Ethylene glycol (CHEM000695)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2009-05-06 21:42:19 UTC
Update Date2026-03-26 21:21:12 UTC
Accession NumberCHEM000695
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. (9)
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Coolant
  • Cosmetic Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-DihydroxyethaneChEBI
1,2-EthanediolChEBI
2-HydroxyethanolChEBI
EthanediolChEBI
GlycolChEBI
HO-CH2-CH2-OHChEBI
Monoethylene glycolChEBI
1,2 EthanediolHMDB
Glycol, monoethyleneHMDB
2 HydroxyethanolHMDB
Glycol, ethyleneHMDB
Poly(ethylene glycol)HMDB
Polyethylene oxideHMDB
Poly(ethylene oxide)HMDB
PolyoxyethyleneHMDB
Poly(oxyethylene)HMDB
PEGHMDB
PEOHMDB
POEHMDB
AlkoxHMDB
CarbowaxHMDB
Carbowax sentryHMDB
MacrogolHMDB
MiraLaxHMDB
Α,ω-hydroxypoly(ethylene oxide)HMDB
Α-hydro-ω-hydroxypoly(oxy-1,2-ethanediyl)HMDB
Α-hydro-ω-hydroxypoly(oxyethylene)HMDB
alpha,Omega-hydroxypoly(ethylene oxide)HMDB
alpha-Hydro-omega-hydroxypoly(oxy-1,2-ethanediyl)HMDB
alpha-Hydro-omega-hydroxypoly(oxyethylene)HMDB
Ethylene glycol homopolymerHMDB
Ethylene glycol polymerHMDB
Ethylene oxide polymerHMDB
Ethylene polyoxideHMDB
Ethylene glycolHMDB
Polyethylene glycolHMDB
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 KeyLYCAIKOWRPUZTN-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 (9).
Experimental Properties
PropertyValue
Melting Point-13°C
Boiling PointNot Available
Solubility1000 mg/mL [RIDDICK,JA et al. (1986)]
Predicted Properties
PropertyValueSource
Water Solubility950 g/LALOGPS
logP-1.5ALOGPS
logS1.18ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-3f04f129d6a8c819d7bcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-eaa1e5b7b88211fa7edbSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-dcef056f352184a24448Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-3f04f129d6a8c819d7bcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-eaa1e5b7b88211fa7edbSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-dcef056f352184a24448Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-9000000000-7d7e99366b74aa908fb5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9300000000-1cb14d2c8cf1747328ebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-1d69e3daf74c74648262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-7060d349c304512b9f75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-3bc95e388ddb6eadd69dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-c649f289b243e440bfa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-7d8813644ca43096609fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-17eed3caf789fe508145Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-bc322895724fc86f7dc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-8057e63671cfd392ae43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f589ce99213e8dfb1d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-8eeb88a032ec50107369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc2940Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-00ba25458eb6c0cc2940Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2fa6f85cb914a856ccc3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (13) ; dermal (13)
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. (2, 3, 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. (13)
Toxicity ValuesLD50: 4700 mg/kg (Oral, Rat) (10) LD50: 5010 mg/kg (Intraperitoneal, Rat) (11) LD50: 3260 mg/kg (Intravenous, Rat) (11) LD50: 2800 mg/kg (Subcutaneous, Rat) (12) LD50: 9530 mg/kg (Dermal, Rabbit) (12)
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. (9)
Minimum Risk LevelAcute Inhalation: 2 mg/m3 (8) Acute Oral: 0.8 mg/kg/day (8)
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 (9).
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. (9, 5)
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. (4, 6, 7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0037790
FooDB IDFDB009379
Phenol Explorer IDNot Available
KNApSAcK IDC00007409
BiGG IDNot Available
BioCyc IDGLYCOL
METLIN IDNot Available
PDB IDEDO
Wikipedia LinkEthylene_Glycol
Chemspider ID13835235
ChEBI ID30742
PubChem Compound ID174
Kegg Compound IDC15588
YMDB IDYMDB00905
ECMDB IDECMDB20146
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10349109
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716482
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16901854
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17186009
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17336832
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17979222
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18612987
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23764541
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23827374
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24045699
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24643482
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25108762
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9463526
15. Tonini M: Polyethylene glycol as a non-absorbable prokinetic agent in the lower gastrointestinal tract. Ital J Gastroenterol Hepatol. 1999 Nov;31 Suppl 3:S238-41.
16. Estrela C, Pesce HF: Chemical analysis of the formation of calcium carbonate and its influence on calcium hydroxide pastes in connective tissue of the dog--Part II. Braz Dent J. 1997;8(1):49-53.
17. Armstead WM: Role of altered cyclooxygenase metabolism in impaired cerebrovasodilation to nociceptin/orphanin FQ following brain injury. Brain Res Bull. 2000 Dec;53(6):807-12.
18. Carreira Cde M, dos Santos SS, Jorge AO, Lage-Marques JL: Antimicrobial effect of intracanal substances. J Appl Oral Sci. 2007 Oct;15(5):453-8.
19. Pashankar DS: Childhood constipation: evaluation and management. Clin Colon Rectal Surg. 2005 May;18(2):120-7. doi: 10.1055/s-2005-870894.
20. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
21. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
22. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
23. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
24. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
25. The lipid handbook with CD-ROM