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Chemistry

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Also known as: 2-butanone, Butan-2-one, Butanone, 78-93-3, Ethyl methyl ketone, Methylethyl ketone
Molecular Formula
C4H8O
Molecular Weight
72.11  g/mol
InChI Key
ZWEHNKRNPOVVGH-UHFFFAOYSA-N
FDA UNII
6PT9KLV9IO

2-Butanone
methyl(ethyl) ketone is a natural product found in Aloe africana, Psidium guajava, and other organisms with data available.
1 2D Structure

2-Butanone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butan-2-one
2.1.2 InChI
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
2.1.3 InChI Key
ZWEHNKRNPOVVGH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)C
2.2 Other Identifiers
2.2.1 UNII
6PT9KLV9IO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-butanone

2. Ethyl Methyl Ketone

3. Methylethyl Ketone

2.3.2 Depositor-Supplied Synonyms

1. 2-butanone

2. Butan-2-one

3. Butanone

4. 78-93-3

5. Ethyl Methyl Ketone

6. Methylethyl Ketone

7. Meetco

8. Methyl Acetone

9. Methylethylketone

10. 3-butanone

11. Ethylmethylketon

12. Ethylmethylketone

13. Aethylmethylketon

14. Butanone 2

15. Acetone, Methyl-

16. Mek

17. Ethyl Methyl Cetone

18. Ketone, Ethyl Methyl

19. Metiletilchetone

20. Metyloetyloketon

21. 2-butanon

22. Ethylmethyl Ketone

23. Rcra Waste Number U159

24. Fema No. 2170

25. Oxobutane

26. Methylethylketon

27. Methyl Ethylketone

28. Mfcd00011648

29. 6pt9klv9io

30. 2-butanone, Hplc Grade

31. C2h5coch3

32. Chebi:28398

33. Metyl Ethyl Ketone

34. Caswell No. 569

35. Butanone 2 [french]

36. Methylacetone

37. Metiletilcetona

38. Ethylmethylketon [dutch]

39. Ethylmethylcetone

40. Metiletilcetona [spanish]

41. Metyloetyloketon [polish]

42. Aethylmethylketon [german]

43. Ethylmethylcetone [french]

44. Metiletilchetone [italian]

45. 2-butanone, Acs Reagent, >=99.0%

46. Methyl-ethyl Ketone

47. Hsdb 99

48. Ethyl Methyl Cetone [french]

49. Methyl(ethyl) Ketone

50. Ccris 2051

51. Ai3-07540 (usda)

52. Einecs 201-159-0

53. Unii-6pt9klv9io

54. Un1193

55. Rcra Waste No. U159

56. Epa Pesticide Chemical Code 044103

57. N-butanone

58. Ai3-07540

59. 2-butanal

60. 2-oxobutane

61. Ethyl Methylketone

62. Ethylmathyl Ketone

63. Methyl-ethylketone

64. Methylethyl-ketone

65. Butane-2-one

66. 2 -butanone

67. 2- Butanone

68. Butan-3-one

69. Methyl Etyl Ketone

70. Ethyl-methyl Ketone

71. Methyl Ethyl Cetone

72. Methyl-ethyl-ketone

73. Ethyl(methyl) Ketone

74. Ketone, Methyl Ethyl

75. 2-butanone, Acs Grade

76. Dsstox_cid_1516

77. Mek [inci]

78. 2-butanone [fcc]

79. Ec 201-159-0

80. 2-butanone [fhfi]

81. Dsstox_rid_76193

82. Dsstox_gsid_21516

83. Ghl.pd_mitscher_leg0.417

84. Astm-d740

85. Chembl15849

86. 2-butanone, Analytical Standard

87. 2-butanone, Lr, >=99%

88. Dtxsid3021516

89. Methyl Ethyl Ketone - Mil Spec

90. Methyl Ethyl Ketone [ii]

91. Methyl Ethyl Ketone [mi]

92. Methyl Ethyl Ketone, Acs Reagent

93. Zinc901514

94. Methyl Ethyl Ketone [hsdb]

95. 2-butanone, Ar, >=99.5%

96. Methyl Ethyl Ketone [vandf]

97. 2-butanone, Technical Grade, 99%

98. Methyl Ethyl Ketone [mart.]

99. Tox21_200041

100. Lmfa12000043

101. Stl146562

102. 2-butanone, Natural, >=99%, Fg

103. Methyl Ethyl Ketone [usp-rs]

104. Akos000118991

105. 2-butanone, For Hplc, >=99.7%

106. Methyl Ethyl Ketone Reagent Grade Acs

107. Un 1193

108. 2-butanone, Puriss., >=99% (gc)

109. 2-butanone, Reagentplus(r), >=99%

110. Cas-78-93-3

111. 2-butanone, >=99.5%, Fcc, Fg

112. Ncgc00090973-01

113. Ncgc00090973-02

114. Ncgc00257595-01

115. Bp-30009

116. 2-butanone 100 Microg/ml In Acetonitrile

117. Ethyl Methyl Ketone Or Methyl Ethyl Ketone

118. 2-butanone, Saj First Grade, >=99.0%

119. 2-butanone, Jis Special Grade, >=99.0%

120. E0140

121. Ft-0628728

122. C02845

123. 2-butanone, Hplc Grade, For Hplc, >=99.5%

124. A839534

125. Q372291

126. 2-butanone, Puriss., Acs Reagent, Reag. Ph. Eur., 99.5%

127. 2-butanone, 5000 Mug/ml In Methanol: Water (9:1), Analytical Standard

128. 2-butanone, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99.5% (gc)

129. Ethyl Methyl Ketone Or Methyl Ethyl Ketone [un1193] [flammable Liquid]

130. Methyl Ethyl Ketone, United States Pharmacopeia (usp) Reference Standard

131. 2-butanone Solution, Certified Reference Material, 2000 Mug/ml In Methanol: Water (9:1)

132. Methyl Ethyl Ketone, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 72.11 g/mol
Molecular Formula C4H8O
XLogP30.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass72.057514874 g/mol
Monoisotopic Mass72.057514874 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count5
Formal Charge0
Complexity38.9
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

The pharmacokinetics of MEK in 70 male and female volunteers following a 4-hr inhalation exposure either alone (200 ppm) or in combination with acetone (225 ppm, 1:1.25 ratio) /was described./ Blood and expired air elimination data for the MEK-exposed individuals revealed on average that MEK steady-state breath levels of about 10 to 12 ppm were attained, non-steady-state peak blood levels of 3 to 4 ug/ml occurred, no significant difference in uptake or elimination was observed for males and females, and no appreciable interaction affecting elimination took place with the combined exposures.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6: 149


Measurable (2.54 to 13 ug/L) quantities of methyl ethyl ketone appeared in expired air of adult humans 3 min following dermal exposure to 100 mL methyl ethyl ketone applied to 91.5 sq cm of skin.

PMID:5842337 Wurster; J Pharm Sci 54: 554 (1965)


Ketones are readily absorbed through the intact skin. Usually they are rapidly excreted ... in the expired air. /Ketones/

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1170


Workers occupationally exposed to methyl ethyl ketone (MEK) were examined. ... Workers exposed to 300 micrograms per liter MEK, the aveolar concn was 30% of the environmental concn. Lung uptake averaged 1.05 mg/min. The blood concn of MEK ranged from 842 to 9573 ug/L, with a mean of 2630 ug/L. Blood concn of MEK were strongly correlated with alveolar concn. MEK was more soluble in heart and muscle tissue than in lung tissue or fat. Urinary MEK excretion ranged from 120 to 1120 mg/L, with a mean of 487 mg/L. ... MEK was not persistent in the tissues. ... Urinary excretion of MEK and acetylmethylcarbinol are only around 0.1% of MEK lung absorption, the main pathway through which MEK is eliminated is unknown.

Perbellini L et al; Intern Arch Occup Environ Health 54 (1): 73-81 (1984)


For more Absorption, Distribution and Excretion (Complete) data for METHYL ETHYL KETONE (22 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Methyl ethyl ketone (MEK) occurs ... in normal human urine and ... has possible dietary origin; its more probable precursor is alpha-methylacetoacetic acid. Like other ketones ... MEK is reduced ... in the body. Only 30-40% ... is eliminated in expired air ... .

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 422


Guinea pigs were given single 450 mg/kg ip doses of methyl ethyl ketone (MEK). MEK produced 2-butanol, 3-hydroxy-2-butanone, and 2,3-butanediol.

PMID:941151 DiVincenzo GD et al; Toxicol Appl Pharmacol 36 (3): 511 (1976)


Milk cultures of five Leuconostoc dextranicum strains were capable of reducing methyl ethyl ketone (MEK) to 2-butyl alcohol.

PMID:5726160 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC547789 Keenan TW; Appl Microbiol 16: 1881-5 (1968)


Resting cells of Lactobacillus brevis 24 reduced methyl ethyl ketone (MEK) quantitatively to 2-butyl alcohol when incubated in phosphate buffer for 24 hr at 30 C.

Keen AR et al; J Dairy Res 41: 249-57 (1974)


For more Metabolism/Metabolites (Complete) data for METHYL ETHYL KETONE (11 total), please visit the HSDB record page.


4.3 Biological Half-Life

Blood: 49-96 minutes; urine: 4 hours; [TDR, p. 1700]

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. 1700


MEK is rapidly cleared from the blood with a reported plasma half-life in humans of 49-96 minutes, exhibiting a biphasic elimination: t(1/2) alpha = 30 minutes and t(1/2) beta = 81 Minutes.

U.S. Environmental Protection Agency's Toxicological Review of Methyl Ethyl Ketone (CAS No. 78-93-3) In Support of Summary Information on the Integrated Risk Information system (IRIS). Available from the Database Query page at: https://www.epa.gov/iris/subst/index.html on the Substance File List as of October 10, 2007


Guinea pigs were given a single dose of methyl ethyl ketone (MEK) ip at 450 mg/kg. Blood samples were taken via cardiac puncture at 1, 2, 4, 6, 8, 12 and 16 hr after dosing. Serum half-life of MEK was estimated at 270 minutes.

Divincenzo GD et al; Toxicol Appl Pharm 36: 511-22 (1976)


... The biological half lives for elimination of acetone and MEK calculated on the basis of a first order kinetic assumption were 3.9 hours and 49 minutes, respectively. ... Workers exposed to acetone or MEK for 6 to 8 hours could expect to have a residual body burden of acetone the next morning, whereas MEK would be essentially eliminated.

Brown WD et al; The Changing Nature of Work and Workforce, Proceedings of the Third Joint US-Finish Science Symposium p.111-14 (1986)


The distribution of MEK in human tissues was examined ... in two solvent-exposed workers who died suddenly of heart attacks at the workplace. ... Distribution volumes were 6.0 for vessel-rich tissues, 39.6 for muscle and 12.8 for fat. Biological half-lives for the same tissues were 0.8, 21.8 and 23.3 min, respectively.

WHO; Environ Health Criteria 143: Methyl Ethyl Ketone p.51 (1993)


For more Biological Half-Life (Complete) data for METHYL ETHYL KETONE (8 total), please visit the HSDB record page.


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