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L-Tartaric Acid

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Also known as: (+)-l-tartaric acid, (+)-tartaric acid, 87-69-4, L-(+)-tartaric acid, L(+)-tartaric acid, Tartaric acid

Molecular Formula

C₄H₆O₆

Molecular Weight

150.09 g/mol

InChI Key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

FDA UNII

W4888I119H

Tartaric Acid is a white crystalline dicarboxylic acid found in many plants, particularly tamarinds and grapes. Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration. Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography. In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

1 2D Structure

L-Tartaric Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-2,3-dihydroxybutanedioic acid

2.1.2 InChI

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

2.1.3 InChI Key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

W4888I119H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (r*,r*)-(+-)-2,3-dihydroxybutanedioic Acid, Monoammonium Monosodium Salt

2. Aluminum Tartrate

3. Ammonium Tartrate

4. Calcium Tartrate

5. Calcium Tartrate Tetrahydrate

6. Mn(iii) Tartrate

7. Potassium Tartrate

8. Seignette Salt

9. Sodium Ammonium Tartrate

10. Sodium Potassium Tartrate

11. Sodium Tartrate

12. Stannous Tartrate

13. Tartaric Acid

14. Tartaric Acid, ((r*,r*)-(+-))-isomer

15. Tartaric Acid, (r*,s*)-isomer

16. Tartaric Acid, (r-(r*,r*))-isomer

17. Tartaric Acid, (s-(r*,r*))-isomer

18. Tartaric Acid, Ammonium Sodium Salt, (1:1:1) Salt, (r*,r*)-(+-)-isomer

19. Tartaric Acid, Calcium Salt, (r-r*,r*)-isomer

20. Tartaric Acid, Monoammonium Salt, (r-(r*,r*))-isomer

21. Tartrate

2.3.2 Depositor-Supplied Synonyms

1. (+)-l-tartaric Acid

2. (+)-tartaric Acid

3. 87-69-4

4. L-(+)-tartaric Acid

5. L(+)-tartaric Acid

6. Tartaric Acid

7. (2r,3r)-2,3-dihydroxysuccinic Acid

8. (2r,3r)-2,3-dihydroxybutanedioic Acid

9. (r,r)-tartaric Acid

10. Threaric Acid

11. L-threaric Acid

12. Dextrotartaric Acid

13. Dl-tartaric Acid

14. Natural Tartaric Acid

15. (2r,3r)-(+)-tartaric Acid

16. (+)-(r,r)-tartaric Acid

17. Tartaric Acid, L-

18. Rechtsweinsaeure

19. (2r,3r)-tartaric Acid

20. (2r,3r)-rel-2,3-dihydroxysuccinic Acid

21. Tartrate

22. (r,r)-(+)-tartaric Acid

23. Fema No. 3044

24. 133-37-9

25. Lamb Protein (fungal)

26. Butanedioic Acid, 2,3-dihydroxy- (2r,3r)-

27. (r,r)-tartrate

28. Tartaric Acid (van)

29. Kyselina Vinna [czech]

30. Ins No.334

31. Uvic Acid

32. Chebi:15671

33. (+)-(2r,3r)-tartaric Acid

34. Ins-334

35. Tartaric Acid [usan:jan]

36. Weinsaeure

37. Mfcd00064207

38. Nsc-62778

39. L-tartarate

40. 4j4z8788n8

41. W4888i119h

42. 138508-61-9

43. Butanedioic Acid, 2,3-dihydroxy-, (2r,3r)-rel-

44. 1,2-dihydroxyethane-1,2-dicarboxylic Acid

45. Resolvable Tartaric Acid

46. D-alpha,beta-dihydroxysuccinic Acid

47. E 334

48. E-334

49. L-(+)-tartrate

50. 144814-09-5

51. Kyselina 2,3-dihydroxybutandiova [czech]

52. Ai3-06298

53. (1r,2r)-1,2-dihydroxyethane-1,2-dicarboxylic Acid

54. 2, 3-dihydroxybutanedioic Acid

55. Butanedioic Acid, 2,3-dihydroxy- (2r,3r)-, Homopolymer

56. Kyselina Vinna

57. Tartaric Acid D,l

58. Butanedioic Acid, 2,3-dihydroxy- (r-(r*,r*))-

59. Tartarate

60. 132517-61-4

61. (+/-)-tartaric Acid

62. Succinic Acid, 2,3-dihydroxy

63. L(+) Tartaric Acid

64. L-2,3-dihydroxybutanedioic Acid

65. (2rs,3rs)-tartaric Acid

66. Einecs 201-766-0

67. Nsc 62778

68. Weinsteinsaeure

69. Weinsaure

70. Tartaric-acid

71. L-threaric Aci

72. Unii-w4888i119h

73. Kyselina 2,3-dihydroxybutandiova

74. 4ebt

75. Nsc 148314

76. Nsc-148314

77. (r,r)-tartarate

78. (2r,3r)-2,3-dihydroxybernsteinsaeure

79. (+)-tartarate

80. (+)-weinsaeure

81. L(+)tartaric Acid

82. Tartaric Acid; L-(+)-tartaric Acid

83. Tartaric Acid (tn)

84. (+-)-tartaric Acid

85. Butanedioic Acid, 2,3-dihydroxy-, (r*,r*)-

86. L-(+) Tartaric Acid

87. (2r,3r)-tartarate

88. 1d5r

89. Dl Tartaric Acid

90. Tartaricum Acidum

91. 2,3-dihydroxy-succinate

92. Tartaric Acid,dl-

93. Dsstox_cid_3632

94. Ec 201-766-0

95. Schembl5762

96. Tartaric Acid [ii]

97. Tartaric Acid, Dl-

98. Dsstox_rid_77120

99. Tartaric Acid (jp17/nf)

100. Tartaric Acid [fcc]

101. Tartaric Acid [jan]

102. D-a,b-dihydroxysuccinic Acid

103. Dsstox_gsid_23632

104. Tartaric Acid [inci]

105. Mls001336057

106. L-tartaric Acid [mi]

107. Tartaric Acid [vandf]

108. Dl-tartaric Acid [mi]

109. Tartaric Acid [mart.]

110. Ccris 8978

111. L-(+)-tartaric Acid, Acs

112. Tartaric Acid [usp-rs]

113. Tartaric Acid [who-dd]

114. Chembl1236315

115. Dtxsid8023632

116. L-(+)-tartaric Acid, Bioxtra

117. Tartaricum Acidum [hpus]

118. Unii-4j4z8788n8

119. (2r,3r)-2,3-tartaric Acid

120. Tartaric Acid (l(+)-)

121. Hms2270g22

122. Pharmakon1600-01300044

123. Tartaric Acid, Dl- [ii]

124. Zinc895301

125. Tartaric Acid, (+/-)-

126. Tartaric Acid,dl- [vandf]

127. Hy-y0293

128. Str02377

129. Tartaric Acid [orange Book]

130. Baros Component Tartaric Acid

131. Einecs 205-105-7

132. Tox21_300155

133. (2r,3r)-2,3-dihydroxysuccinicacid

134. Nsc759609

135. S6233

136. Tartaric Acid [ep Monograph]

137. L-2,3-dihydroxysuccinic Acid

138. Akos016843282

139. L-(+)-tartaric Acid, >=99.5%

140. Cs-w020107

141. Db09459

142. Nsc-759609

143. (2r,3r)-2,3-dihydroxy-succinic Acid

144. Butanedioic Acid, 2,3-dihydroxy-; Butanedioic Acid, 2,3-dihydroxy-, (r-(r*,r*))-

145. Cas-87-69-4

146. L-(+)-tartaric Acid, Ar, >=99%

147. Tartaric Acid Component Of Baros

148. Ncgc00247911-01

149. Ncgc00254043-01

150. Bp-31012

151. Smr000112492

152. Sbi-0207063.p001

153. T0025

154. C00898

155. D00103

156. D70248

157. Dl-tartaric Acid 100 Microg/ml In Acetonitrile

158. L-(+)-tartaric Acid, >=99.7%, Fcc, Fg

159. L-(+)-tartaric Acid, Acs Reagent, >=99.5%

160. L-(+)-tartaric Acid, Bioultra, >=99.5% (t)

161. J-500964

162. J-520420

163. L-(+)-tartaric Acid, Reagentplus(r), >=99.5%

164. L-(+)-tartaric Acid, Saj First Grade, >=99.5%

165. L-(+)-tartaric Acid, Tested According To Ph.eur.

166. Rel-(2r,3r)-2,3-dihydroxybutanedioic Acid

167. Butanedioic Acid, 2,3-dihydroxy-, (r*,r*)-(+-)-

168. L-(+)-tartaric Acid, Jis Special Grade, >=99.5%

169. L-(+)-tartaric Acid, Natural, >=99.7%, Fcc, Fg

170. L-(+)-tartaric Acid, P.a., Acs Reagent, 99.0%

171. L-(+)-tartaric Acid, Vetec(tm) Reagent Grade, 99%

172. Q18226455

173. F8880-9012

174. Z1262250859

175. Butanedioic Acid, 2,3-dihydroxy-, (r-(r*,r*))-

176. Butanedioic Acid, 2,3-dihydroxy-, (theta,theta)-(+-)-

177. 000189e3-11d0-4b0a-8c7b-31e02a48a51f

178. L-(+)-tartaric Acid, Puriss. P.a., Acs Reagent, >=99.5%

179. L-(+)-tartaric Acid, Certified Reference Material, Tracecert(r)

180. Tartaric Acid, United States Pharmacopeia (usp) Reference Standard

181. L-(+)-tartaric Acid, Anhydrous, Free-flowing, Redi-dri(tm), Acs Reagent, >=99.5%

182. L-(+)-tartaric Acid, P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., 99.5%

183. Tartaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material

184. L-(+)-tartaric Acid, Puriss. P.a., Reag. Iso, Reag. Ph. Eur., 99.5-101.0% (calc. To The Dried Substance)

185. L-(+)-tartaric Acid, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Nf, Fcc, E334, 99.7-100.5% (calc. To The Dried Substance), Grit

186. L-(+)-tartaric Acid, Puriss., Meets Analytical Specification Of Ph. Eur., Nf, 99.7-100.5% (calc. To The Dried Substance), Powder

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄H₆O₆
Molecular Weight	150.09 g/mol
XLogP3	-1.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	150.01643791 g/mol
Monoisotopic Mass	150.01643791 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	134
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Indication

Tartaric Acid is primarily indicated in conditions like Antiscorbutic, Antiseptic.

Stress incontinence, female

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration. Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography. In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

5.2 Absorption, Distribution and Excretion

Absorption

Oral or parenteral doses of monosodium 14C-L(+)-tartrate (400 mg/kg) are rapidly excreted by rats and a proportion completely metabolized to CO2. The oral dose was well-absorbed.

Route of Elimination

Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.

5.3 Metabolism/Metabolites

Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract , primarily in the large instestine.

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