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Ethanol (FDB000753)

Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2020-09-17 15:42:10 UTC
Primary IDFDB000753
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEthanol
DescriptionEthanol, 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).
CAS Number64-17-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility579 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.01 m³·mol⁻¹ChemAxon
Polarizability5.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H6O
IUPAC nameethanol
InChI IdentifierInChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
InChI KeyLFQSCWFLJHTTHZ-UHFFFAOYSA-N
Isomeric SMILESCCO
Average Molecular Weight46.0684
Monoisotopic Molecular Weight46.041864814
Classification
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).
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 52.14%; H 13.13%; O 34.73%DFC
Melting PointFp -117.3° (-112.3°)DFC
Boiling PointBp16 4°DFC
Experimental Water Solubility1000 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP-0.31HANSCH,C ET AL. (1995)
Experimental pKapKa 15.93 (25°)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.79DFC
Refractive Indexn20.5D 1.3610DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-003s-9000000000-dabf5a61c5a7da9fbe132014-09-20View Spectrum
GC-MSEthanol, non-derivatized, GC-MS Spectrumsplash10-001j-9000000000-a705823ce4aeba7f89e1Spectrum
GC-MSEthanol, non-derivatized, GC-MS Spectrumsplash10-001j-9000000000-a705823ce4aeba7f89e1Spectrum
Predicted GC-MSEthanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-9000000000-7fa80a491183c1cdd23eSpectrum
Predicted GC-MSEthanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-9200000000-587cc3c48ab7fbf9cd3aSpectrum
Predicted GC-MSEthanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthanol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001j-9000000000-a705823ce4aeba7f89e12012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-d75d9996bc68c673f0902015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-893c2599624722912f252015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-8af4124822065023744f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-22231ed69c5f28bfed792015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-d2881505c47bbef13f182015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-2ed988bb761ac20ba44a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-5c5e98353b75870c1c552021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-326f4f38d260a85ea4692021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9000000000-f850ab2a079485c4a2762021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-b6602db69e5662ad67a92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-b6602db69e5662ad67a92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-4d0d1c69f8440a7fda182021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H 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
ChemSpider ID682
ChEMBL IDCHEMBL545
KEGG Compound IDC00469
Pubchem Compound ID702
Pubchem Substance IDNot Available
ChEBI ID16236
Phenol-Explorer IDNot Available
DrugBank IDDB00898
HMDB IDHMDB00108
CRC / DFC (Dictionary of Food Compounds) IDBGT97-X:BGT97-X
EAFUS ID1148
Dr. Duke IDETHANOL|ETHYL-ALCOHOL
BIGG ID35062
KNApSAcK IDC00019560
HET IDEOH
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID64-17-5
GoodScent IDrw1000511
SuperScent IDNot Available
Wikipedia IDEthanol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anhydroticDUKE
anti atherosclerotic38070 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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti pruritic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypertensiveDUKE
hypnoticDUKE
hypocalcemicDUKE
hypotensiveDUKE
mucotropicDUKE
neurolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
rubefacientDUKE
sclerosantDUKE
surfactant35195 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
teratogenic50905 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
tremorilyticDUKE
ulcerogenicDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.CHEBI
Enzymes
NameGene NameUniProt ID
Serum paraoxonase/lactonase 3PON3Q15166
Serum paraoxonase/arylesterase 1PON1P27169
Serum paraoxonase/arylesterase 2PON2Q15165
Lysosomal acid phosphataseACP2P11117
Sulfotransferase family cytosolic 2B member 1SULT2B1O00204
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
3-mercaptopyruvate sulfurtransferaseMPSTP25325
Beta-glucuronidaseGUSBP08236
Plasma alpha-L-fucosidaseFUCA2Q9BTY2
Lecithin retinol acyltransferaseLRATO95237
Nuclear receptor subfamily 1 group I member 3NR1I3Q14994
Fatty acyl-CoA reductase 2FAR2Q96K12
Acyl-CoA wax alcohol acyltransferase 2AWAT2Q6E213
Testicular acid phosphataseACPTQ9BZG2
Carboxylesterase 5ACES5AQ6NT32
Acid phosphatase-like protein 2ACPL2Q8TE99
Synaptic vesicle membrane protein VAT-1 homolog-likeVAT1LQ9HCJ6
Quinone oxidoreductase PIG3TP53I3Q53FA7
Synaptic vesicle membrane protein VAT-1 homologVAT1Q99536
Pathways
NameSMPDB LinkKEGG Link
Ethanol DegradationSMP00449 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. 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
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
alcoholic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.