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Chemistry

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Also known as: 110-16-7, Cis-butenedioic acid, Toxilic acid, Maleinic acid, Malenic acid, (2z)-but-2-enedioic acid

Molecular Formula

C₄H₄O₄

Molecular Weight

116.07 g/mol

InChI Key

VZCYOOQTPOCHFL-UPHRSURJSA-N

FDA UNII

91XW058U2C

Maleic acid is a metabolite found in the aging mouse brain.

1 2D Structure

Maleic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-but-2-enedioic acid

2.1.2 InChI

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

2.1.3 InChI Key

VZCYOOQTPOCHFL-UPHRSURJSA-N

2.1.4 Canonical SMILES

C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

C(=C\C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

91XW058U2C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydrogen Maleate

2. Maleate

3. Maleic Acid, Ammonium Salt

4. Maleic Acid, Calcium Salt

5. Maleic Acid, Dipotassium Salt

6. Maleic Acid, Disodium Salt

7. Maleic Acid, Iron Salt

8. Maleic Acid, Monoammonium Salt

9. Maleic Acid, Monocopper (2+) Salt

10. Maleic Acid, Monosodium Salt

11. Maleic Acid, Neodymium Salt

12. Maleic Acid, Potassium Salt

13. Maleic Acid, Sodium Salt

14. Sodium Maleate

2.3.2 Depositor-Supplied Synonyms

1. 110-16-7

2. Cis-butenedioic Acid

3. Toxilic Acid

4. Maleinic Acid

5. Malenic Acid

6. (2z)-but-2-enedioic Acid

7. 2-butenedioic Acid (2z)-

8. (z)-butenedioic Acid

9. 2-butenedioic Acid (z)-

10. Maleate

11. Cis-1,2-ethylenedicarboxylic Acid

12. Kyselina Maleinova

13. (z)-2-butenedioic Acid

14. Butenedioic Acid, (z)-

15. 2-butenedioic Acid, (z)-

16. 2-butenedioic Acid

17. 1,2-ethylenedicarboxylic Acid, (z)

18. Ccris 1115

19. Hsdb 666

20. Cis-2-butenedioic Acid

21. Malezid Cm

22. H2male

23. (z)-but-2-enedioic Acid

24. Ai3-01002

25. Cis-but-2-enedioic Acid

26. Mfcd00063177

27. Scotchbond Multipurpose Etchant

28. Chebi:18300

29. 91xw058u2c

30. Nsc-25940

31. 2-butenedioic Acid (2z)-, Monocastor Oil Alkyl Esters

32. Dsstox_cid_1517

33. (z)-2-butenedioate

34. Dsstox_rid_76194

35. Dsstox_gsid_21517

36. 68307-91-5

37. Mae

38. (2z)-but-2-enedioate

39. Kyselina Maleinova [czech]

40. Cas-110-16-7

41. Maleic Acid [nf]

42. Einecs 203-742-5

43. Na2215

44. Nsc 25940

45. (2z)-2-butenedioic Acid

46. Brn 0605762

47. Maleic-acid

48. Unii-91xw058u2c

49. Cis-butenedioate

50. 2-butenedioate

51. (z)-butenedioate

52. 1ahy

53. 1tok

54. Ncgc00091192-02

55. Cis-2-butenedioate

56. Bis-hydrogen Maleate

57. Maleic Acid [na2215] [corrosive]

58. Cis-but-2-enedioate

59. Maleic Acid, 99%

60. Maleic Acid (8ci)

61. Maleic Anhydride, Mono(castor Oil) Ester

62. (2z)-2-butenedioate

63. Butenedioic Acid,(z)-

64. (2z)-butene-2-dioate

65. Maleic Acid [ii]

66. Maleic Acid [mi]

67. Schembl613

68. Bmse000212

69. Ec 203-742-5

70. Maleic Acid [na2215]

71. Wln: Qv1u1vq-c

72. Maleic Acid [hsdb]

73. Maleic Acid [inci]

74. (2z)-butene-2-dioic Acid

75. Maleic Acid [mart.]

76. 4-02-00-02199 (beilstein Handbook Reference)

77. Mls002153468

78. 2-butenedioic Acid, (2z)-

79. Maleic Acid [usp-rs]

80. Maleic Acid [who-dd]

81. (2z)-2-butenedioic Acid #

82. Chembl539648

83. Gtpl9630

84. Dtxsid8021517

85. 1-(o-tolyl)piperazinehydrochloride

86. Hms2236f09

87. Maleic Acid, For Synthesis, 99%

88. Maleic Acid [ep Monograph]

89. Maleic Acid [usp Impurity]

90. Hy-y0367

91. Nsc25940

92. Str03481

93. Tox21_113105

94. Tox21_202193

95. Tox21_303045

96. 1,2-ethylenedicarboxylic Acid, Cis-

97. 2-butenedioic Acid (2z)- (9ci)

98. S3086

99. Zinc12358683

100. Akos000268822

101. Tox21_113105_1

102. Db04299

103. Maleic Acid [na2215] [corrosive]

104. Ncgc00090970-01

105. Ncgc00090970-02

106. Ncgc00090970-03

107. Ncgc00257215-01

108. Ncgc00259742-01

109. Maleic Acid, Tested According To Ph.eur.

110. Smr001230824

111. Maleic Acid 100 Microg/ml In Acetonitrile

112. Malic Acid Impurity B [ep Impurity]

113. Cs-0015079

114. M0006

115. Maleic Acid, Saj Special Grade, >=99.0%

116. Maleic Acid, Vetec(tm) Reagent Grade, 98%

117. 1, (z)

118. C01384

119. Q42038

120. A802156

121. Maleic Acid, Reagentplus(r), >=99.0% (hplc)

122. J-521667

123. J-610085

124. Sodium Aurothiomalate Impurity A [ep Impurity]

125. F2191-0240

126. 3b685b85-c1f3-4e32-9dbc-3854162a8de1

127. Maleic Acid, European Pharmacopoeia (ep) Reference Standard

128. Maleic Acid, Standard For Quantitative Nmr, Tracecert(r)

129. Maleic Acid, United States Pharmacopeia (usp) Reference Standard

130. Maleic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄H₄O₄
Molecular Weight	116.07 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	116.01095860 g/mol
Monoisotopic Mass	116.01095860 g/mol
Topological Polar Surface Area	74.6 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	119
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

4.2 Mechanism of Action

Kidney damage has been observed as a systemic toxic action of maleic acid. Morphological-functional changes in the kidneys were produced by intraperitoneal injection (100-350 mg/kg; rats, dogs) and also by inhalation exposure to ca. 720 mg/mc (rats). The damage to distal and proximal tubular resorption produced by maleic acid is reminiscent of the known (congenital or acquired) Fanconi syndrome in humans. This damage seems to be caused by the interaction of maleic acid with glutathione in tubular renal cells, leading to intolerable concentration of free radicals and peroxides. In addition to the resultant cellular damage, maleic acid appears to affect Na+ and H+ ion transport in the proximal tubes [RE5]. After chronic exposure of male rats (250, 500, 750 mg/kg /per/ day for up to two years), an increased mortality as well as kidney damage and delayed growth was observed in all dosage groups. Liver and testicular damage has also been found in highest dosage group. No signs of carcinogenic activity of maleic acid were discovered with long-term dosage, which however was not designed as a carcinogenicity study.

European Commission/European Chemical Substances Information System (ESIS); IUCLID Dataset, Maleic acid (CAS 110-16-7) p. 31 (2000). Available from, as of February 19, 2015: https://esis.jrc.ec.europa.eu/

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