Record Information
Version2.0
Creation Date2012-05-31 09:57:31 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00108
Identification
Name:Ethanol
Description:Ethanol is a clear, colorless liquid. Many bacteria species, including gut microflora such as E. coli, produce ethanol through fermentation in glucose metabolism. (HMDB, KEGG)
Structure
Thumb
Synonyms:
  • 1-Hydroxyethane
  • Absolute alcohol
  • Absolute ethanol
  • Absolute ethyl alcohol
  • Aethanol
  • Aethylalkohol
  • Alcare Hand Degermer
  • Alcohol
  • Alcohols
  • Alcool ethylique
  • Alcool etilico
  • Algrain
  • Alkohol
  • Alkoholu etylowego
  • Anhydrol
  • Anhydrous alcohol
  • Cologne spirit
  • Cologne spirits
  • Dehydrated alcohol
  • Dehydrated ethanol
  • Denatured alcohol
  • Denatured ethanol
  • Desinfektol EL
  • Diluted Alcohol
  • Distilled spirits
  • Eth
  • Ethanol 200 proof
  • Ethanol solution
  • Ethicap
  • Ethyl alc
  • Ethyl alcohol
  • Ethyl alcohol anhydrous
  • Ethyl alcohol in alcoholic beverages
  • Ethyl alcohol usp
  • Ethyl hydrate
  • Ethyl hydric acid
  • Ethyl hydroxide
  • EtOH
  • Fermentation alcohol
  • Grain alcohol
  • Hinetoless
  • Hydroxyethane
  • Infinity Pure
  • Jaysol
  • Jaysol S
  • Lux
  • Methylcarbinol
  • Molasses alcohol
  • Potato alcohol
  • Punctilious ethyl alcohol
  • Pyro
  • Silent spirit
  • Spirit
  • Spirits of wine
  • Spirt
  • Synasol
  • Tecsol
  • Tecsol C
  • Thanol
  • Undenatured Ethanol
Chemical Formula:C2H6O
Weight:Average: 46.0684
Monoisotopic: 46.041864814
InChI Key:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
InChI:InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
CAS number:64-17-5
IUPAC Name:ethanol
Traditional IUPAC Name:ethyl alcohol
SMILES:CCO
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:-114.1 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [RIDDICK,JA et al. (1986)]PhysProp
LogP:-0.31 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility579.0 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.16ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)16.47ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.01 m3·mol-1ChemAxon
Polarizability5.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Glycolysis / Gluconeogenesis ec00010
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-002b-9000000000-7fa80a491183c1cdd23eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001j-9000000000-a705823ce4aeba7f89e1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fmi-9200000000-587cc3c48ab7fbf9cd3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001j-9000000000-a705823ce4aeba7f89e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-d75d9996bc68c673f090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-893c2599624722912f25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-8af4124822065023744fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-22231ed69c5f28bfed79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-d2881505c47bbef13f18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-2ed988bb761ac20ba44aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-003s-9000000000-dabf5a61c5a7da9fbe13View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Aye MM, Ma C, Lin H, Bower KA, Wiggins RC, Luo J: Ethanol-induced in vitro invasion of breast cancer cells: the contribution of MMP-2 by fibroblasts. Int J Cancer. 2004 Dec 10;112(5):738-46. Pubmed: 15386367
  • Barceloux DG, Bond GR, Krenzelok EP, Cooper H, Vale JA: American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning. J Toxicol Clin Toxicol. 2002;40(4):415-46. Pubmed: 12216995
  • Boschmann M, Adams F, Schaller K, Franke G, Sharma AM, Klaus S, Luft FC, Jordan J: Hemodynamic and metabolic responses to interstitial angiotensin II in normal weight and obese men. J Hypertens. 2006 Jun;24(6):1165-71. Pubmed: 16685217
  • Chastain G: Alcohol, neurotransmitter systems, and behavior. J Gen Psychol. 2006 Oct;133(4):329-35. Pubmed: 17128954
  • Collins JW, Macdermott S, Bradbrook RA, Keeley FX Jr, Timoney AG: Is using ethanol-glycine irrigating fluid monitoring and 'good surgical practice' enough to prevent harmful absorption during transurethral resection of the prostate? BJU Int. 2006 Jun;97(6):1247-51. Pubmed: 16686720
  • De Martinis BS, de Paula CM, Braga A, Moreira HT, Martin CC: Alcohol distribution in different postmortem body fluids. Hum Exp Toxicol. 2006 Feb;25(2):93-7. Pubmed: 16539214
  • Dean RA, Zhang J, Brzezinski MR, Bosron WF: Tissue distribution of cocaine methyl esterase and ethyl transferase activities: correlation with carboxylesterase protein. J Pharmacol Exp Ther. 1995 Nov;275(2):965-71. Pubmed: 7473189
  • Elias AN, Meshkinpour H, Valenta LJ, Grossman MK: Pseudo-Cushing's syndrome: the role of alcohol. J Clin Gastroenterol. 1982 Apr;4(2):137-9. Pubmed: 6282953
  • Enocksson S, Shimizu M, Lonnqvist F, Nordenstrom J, Arner P: Demonstration of an in vivo functional beta 3-adrenoceptor in man. J Clin Invest. 1995 May;95(5):2239-45. Pubmed: 7738189
  • Friedman GD, Klatsky AL, Siegelaub AB: Alcohol, tobacco, and hypertension. Hypertension. 1982 Sep-Oct;4(5 Pt 2):III143-50. Pubmed: 7049929
  • Gordon Z, Parsons CL, Monga M: Intravesical ethanol test: an ineffective measure of bladder hyperpermeability. Urology. 2003 Mar;61(3):555-7. Pubmed: 12639646
  • Hemmingsen R, Barry DI, Hertz MM, Klinken L: Cerebral blood flow and oxygen consumption during ethanol withdrawal in the rat. Brain Res. 1979 Sep 14;173(2):259-69. Pubmed: 573652
  • Henriksson J, Knol M: A single bout of exercise is followed by a prolonged decrease in the interstitial glucose concentration in skeletal muscle. Acta Physiol Scand. 2005 Dec;185(4):313-20. Pubmed: 16266372
  • Hingson R, Winter M: Epidemiology and consequences of drinking and driving. Alcohol Res Health. 2003;27(1):63-78. Pubmed: 15301401
  • Huang JS, She QB, Crilly KS, Kiss Z: Ethanol, Zn2+ and insulin interact as progression factors to enhance DNA synthesis synergistically in the presence of Ca2+ and other cell cycle initiators in fibroblasts. Biochem J. 2000 Feb 15;346 Pt 1:241-7. Pubmed: 10657263
  • Igawa Y, Satoh T, Mizusawa H, Seki S, Kato H, Ishizuka O, Nishizawa O: The role of capsaicin-sensitive afferents in autonomic dysreflexia in patients with spinal cord injury. BJU Int. 2003 May;91(7):637-41. Pubmed: 12699475
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lopez JM, Bombi JA, Valderrama R, Gimenez A, Pares A, Caballeria J, Imperial S, Navarro S: Effects of prolonged ethanol intake and malnutrition on rat pancreas. Gut. 1996 Feb;38(2):285-92. Pubmed: 8801213
  • Maddula, S., Blank, L. M., Schmid, A., Baumbach, J. I. (2009). "Detection of volatile metabolites of Escherichia coli by multi capillary column coupled ion mobility spectrometry." Anal Bioanal Chem 394:791-800. Pubmed: 19330511
  • McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. Pubmed: 9880479
  • Pohorecky LA: Influence of alcohol on peripheral neurotransmitter function. Fed Proc. 1982 Jun;41(8):2452-5. Pubmed: 6123447
  • Rosdahl H, Lind L, Millgard J, Lithell H, Ungerstedt U, Henriksson J: Effect of physiological hyperinsulinemia on blood flow and interstitial glucose concentration in human skeletal muscle and adipose tissue studied by microdialysis. Diabetes. 1998 Aug;47(8):1296-301. Pubmed: 9703331
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Snyder R, Kalf GF: A perspective on benzene leukemogenesis. Crit Rev Toxicol. 1994;24(3):177-209. Pubmed: 7945890
  • Sokolik VV, Chursina VS, Artemchuk AA, Artemchuk AF, Bozhko GKh: [Depression of serum esterase and lipoprotein lipase activities in acute and longitudinal actions of ethanol] Biomed Khim. 2006 Jan-Feb;52(1):95-100. Pubmed: 16739925
  • Uemura M, Lehmann WD, Schneider W, Seitz HK, Benner A, Keppler-Hafkemeyer A, Hafkemeyer P, Kojima H, Fujimoto M, Tsujii T, Fukui H, Keppler D: Enhanced urinary excretion of cysteinyl leukotrienes in patients with acute alcohol intoxication. Gastroenterology. 2000 Jun;118(6):1140-8. Pubmed: 10833489
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yamashina S, Ikejima K, Enomoto N, Takei Y, Sato N: [Ethanol changes sensitivity of Kupffer cells to endotoxin] Nihon Arukoru Yakubutsu Igakkai Zasshi. 2003 Oct;38(5):415-24. Pubmed: 14639920
Synthesis Reference:Lashley, David. Process for producing an alcoholic sugar cane juice beverage. U.S. (1988), 3 pp. CODEN: USXXAM US 4784859 A 19881115 CAN 110:113222 AN 1989:113222
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16236
HMDB IDHMDB00108
Pubchem Compound ID702
Kegg IDC00469
ChemSpider ID682
WikipediaEthanol
BioCyc IDETOH
EcoCyc IDETOH
Ligand ExpoOXA

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This enzyme has three activities:ADH, ACDH, and PFL- deactivase. In aerobic conditions it acts as a hydrogen peroxide scavenger. The PFL deactivase activity catalyzes the quenching of the pyruvate-formate-lyase catalyst in an iron, NAD, and CoA dependent reaction
Gene Name:
adhE
Uniprot ID:
P0A9Q7
Molecular weight:
96126
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
Preferred specificity is towards 1-propanol
Gene Name:
adhP
Uniprot ID:
P39451
Molecular weight:
35379
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yiaY
Uniprot ID:
P37686
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
eutG
Uniprot ID:
P76553
Molecular weight:
Not Available

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368