Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:54 UTC
HMDB IDHMDB00108
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthanol
DescriptionEthanol 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 clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver,[77] 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.
Structure
Thumb
Synonyms
  1. 1-Hydroxyethane
  2. Absolute alcohol
  3. Absolute ethanol
  4. Absolute ethyl alcohol
  5. Aethanol
  6. Aethylalkohol
  7. Alcare Hand Degermer
  8. Alcohol
  9. Alcohols
  10. Alcool ethylique
  11. Alcool etilico
  12. Algrain
  13. Alkohol
  14. Alkoholu etylowego
  15. Anhydrol
  16. Anhydrous alcohol
  17. Cologne spirit
  18. Cologne spirits
  19. Dehydrated alcohol
  20. Dehydrated ethanol
  21. Denatured alcohol
  22. Denatured ethanol
  23. Desinfektol EL
  24. Diluted Alcohol
  25. Distilled spirits
  26. Ethanol 200 proof
  27. Ethanol solution
  28. Ethicap
  29. Ethyl alc
  30. Ethyl alcohol
  31. Ethyl alcohol anhydrous
  32. Ethyl alcohol in alcoholic beverages
  33. Ethyl alcohol usp
  34. Ethyl hydrate
  35. Ethyl hydroxide
  36. Fermentation alcohol
  37. Grain alcohol
  38. Hinetoless
  39. Hydroxyethane
  40. Infinity Pure
  41. Jaysol
  42. Jaysol S
  43. Lux
  44. Methylcarbinol
  45. Molasses alcohol
  46. Potato alcohol
  47. Punctilious ethyl alcohol
  48. Pyro
  49. Silent spirit
  50. Spirit
  51. Spirits of wine
  52. Spirt
  53. Synasol
  54. Tecsol
  55. Tecsol C
  56. Thanol
  57. Undenatured Ethanol
Chemical FormulaC2H6O
Average Molecular Weight46.0684
Monoisotopic Molecular Weight46.041864814
IUPAC Nameethanol
Traditional IUPAC Nameethyl alcohol
CAS Registry Number64-17-5
SMILES
CCO
InChI Identifier
InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
InChI KeyLFQSCWFLJHTTHZ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassPrimary Alcohols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a primary alcohol(Cyc)
  • a short-chain alcohol(Cyc)
  • alkyl alcohol(ChEBI)
  • ethanols(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct ParentPrimary Alcohols
Ontology
StatusDetected and Quantified
Origin
  • Food
Biofunction
  • Component of Androgen and estrogen metabolism
  • Component of Bile acid biosynthesis
  • Component of C21-Steroid hormone metabolism
  • Component of Fatty acid metabolism
  • Component of Glycerolipid metabolism
  • Component of Sulfur metabolism
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Peroxisome
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-114.1 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-0.31HANSCH,C ET AL. (1995)
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 area20.23ChemAxon
rotatable bond count0ChemAxon
refractivity13.01ChemAxon
polarizability5.3ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fetus
  • Fibroblasts
  • Gonads
  • Gut
  • Heart
  • Intestine
  • Kidney
  • Liver
  • Lung
  • Mouth
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Ethanol DegradationSMP00449Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified40.0 (0.0-80.0) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified15.0 (0.0-33.0) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified<0.01 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.0105 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified5-500 umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified3.1 umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified40.2 +/- 12.1 uMAdult (>18 years old)Not SpecifiedHeart Transplant
BloodDetected and Quantified45393.0 (18027.0-74063.0) uMAdult (>18 years old)BothAlcohol intoxication
BloodDetected and Quantified40615.0 +/- 17158.0 uMAdult (>18 years old)MaleDrunk driver
BloodDetected and Quantified90.0 (10.0-170.0) uMAdult (>18 years old)BothCommentKidney disease
Cerebrospinal Fluid (CSF)Detected and Quantified230 +/- 30 uMAdult (>18 years old)Not SpecifiedCervical myelopathy
UrineDetected and Quantified54.0 (0.0-661.0) umol/mmol creatinineNot SpecifiedBothLung cancer
UrineDetected and Quantified0.0039 - 0.0617 umol/mmol creatinineAdult (>18 years old)BothADPKD
UrineDetected and Quantified3543.6 +/- 1414.6 umol/mmol creatinineAdult (>18 years old)MaleDrunk driver
Associated Disorders and Diseases
Disease References
Alcoholism
  • Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. Pubmed: 2779169
  • Jones AW, Helander A: Changes in the concentrations of ethanol, methanol and metabolites of serotonin in two successive urinary voids from drinking drivers. Forensic Sci Int. 1998 May 11;93(2-3):127-34. Pubmed: 9717263
Cervical myelopathy
  • Meshitsuka S, Morio Y, Nagashima H, Teshima R: 1H-NMR studies of cerebrospinal fluid: endogenous ethanol in patients with cervical myelopathy. Clin Chim Acta. 2001 Oct;312(1-2):25-30. Pubmed: 11580906
Kidney disease
  • Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. Pubmed: 914932
Lung Cancer
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
Abnormal
  • Schneider H, Glatt H: Sulpho-conjugation of ethanol in humans in vivo and by individual sulphotransferase forms in vitro. Biochem J. 2004 Nov 1;383(Pt. 3):543-9. Pubmed: 15281911
Associated OMIM IDs
DrugBank IDDB00898
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000753
KNApSAcK IDC00019560
Chemspider ID682
KEGG Compound IDC00469
BioCyc IDETOH
BiGG ID35062
Wikipedia LinkEthanol
NuGOwiki LinkHMDB00108
Metagene LinkHMDB00108
METLIN ID3203
PubChem Compound702
PDB IDEOH
ChEBI ID16236
References
Synthesis ReferenceLashley, 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)Not Available
General References
  1. 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
  2. Gordon Z, Parsons CL, Monga M: Intravesical ethanol test: an ineffective measure of bladder hyperpermeability. Urology. 2003 Mar;61(3):555-7. Pubmed: 12639646
  3. 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
  4. Friedman GD, Klatsky AL, Siegelaub AB: Alcohol, tobacco, and hypertension. Hypertension. 1982 Sep-Oct;4(5 Pt 2):III143-50. Pubmed: 7049929
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. Pohorecky LA: Influence of alcohol on peripheral neurotransmitter function. Fed Proc. 1982 Jun;41(8):2452-5. Pubmed: 6123447
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. Snyder R, Kalf GF: A perspective on benzene leukemogenesis. Crit Rev Toxicol. 1994;24(3):177-209. Pubmed: 7945890
  22. McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. Pubmed: 9880479
  23. 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
  24. Hingson R, Winter M: Epidemiology and consequences of drinking and driving. Alcohol Res Health. 2003;27(1):63-78. Pubmed: 15301401
  25. Chastain G: Alcohol, neurotransmitter systems, and behavior. J Gen Psychol. 2006 Oct;133(4):329-35. Pubmed: 17128954

Only showing the first 50 proteins. There are 52 proteins in total.

Enzymes

Gene Name:
PON3
Uniprot ID:
Q15166
Gene Name:
PON1
Uniprot ID:
P27169
Gene Name:
PON2
Uniprot ID:
Q15165
Gene Name:
ACP2
Uniprot ID:
P11117
Gene Name:
ALPPL2
Uniprot ID:
P10696
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Gene Name:
SORD
Uniprot ID:
Q00796
Gene Name:
AKR1A1
Uniprot ID:
P14550
Reactions
Ethanol + NADP unknown Acetaldehyde + NADPH + Hydrogen Iondetails
Gene Name:
ADH4
Uniprot ID:
P08319
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Gene Name:
ADH5
Uniprot ID:
P11766
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
MPST
Uniprot ID:
P25325
Gene Name:
ADH1B
Uniprot ID:
P00325
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH7
Uniprot ID:
P40394
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH1A
Uniprot ID:
P07327
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH6
Uniprot ID:
P28332
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ADH1C
Uniprot ID:
P00326
Reactions
Ethanol + NAD unknown Acetaldehyde + NADH + Hydrogen Iondetails
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
FUCA2
Uniprot ID:
Q9BTY2
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
LRAT
Uniprot ID:
O95237
Gene Name:
FAR2
Uniprot ID:
Q96K12
Gene Name:
AWAT2
Uniprot ID:
Q6E213
41. Klotho
Gene Name:
KL
Uniprot ID:
Q9UEF7
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Gene Name:
GLRA1
Uniprot ID:
P23415
Gene Name:
GLRA2
Uniprot ID:
P23416
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Gene Name:
ACPL2
Uniprot ID:
Q8TE99
Gene Name:
TP53I3
Uniprot ID:
Q53FA7

Only showing the first 50 proteins. There are 52 proteins in total.