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Chemistry

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Also known as: Ethane-1,2-diol, 1,2-ethanediol, 107-21-1, Glycol, Monoethylene glycol, 1,2-dihydroxyethane
Molecular Formula
C2H6O2
Molecular Weight
62.07  g/mol
InChI Key
LYCAIKOWRPUZTN-UHFFFAOYSA-N
FDA UNII
FC72KVT52F

Macrogol
A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.
1 2D Structure

Macrogol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethane-1,2-diol
2.1.2 InChI
InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
2.1.3 InChI Key
LYCAIKOWRPUZTN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CO)O
2.2 Other Identifiers
2.2.1 UNII
FC72KVT52F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2 Ethanediol

2. 1,2-ethanediol

3. 2 Hydroxyethanol

4. 2-hydroxyethanol

5. Glycol, Ethylene

6. Glycol, Monoethylene

7. Monoethylene Glycol

2.3.2 Depositor-Supplied Synonyms

1. Ethane-1,2-diol

2. 1,2-ethanediol

3. 107-21-1

4. Glycol

5. Monoethylene Glycol

6. 1,2-dihydroxyethane

7. 2-hydroxyethanol

8. Glycol Alcohol

9. Ethylene Alcohol

10. Polyethylene Glycol

11. Macrogol

12. Fridex

13. Tescol

14. Ethylene Dihydrate

15. Norkool

16. Macrogol 400 Bpc

17. Dowtherm Sr 1

18. Ethanediol

19. Zerex

20. Poly(ethylene Glycol)

21. Ucar 17

22. Lutrol-9

23. Polyethylene Glycol 200

24. Ethyleneglycol

25. Aethylenglykol

26. Ethylenglycol

27. 1,2-ethandiol

28. Polyethylene Glycol 1000

29. 1,2-ethylene Glycol

30. 1,2-dihydroxy Ethane

31. Ethylen Glycol

32. Ethylene-glycol

33. 146ar

34. Polyethylene Glycol 3350

35. Lutrol 9

36. Mfcd00002885

37. Nsc 93876

38. Carbowax 300

39. Peg

40. Hoch2ch2oh

41. Union Carbide Xl 54 Type I De-icing Fluid

42. Peg 1000

43. M.e.g.

44. Fc72kvt52f

45. Dtxsid8020597

46. Chebi:30742

47. 1, 2-ethanediol

48. Nsc-93876

49. Dsstox_cid_597

50. Dsstox_rid_75680

51. Dsstox_gsid_20597

52. Glycol, Ethylene-

53. Glycol, Polyethylene

54. Glycols, Polyethylene

55. Caswell No. 441

56. Aethylenglykol [german]

57. Polyethylene Oxide

58. Carbowax 20

59. Cas-107-21-1

60. Polyethylene Glycols

61. Carbowax 400

62. Carbowax 1000

63. Ccris 3744

64. Dowtherm 4000

65. Hsdb 5012

66. Ethylene Glycol Polymer

67. Nci-c00920

68. Peg 3350

69. Einecs 203-473-3

70. Ethylene Glycol Homopolymer

71. Polyethylene Glycol 6000

72. Unii-fc72kvt52f

73. Epa Pesticide Chemical Code 042203

74. 1,2-ethanediol Homopolymer

75. Wln: Q2q

76. Ethyleneglycole

77. Athylenglykol

78. Ehtylene Glycol

79. Etylene Glycol

80. Ai3-03050

81. 2-ethanediol

82. Polyaethylenglykol

83. Ilexan E

84. 4-vinyl Cathecol

85. Polyaethylenglykole

86. Meg 100

87. Solbanon (tn)

88. 1,2-ethane Diol

89. 1,2-ethane-diol

90. Ethane-1.2-diol

91. Gxt

92. Peg 4000

93. 1,2-ethyleneglycol

94. Ethan-1,2-diol

95. Mono-ethylene Glycol

96. Macrogol 400

97. Carbowax 1540

98. 1,2-ethylene-glycol

99. Lutrol E (tn)

100. Nanosilver+eg

101. Ylene Glycol

102. Dupont Zonyl Fso Fluorinated Surfactants

103. Ethylene Glycol-[d6]

104. Alpha-hydro-omega-hydroxypoly(oxyethylene)

105. Glycol [inci]

106. Polyethylene Glycol-400

107. Macrogol 400 (tn)

108. Polyethylene Oxide (nf)

109. Polyethylene Glycol (nf)

110. Sentry Polyox Wsr (tn)

111. Ethyleneglycol, Reagentplus

112. Macrogol 1500 (tn)

113. Macrogol 4000 (tn)

114. Macrogol 6000 (tn)

115. Ec 203-473-3

116. Lowenol T-163a

117. Macrogol Ointment (jp17)

118. Glycol, Polyethylene(300)

119. Ho(ch2)2oh

120. Nciopen2_001979

121. Nciopen2_002019

122. Nciopen2_002100

123. Macrogol 400 (jp17)

124. Ethylene Glycol [ii]

125. Ethylene Glycol [mi]

126. Polyethylene Glycol 300 Nf

127. Alpha-hydro-omega-hydroxypoly(oxy-1,2-ethanediyl)

128. Ethylene Glycol 5 M Solution

129. Mls002454404

130. Polyethylene Glycol, Diglycidyl Bisphenol A Polymer

131. Bidd:er0283

132. Fisherfresh™ Concentrate

133. Macrogol 1500 (jp17)

134. Macrogol 4000 (jp17)

135. Macrogol 6000 (jp17)

136. Ethylene Glycol [hsdb]

137. Chembl457299

138. Ethylene Glycol [mart.]

139. Ethylene Glycol, Ar, >=99%

140. Ethylene Glycol, Lr, >=99%

141. Macrogol 20000 (jp17)

142. Chebi:46793

143. Ethylene Glycol [usp-rs]

144. Ethylene Glycol [who-dd]

145. Peg1000

146. Hms2267f07

147. Poly(ethylene Glycol) Methyl Ether

148. Polyethylene Glycol 3350 (usp)

149. Ethylene Glycol, P.a., 99.5%

150. Lowenol Copolymer 1985-a

151. Lowenol Copolymer 1985-b

152. 1,2-ethanediol (glycol)

153. Amy22336

154. Nsc32853

155. Nsc32854

156. Nsc57859

157. Nsc93876

158. Peg 3600

159. Peg-1000

160. Poly (ethylene Glycol) Methyl Ether

161. Str01171

162. Zinc5224354

163. Ethylene Glycol, Analytical Standard

164. Tox21_202038

165. Tox21_300637

166. Ethane-1,2-diol (ethylene Glycol)

167. Ethylene Glycol, Anhydrous, 99.8%

168. Nsc-32853

169. Nsc-32854

170. Nsc-57859

171. Nsc152324

172. Nsc152325

173. Nsc155081

174. Polyethylene Glycol 8000, Nf Fcc

175. Stl264188

176. Akos000119039

177. Alpha,omega-hydroxypoly(ethylene Oxide)

178. Nsc-152324

179. Nsc-152325

180. Nsc-155081

181. Ethylene Glycol, Spectrophotometric Grade

182. Ncgc00091510-01

183. Ncgc00091510-02

184. Ncgc00091510-03

185. Ncgc00254292-01

186. Ncgc00259587-01

187. Bp-13454

188. Bp-31056

189. Glycerol Impurity B [ep Impurity]

190. Oxirane, 2,2'-((1-methylethylidene)bis(4,1-phenyleneoxymethylene))bis-, Polymer With Alpha-hydro-omega-hydroxypoly(oxy-1,2-ethanediyl)

191. Smr001262244

192. Dihydrocarveol, (-)-, Mixture Of Isomers

193. Ethylene Glycol High Purity Grd 1l

194. Ethylene Glycol, Reagentplus(r), >=99%

195. Dupont Zonyl Fse Fluorinated Surfactants

196. Ethylene Glycol 100 Microg/ml In Methanol

197. Residual Solvent Class 2 - Ethylene Glycol

198. E0105

199. Ethylene Glycol 1000 Microg/ml In Methanol

200. Ethylene Glycol, Puriss., >=99.5% (gc)

201. Ft-0626292

202. Ft-0692978

203. 1,2-ethane-1,1,2,2-d4-diol-d2(9ci)

204. Ethylene Glycol, Bioultra, >=99.5% (gc)

205. Ethylene Glycol, Saj First Grade, >=99.0%

206. C01380

207. D03370

208. D06418

209. D06419

210. D06420

211. D06421

212. D06422

213. D06423

214. Ethylene Glycol, Jis Special Grade, >=99.5%

215. Ethylene Glycol, Anhydrous, Zero2(tm), 99.8%

216. Ethylene Glycol, Vetec(tm) Reagent Grade, 98%

217. A851234

218. Ethylene Glycol, Spectrophotometric Grade, >=99%

219. Q194207

220. J-001731

221. F0001-0142

222. 004143f9-240e-472f-9d5a-b1b13bba2a18

223. Poly(oxy-1,2-ethanediyl), .alpha.-hydro-.omega.-hydroxy-

224. Ethylene Glycol, United States Pharmacopeia (usp) Reference Standard

225. Propylene Glycol Related Compound Ethylene Glycol [usp Impurity]

226. Ethylene Glycol, Pharmaceutical Secondary Standard; Certified Reference Material

227. Ethylene Glycol Solution, Nmr Reference Standard, 80% In Dmso-d6 (99.9 Atom % D), Nmr Tube Size 3 Mm X 8 In.

228. Ethylene Glycol Solution, Nmr Reference Standard, 80% In Dmso-d6 (99.9 Atom % D), Nmr Tube Size 5 Mm X 8 In.

229. Ethylene Glycol;1,2-ethanediol;ethane-1,2-diol;glycolethylene Glycol;ethanediol;ethylene Glycol 1,2-ethanediol Ethane-1,2-diol Glycolethylene Glycol Ethanediol

230. Residual Solvent Class 2 - Ethylene Glycol, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 62.07 g/mol
Molecular Formula C2H6O2
XLogP3-1.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass62.036779430 g/mol
Monoisotopic Mass62.036779430 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count4
Formal Charge0
Complexity6
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

Lethal dose = 1.4 mL/kg (approximately 1.5 g/kg), or 100 mL for adults (70 kg).

inchem - pim


Doses of 1.0 to 2.0 g/kg bw (100 mL) are lethal in humans.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 726


4.2 Drug Indication

Polyethylene glycol is indicated for use as an over-the-counter osmotic laxative to relieve occasional constipation. When used in combination with sodium ascorbate, sodium sulfate, ascorbic acid, sodium chloride and potassium chloride, it is used for cleansing of the colon in preparation for colonoscopy in adults.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

The osmotic effect of PEG produces a copious watery diarrhea. The onset of action of PEG 3350 is about 1 to 2 hours after oral ingestion. The colonic transit of polyethylene glycol occurs in a dose-dependent manner. When used for bowel preparation before colonscopy, electrolytes are typically added in the oral solution to prevent dehydration and electrolyte disturbances. As an over-the-counter laxative, the OTC product does not contain any salts that can be absorbed. In a study involving healthy subjects, PEG 3350 had negligible effects on colonic fluid absorption or with the ability of the colonic mucosa to generate and sustain steep electrochemical gradients.


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Osmotic Laxative [EPC]; Stimulation Large Intestine Fluid/Electrolyte Secretion [PE]; Osmotic Activity [MoA]
5.3 ATC Code

A - Alimentary tract and metabolism

A06 - Drugs for constipation

A06A - Drugs for constipation

A06AD - Osmotically acting laxatives

A06AD15 - Macrogol


5.4 Absorption, Distribution and Excretion

Absorption

Following a two-day split-dosing regimen of an oral suspension containing 140 grams of PEG 3350 in healthy subjects, the mean Cmax was 2.7 mcg/mL and the mean Tmax was 3 hours. Typically, polyethylene glycols with a high molecular weight are poorly absorbed from the gastrointestinal tract following oral administration.


Route of Elimination

Following administration of an oral suspension containing 140 grams of PEG 3350 in healthy subjects, up to 85% to 99% of the compound was excreted in the feces.


Volume of Distribution

Following a two-day split-dosing regimen of an oral suspension containing 140 grams of PEG 3350 in healthy subjects, the mean volume of distribution was 48,481 L.


Clearance

There is limited information on the clearance rate of polyethylene glycols.


During 4 hr following iv dose of (14)C-ethylene glycol, urinary excretion of (14)C was more rapid from rats (38%) than from rhesus monkeys (10%), but excretion in expired air was similar (about 5%). Some (14)C entered body carbon pool. Oral dose was also more rapidly excreted by rats.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 157


Study of renal clearance of ethylene glycol suggests that glomerular filtration and passive reabsorption are main mechanisms involved in renal excretion of ethylene glycol.

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 481


The proportion of administered (14)C (as ethylene glycol) excreted in urine of rats varied with dosage, being 21% at dose of 0.1 g/kg and 78% at dose of 7.5 g/kg. Distribution of radioactivity 24 hr after administration ...to rats was highest in bones (2-10%); highest in muscle of rabbits (3.4%), although liver contained 1.4 and bone 1.7% of dose.

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1501


A dose-dependent change was observed in disposition of (14)C-labeled ethylene glycol after iv administration of 20, 200, 1000, and 2000 mg/kg to Fischer 344 rats. Part of the dose was expired as carbon dioxide and decreased from 39% at 20 and 200 mg/kg to 26% at 1000 and 2000 mg/kg, while urinary excretion of radiocarbon increased from 35 to 56%. As dose increased from 20 to 2,000 mg/kg increases in urinary (14)C was almost entirely attributable to (14)C-glycolate, which comprised 20% of dose in 24 hrs at two higher dose levels and only 2% at lower doses. Blood clearance of (14)C occurred in initial rapid phase (half-life, 3-5 hr), when plasma comprised predominantly of ethylene glycol, that persisted for 12 hrs at 20 mg/kg and 30 hr at 2000 mg/kg administered iv to Fischer 344 rats.

PMID:7175970 Marshall TC; J Toxicol Environ Health 10 (3): 397-409 (1982)


For more Absorption, Distribution and Excretion (Complete) data for ETHYLENE GLYCOL (16 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Polyethylene glycol is a metabolically inert laxative that does not undergo intestinal enzymatic degradation or bacterial metabolism.


Multiple metabolites contribute to the toxic effects. Glycolaldehyde and glyoxylate are more toxic than glycolate, although the latter is the only metabolite that accumulates in appreciable amounts, owing to the rate-limiting effect of lactate dehydrogenase or glycolate oxidase. Glyoxylate can be converted to numerous metabolites, the most toxic of which is oxalic acid (oxalate). Oxalate complexes with calcium to form calcium oxalate crystals, which are deposited in various tissues.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 758


Although oxalate normally is a minor metabolic product of ethylene glycol metabolism, urinary oxalate crystals are a common, but not invariable, feature of ethylene glycol intoxication. There are two forms of urinary calcium oxalate crystals: the octahedral or tent-shaped form of the dihydrate crystals, and the prism or dumbell-shaped monohydrate. The latter form is stable under normal physiologic conditions; the dihydrate form appears only during high urinary calcium and oxalate concentrations, as seen in ethylene glycol poisoning. The dihydrate form can transform into the monohydrate form.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1153


In oxidative metabolism of ethylene glycol in mammals, species variations occur which explain... differences in toxicity. Glycol is oxidized by major pathway into carbon dioxide, and by minor pathway to ... oxalic acid. Extent of formation of oxalic acid is dependent on dose level, but has ... been shown to vary with species ...

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 118


Rabbits and rats were given doses of 0.1-2.0 g/kg /of (14)C-ethylene glycol/. Rabbits received the doses orally or by subcutaneous injection, rats were given subcutaneous injections. In rabbits and rats, approximately 20% to 30% of the (14)C label from ethylene glycol (14)C was eliminated in the urine. Metabolites found in the 24-hr urine incl unchanged ethylene glycol (6.0 to 15.1%) and a trace of oxalic acid (0.1%

PMID:13704828 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1205673 Gessner PK et al; Biochem J 79: 482-89 (1961)


For more Metabolism/Metabolites (Complete) data for ETHYLENE GLYCOL (10 total), please visit the HSDB record page.


5.6 Biological Half-Life

Following a two-day split-dosing regimen of an oral suspension containing 140 grams of PEG 3350 in healthy subjects, the mean half life was 4.1 hours.


Serum: 2-3 hours; not detectable in urine or tissues after 24-48 hours (metabolites present for longer periods); [TDR, p. 659]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 659


... Ingestion of the 2 alcohols resulted in a peculiar intoxication due to their metabolic interaction. The half-life of ethylene glycol was prolonged to 14 hr.

Divanon F et al; J. Pharm. Clin 16(3): 177-182 (1997)


Hepatic metabolism occurs through successive oxidations by the enzyme alcohol dehydrogenase. The elimination half life of ethylene glycol in the absence of alcohol dehydrogenase inhibitors is 2.5 to 3.0 hours. If alcohol dehydrogenase inhibitor therapy is instituted before the development of renal insufficiency, the elimination half life lengthens to approximately 17 hours, mostly via normal renal elimination. In the presence of fomepizole, the elimination half life is increased to approximately 20 hours.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1224


...After iv administration of 20, 200, 1000, and 2000 mg/kg /ethylene glycol/ to Fischer 344 rats. ...Blood clearance of (14)C occurred in initial rapid phase (half-life, 3-5 hr)... .

PMID:7175970 Marshall TC; J Toxicol Environ Health 10 (3): 397-409 (1982)


... Rats /were exposed/ (nose only) to (14)C-ethylene glycol vapor at a concentration of 32 mg/L for 30 min. ...After 6 hr, blood levels declined by apparent first order kinetics with a half life of 53 hr.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 9


Plasma half-lives in rodents, monkeys, and dogs (receiving 1-1000 mg/kg body weight) range from 1 to 4 hr.

International Programme on Chemical Safety; Concise International Chemical Assessment Document Number 45 Ethylene Glycol: Human Health Effects (2002). Available from, as of October 6, 2011: https://www.inchem.org/pages/cicads.html


5.7 Mechanism of Action

Osmotic laxatives contain substances that are poorly absorbable and draw water into the lumen of the bowel. Polyethylene glycol functions is an osmotic laxative that causes increased water retention in the lumen of the colon by binding to water molecules, thereby producing loose stools.


Ethylene 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.

Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 193


API Reference Price

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24-Jan-2021
28-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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