material remain. Numerous other spirits and liqueurs are prepared by infusing flavors from fruits, herbs, and spices into distilled spirits. A traditional example is gin, which is created by infusing juniper berries into a neutral grain alcohol. Alcoholic beverages can also be made into culinary/household vinegar: Wine and cider vinegar are both named for their respective source alcohols, whereas malt vinegar is derived from beer. Ethanol is also a psychoactive drug and one of the oldest known recreational drugs. Ethanol binds to acetylcholine, GABA, serotonin, and NMDA receptors with depressant effects on the central nervous system. |
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Structure | |
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Synonyms | - 1-Hydroxyethane
- Aethanol
- Aethylalkohol
- Alcohol
- Ethyl alc
- Ethyl alcohol
- Ethyl hydrate
- Ethyl hydroxide
- Hydroxyethane
- [CH2Me(OH)]
- [OEtH]
- Alcohol etilico
- Alcool ethylique
- Alkohol
- C2H5OH
- Dehydrated ethanol
- Etanol
- EtOH
- Methylcarbinol
- Spiritus vini
- Anhydrous ethanol
- Absolute alcohol
- Absolute ethanol
- Absolute ethyl alcohol
- Alcare hand degermer
- Alcohols
- Alcool etilico
- Algrain
- Alkoholu etylowego
- Anhydrol
- Anhydrous alcohol
- Cologne spirit
- Cologne spirits
- Dehydrated alcohol
- Denatured alcohol
- Denatured ethanol
- Desinfektol el
- Diluted alcohol
- Distilled spirits
- Ethanol 200 proof
- Ethanol solution
- Ethicap
- Ethyl alcohol anhydrous
- Ethyl alcohol in alcoholic beverages
- Ethyl alcohol usp
- Fermentation alcohol
- Grain alcohol
- Hinetoless
- Infinity pure
- Jaysol
- Jaysol S
- Lux
- Molasses alcohol
- Potato alcohol
- Punctilious ethyl alcohol
- Pyro
- Silent spirit
- Spirit
- Spirits OF wine
- Spirt
- Synasol
- Tecsol
- Tecsol C
- Thanol
- Undenatured ethanol
- Alcohol, absolute
- Alcohol, ethyl
- Alcohol, grain
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CAS number | 64-17-5 |
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Weight | Average: 46.0684 Monoisotopic: 46.041864814 |
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InChI Key | LFQSCWFLJHTTHZ-UHFFFAOYSA-N |
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InChI | InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 |
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IUPAC Name | ethanol |
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Traditional IUPAC Name | ethyl alcohol |
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Chemical Formula | C2H6O |
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SMILES | [H]OC([H])([H])C([H])([H])[H] |
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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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Physical Properties |
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State | Liquid |
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Charge | 0 |
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Melting point | -114.1 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)] | PhysProp | LogP | -0.31 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - extracellular
- mitochondrion
- cytoplasm
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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325823 ± 68594 µM | YEPD media 200g/L glucose | anaerobic;30C;12h | Brewer's yeast | PMID: 3513699 | 583052 ± 120040 µM | YEPD media 200g/L glucose | anaerobic;30C;24h | Brewer's yeast | PMID: 3513699 | 1406185 ± 291526 µM | YEPD media 200g/L glucose | anaerobic;30C;48h | Brewer's yeast | PMID: 3513699 | 1825 ± 91 µM | YEB media with 0.5 mM glucose | aerobic | Brewer's yeast | Experimentally Determined Not Available | Conversion Details Here |
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Extracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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868282 ± 8000 µM | hops, malted barley | anaerobic | Brewer's yeast | PMID: 16448171 | 291526 ± 17149 µM | YEPD media 200g/L glucose | anaerobic;30C;12h | Brewer's yeast | PMID: 3513699 | 943173 ± 17149 µM | YEPD media 200g/L glucose | anaerobic;30C;24h | Brewer's yeast | PMID: 3513699 | 1920643 ± 171486 µM | YEPD media 200g/L glucose | anaerobic;30C;48h | Brewer's yeast | PMID: 3513699 | 846575 ± 6946 µM | hops, malted barley | anaerobic | Brewer's yeast | Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page | 2300946 ± 4341 µM | grape juice | anaerobic | Brewer's yeast | Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page | 1500 ± 1000 µM | Synthetic medium with 1% glucose and 0.1% yeast extract | aerobic | Brewer's yeast | PMID: 16623706 | 543 ± 0 uM | Glucose 1.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 2952 ± 0 uM | Glucose 2.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 12807 ± 0 uM | Glucose 5.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 31258 ± 0 uM | Glucose 10.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 39072 ± 0 uM | Glucose 50.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 195 ± 0 uM | Galatose 1.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 304 ± 0 uM | Galactose 2.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 3668 ± 0 uM | Galactose 5.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 12677 ± 0 uM | Galactose 10.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | 23574 ± 0 uM | Galactose 50.0 g/l as carbon source | Aerobic, 25 oC | Brewer's yeast | PMID: 5516454 | Conversion Details Here |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001j-9000000000-a705823ce4aeba7f89e1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001j-9000000000-a705823ce4aeba7f89e1 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002b-9000000000-7fa80a491183c1cdd23e | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0fmi-9200000000-587cc3c48ab7fbf9cd3a | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-001j-9000000000-a705823ce4aeba7f89e1 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-d75d9996bc68c673f090 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-893c2599624722912f25 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-8af4124822065023744f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-22231ed69c5f28bfed79 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-d2881505c47bbef13f18 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9000000000-2ed988bb761ac20ba44a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-5c5e98353b75870c1c55 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-326f4f38d260a85ea469 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002b-9000000000-f850ab2a079485c4a276 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-b6602db69e5662ad67a9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-b6602db69e5662ad67a9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9000000000-4d0d1c69f8440a7fda18 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-003s-9000000000-dabf5a61c5a7da9fbe13 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
- Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
- Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
- Dombek, K. M., Ingram, L. O. (1986). "Determination of the intracellular concentration of ethanol in Saccharomyces cerevisiae during fermentation." Appl Environ Microbiol 51:197-200.3513699
- Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
- Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
- Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
- Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. (2000). "Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli." Appl Microbiol Biotechnol 53:596-600.10855721
- Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
- Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
- Xu, Z., Tsurugi, K. (2006). "A potential mechanism of energy-metabolism oscillation in an aerobic chemostat culture of the yeast Saccharomyces cerevisiae." FEBS J 273:1696-1709.16623706
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Synthesis Reference: | Hennell, H. (1828). On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed. Philosophical Transactions 118: 365. |
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