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DSSTox_CID_3602
Also known as: Butanedioic acid, 110-15-6, Amber acid, Wormwood acid, Asuccin, Dihydrofumaric acid
Molecular Formula
C4H6O4
Molecular Weight
118.09  g/mol
InChI Key
KDYFGRWQOYBRFD-UHFFFAOYSA-N
FDA UNII
AB6MNQ6J6L

A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851)
1 2D Structure

DSSTox_CID_3602

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butanedioic acid
2.1.2 InChI
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
2.1.3 InChI Key
KDYFGRWQOYBRFD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CC(=O)O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
AB6MNQ6J6L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2 Ethanedicarboxylic Acid

2. 1,2-ethanedicarboxylic Acid

3. 1,4 Butanedioic Acid

4. 1,4-butanedioic Acid

5. Ammonium Succinate

6. Butanedioic Acid

7. Potassium Succinate

8. Succinate

9. Succinate, Ammonium

10. Succinate, Potassium

2.3.2 Depositor-Supplied Synonyms

1. Butanedioic Acid

2. 110-15-6

3. Amber Acid

4. Wormwood Acid

5. Asuccin

6. Dihydrofumaric Acid

7. Katasuccin

8. 1,2-ethanedicarboxylic Acid

9. Bernsteinsaure

10. Ethylenesuccinic Acid

11. 1,4-butanedioic Acid

12. Wormwood

13. Succinicum Acidum

14. Butandisaeure

15. Acidum Succinicum

16. Butanedionic Acid

17. Kyselina Jantarova

18. Butane Diacid

19. Ethylene Dicarboxylic Acid

20. Spirit Of Amber

21. Bernsteinsaure [german]

22. Kyselina Jantarova [czech]

23. Ammonium Succinate

24. Hsdb 791

25. Succinic-acid

26. Mfcd00002789

27. Succ

28. Nsc 106449

29. Ai3-06297

30. Ab6mnq6j6l

31. Nsc-106449

32. Butanedioic Acid, Homopolymer

33. E363

34. Fema No. 4719

35. Chebi:15741

36. C4-beta-polymorph

37. Nsc25949

38. Succinicacid(industrialgrade&foodgrade)

39. Ncgc00159372-02

40. Ncgc00159372-04

41. Succinellite

42. Acide Succinique

43. Sal Succini

44. Acid Of Amber

45. Dsstox_cid_3602

46. Wln: Qv2vq

47. Dsstox_rid_77102

48. Dsstox_gsid_23602

49. 26776-24-9

50. Sin

51. Ethylene Succinic Acid

52. Ethanedicarboxylic Acid

53. Bernsteinsaeure

54. Sodium Succinate (anhydrous)

55. Succinate, 9

56. Acide Butanedioique

57. Cas-110-15-6

58. Succinic Acid [nf]

59. Succinic Acid (8ci)

60. Butanedioic Acid (9ci)

61. Einecs 203-740-4

62. Unii-ab6mnq6j6l

63. Brn 1754069

64. Dihydrofumarate

65. Succinicate

66. Butanedioic Acid Diammonium Salt

67. Salt Of Amber

68. 1cze

69. Nat.succinic Acid

70. 1,4-butanedioate

71. Succinic Acid, 6

72. Succinic Acid, Fcc

73. Succinic Acide,(s)

74. Succinic Acid (sa)

75. 1,4-butandioic Acid

76. Succinic Acid, 99%

77. Succinic Acid, Natural

78. 4lh2

79. 1,2-ethanedicarboxylate

80. Substrate Analogue, 11

81. Suc

82. Succinic Acid, Acs Grade

83. Bmse000183

84. Bmse000968

85. Chembl576

86. Ec 203-740-4

87. Succinic Acid [ii]

88. Succinic Acid [mi]

89. Hooc-ch2-ch2-cooh

90. Succinic Acid [fcc]

91. A 12084

92. Succinic Acid [hsdb]

93. Succinic Acid [inci]

94. 4-02-00-01908 (beilstein Handbook Reference)

95. Succinic Acid [vandf]

96. Succinic Acid [mart.]

97. Gtpl3637

98. Succinic Acid [usp-rs]

99. Succinic Acid [who-dd]

100. Dtxsid6023602

101. Succinicum Acidum [hpus]

102. Bdbm26121

103. Succinic Acid (butanedioic Acid)

104. Hms3885o04

105. Zinc895030

106. Hy-n0420

107. Str02803

108. Tox21_111612

109. Tox21_201918

110. Tox21_303247

111. Bbl002473

112. Lmfa01170043

113. Nsc-25949

114. Nsc106449

115. S3791

116. Stk387105

117. Succinic Acid [usp Impurity]

118. Succinic Acid, >=99%, Fcc, Fg

119. Succinic Acid, Bioxtra, >=99.0%

120. Akos000118899

121. Tox21_111612_1

122. Ccg-266069

123. Db00139

124. Ncgc00159372-03

125. Ncgc00159372-05

126. Ncgc00159372-06

127. Ncgc00257092-01

128. Ncgc00259467-01

129. Succinic Acid, Acs Reagent, >=99.0%

130. Bp-21128

131. Succinic Acid, Reagentplus(r), >=99.0%

132. Adipic Acid Impurity B [ep Impurity]

133. Cs-0008946

134. Ft-0652509

135. Ft-0773657

136. N1941

137. S0100

138. Succinic Acid 100 Microg/ml In Acetonitrile

139. Succinic Acid, P.a., Acs Reagent, 99.0%

140. Succinic Acid, Saj First Grade, >=99.0%

141. Succinic Acid High Purity Grade 2.5kg

142. Succinic Acid, Purum P.a., >=99.0% (t)

143. Succinic Acid, Saj Special Grade, >=99.5%

144. 1,4-butanedioic Acid (succinic Acid)

145. A14596

146. C00042

147. D85169

148. Succinic Acid, Vetec(tm) Reagent Grade, 98%

149. Ab01332192-02

150. Q213050

151. Sr-01000944556

152. J-002386

153. Sr-01000944556-2

154. Z57127453

155. F2191-0239

156. 37e8fffb-70da-4399-b724-476bd8715ef0

157. Succinic Acid, Certified Reference Material, Tracecert(r)

158. Succinic Acid, Puriss. P.a., Acs Reagent, >=99.5% (t)

159. Succinic Acid, United States Pharmacopeia (usp) Reference Standard

160. Succinic Acid, Matrix Substance For Maldi-ms, >=99.5% (t), Ultra Pure

161. Succinic Acid, Anhydrous, Free-flowing, Redi-dri(tm), Acs Reagent, >=99.0%

162. Succinic Acid, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

163. Succinic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 118.09 g/mol
Molecular Formula C4H6O4
XLogP3-0.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass118.02660867 g/mol
Monoisotopic Mass118.02660867 g/mol
Topological Polar Surface Area74.6 Ų
Heavy Atom Count8
Formal Charge0
Complexity92.6
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPTL THER/ Succinic acid (100 mM) significantly inhibited systemic anaphylaxis induced by compound 48/80 /a potent mast cell degranulator/ in mice and dose-dependently inhibited local anaphylaxis activated by anti-dinitrophenyl IgE. Further 10 and 100 mM significantly inhibited histamine release from rat peritoneal mast cells activated by compound 48/80 or anti-dinitrophenyl IgE. In addition succinic acid (0.1 and 1 mM) had a significant inhibitory effect on anti-dinitrophenyl IgE-induced tumor necrosis factor-alpha secretion from rat peritoneal mast cells. The level of cyclic AMP in rat peritoneal mast cells, when succinic acid (100 mM) was added, transiently and significantly increased about 4 times compared with that of basal cells. These results suggest a possible use of succinic acid in managing mast cell-dependent anaphylaxis.

Kim HM et al;


4.2 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Succinic acid occurs normally in human urine (1.9-8.8 mg/L).

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 758


5.2 Metabolism/Metabolites

Succinic acid is a normal intermediary metabolite and a constituent of the citric acid cycle. It is readily metabolized when administered to animals, but may be partly excreted unchanged in the urine if large doses are fed.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 757


5.3 Mechanism of Action

Succinate is an essential component of the Krebs or citric acid cycle and serves an electron donor in the production of fumaric acid and FADH2. It also has been shown to be a good "natural" antibiotic because of its relative acidic or caustic nature (high concentrations can even cause burns). Succinate supplements have been shown to help reduce the effects of hangovers by activating the degradation of acetaldehyde - a toxic byproduct of alcohol metabolism - into CO2 and H2O through aerobic metabolism. Succinic acid has been shown to stimulate neural system recovery and bolster the immune system. Claims have also been made that it boosts awareness, concentration and reflexes.


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