AFCDB: 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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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

Physico-Chemical Properties - Experimental

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

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
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

MS/MS

Type	Description	Splash Key	View
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

NMR

Type	Description	View
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

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

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Food	Content Range	Average	Reference

Nanking cherry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Orange bell pepper	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Saskatoon berry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB
Sea-buckthornberry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, HMDB

Showing 1 to 4 of 4 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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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

Showing 1 to 10 of 24 entries

Enzymes

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Name	Gene Name	UniProt ID
3-mercaptopyruvate sulfurtransferase	MPST	P25325
Acid phosphatase-like protein 2	ACPL2	Q8TE99
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Q6E213
Alcohol dehydrogenase [NADP(+)]	AKR1A1	P14550
Beta-glucuronidase	GUSB	P08236
Carboxylesterase 5A	CES5A	Q6NT32
Fatty acyl-CoA reductase 2	FAR2	Q96K12
Lecithin retinol acyltransferase	LRAT	O95237
Lysosomal acid phosphatase	ACP2	P11117
Nuclear receptor subfamily 1 group I member 3	NR1I3	Q14994

Showing 1 to 10 of 19 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
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.
strong	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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

Showing 1 to 5 of 5 entries

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Ethanol (FDB000753)

Structure for FDB000753 (Ethanol)