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Chemistry

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Also known as: 112-27-6, Triglycol, 2,2'-(ethane-1,2-diylbis(oxy))diethanol, 2-[2-(2-hydroxyethoxy)ethoxy]ethanol, Triethyleneglycol, Trigen
Molecular Formula
C6H14O4
Molecular Weight
150.17  g/mol
InChI Key
ZIBGPFATKBEMQZ-UHFFFAOYSA-N
FDA UNII
3P5SU53360

Triethylene Glycol
1 2D Structure

Triethylene Glycol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[2-(2-hydroxyethoxy)ethoxy]ethanol
2.1.2 InChI
InChI=1S/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2
2.1.3 InChI Key
ZIBGPFATKBEMQZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(COCCOCCO)O
2.2 Other Identifiers
2.2.1 UNII
3P5SU53360
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2-bis(2-hydroxyethoxy)ethane

2. 2,2'-(1,2-ethanediylbis(oxy))bisethanol

3. 2,2'-(ethylenedioxy)diethanol

4. 2,2'-ethylenedioxybis(ethanol)

5. 3,6-dioxaoctane-1,8-diol

6. Bis(2-hydroxyethoxyethane)

7. Ethylene Glycol Dihydroxydiethyl Ether

8. Polyethylene Glycol (3)

9. Polyethylene Glycol 150

10. Triethylene Glycol, Dipotassium Salt

11. Triethylene Glycol, Disodium Salt

12. Triethylene Glycol, Sodium Salt

2.3.2 Depositor-Supplied Synonyms

1. 112-27-6

2. Triglycol

3. 2,2'-(ethane-1,2-diylbis(oxy))diethanol

4. 2-[2-(2-hydroxyethoxy)ethoxy]ethanol

5. Triethyleneglycol

6. Trigen

7. Triethylenglykol

8. 2,2'-ethylenedioxydiethanol

9. 1,2-bis(2-hydroxyethoxy)ethane

10. 2,2'-(ethylenedioxy)diethanol

11. 2,2'-ethylenedioxybis(ethanol)

12. 3,6-dioxaoctane-1,8-diol

13. Di-beta-hydroxyethoxyethane

14. 2,2'-ethylenedioxyethanol

15. 2,2'-[ethane-1,2-diylbis(oxy)]diethanol

16. Ethanol, 2,2'-[1,2-ethanediylbis(oxy)]bis-

17. Triethylene Glcol

18. Glycol Bis(hydroxyethyl) Ether

19. Ethylene Glycol Dihydroxydiethyl Ether

20. Trigol

21. Teg

22. 2,2'-(1,2-ethanediylbis(oxy))bisethanol

23. Ethanol, 2,2'-(ethylenedioxy)di-

24. Nsc 60758

25. 2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethanol

26. Ethylene Glycol-bis-(2-hydroxyethyl Ether)

27. Di-.beta.-hydroxyethoxyethane

28. 119438-10-7

29. Chebi:44926

30. Ethanol, 2,2'-(1,2-ethanediylbis(oxy))bis-

31. Nsc-60758

32. 3p5su53360

33. Ncgc00163798-03

34. 2-[2-(2-hydroxyethoxy)ethoxy]ethan-1-ol

35. Dsstox_cid_1393

36. Poly(ethylene Glycol) 4-nonylphenyl 3-sulfopropyl Ether, Potassium Salt

37. Dsstox_rid_76135

38. Dsstox_gsid_21393

39. 103734-98-1

40. 122784-99-0

41. 137800-98-7

42. 145112-98-7

43. 2,2'-(ethane-1,2-diylbis(oxy))bis(ethan-1-ol)

44. Caswell No. 888

45. Triethylenglykol [czech]

46. Mfcd00081839

47. Bis(2-hydroxyethoxyethane)

48. Polyethylene Glycol 6,000

49. Cas-112-27-6

50. Hsdb 898

51. Einecs 203-953-2

52. Oh-peg3-oh

53. Epa Pesticide Chemical Code 083501

54. Brn 0969357

55. Trigenos

56. Triethylenglycol

57. Polyethylene Glycol 12,000

58. Polyethylene Glycol 20,000

59. Ai3-01453

60. Ccris 8926

61. Unii-3p5su53360

62. Triethylene-glycol

63. Triethyleneglycol,

64. Tri-ethylene Glycol

65. 3,8-diol

66. Polyethyleneglycol 300

67. Macrogol 150

68. Polyethylene Glycol 1500

69. Ec 203-953-2

70. Polyethylene Glycol 2000

71. Triethylene Glycol, Puriss.

72. Peg-3

73. Polyethylene Glycol 8,000

74. Schembl14929

75. Wln: Q2o2o2q

76. 3,6-dioxa-1,8-octanediol

77. 4-01-00-02400 (beilstein Handbook Reference)

78. Polyethylene Glycol 10,000

79. Amy375

80. Di(2-ethylbutyrate), Diacetate

81. Ethanol,2'-(ethylenedioxy)di-

82. Triethylene Glycol [mi]

83. Chembl1235259

84. Dtxsid4021393

85. Polyethylene Glycol (3)

86. Polyethylene Glycol 150

87. Triethylene Glycol Reagent Grade

88. Triethylene Glycol [hsdb]

89. Triethylene Glycol [inci]

90. Nsc60758

91. Str02345

92. Triethylene Glycol [usp-rs]

93. Triethylene Glycol [who-dd]

94. Zinc1690436

95. Tox21_112073

96. Tox21_202440

97. Tox21_300306

98. Mfcd00002880

99. Mfcd01779596

100. Mfcd01779599

101. Mfcd01779601

102. Mfcd01779603

103. Mfcd01779605

104. Mfcd01779609

105. Mfcd01779611

106. Mfcd01779612

107. Mfcd01779614

108. Mfcd01779615

109. Mfcd01779616

110. Stl282716

111. Akos000120013

112. Triethylene Glycol (industrial Grade)

113. Cs-w018156

114. Db02327

115. Hy-w017440

116. Polyethylene Oxide, M.w. 100,000

117. Polyethylene Oxide, M.w. 300,000

118. Ncgc00163798-01

119. Ncgc00163798-02

120. Ncgc00163798-04

121. Ncgc00163798-05

122. Ncgc00163798-06

123. Ncgc00254097-01

124. Ncgc00259989-01

125. 2-[2-(2-hydroxyethoxy)ethoxy]ethanol #

126. Bp-21036

127. Polyethylene Oxide, M.w. 1,000,000

128. Polyethylene Glycol (peg), 50% Solution

129. Triethylene Glycol, Reagentplus(r), 99%

130. Ethanol,2'-[1,2-ethanediylbis(oxy)]bis-

131. Polyethylene Oxide, M.w. >5,000,000

132. Ft-0652416

133. Ft-0659862

134. T0428

135. F71165

136. Triethylene Glycol, Saj First Grade, >=96.0%

137. Q420630

138. Sr-01000944720

139. Triethylene Glycol, Vetec(tm) Reagent Grade, 98%

140. J-506706

141. Sr-01000944720-1

142. F0001-0256

143. Triethylene Glycol, Bioultra, Anhydrous, >=99.0% (gc)

144. Z1318198494

145. Alpha,omega-bis-hydroxy Poly(ethylene Glycol) (peg-wm 3.000 Dalton)

146. Triethylene Glycol, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 150.17 g/mol
Molecular Formula C6H14O4
XLogP3-1.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass150.08920892 g/mol
Monoisotopic Mass150.08920892 g/mol
Topological Polar Surface Area58.9 Ų
Heavy Atom Count10
Formal Charge0
Complexity49.7
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Four male albino rats weighing 112 to 145 g were given a single oral dose of 22.5 mg randomly radiolabeled 14-C-triethylene glycol. The rats were then placed in a metabolic chamber in which urine, feces, and expired air were collected over a period of 5 days. The radioactivity recovered (in percent of the administered dose) amounted to 0.8 to 1.2% in expired air, 2.0 to 5.3% in feces, and 86.1 to 94.0% in urine. The total recovery of radioactivity was 90.6% to 98.3% of the administered dose.

PMID:17090481 Cosmetic Ingredient Review Expert Panel; Int J Toxicol 25 (Supp 2): 121-38 (2006)


Following oral dosing, the rat and rabbit excreted most of the triethylene glycol in both unchanged and/or oxidized forms (mono- and dicarboxylic acid derivatives of triethylene glycol). In rabbits dosed with 200 or 2000 mg/kg triethylene glycol respectively excreted 34.3% or 28%, of the administered dose in the urine as unchanged triethylene glycol and 35.2% as a hydroxyacid form of this chemical. In the studies with rats, little if any 14-C-oxalate or 14-C-triethylene glycol in conjugated form was found in the urine. Trace amounts of orally administered 14-C triethylene glycol were excreted in expired air as carbon dioxide (<1%) and in detectable amounts in feces (2 to 5 %). The total elimination of radioactivity (urine, feces and CO2) during the five day period following an oral dose of labeled compound (22.5 mg) ranged from 91 to 98%. The majority of the radioactivity appeared in the urine.

U.S. EPA; TRIETHYLENE GLYCOL - Revised Report of the Antimicrobials Division Toxicology Endpoint Selection Committee. 13 pp. November 21, 2005. Avaliable at https://www.epa.gov.edocket as OPP-2005-0250-0003.


No studies have been reported dealing with the skin absorption of triethylene glycol. Although it is possible that under conditions of very severe prolonged exposures to this chemical, absorption through the skin can occur, it is doubtful any appreciable systemic/dermal injury would occur because triethylene glycol has (1) a low order of dermal irritancy, (2) is not a dermal sensitizer, and (3) showed no evidence of dermal or systemic toxicity following repeated dermal applications of 2 mL (approximately 600 mg/kg) triethylene glycol applied to the skin of rabbits in a 21-day dermal toxicity study.

U.S. EPA; TRIETHYLENE GLYCOL - Revised Report of the Antimicrobials Division Toxicology Endpoint Selection Committee. 13 pp. November 21, 2005. Avaliable at https://www.epa.gov.edocket as OPP-2005-0250-0003.


4.2 Metabolism/Metabolites

Two female New Zealand white rabbits triethylene glycol by stomach tube. Urine from the dosed animals was subsequently collected for 24 hrs. Rabbits dosed with 200 or 2,000 mg/kg respectively excreted 34.3% or 28% of the dose amount as unchanged triethylene glycol. The urine of one rabbit contained 35.2% of the administered dose as a hydroxyacid form of triethylene glycol.

PMID:17090481 Cosmetic Ingredient Review Expert Panel; Int J Toxicol 25 (Supp 2): 121-38 (2006)


Triethylene glycol is believed to be metabolized in mammals by alcohol dehydrogenase to acidic products causing metabolic acidosis. Triethylene glycol metabolism by alcohol dehydrogenase can be inhibited by 4-methyl pyrazole or ethanol.

PMID:17090481 Cosmetic Ingredient Review Expert Panel; Int J Toxicol 25 (Supp 2): 121-38 (2006)


... Eliminated ... possibly as mono- and dicarboxylic acid derivatives or triethylene glycol. In studies with rats, little if any 14-C-oxalate or 14-C-triethylene glycol in conjugated form was found in urine.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 3842


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