1. 3-buten-2-one
2. Methylvinyl Ketone
1. 3-buten-2-one
2. 78-94-4
3. But-3-en-2-one
4. Butenone
5. Vinyl Methyl Ketone
6. Methylene Acetone
7. 2-butenone
8. Methylvinylketon
9. Acetyl Ethylene
10. 1-buten-3-one
11. 3-butene-2-one
12. Methyl Ethenyl Ketone
13. Methylvinyl Ketone
14. Methylvinylketone
15. 3-butenone-2
16. Acetone, Methylene-
17. Ketone, Methyl Vinyl
18. Gamma-oxo-alpha-butylene
19. Methyl-vinyl-cetone
20. 3-oxo-1-butene
21. But-1-en-3-one
22. Methylvinylcetone
23. Poly(vinyl Methyl Ketone)
24. 3-oxobutene
25. Nsc 4853
26. Un1251
27. Chebi:48058
28. Delta(3)-2-butenone
29. Ch2=chcoch3
30. Ar7642i1mp
31. Chembl1600824
32. Nsc-4853
33. 25038-87-3
34. Polyvinyl Methyl Ketone
35. Methgl Vinyl Ketone
36. Methylvinylketon [german]
37. Delta(sup 3)-2-butenone
38. Methyl-vinyl-cetone [french]
39. Ccris 3423
40. Hsdb 716
41. Einecs 201-160-6
42. Unii-ar7642i1mp
43. Ai3-16048
44. 3-butenone
45. Methyl Vinylketone
46. Methyl-vinylketone
47. Methylvinyl-ketone
48. But-3-enone
49. Buten-2-one
50. G-oxo-a-butylene
51. Metyl Vinyl Ketone
52. 3-oxo-l-butene
53. Methly Vinyl Ketone
54. Methyl-vinyl-ketone
55. 1-butene-3-one
56. 3-butenen-2-one
57. 1-propen-3-one
58. Mfcd00008777
59. 3-oxo-but-1-ene
60. Dsstox_cid_5671
61. Ec 201-160-6
62. Dsstox_rid_77878
63. Dsstox_gsid_25671
64. .delta.3-2-butenone
65. .gamma.-oxo-.alpha.-butylene
66. Methyl Vinyl Ketone, Stabilized
67. Wln: 1v1u1
68. Dtxsid3025671
69. Methyl Vinyl Ketone [mi]
70. Nsc4853
71. Act09262
72. Bcp24759
73. Zinc1680420
74. Tox21_200363
75. Bdbm50245462
76. Lmfa12000018
77. Stl299803
78. .delta.-oxo-.alpha.-butylene
79. Akos000120352
80. Un 1251
81. Un-1251
82. Cas-78-94-4
83. Ncgc00091118-01
84. Ncgc00091118-02
85. Ncgc00257917-01
86. M0460
87. 3-buten-2-one, Purum, >=95.0% (gc)
88. C20701
89. F71092
90. M-6580
91. Q417525
92. Methyl Vinyl Ketone, Stabilized [un1251] [poison]
93. 3-buten-2-one, Contains 0.3-1.0% Hydroquinone As Stabilizer, Technical Grade, 90%
94. 3-buten-2-one, Contains 0.5% Hydroquinone And 0.1% Acetic Acid As Stabilizer, 99%
| Molecular Weight | 70.09 g/mol |
|---|---|
| Molecular Formula | C4H6O |
| XLogP3 | 0.5 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Exact Mass | 70.041864811 g/mol |
| Monoisotopic Mass | 70.041864811 g/mol |
| Topological Polar Surface Area | 17.1 Ų |
| Heavy Atom Count | 5 |
| Formal Charge | 0 |
| Complexity | 54.7 |
| 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 |
... /Methyl vinyl ketone/ can be absorbed into the body by inhalation, through the skin and by ingestion.
IPCS, CEC; International Chemical Safety Card on Methyl vinyl ketone. (November 2003). Available from, as of November 02, 2006: https://www.inchem.org/documents/icsc/icsc/eics1495.htm
Readily absorbed through skin causing general poisoning of the organism.
The Merck Index. 10th ed. Rahway, New Jersey: Merck Co., Inc., 1983., p. 878
... In a study of alpha,beta-unsaturated ketone reactivity toward glutathione (GSH) ... methyl vinyl ketone (MVK) /was compared/ to N-ethylmaleimide which has been documented to have high selectivity and reactivity toward sulfhydryl groups ... /and was found/ that MVK reacted 30 times slower with GSH than N-ethylmaleimide. /Alpha,beta-unsaturated ketones/
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
Compounds with ketone functionality are known to react reversibly with glutathione (GSH). Alpha,beta-unsaturated ketones are considered classic substrates for a reversible Michael 1,4-addition reaction in which the whole GSH molecule is added to the substrate to form conjugates ... /which/ may not always be the endpoint; reformation of reactive species may occur with significant implications relative to effects at sites distant from the site of initial exposure and/or initial conjugation. /Alpha,beta-unsaturated ketones/
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
... The interaction of MVK with hepatic microsomal cytochrome P-450 and its effect on hepatic microsomal drug metabolizing enzymes /was studied/ ... MVK bound to hepatic microsomal P-450 in a type I manner and that it enhanced CO-inhibitable NADPH oxidation in vitro. In rat liver mitochondria, MVK is an alkylating agent and inhibitor of cellular (mitochondrial) respiration, less potent than acrolein by one order of magnitude. It is an inhibitor of glutamate transport, inorganic phosphate transport, and succinate dehydrogenase activity.
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
Ketones are known to undergo metabolic transformations to the corresponding alcohols, diols, epoxides and various other metabolites. Conversion in mammals to the relatively less toxic alcohols is reported to proceed slowly. /ketones/
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
3-buten-2-one is a known human metabolite of butadiene.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
... Alpha,beta-unsaturated ketones occurring in the neutral fraction (28% of the semi-volatile fraction) of cigarette smoke concentrates, including MVK, /was described/ as highly reactive electrophiles that can combine with biochemical nucleophiles and constitute a highly cytotoxic group of compounds ...
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
MVK has been described as a model alkylating agent and Michael acceptor which binds to cellular protein sulfhydryl groups and glutathione (GSH) ... The effect of MVK on respiration of isolated rat liver mitochondria /was examined/ and ... /MVK's/ high affinity for sulfhydryl groups /was documented/ ... MVK's cytotoxicity to freshly isolated rat kidney nephron cells /was/ described /as causing/ irreversible cellular injury with distal tubular cells showing greater susceptibility to injury from MVK than proximal tubular cells. Incubation of cells with MVK led to altered cellular GSH status and pronounced inhibition of mitochondria. MVK has been reported ... to be an excellent substrate for induction of glutathione-S-transferase based on studies with Hepa 1c1c7 murine hepatoma cells ... /It was/ postulated that such Phase II enzyme inducers may have potential chemoprotective properties.
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
In the study of the sensitivity of rat liver mitochondrial processes to inhibition by methyl vinyl ketone, 3 different sites were apparent: glutamate transport, inorganic phosphate transport, and succinate dehydrogenase. Methyl vinyl ketone was less effective than acrolein by one order of magnitude.
PMID:4350554 Zollner H; Biochem Pharmacol 22 (10): 1171-8 (1973)
... Evidence of the mutagenicity of MVK /was cited/ as strongly suggestive that this chemical is capable of reacting with cellular DNA ... The formation under mild experimental conditions (24.3 mmoles added to 75 mL of phosphate buffer at pH 7.0 containing 1.1 mmoles of deoxyguanosine) of 2 major deoxyguanosine-MVK adducts /was demonstrated/. Two guanine adducts produced under basic conditions were also identified ... These adducts formed in vitro could play a role in the mutagenicity and/or potential tumorigenicity of this chemical /was speculated/ ...
NTP; Executive Summary Methyl Vinyl Ketone (78-94-4) (January 1992). Available from, as of November 02, 2006: https://ntp.niehs.nih.gov/index.cfm?objectid=03DB450B-B5DE-6081-1DF1947BFBD4EEF0
For more Mechanism of Action (Complete) data for METHYL VINYL KETONE (6 total), please visit the HSDB record page.
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