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Chemistry

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Also known as: Dl-mandelic acid, 90-64-2, 2-hydroxy-2-phenylacetic acid, 611-72-3, Phenylglycolic acid, Amygdalic acid

Molecular Formula

C₈H₈O₃

Molecular Weight

152.15 g/mol

InChI Key

IWYDHOAUDWTVEP-UHFFFAOYSA-N

FDA UNII

NH496X0UJX

Mandelic Acid is an aromatic alpha hydroxy acid used in the treatment of urinary tract infections and as an oral antibiotic.

1 2D Structure

Mandelic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-2-phenylacetic acid

2.1.2 InChI

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

2.1.3 InChI Key

IWYDHOAUDWTVEP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

NH496X0UJX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mandelic Acid, (+-)-isomer

2. Mandelic Acid, (11)c-labeled

3. Mandelic Acid, (r)-isomer

4. Mandelic Acid, (s)-isomer

5. Mandelic Acid, Calcium (2:1) Salt

6. Mandelic Acid, Monoammonium Salt

7. Mandelic Acid, Monocalcium Salt

8. Mandelic Acid, Monolithium Salt

9. Mandelic Acid, Monosodium Salt

10. Mandelic Acid, Monosodium Salt, (r)-isomer

11. Mandelic Acid, Monosodium Salt, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Dl-mandelic Acid

2. 90-64-2

3. 2-hydroxy-2-phenylacetic Acid

4. 611-72-3

5. Phenylglycolic Acid

6. Amygdalic Acid

7. Paramandelic Acid

8. Racemic Mandelic Acid

9. Almond Acid

10. Uromaline

11. P-mandelic Acid

12. (rs)-mandelic Acid

13. 2-phenylglycolic Acid

14. Hydroxy(phenyl)acetic Acid

15. Phenylhydroxyacetic Acid

16. Glycolic Acid, Phenyl-

17. Alpha-hydroxyphenylacetic Acid

18. Kyselina Mandlova

19. 2-phenyl-2-hydroxyacetic Acid

20. Dl-hydroxy(phenyl)acetic Acid

21. (+/-)-mandelic Acid

22. 2-hydroxy-2-phenyl-acetic Acid

23. Benzeneacetic Acid, Alpha-hydroxy-

24. Nsc 7925

25. Benzeneacetic Acid, .alpha.-hydroxy-

26. (+/-)-alpha-hydroxyphenylacetic Acid

27. .alpha.-hydroxyphenylacetic Acid

28. Alpha-hydroxy-alpha-toluic Acid

29. Kyselina 2-fenyl-2-hydroxyethanova

30. Nsc-7925

31. Nh496x0ujx

32. Chebi:35825

33. (+-)-alpha-hydroxybenzeneacetic Acid

34. Alpha-hydroxybenzeneacetic Acid

35. .alpha.-hydroxy-.alpha.-toluic Acid

36. .alpha.-toluic Acid, .alpha.-hydroxy-

37. Ammonium Mandelate

38. (+)-mandelate, Xxi

39. Acido Mandelico

40. (+-)-mandelic Acid

41. Benzeneacetic Acid, Alpha-hydroxy-, Homopolymer

42. 32518-00-6

43. Benzeneacetic Acid, .alpha.-hydroxy-, (.+/-.)-

44. Mandelic-acid

45. 2-hydroy-2-phenylacetic Acid

46. Mandelic Acid [usp]

47. Dl-amygdalic Acid

48. Dl-mandelicacid

49. Acido Mandelico [italian]

50. Dl-2-hydroxy-2-phenylacetic Acid

51. Kyselina Mandlova [czech]

52. (+-)-2-hydroxy-2-phenylethanoic Acid

53. Alpha-toluic Acid, Alpha-hydroxy-

54. (+-)-alpha-hydroxyphenylacetic Acid

55. Einecs 202-007-6

56. Einecs 210-277-1

57. Unii-nh496x0ujx

58. 2-hydroxy-2-phenylethanoic Acid

59. Acidomandelico

60. Alpha-hydroxybenzeneacetic Acid, (+-)-

61. Ai3-06293

62. Kyselina 2-fenyl-2-hydroxyethanova [czech]

63. Mfcd00004495

64. Mfcd00064251

65. Benzoglycolic Acid

66. Phenylacetic Acid, Alpha-hydroxy-

67. Ncgc00166022-01

68. L(+)mandelic Acid

69. (+) Mandelic Acid

70. (+)-mandelic Acid

71. Ppcm

72. Samma

73. Hyroxyphenylacetic Acid

74. Pregabalin Impurity C

75. (+/-)-alpha-hydroxybenzeneacetic Acid

76. Mandelic Acid, 99%

77. (-)-mandelate, Xx

78. Hydroxyphenyl Acetic Acid

79. 81432-25-9

80. Benzeneacetic Acid, .alpha.-hydroxy-, (.alpha.r)-

81. Pregabalin Ep Impurity C

82. Wln: Qyr&vq

83. Hydroxy-phenyl-acetic Acid

84. Mandelic Acid, >=99%

85. Dl-mandelic Acid, 99%

86. Mandelic Acid [mi]

87. Schembl1050

88. (.+/-.)-mandelic Acid

89. Chembl1609

90. (+)-phenylhydroxyacetic Acid

91. (?)-phenylhydroxyacetic Acid

92. 2-hydroxy-2-phenylaceticacid

93. Mandelic Acid [inci]

94. Mls001074208

95. Mandelic Acid [mart.]

96. Mandelic Acid [usp-rs]

97. Mandelic Acid [who-dd]

98. .alpha.-phenylhydroxyacetic Acid

99. Dtxsid6023234

100. Bdbm92715

101. Nsc7925

102. Mandelic Acid Condensation Polymer

103. 2-oxidanyl-2-phenyl-ethanoic Acid

104. Hms2230f19

105. Hms3371m20

106. Hms3373a03

107. (2rs)-hydroxy(phenyl)ethanoic Acid

108. Bbl028097

109. Mfcd00064250

110. S3363

111. Stl283951

112. Akos000118795

113. Akos016050628

114. Cs-w016307

115. Db13218

116. Hy-w015591

117. Ks-1423

118. Ncgc00166023-01

119. Ncgc00166269-01

120. (.+/-.)-alpha-hydroxybenzeneacetic Acid

121. Ac-12228

122. Smr000653543

123. Sy001645

124. Sy001670

125. Db-016128

126. Db-016158

127. Ds-000887

128. Am20060842

129. Ft-0600010

130. Ft-0601504

131. Ft-0625487

132. Ft-0628148

133. M0038

134. Benzeneacetic Acid, .alpha.-hydroxy-, ( )-

135. Benzeneacetic Acid, .alpha.-hydroxy-, (s)-

136. Phenylacetic Acid, .alpha.--hydroxy-

137. A19434

138. Dl-mandelic Acid, Analytical Reference Material

139. Mls-0090887.0001

140. A833072

141. Ae-562/40233036

142. Q412293

143. (2rs)-2-hydroxy-2-phenylacetic Acid (mandelic Acid)

144. Glycopyrronium Bromide Impurity C [ep Impurity]

145. Mandelic Acid ((2rs)-2-hydroxy-2-phenylacetic Acid)

146. 14a53e4a-8315-42a7-9d60-de06ccbb1af9

147. F2191-0202

148. Homatropine Hydrobromide Impurity C [ep Impurity]

149. Z955123532

150. Homatropine Methylbromide Impurity C [ep Impurity]

151. Mandelic Acid, United States Pharmacopeia (usp) Reference Standard

152. Mandelic Acid; (2rs)-2-hydroxy-2-phenylacetic Acid ; ?-hydroxy-benzeneacetic Acid;\

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₈H₈O₃
Molecular Weight	152.15 g/mol
XLogP3	0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	152.047344113 g/mol
Monoisotopic Mass	152.047344113 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	138
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 ATC Code

B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05C - Irrigating solutions

B05CA - Antiinfectives

B05CA06 - Mandelic acid

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XX - Other antibacterials

J01XX06 - Mandelic acid

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