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2D Structure
Also known as: 4-methylpent-3-en-2-one, 141-79-7, 4-methyl-3-penten-2-one, 3-penten-2-one, 4-methyl-, Methyl isobutenyl ketone, Isopropylideneacetone
Molecular Formula
C6H10O
Molecular Weight
98.14  g/mol
InChI Key
SHOJXDKTYKFBRD-UHFFFAOYSA-N
FDA UNII
77LAC84669

mesityl oxide is a natural product found in Lepidium meyenii, Bistorta manshuriensis, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-methylpent-3-en-2-one
2.1.2 InChI
InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
2.1.3 InChI Key
SHOJXDKTYKFBRD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=CC(=O)C)C
2.2 Other Identifiers
2.2.1 UNII
77LAC84669
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 4-methylpent-3-en-2-one

2. 141-79-7

3. 4-methyl-3-penten-2-one

4. 3-penten-2-one, 4-methyl-

5. Methyl Isobutenyl Ketone

6. Isopropylideneacetone

7. Isobutenyl Methyl Ketone

8. Mesityloxid

9. Mesityloxyde

10. Ossido Di Mesitile

11. 3-isohexen-2-one

12. Isopropylidene Acetone

13. Oxyde De Mesityle

14. Acetone, Isopropylidene-

15. Methyl 2-methyl-1-propenyl Ketone

16. Methyl 2,2-dimethylvinyl Ketone

17. 2-methyl-4-oxo-2-pentene

18. 2-methyl-2-pentenone-4

19. 2,2-dimethylvinyl Methyl Ketone

20. 4-metil-3-penten-2-one

21. 4-methyl-3-pentene-2-one

22. 4-methyl-3-penten-2-on

23. 2-methyl-2-penten-4-one

24. Fema No. 3368

25. Nsc 38717

26. 4-methyl-3-penten-2-one, 9ci

27. 4-methyl-pent-3-en-2-one

28. Chebi:89993

29. (ch3)2c=chc(=o)ch3

30. Nsc-38717

31. 77lac84669

32. Dsstox_cid_9170

33. Dsstox_rid_78697

34. Dsstox_gsid_29170

35. Mesityloxid [german]

36. Mesityloxyde [dutch]

37. Caswell No. 547

38. Fema Number 3368

39. Oxyde De Mesityle [french]

40. Cas-141-79-7

41. Ossido Di Mesitile [italian]

42. Hsdb 1195

43. Einecs 205-502-5

44. 4-metil-3-penten-2-one [italian]

45. Un1229

46. Epa Pesticide Chemical Code 052401

47. Brn 1361550

48. 4-methyl-3-penten-2-on [dutch, German]

49. Ai3-07702

50. Unii-77lac84669

51. Mesityloxid(german)

52. Mfcd00008900

53. Isopropylidene-acetone

54. Mesityl Oxide [un1229] [flammable Liquid]

55. Ec 205-502-5

56. 2-methylpent-2-en-4-one

57. Mesityl Oxide [mi]

58. 1-methylpent-2-en-4-one

59. Mesityl Oxide [hsdb]

60. Chembl3185916

61. Dtxsid1029170

62. Fema 3368

63. Wln: 1y1 & U1v1

64. 4-methyl-3-penten-2-one, 90%

65. Amy23356

66. Nsc38717

67. Tox21_202080

68. Tox21_303606

69. Lmfa12000030

70. Stl146350

71. Mesityl Oxide, Technical Grade, 90%

72. Akos000118892

73. Zinc100019800

74. Un 1229

75. Ncgc00249161-01

76. Ncgc00257514-01

77. Ncgc00259629-01

78. 4-methyl-3-penten-2-one (mesityl Oxide)

79. 4-methyl-3-penten-2-on(dutch, German)

80. 4-methyl-3-pentene-2-one [fhfi]

81. Ft-0628235

82. M0069

83. M1340

84. Mesityl Oxide 100 Microg/ml In Acetonitrile

85. Teicoplanin Impurity A [ep Impurity]

86. 3-penten,2-one,4-methyl Mesityloxide

87. Mesityl Oxide [un1229] [flammable Liquid]

88. 3-penten,2-one,4-methyl Mesityloxide

89. A807813

90. Cilastatin Sodium Impurity D [ep Impurity]

91. Q425668

92. Q-201356

93. 4-methyl-3-penten-2-one, Analytical Reference Material

94. Mesityl Oxide, 90%, Remainder 4-methyl-4-penten-2-one

95. Mesityl Oxide, European Pharmacopoeia (ep) Reference Standard

96. Mesityl Oxide, Pharmaceutical Secondary Standard; Certified Reference Material

97. Mesityl Oxide, Suitable For Neutral Marker For Measuring Electroosmotic Flow (eof), ~98%

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 98.14 g/mol
Molecular Formula C6H10O
XLogP31.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass98.073164938 g/mol
Monoisotopic Mass98.073164938 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count7
Formal Charge0
Complexity96.7
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

Mesityl oxide ... reduced in body to apprecialbe extent. ... Shown to increase glucuronic output in rabbits. ... Repeated exposure of animals to non-lethal concentrations, suggests that it is probably not rapidly eliminated, and that with frequent exposures, blood concentration reaches anesthetic level.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 441


It is readily absorbed through the intact skin.

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1172


... /Mesityl oxide/ can be absorbed into the body by inhalation of its vapor, through the skin and by ingestion.

IPCS, CEC; International Chemical Safety Card on Mesityl oxide. (March 1998). Available from, as of November 01, 2006: https://www.inchem.org/documents/icsc/icsc/eics0814.htm


4.2 Metabolism/Metabolites

Some mesityl oxide remains unchanged, some reduction and conjugation occurs. Metabolite is believed to be a glucuronide, but has not been demonstrated. /From table/

Casarett, L.J., and J. Doull. Toxicology: The Basic Science of Poisons. New York: MacMillan Publishing Co., 1975., p. 81


... Mesityl oxide reacts with certain sulfur-containing compounds in body, probably sulfhydryls and that this forms odorous product which ... /is/ believed to be sulfur substituted ketone.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 441