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Chemistry

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Also known as: Ethanedioic acid, 144-62-7, Aktisal, Aquisal, Oxalate, Oxiric acid

Molecular Formula

C₂H₂O₄

Molecular Weight

90.03 g/mol

InChI Key

MUBZPKHOEPUJKR-UHFFFAOYSA-N

FDA UNII

9E7R5L6H31

A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.

1 2D Structure

Oxalic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

oxalic acid

2.1.2 InChI

InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)

2.1.3 InChI Key

MUBZPKHOEPUJKR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

9E7R5L6H31

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Oxalic

2. Aluminum Oxalate

3. Ammonium Oxalate

4. Chromium (2+) Oxalate

5. Chromium (3+) Oxalate (3:2)

6. Chromium Oxalate

7. Diammonium Oxalate

8. Dilithium Oxalate

9. Dipotassium Oxalate

10. Disodium Oxalate

11. Ferric Oxalate

12. Iron (2+) Oxalate (1:1)

13. Iron (3+) Oxalate

14. Iron Oxalate

15. Magnesium Oxalate

16. Magnesium Oxalate (1:1)

17. Manganese (2+) Oxalate (1:1)

18. Monoammonium Oxalate

19. Monohydrogen Monopotassium Oxalate

20. Monopotassium Oxalate

21. Monosodium Oxalate

22. Oxalate, Aluminum

23. Oxalate, Chromium

24. Oxalate, Diammonium

25. Oxalate, Dilithium

26. Oxalate, Dipotassium

27. Oxalate, Disodium

28. Oxalate, Ferric

29. Oxalate, Iron

30. Oxalate, Magnesium

31. Oxalate, Monoammonium

32. Oxalate, Monohydrogen Monopotassium

33. Oxalate, Monopotassium

34. Oxalate, Monosodium

35. Oxalate, Potassium

36. Oxalate, Potassium Chromium

37. Oxalate, Sodium

38. Potassium Chromium Oxalate

39. Potassium Oxalate

40. Potassium Oxalate (2:1)

41. Sodium Oxalate

2.3.2 Depositor-Supplied Synonyms

1. Ethanedioic Acid

2. 144-62-7

3. Aktisal

4. Aquisal

5. Oxalate

6. Oxiric Acid

7. Oxalsaeure

8. Oxaalzuur

9. Kyselina Stavelova

10. Acide Oxalique

11. Acido Ossalico

12. Acidum Oxalicum

13. Caswell No. 625

14. Oxaalzuur [dutch]

15. Oxalsaeure [german]

16. Oxalicacid

17. Nci-c55209

18. Ethanedionic Acid

19. Acide Oxalique [french]

20. Ethane-1,2-dioic Acid

21. Acido Ossalico [italian]

22. Kyselina Stavelova [czech]

23. Ccris 1454

24. Epa Pesticide Chemical Code 009601

25. Hsdb 1100

26. Ai3-26463

27. Nsc 62774

28. Brn 0385686

29. Hooccooh

30. Oxalic Acid Anhydrous

31. Mfcd00002573

32. Chebi:16995

33. 9e7r5l6h31

34. C2-beta-polymorph

35. Nsc-62774

36. Ethanedioic Acid Dihydrate

37. Ethanedioic Acid-d2

38. Oxalic Acid Dianion

39. Dsstox_cid_5816

40. C00209

41. Dsstox_rid_77935

42. Dsstox_gsid_25816

43. Oxalic Acid Diammonium Salt

44. Wood Bleach

45. Oxaliplatin Related Compound A

46. Cas-144-62-7

47. Oxd

48. C2h2o4

49. Nsc115893

50. Einecs 205-634-3

51. Ethandisaeure

52. Ethanedionate

53. Oxagel

54. Unii-9e7r5l6h31

55. 2dua

56. 2hwg

57. H2ox

58. Anhydrous Oxalic Acid

59. Ethane-1,2-dioate

60. Oxalic Acid, 98%

61. Oxalic Acid (8ci)

62. Oxalic Acid 2 Hydrate

63. Oxalic Acid, Anhydrous

64. Oxalic Acid 2-hydrate

65. 1o4n

66. 1t5a

67. Oxalate Standard For Ic

68. Wln: Qvvq

69. Ethanedioic Acid (9ci)

70. Oxalic Acid [mi]

71. Oxalic Acid Dihydrate Acs

72. Ultraplast Activate S 52

73. Bmse000106

74. Ec 205-634-3

75. Oxalic Acid Low Ash Grade

76. Oxalic Acid [hsdb]

77. Oxalic Acid [inci]

78. Nciopen2_000770

79. Nciopen2_001022

80. Nciopen2_001042

81. Nciopen2_001202

82. Nciopen2_008831

83. Oxalic Acid [vandf]

84. Tetradecanoic-d27acid

85. 4-02-00-01819 (beilstein Handbook Reference)

86. Oxalic Acid [who-dd]

87. Oxalic Acid Solution, 0.5 M

88. Oxalic Acid, Ar, >=99%

89. Oxalic Acid, Lr, >=98%

90. Chembl146755

91. Dtxsid0025816

92. Oxalic Acid Solution, 0.05 M

93. Oxalic Acid, Analytical Standard

94. Bdbm14674

95. Bis(5-azaspiro[2.5]octan-8-ol)

96. Hy-y0262

97. Nsc62774

98. Oxalicacid,0.1nstandardizedsolution

99. Str01359

100. Zinc6021239

101. Tox21_202122

102. Tox21_303346

103. Bbl003000

104. Bis((2r)-azetidine-2-carbonitrile)

105. S9354

106. Stk379550

107. Akos005449445

108. Oxalic Acid, 5% W/v Aqueous Solution

109. Ccg-266020

110. Db03902

111. Sb40938

112. Sb40959

113. Sb40985

114. Oxalic Acid, 10% W/v Aqueous Solution

115. Oxalic Acid, Reagentplus(r), >=99%

116. Ncgc00249170-01

117. Ncgc00257376-01

118. Ncgc00259671-01

119. Bp-21133

120. Oxalic Acid 10 Microg/ml In Acetonitrile

121. Oxalic Acid, 0.1n Standardized Solution

122. Oxalic Acid, Saj First Grade, >=97.0%

123. Bis(1-(3-methyloxetan-3-yl)ethan-1-amine)

124. Cs-0013716

125. Ft-0657506

126. Oxalic Acid, Vetec(tm) Reagent Grade, 98%

127. Oxaliplatin Impurity A [ep Impurity]

128. Oxaliplatin Related Compound A [usp-rs]

129. Oxalic Acid, Purum, Anhydrous, >=97.0% (rt)

130. Q184832

131. J-007978

132. Oxaliplatin Related Compound A [usp Impurity]

133. F1b1b2d7-c290-4ce6-8550-f25b202afade

134. F2191-0257

135. Oxalic Acid, Puriss. P.a., Anhydrous, >=99.0% (rt)

136. Oxalic Acid, Purified Grade, 99.999% Trace Metals Basis

137. Oxalate Standard For Ic, 1.000 G/l In H2o, Analytical Standard

138. Oxalic Acid Concentrate, 0.1 M (cooh)2 (0.2n), Eluent Concentrate For Ic

139. 48j

2.3.3 Other Synonyms

1. 6153-56-6

2. Ethanedioic Acid, Dihydrate

3. Oxalic Acid Dihydrate

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂H₂O₄
Molecular Weight	90.03 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	89.99530854 g/mol
Monoisotopic Mass	89.99530854 g/mol
Topological Polar Surface Area	74.6 Å²
Heavy Atom Count	6
Formal Charge	0
Complexity	71.5
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

4 Drug and Medication Information

4.1 Drug Warning

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients. /Oxalates/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 702

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Reducing Agents

Materials that add an electron to an element or compound, that is, decrease the positiveness of its valence. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) (See all compounds classified as Reducing Agents.)

5.2 Absorption, Distribution and Excretion

TARTARIC & OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGED.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 141

The absorption of (14)C-labelled oxalic acid was studied in Wistar rats, CD-1 mice and NMRI mice. Oxalic acid in solution was given to the animals by gavage either with water alone or with 0.625 g/kg body wt of xylitol. Both xylitol adapted animals and animals not previously exposed to xylitol were used. Adaptation to xylitol diets enhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in rats. Earlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitol. The results of the present study offer one likely explanation for the increased formation of bladder calculi as a result of over saturation of urine with oxalate.

PMID:3188068 Salminen S et al; Toxicol Lett 44 (1-2): 113-20 (1988)

5.3 Metabolism/Metabolites

IN RABBIT, MAJOR END-PRODUCT OF METAB OF (14)C-ETHYLENE GLYCOL IS RESP CARBON DIOXIDE (60% OF DOSE IN 3 DAYS), & METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENE GLYCOL (10%) & OXALIC ACID (0.1%). ... GLYCOLALDEHYDE, GLYCOLLIC ACID & GLYOXYLIC ACID ARE INTERMEDIATES IN CONVERSION TO CARBON DIOXIDE.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 214

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS, SPECIES VARIATIONS OCCUR WHICH EXPLAIN ... DIFFERENCES IN TOXICITY. GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBON DIOXIDE, & BY MINOR PATHWAY TO ... OXALIC ACID. EXTENT OF FORMATION OF OXALIC ACID IS DEPENDENT ON DOSE LEVEL, BUT HAS ... BEEN SHOWN TO VARY WITH SPECIES ...

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 118

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) & TO GLYOXYLIC ACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE; DECARBOXYLATION OF GLYOXYLIC ACID YIELDS CARBON DIOXIDE & FORMIC ACID. GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1637

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivo transformation of glyoxylic acid to glycine rather than to oxalic acid. However, it has recently been shown that long term treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis. A patient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renal insufficiency, an association that has not been previously described, was reported. Therefore, piridoxilate should be added to the list of chemicals responsible for chronic oxalate nephropathy.

PMID:3118272 Vigeral P et al; Nephrol Dial Transplant 2 (4): 275-8 (1987)

Cyclosporin A interferes with oxalate metabolism and, therefore, should be given with utmost caution in patients with primary hyperoxaluria.

PMID:3075154 Drachman R et al; Child Nephrol Urol 9 (1-2): 90-2 (1988)

5.4 Mechanism of Action

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset the calcium-potassium ratio in critical tissues.

American Conference of Governmental Industrial Hygienists. Documentation of the Threshold Limit Values and Biological Exposure Indices. 5th ed. Cincinnati, OH: American Conference of Governmental Industrial Hygienists, 1986., p. 451

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