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Methacrylic Acid
Also known as: 79-41-4, 2-propenoic acid, 2-methyl-, 2-methylacrylic acid, Methylacrylic acid, 2-methylpropenoic acid, 2-methylprop-2-enoic acid
Molecular Formula
C4H6O2
Molecular Weight
86.09  g/mol
InChI Key
CERQOIWHTDAKMF-UHFFFAOYSA-N
FDA UNII
1CS02G8656

methacrylic acid is a natural product found in Coffea arabica, Euryops arabicus, and Scarites subterraneus with data available.
1 2D Structure

Methacrylic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methylprop-2-enoic acid
2.1.2 InChI
InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
2.1.3 InChI Key
CERQOIWHTDAKMF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
1CS02G8656
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-methylacrylic Acid

2. Methacrylic Acid, Calcium Salt

3. Methacrylic Acid, Sodium Salt

4. Sodium Methacrylate

2.3.2 Depositor-Supplied Synonyms

1. 79-41-4

2. 2-propenoic Acid, 2-methyl-

3. 2-methylacrylic Acid

4. Methylacrylic Acid

5. 2-methylpropenoic Acid

6. 2-methylprop-2-enoic Acid

7. 2-methyl-2-propenoic Acid

8. Alpha-methylacrylic Acid

9. 2-methylenepropionic Acid

10. Acrylic Acid, 2-methyl-

11. Alpha-methacrylic Acid

12. Propionic Acid, 2-methylene-

13. Polymethacrylic Acid

14. Kyselina Methakrylova

15. Methacrylsaeure

16. Methakrylsaeure

17. Nsc 7393

18. 25087-26-7

19. 2-methylpropensaeure

20. 2-methyl-acrylic Acid

21. .alpha.-methacrylic Acid

22. .alpha.-methylacrylic Acid

23. Chebi:25219

24. Nsc-7393

25. 1cs02g8656

26. 2-methacrylic Acid

27. Methacrylicacid

28. Propenoic Acid, 2-methyl

29. Acido Metacrilico

30. Acide Methacrylique

31. Acido Metacrilico [spanish]

32. Acide Methacrylique [french]

33. Kyselina Methakrylova [czech]

34. Ccris 5925

35. 2-propenoic Acid, 2-methyl-, Homopolymer

36. Hsdb 2649

37. Einecs 201-204-4

38. Un2531

39. Methacrylic Acid Homopolymer

40. Brn 1719937

41. Ai3-15724

42. Unii-1cs02g8656

43. Methyl Acrylic Acid

44. Gmaa Methacrylic Acid

45. Methacrylic Acid Glacial

46. Methacrylic Acid Monomer

47. Glacial Methacrylic Acid

48. Methacrylic Ac Id

49. Dsstox_cid_5542

50. Ch2=c(ch3)cooh

51. Ec 201-204-4

52. Methacrylic Acid, Inhibited

53. Methacrylic Acid, Stabilized

54. Dsstox_rid_77824

55. Dsstox_gsid_25542

56. Wln: Qvy1&u1

57. 4-02-00-01518 (beilstein Handbook Reference)

58. Un 2531 (salt/mix)

59. Methacrylic Acid [mi]

60. Methacrylic Acid [hsdb]

61. Methacrylic Acid [inci]

62. Chembl1213531

63. Dtxsid3025542

64. Nsc7393

65. Methacrylic Acid [who-dd]

66. Str02118

67. Zinc1683524

68. Tox21_200826

69. Bbl011616

70. Mfcd00002651

71. Stl163339

72. Akos000121138

73. Cas-79-41-4

74. Methacrylic Acid, Inhibited (salt/mix)

75. Ncgc00248843-01

76. Ncgc00258380-01

77. Bp-30227

78. Ft-0613003

79. M0079

80. Methacrylic Acid, Saj First Grade, >=98.0%

81. Q165949

82. J-521686

83. Methacrylic Acid, Inhibited [un2531] [corrosive]

84. Methacrylic Acid, Contains 250 Ppm Mehq As Inhibitor, 99%

85. 25068-55-7

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 86.09 g/mol
Molecular Formula C4H6O2
XLogP30.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass86.036779430 g/mol
Monoisotopic Mass86.036779430 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count6
Formal Charge0
Complexity83.5
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

Methacrylic acid is readily absorbed through mucous membranes of the lungs and gastrointestinal tract and the skin; and is rapidly distributed to all major tissues.

PMID:16596768 Cosmetic Ingredient Review; International Journal of Toxicology 24(suppl 5):33-51(2005)


Deposition of methacrylic acid vapors in the surgically isolated upper respiratory tract (URT) of anesthetised rats was studied after inhalation of 450 ug/L (133 ppm) using a unidirectional respiratory flow technique (cyclic flow studies were not possible due to vapor absorption on the cyclic flow pump) for 60 min. Deposition of methacrylic acid was measured throughout exposure determining the difference in vapor concentration of methacrylic acid in the inspired and the URT expiring air. Deposition rates (from 30 to 60 min of exposure) of about 95% were observed under 200 mL/min unidirectional flow conditions. However, the degree of penetration to underlying cells could not be derived from this experiment. These results indicate that after inhalation in rats most of the methacrylic acid does not reach the lung.

European Chemicals Bureau, Institute for Health and Consumer Protection, European Union Risk Assessment Report, Methacrylic acid (CAS # 79-41-4) p. 48 (2002). Available from, as of July 9, 2008: https://ecb.jrc.it


After a single oral administration of the sodium salt of methacrylic acid to Wistar rats (540 mg/kg bw) methacrylic acid was detected in the blood serum by means of HPCL. The maximum concentration was found after 10 min, whereas after 60 min no more methacrylic acid was detectable. /Methacrylic acid, sodium salt/

European Chemicals Bureau, Institute for Health and Consumer Protection, European Union Risk Assessment Report, Methacrylic acid (CAS # 79-41-4) p. 48 (2002). Available from, as of July 9, 2008: https://ecb.jrc.it


4.2 Metabolism/Metabolites

Methacrylates are metabolized via two basic pathways, hydrolysis and conjugation. Methacrylic acid is a physiological substrate of the valine pathway and is metabolized toCO2 by two substrates of the citric acid cycle, methylmalonyl and succinyl- CoA.

PMID:16596768 Cosmetic Ingredient Review; International Journal of Toxicology 24(suppl 5):33-51(2005)


Male Wistar rats dosed orally with radiolabelled methyl methacrylate in corn oil revealed that endogenously generated methacrylic acid (0.08% of the dose) was metabolized using the pathway present in mammalian cells for the metabolism of valine, with CO2 and water as the ultimate metabolites.

PMID:16596768 Cosmetic Ingredient Review; International Journal of Toxicology 24(suppl 5):33-51(2005)


Methacrylic acid is a physiological metabolite of the Valine pathway. After activation with Acetyl-CoA it is converted into methyl-malonyl CoA and Succinyl-CoA which enters the citric acid cycle.

European Chemicals Bureau; IUCLID Dataset, Methacrylic Acid (CAS # 79-41-4) p.137 (2000 CD-ROM edition). Available from, as of July 11, 2008: https://esis.jrc.ec.europa.eu/


Methacrylic acid is metabolized primarily through B12-dependent pathway of propionate metabolism. It is first converted to the coenzyme-A ester. This catabolic pathway leads to the tricarboxylic acid (TCA) cycle and ultimately to CO2.

European Chemicals Bureau; IUCLID Dataset, Methacrylic Acid (CAS # 79-41-4) p.130 (2000 CD-ROM edition). Available from, as of July 11, 2008: https://esis.jrc.ec.europa.eu/


METHYL METHACRYLATE, THE MONOMER COMPONENT OF POLY(METHYL METHACRYLATE) CEMENT USED IN ORTHOPEDIC SURGERY, UNDERWENT HYDROLYSIS, TO METHACRYLIC ACID DURING HIP REPLACEMENT OPERATIONS. CIRCULATING LEVELS OF METHACRYLIC ACID WERE COMPARABLE TO THOSE OF METHYL METHACRYLATE, THE CONCENTRATIONS BEING 0-15 UG/CC.

PMID:477128 CROUT DH G; CLIN ORTHOP RELAT RES 141: 90-5 (1979)


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