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Diethylene Glycol Monoethyl Ether

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Also known as: 2-(2-ethoxyethoxy)ethanol, 111-90-0, Carbitol, Transcutol, 2(2-ethoxyethoxy)ethanol, Ethoxy diglycol

Molecular Formula

C₆H₁₄O₃

Molecular Weight

134.17 g/mol

InChI Key

XXJWXESWEXIICW-UHFFFAOYSA-N

FDA UNII

A1A1I8X02B

1 2D Structure

Diethylene Glycol Monoethyl Ether

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(2-ethoxyethoxy)ethanol

2.1.2 InChI

InChI=1S/C6H14O3/c1-2-8-5-6-9-4-3-7/h7H,2-6H2,1H3

2.1.3 InChI Key

XXJWXESWEXIICW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOCCOCCO

2.2 Other Identifiers

2.2.1 UNII

A1A1I8X02B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbitol

2. Ethyl Carbitol

3. Ethylcarbitol

4. Transcutol

5. Transcutol Hp

6. Transcutol P

2.3.2 Depositor-Supplied Synonyms

1. 2-(2-ethoxyethoxy)ethanol

2. 111-90-0

3. Carbitol

4. Transcutol

5. 2(2-ethoxyethoxy)ethanol

6. Ethoxy Diglycol

7. Ethyl Carbitol

8. Ethoxydiglycol

9. Dioxitol

10. Ethanol, 2-(2-ethoxyethoxy)-

11. Ethyl Digol

12. Carbitol Solvent

13. Transcutol P

14. Solvolsol

15. Losungsmittel Apv

16. Dowanol De

17. Carbitol Cellosolve

18. Poly-solv De

19. Diglycol Monoethyl Ether

20. Diethylene Glycol Ethyl Ether

21. Degmee

22. Ektasolve De

23. Ethyl Diethylene Glycol

24. 3,6-dioxa-1-octanol

25. Dowanol 17

26. Karbitol

27. Diethyleneglycol Monoethyl Ether

28. Ethylene Diglycol Monoethyl Ether

29. 2-(2-ethoxyethoxy) Ethanol

30. Monoethyl Ether Of Diethylene Glycol

31. 3,6-dioxa-1-oktanol

32. Ethanol, 2,2'-oxybis-, Monoethyl Ether

33. 2-(ethoxyethoxy)ethanol

34. A1a1i8x02b

35. Chebi:40572

36. Nsc-408451

37. Diethylene Glycol Monoethyl Ether [nf]

38. Dsstox_cid_1941

39. Aqualine™ Complete 1

40. Aqualine™ Complete 2

41. Aqualine™ Complete 5

42. Dsstox_rid_76417

43. Karbitol [czech]

44. Dsstox_gsid_21941

45. 149818-01-9

46. 2-(2-ethoxyethoxy)-ethanol

47. Diethylene Glycol Monoethyl Ether (nf)

48. Acetamide, N-5-(1,2-dihydroxyethyl)-4-hydroxy-3-pyrrolidinyl-, Monohydrochloride, 3s-3.alpha.,4.beta

49. Ae3

50. Cas-111-90-0

51. Hsdb 51

52. Aethyldiaethylenglycol

53. Aethyldiaethylenglycol [german]

54. 3,6-dioxa-1-oktanol [czech]

55. Einecs 203-919-7

56. Nsc 408451

57. Pm 1799

58. Brn 1736441

59. Unii-a1a1i8x02b

60. Diethoxol

61. Ai3-01740

62. O-ethyldigol

63. Eastman De

64. Ethyl Di-icinol

65. Glycol Ether De

66. Mfcd00002872

67. (ethoxyethoxy)ethanol

68. 3,6-dioxaoctan-1-ol

69. 2-(2ethoxyethoxy)ethanol

70. Ec 203-919-7

71. Diethyleneglycolmonoethylether

72. 1-hydroxy-3,6-dioxaoctane

73. Schembl16399

74. 2-(2-ethoxyethoxy);ethanol

75. Aqualine™ Complete 5k

76. Ethoxydiglycol [inci]

77. Diethyleneglycol Monoethylether

78. Wln: Q2o2o2

79. 2-(2-ethoxy-ethoxy)-ethanol

80. 2-(.beta.-ethoxyethoxy)ethanol

81. 3,6-dioxaoctane-1-ol

82. Chembl1230841

83. Diethylene Glycol-monoethyl Ether

84. Dtxsid2021941

85. Zinc1600621

86. Tox21_200413

87. Tox21_300080

88. Ethanol,2'-oxybis-, Monoethyl Ether

89. Nsc408451

90. Stl453580

91. Akos009031390

92. Ehanol, 2,2'-oxybis-, Monoethyl Ether

93. Ncgc00247898-01

94. Ncgc00247898-02

95. Ncgc00254003-01

96. Ncgc00257967-01

97. Di(ethylene Glycol) Ethyl Ether, >=99%

98. Diethylene Glycol Monoethyl Ether, >=99%

99. Cs-0015134

100. E0048

101. Ft-0624897

102. Ft-0693130

103. Diethylene Glycol Monoethyl Ether [ii]

104. Diethylene Glycol Monoethyl Ether [mi]

105. Glycol Ether De (low Gravity) Reagent Grade

106. D08904

107. D72502

108. Diethylene Glycol Monoethyl Ether [hsdb]

109. A802441

110. Diethylene Glycol Monoethyl Ether [usp-rs]

111. Diethylene Glycol Monoethyl Ether [who-dd]

112. Q416399

113. J-505606

114. Diethylene Glycol Monoethyl Ether [ep Monograph]

115. Diethylene Glycol Monoethyl Ether, Reagentplus(r), 99%

116. Diethylene Glycol Monoethyl Ether, Saj First Grade, >=98.0%

117. Diethylene Glycol Monoethyl Ether, Vetec(tm) Reagent Grade, 99%

118. Diethylene Glycol Monoethyl Ether, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₄O₃
Molecular Weight	134.17 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	134.094294304 g/mol
Monoisotopic Mass	134.094294304 g/mol
Topological Polar Surface Area	38.7 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	47.6
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Minimum/Potential Fatal Human Dose

It has been estimated that the single oral dose /of diethylene glycol/ lethal for humans is approximately 1 ml/kg. /Diethylene glycols/

Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 704

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

To assist evaluation of the hazards of skin contact with selected undiluted glycol ethers, their absorption across isolated human abdominal epidermis was measured in vitro. Epidermal membranes were set up in glass diffusion cells and, following an initial determination of permeability to tritiated water, excess undiluted glycol ether was applied to the outer surface for 8 hr. The appearance of glycol ether in an aqueous receptor phase bathing the underside of the epidermis was quantified by a gas chromatographic technique. A final determination of tritiated water permeability was compared with initial values to establish any irreversible alterations in epidermal barrier function induced by contact with the glycol ethers. 2-methoxyethanol (EM) was most readily absorbed (mean steady rate 2.82 mg/sq cm/hr), and a relatively high absorption rate (1.17 mg/sq cm/hr) was also apparent for 1-methoxypropan-2-ol (PM). There was a trend of reducing absorption rate with increasing molecular weight or reducing volatility for monoethylene glycol ethers (EM, 2.82 mg/sq cm/hr; 2-ethoxyethanol, EE, 0.796 mg/sq cm/hr; 2-butoxyethanol, EB, 0.198 mg/sq cm/hr) and also within the diethylene glycol series: 2-(2-methoxyethoxy) ethanol (DM, 0.206 mg/sq cm/hr); 2-(2-ethoxyethoxy) ethanol (DE, 0.125 mg/sq cm/hr) and 2-(2-butoxyethoxy) ethanol (DB, 0.035 mg/sq cm/hr). The rate of absorption of 2-ethoxyethyl acetate (EEAc) was similar to that of the parent alcohol, EE. Absorption rates of diethylene glycol ethers were slower than their corresponding monoethylene glycol equivalents. Combination of intrinsic toxicity and ability to pass across skin contribute to assessment of hazards of contact with undiluted glycol ethers.

PMID:6499804 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1568269 Dugard PH et al; Environ Health Perspect 57: 193-7 (1984)

When a single /oral/ dose of diethylene glycol monoethyl ether (11.2 mmol) was given to an adult human volunteer (sex and age not specified) about 68% of the dose was excreted in the urine as (2-ethoxyethoxy)acetic acid within 12 hr.

FAO/WHO Joint Expert Committee on Food Additives; WHO Food Additives Series 30 Diethylene Glycol Monoethyl Ether. Available from, as of February 20, 2007: https://www.inchem.org/pages/jecfa.html

The quantitative urinary excretion of diethylene glycol monoethyl ether was investigated in the rabbit after oral, intravenous, subcutaneous and percutaneous administration. After oral dosing of two animals at a level of 5 mL/kg bw, both animals died during the first day and total excretion was only 0.8% and 0.33%. After intravenous administration to 15 rabbits at dose levels of 0.5-3.4 mL/kg most of the dose was excreted during the first day (for 13/15 rabbits), the percentage excreted tending to increase with dose. After a single parenteral dose of 1.0-3.0 mL/kg, urinary excretion was monitored for up to 4 consecutive days. Excretion was high in the first 24 hr and the total percentage of the dose excreted in urine increased with dose. After repeated daily parenteral doses of 0.16, 0.32 or 0.63 mL/kg bw, total urinary excretion increased with dose and equalled 4.7, 5.0 and 11.6%, respectively.

FAO/WHO Joint Expert Committee on Food Additives; WHO Food Additives Series 30 Diethylene Glycol Monoethyl Ether. Available from, as of February 20, 2007: https://www.inchem.org/pages/jecfa.html

The oral administration fo 1503 mg Diethylene glycol monoethyl ether to a normal man resulted in the excretion of 1140 mg of 2-ethoxyethoxyacetic acid, 69 % of the total dose, within 12 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 197

5.2 Metabolism/Metabolites

...Carbitol is largely destroyed in body or conjugated with glucuronic acid and excreted as the glucuronate. ...This metabolic peculiarity may explain its lesser toxicity when compared with that of diethyl, methyl and butyl cellosolve.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 630

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