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Record Information
Version2.0
Creation Date2009-05-06 21:42:19 UTC
Update Date2014-12-24 20:22:48 UTC
Accession NumberT3D0772
Identification
Common NameEthylene glycol
ClassSmall Molecule
DescriptionEthylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. Ethylene glycol is toxic, and its accidental ingestion should be considered a medical emergency. (14)
Compound Type
  • Coolant
  • Cosmetic Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,2-Dihydroxyethane
1,2-Ethandiol
1,2-Ethanediol
2-Hydroxyethanol
Aliphatic diol
Dihydroxyethane
Dowtherm SR 1
Ethane-1,2-diol
Ethanediol
Ethylene alcohol
Ethylene dihydrate
Ethylene glycol
Ethylene gycol
Fridex
Glycol
Glycol alcohol
Glycol, polyethylene
Glygen
HO-CH2-CH2-OH
Macrogol 400 BPC
Monoethylene glycol
Norkool
Chemical FormulaC2H6O2
Average Molecular Mass62.068 g/mol
Monoisotopic Mass62.037 g/mol
CAS Registry Number107-21-1
IUPAC NameNot Available
Traditional NameNot Available
SMILESOCCO
InChI IdentifierInChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
InChI KeyInChIKey=LYCAIKOWRPUZTN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceOdorless, colorless, syrupy liquid (14).
Experimental Properties
PropertyValue
Melting Point-13°C
Boiling PointNot Available
Solubility1000 mg/mL [RIDDICK,JA et al. (1986)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility950.0 mg/mLALOGPS
logP-1.5ALOGPS
logS1.18ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-03e9-9000000000-7d7e99366b74aa908fb5View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-3f04f129d6a8c819d7bcView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-eaa1e5b7b88211fa7edbView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-dcef056f352184a24448View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS)splash10-00di-9300000000-1cb14d2c8cf1747328ebView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-3f04f129d6a8c819d7bcView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-eaa1e5b7b88211fa7edbView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-dcef056f352184a24448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-1d69e3daf74c74648262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-7060d349c304512b9f75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-3bc95e388ddb6eadd69dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-c649f289b243e440bfa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-7d8813644ca43096609fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-17eed3caf789fe508145View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2fa6f85cb914a856ccc3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (10) ; dermal (10)
Mechanism of ToxicityEthylene glycol is metabolized by alcohol dehydrogenase to glycoaldehyde, which is then metabolized to glycolic, glyoxylic, and oxalic acids. These acids, along with excess lactic acid are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic and glyoxylic acids. Ethylene glycol produces central nervous system depression. The glycol probably causes the initial CNS depression; oxalate and the other intermediates seem to be responsible for nephrotoxicity. Glycoaldehyde and glyoxylate may be the principal metabolites responsible for EG nephrotoxicity and do so by causing ATP depletion and phospholipid and enzyme destruction. Glycine and acidosis, by-products of EG metabolism, can attenuate glyoxylate-mediated injury. This suggests that naturally occurring but incomplete protective pathways may be operative during the evolution of EG cytotoxicity. (6, 7, 1)
MetabolismThe main steps in degradation of ethylene glycol are as follows: ethylene glycol--> glycoaldehyde--> glycolic and glyoxylic acid. Glyoxylic acid is then metabolized into a number of chemicals that have been identified in expired air, urine, or blood. The metabolism of ethylene glycol to glycoaldehyde is mediated by alcohol dehydrogenase. Glycoaldehyde is metabolized to glycolic acid by aldehyde oxidase or to a lesser extent to glyoxal. Glyoxal is changed both to glycolic acid in the presence of lactic dehydrogenase, aldehyde oxidase, or possibly both enzymes, and to glyoxylic acid via some oxidative mechanism. The main path of the degradation of glycolic acid is to glyoxylic acid. This reaction is mediated by lactic dehydrogenase or glycolic acid oxidase. Once glyoxylic acid is formed, it is apparently degraded very rapidly to a variety of products, a few of which have been observed. Its breakdown to 2-hydroxy-3-oxoadipate it is thought, is mediated by thiamine pyrophosphate in the presence of magnesium ions. The formation of glycine involves pyridoxal phosphate and glyoxylate transaminase, whereas the formation of carbon dioxide and water via formic acid apparently involves coenzyme A (CoA) and flavin mononucleotides. Oxalic acid formation from glyoxylic acid, has been considered to be the results from the action of lactic dehydrogenase or glycolic acid oxidase. (10)
Toxicity ValuesLD50: 4700 mg/kg (Oral, Rat) (15) LD50: 5010 mg/kg (Intraperitoneal, Rat) (8) LD50: 3260 mg/kg (Intravenous, Rat) (8) LD50: 2800 mg/kg (Subcutaneous, Rat) (9) LD50: 9530 mg/kg (Dermal, Rabbit) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThe major use of ethylene glycol is as a coolant or antifreeze in, for example, automobiles and personal computers. Ethylene glycol has become increasingly important in the plastics industry for the manufacture of polyester fibers and resins, including polyethylene terephthalate, which is used to make plastic bottles for soft drinks. (14)
Minimum Risk LevelAcute Inhalation: 2 mg/m3 (13) Acute Oral: 0.8 mg/kg/day (13)
Health EffectsHealth effects of ethylene glycol poisoning include tachycardia, hypertension, hyperventilation, and metabolic acidosis. Stage 3 of ethylene glycol poisoning is the result of kidney injury, leading to acute kidney failure. Oxalic acid reacts with calcium and forms calcium oxalate crystals in the kidney (14).
SymptomsSymptoms of ethylene glycol poisoning usually follow a three-step progression. Stage 1 consists of neurological symptoms including victims appearing to be intoxicated, exhibiting symptoms such as dizziness, headaches, slurred speech, and confusion. Over time, the body metabolizes ethylene glycol into other toxins, it is first metabolized to glycolaldehyde, which is then oxidized to glycolic acid, glyoxylic acid, and finally oxalic acid. Stage 2 is a result of accumulation of these metabolites and consists of tachycardia, hypertension, hyperventilation, and metabolic acidosis. Stage 3 of ethylene glycol poisoning is the result of kidney injury, leading to acute kidney failure. Oxalic acid reacts with calcium and forms calcium oxalate crystals in the kidney. (14, 3)
TreatmentInitial treatment consists of stabilizing the patient and gastric decontamination. Gastric lavage or nasogastric aspiration of gastric contents are the most common methods employed in ethylene glycol poisoning. Ipecac-induced vomiting or activated charcoal. The antidotes for ethylene glycol poisoning are ethanol or fomepizole; antidotal treatment forms the mainstay of management following ingestion. Ethanol (usually given IV as a 5 or 10% solution in 5% dextrose and water, but also sometimes given in the form of a strong spirit such as whisky, vodka or gin) acts by competing with ethylene glycol for the enzyme alcohol dehydrogenase thus limiting the formation of toxic metabolites. Fomepizole acts by inhibiting alcohol dehydrogenase, thus blocking the formation of the toxic metabolites. (2, 4, 5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID174
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC01380
UniProt IDNot Available
OMIM ID
ChEBI ID30742
BioCyc IDCPD-347
CTD IDD019855
Stitch IDEthylene glycol
PDB IDNot Available
ACToR ID607
Wikipedia LinkEthylene_glycol
References
Synthesis ReferenceNot Available
MSDST3D0772.pdf
General References
  1. Poldelski V, Johnson A, Wright S, Rosa VD, Zager RA: Ethylene glycol-mediated tubular injury: identification of critical metabolites and injury pathways. Am J Kidney Dis. 2001 Aug;38(2):339-48. [11479160 ]
  2. Brent J: Current management of ethylene glycol poisoning. Drugs. 2001;61(7):979-88. [11434452 ]
  3. Field DL: Acute ethylene glycol poisoning. Crit Care Med. 1985 Oct;13(10):872-3. [4028762 ]
  4. Barceloux DG, Krenzelok EP, Olson K, Watson W: American Academy of Clinical Toxicology Practice Guidelines on the Treatment of Ethylene Glycol Poisoning. Ad Hoc Committee. J Toxicol Clin Toxicol. 1999;37(5):537-60. [10497633 ]
  5. Brent J, McMartin K, Phillips S, Burkhart KK, Donovan JW, Wells M, Kulig K: Fomepizole for the treatment of ethylene glycol poisoning. Methylpyrazole for Toxic Alcohols Study Group. N Engl J Med. 1999 Mar 18;340(11):832-8. [10080845 ]
  6. Yamamoto N, Naraparaju VR: Vitamin D3-binding protein as a precursor for macrophage activating factor in the inflammation-primed macrophage activation cascade in rats. Cell Immunol. 1996 Jun 15;170(2):161-7. [8660814 ]
  7. Yamamoto N, Naraparaju VR: Role of vitamin D3-binding protein in activation of mouse macrophages. J Immunol. 1996 Aug 15;157(4):1744-9. [8759764 ]
  8. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  9. American Conference of Governmental Industrial Hygienists (2001). Documentation of Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices for 2001. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  10. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  11. Olson, KR (ed) (1999). Poisoning & Drug Overdose. 3rd edition. New York, NY: Lange Medical Books/McGraw-Hill.
  12. Gilman AG, Goodman LS, and Gilman A (eds) (1980). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York, NY: Macmillan Publishing Co., Inc.
  13. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  14. Wikidoc. Ethylene glycol. Last Updated 11 June 2009. [Link]
  15. The Physical and Theoretical Chemistry Laboratory of Oxford University (2009). Material Safety Data Sheet (MSDS) for ethylene glycol. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available