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Chemistry

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Also known as: 111-77-3, Diethylene glycol monomethyl ether, Methyl carbitol, Methoxydiglycol, Methyl digol, Ethanol, 2-(2-methoxyethoxy)-
Molecular Formula
C5H12O3
Molecular Weight
120.15  g/mol
InChI Key
SBASXUCJHJRPEV-UHFFFAOYSA-N
FDA UNII
465DDJ8G8K

Diethylene Glycol Methyl Ether
1 2D Structure

Diethylene Glycol Methyl Ether

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-methoxyethoxy)ethanol
2.1.2 InChI
InChI=1S/C5H12O3/c1-7-4-5-8-3-2-6/h6H,2-5H2,1H3
2.1.3 InChI Key
SBASXUCJHJRPEV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COCCOCCO
2.2 Other Identifiers
2.2.1 UNII
465DDJ8G8K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-mee Cpd

2.3.2 Depositor-Supplied Synonyms

1. 111-77-3

2. Diethylene Glycol Monomethyl Ether

3. Methyl Carbitol

4. Methoxydiglycol

5. Methyl Digol

6. Ethanol, 2-(2-methoxyethoxy)-

7. Dowanol Dm

8. Poly-solv Dm

9. Methyl Dioxitol

10. 3,6-dioxa-1-heptanol

11. Mecb

12. Ektasolve Dm

13. Diethylene Glycol Methyl Ether

14. Diglycol Monomethyl Ether

15. Degme

16. 2-(2-methoxyethoxy)-ethanol

17. Diethyleneglycol Monomethyl Ether

18. Methyl Karbitol

19. Methyl-peg2-alcohol

20. Ethylene Diglycol Monomethyl Ether

21. Nsc 2261

22. Ethanol, 2,2'-oxybis-, Monomethyl Ether

23. 465ddj8g8k

24. .beta.-methoxy-.beta.'-hydroxydiethyl Ether

25. Dtxsid3025049

26. Chebi:44836

27. Nsc-2261

28. Ncgc00163771-03

29. Jeffersol Dm

30. Dowanol 16

31. Caswell No. 338b

32. Methyldiglycol

33. Egme, Di-

34. Diethylene Glycol Monome Methylether

35. Methyl Karbitol [czech]

36. Hsdb 96

37. Pg0

38. Mpeg2-oh

39. Einecs 203-906-6

40. Epa Pesticide Chemical Code 042204

41. Beta-methoxy-beta'-hydroxydiethyl Ether

42. Brn 1697812

43. Methylcarbitol

44. Unii-465ddj8g8k

45. 2-(2-methoxy-ethoxy)ethanol

46. 2-(2-methoxyethoxy) Ethanol

47. Ai3-18364

48. 2-(2-methoxyethoxy)ethan-1-ol

49. Hicotol Car

50. Diethylene Glycol-monomethyl Ether

51. 2-(methoxyethoxy)ethanol

52. Dsstox_cid_5049

53. 2-(methoxyethoxy)-ethanol

54. Ec 203-906-6

55. Dsstox_rid_77640

56. 2-(2-methoxyethoxyl)ethanol

57. Dsstox_gsid_25049

58. Schembl15778

59. 4-01-00-02392 (beilstein Handbook Reference)

60. Methoxydiglycol [inci]

61. Wln: Q2o2o1

62. Diethyleneglycol Monomethylether

63. Glycol Ether Dm Reagent Grade

64. 2-(2'-methoxyethoxy) Ethanol

65. 2-(2-methoxy Ethoxy) Ethanol

66. 2-(2-methoxy-ethoxy)-ethanol

67. Diethylene Glycol Monomethylether

68. Chembl1235250

69. Nsc2261

70. M-peg-oh, Mw 2,000

71. M-peg-oh, Mw 5,000

72. Zinc1577245

73. M-peg-oh, Mw 30,000

74. Tox21_400009

75. Diethylene Glycol Methyl Ether, 99%

76. Mfcd00002871

77. Stl280434

78. Akos009156476

79. Ethanol,2'-oxybis-, Monomethyl Ether

80. Cs-w013578

81. Hy-w012862

82. Ncgc00163771-01

83. Ncgc00163771-02

84. Ncgc00163771-04

85. As-12944

86. Bp-13446

87. Bp-23184

88. Bp-23185

89. Bp-27937

90. Cas-111-77-3

91. Ft-0624900

92. M0537

93. D78002

94. Diethylene Glycol Monomethyl Ether [mi]

95. Diethylene Glycol Monomethyl Ether [hsdb]

96. Poly(oxy-1,2-ethanediyl), A-methyl-w-hydroxy-

97. Q1925579

98. W-109062

99. Diethylene Glycol Monomethyl Ether (stabilized With Bht)

100. Z1251171284

101. Diethylene Glycol Methyl Ether, Reagentplus(r), >=99.0%

102. Diethylene Glycol Methyl Ether, Saj First Grade, >=99.0%

103. Diethylene Glycol Monomethyl Ether, Purum, >=99.0% (gc)

104. Diethylene Glycol Methyl Ether, Vetec(tm) Reagent Grade, 98%

105. 2-(2-methoxyethoxy)ethanol Stabilized With ~100ppm 2,6-di-tert-butyl-4-methylphenol

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 120.15 g/mol
Molecular Formula C5H12O3
XLogP3-0.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass120.078644241 g/mol
Monoisotopic Mass120.078644241 g/mol
Topological Polar Surface Area38.7 Ų
Heavy Atom Count8
Formal Charge0
Complexity38.7
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

EXPL : Structure activity studies with nine glycol alkyl ethers were conducted with a cellular leukemia transplant model in male Fischer rats to measure the effects on neoplastic progression in transplant recipients. Chemicals were given ad libitum in the drinking water simultaneously with the transplants and continued throughout the study. In all, 20 million leukemic cells were injected sc into syngeneic rats, which after 60 days resulted in a 10-fold increase in relative spleen weights, a 100-fold increase in white blood cell counts, and a 50% reduction in red blood cell indices and platelet counts. Ethylene glycol monomethyl ether given at a dose of 2.5 mg/mL in the drinking water completely eliminated all clinical, morphological, and histopathological evidence of leukemia, whereas the same dose of ethylene glycol monoethyl ether reduced these responses by about 50%. Seven of the glycol ethers were ineffective as anti-leukemic agents, including ethylene glycol, the monopropyl, monobutyl, and monophenyl ethylene glycol ethers, diethylene glycol, and the monomethyl and monoethyl diethylene glycol ethers.

PMID:2357763 Dieter MP et al; Cancer Chemother Pharmacol 26 (3): 173-80 (1990)


4.2 Drug Warning

Retrocaval ureter is a very rare condition. In light of the experimental studies, one of the etiologic factors seems to be maternal contact with diethylene glycol monomethyl ether or ethylene glycol monomethyl ether. A case of cardiovascular, skeletal, and retrocaval ureter anomalies caused by possible maternal contact while pregnant with these materials at her work in a textile factory is presented.

PMID:12149723 Karaman MI et al; J Pediatr Surg 37 (8): E23 (2002)


4.3 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/

Doull, J., C.D.Klassen, and M.D. Amdur (eds.). Casarett and Doull's Toxicology. 3rd ed., New York: Macmillan Co., Inc., 1986., p. 656


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

... /It is/ absorbed by skin ... .

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 633


... Material can be absorbed through skin of rabbits in toxic amounts... .

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 634


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)


The toxicity of bis(2-methoxyethyl)ether was studied in rats. Male Sprague-Dawley rats were given 0.051, or 5.1 mmol/kg (14)C labeled bis(2-methoxyethyl)ether orally. The principal urinary metabolites were (2-methoxyethoxy)acetic acid and methoxyacetic acid which accounted for around 70 and 6% of the doses, respectively. Smaller amounts of N-(methoxyacetyl)glycine, diglycolic acid, 2-methoxyethanol, and 2-(2-methoxyethoxy)ethanol were found. Only unchanged bis(2-methoxyethyl)ether was found in the volatile organic fraction of the expired air. Additionally, rats were given up to 20 daily doses of 5.1 mmol/kg 2-(2-methoxyethoxy)ethanol or (2-methoxyethoxy)acetic acid at on days 3 through 21. 2-(2-Methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid induced no gross or histopathological testicular changes. Bis(2-methoxyethyl)ether metabolism proceeds primarily through an O-demethylation pathway, followed by oxidation to (2-methoxyethoxy)acetic acid. The lack of toxicity of 2-(2-methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid suggests that the testicular toxicity of bis(2-methoxyethyl)ether may be due to methoxyacetic acid, a minor metabolite.

Cheever KL et al; Toxicol and Appl Pharmacol 94 (1): 150-9 (1988)


5.2 Metabolism/Metabolites

...Male Sprague-Dawley rats were given 0.051, or 5.1 mmol/kg (14)C labeled bis(2-methoxyethyl)ether orally. The principal urinary metabolites were (2-methoxyethoxy)acetic acid and methoxyacetic acid which accounted for around 70 and 6% of the doses, respectively. Smaller amounts of N-(methoxyacetyl)glycine, diglycolic acid, 2-methoxyethanol, and 2-(2-methoxyethoxy)ethanol were found. Only unchanged bis(2-methoxyethyl)ether was found in the volatile organic fraction of the expired air. ...Bis(2-methoxyethyl)ether metabolism proceeds primarily through an O-demethylation pathway, followed by oxidation to (2-methoxyethoxy)acetic acid. The lack of toxicity of 2-(2-methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid suggests that the testicular toxicity of bis(2-methoxyethyl)ether may be due to methoxyacetic acid, a minor metabolite.

Cheever KL et al; Toxicol and Appl Pharmacol 94 (1): 150-9 (1988)


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