Showing Compound Ethanol (FDB000753)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:42 UTC

Update date

2020-09-17 15:42:10 UTC

Primary ID

FDB000753

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ethanol

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).

CAS Number

64-17-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
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

Predicted Properties

Property	Value	Source
Water Solubility	579 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-0.16	ChemAxon
logS	1.1	ALOGPS
pKa (Strongest Acidic)	16.47	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	13.01 m³·mol⁻¹	ChemAxon
Polarizability	5.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C2H6O

IUPAC name

ethanol

InChI Identifier

InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3

InChI Key

LFQSCWFLJHTTHZ-UHFFFAOYSA-N

Isomeric SMILES

CCO

Average Molecular Weight

46.0684

Monoisotopic Molecular Weight

46.041864814

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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:16236 )
alkyl alcohol (CHEBI:16236 )
ethanols (CHEBI:16236 )
a primary alcohol (ETOH )
a short-chain alcohol (ETOH )

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Psychiatric disorders:

Depression

Cancer:

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Microbe:

Hansenula:

Hansenula polymorpha

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Alcoholism

Role

Indirect biological role:

Industrial application:

Household products:

Antimicrobial agent:

Disinfectant

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 52.14%; H 13.13%; O 34.73%	DFC
Melting Point	Fp -117.3° (-112.3°)	DFC
Boiling Point	Bp16 4°	DFC
Experimental Water Solubility	1000 mg/mL at 25 oC	RIDDICK,JA et al. (1986)
Experimental logP	-0.31	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 15.93 (25°)	DFC
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 0.79	DFC
Refractive Index	n20.5D 1.3610	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-003s-9000000000-dabf5a61c5a7da9fbe13	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

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-001j-9000000000-a705823ce4aeba7f89e1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-d75d9996bc68c673f090	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-893c2599624722912f25	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-8af4124822065023744f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-22231ed69c5f28bfed79	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-d2881505c47bbef13f18	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-2ed988bb761ac20ba44a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-5c5e98353b75870c1c55	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-326f4f38d260a85ea469	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9000000000-f850ab2a079485c4a276	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-b6602db69e5662ad67a9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-b6602db69e5662ad67a9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-4d0d1c69f8440a7fda18	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16236

Phenol-Explorer ID

Not Available

DrugBank ID

DB00898

HMDB ID

HMDB00108

CRC / DFC (Dictionary of Food Compounds) ID

BGT97-X:BGT97-X

EAFUS ID

1148

Dr. Duke ID

ETHANOL|ETHYL-ALCOHOL

BIGG ID

35062

KNApSAcK ID

C00019560

HET ID

EOH

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

64-17-5

GoodScent ID

rw1000511

SuperScent ID

Not Available

Wikipedia ID

Ethanol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
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

Enzymes

Name	Gene Name	UniProt ID
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

Pathways

Name	SMPDB Link	KEGG Link
Ethanol Degradation	SMP00449	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
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.