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Chemistry

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Also known as: 3,4,5-trihydroxybenzoic acid, 149-91-7, Gallate, Benzoic acid, 3,4,5-trihydroxy-, Gallic acid, tech., Galop
Molecular Formula
C7H6O5
Molecular Weight
170.12  g/mol
InChI Key
LNTHITQWFMADLM-UHFFFAOYSA-N
FDA UNII
632XD903SP

Gallic Acid
A colorless or slightly yellow crystalline compound obtained from nutgalls. It is used in photography, pharmaceuticals, and as an analytical reagent.
1 2D Structure

Gallic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3,4,5-trihydroxybenzoic acid
2.1.2 InChI
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
2.1.3 InChI Key
LNTHITQWFMADLM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(C=C(C(=C1O)O)O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
632XD903SP
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3,4,5-trihydroxybenzoic Acid

2. Acid, Gallic

2.3.2 Depositor-Supplied Synonyms

1. 3,4,5-trihydroxybenzoic Acid

2. 149-91-7

3. Gallate

4. Benzoic Acid, 3,4,5-trihydroxy-

5. Gallic Acid, Tech.

6. Galop

7. Pyrogallol-5-carboxylic Acid

8. Kyselina Gallova

9. Hsdb 2117

10. 3,4,5-trihydroxybenzoate

11. Mfcd00002510

12. Ccris 5523

13. Gallic Acid Polymer

14. Nsc 674319

15. Chebi:30778

16. Ai3-16412

17. Kyselina 3,4,5-trihydroxybenzoova

18. Nsc-20103

19. Nsc-674319

20. Chembl288114

21. 3,4,5-trihydroxy-benzoic Acid

22. 632xd903sp

23. Nsc20103

24. Nsc674319

25. Ncgc00091125-01

26. Dsstox_cid_650

27. Benzoic Acid, 3,4,5-trihydroxy-, Homopolymer

28. Dsstox_rid_75711

29. Dsstox_gsid_20650

30. Gallic Acid Anhydrous

31. Kyselina Gallova [czech]

32. 31387-49-2

33. Cas-149-91-7

34. Gallic Acid [nf]

35. Sr-05000001537

36. Einecs 205-749-9

37. Nsc 20103

38. Brn 2050274

39. Gallic-acid

40. Unii-632xd903sp

41. Kyselina 3,4,5-trihydroxybenzoova [czech]

42. Gallic Acid Tech.

43. Gallic Acid, F

44. Gde

45. (?)-gallic Acid

46. Spectrum_000342

47. 3,4,5-trihydroxybenzoic Acid, Anhydrous

48. Specplus_000307

49. 5-trihydroxybenzoic Acid

50. Spectrum2_000399

51. Spectrum3_000254

52. Spectrum4_001544

53. Spectrum5_000108

54. Gallic Acid [mi]

55. Bmse000389

56. 3,5-trihydroxybenzoic Acid

57. Gallic Acid [hsdb]

58. Gallic Acid [inci]

59. Wln: Qvr Cq Dq Eq

60. 3,4,5-trihydroxy-benzoate

61. Oprea1_087792

62. Schembl15012

63. 3,4,5-trihydroxybenzoicacid

64. Bspbio_001668

65. Kbiogr_002008

66. Kbioss_000822

67. Spectrum210369

68. 3-10-00-02070 (beilstein Handbook Reference)

69. Bidd:er0374

70. Divk1c_006403

71. Gallic Acid [who-dd]

72. Spbio_000617

73. 3,4,5-trihydroxybenzoate, X

74. Benzoic Acid,4,5-trihydroxy-

75. Gtpl5549

76. Zinc1504

77. 3,4,5-trihydroxybenzoic Acid;

78. Dtxsid0020650

79. Kbio1_001347

80. Kbio2_000822

81. Kbio2_003390

82. Kbio2_005958

83. Kbio3_001168

84. Cpd-183

85. Gallic Acid, Puriss., 98.0%

86. Hms1923k07

87. Hms2091a07

88. Pharmakon1600-00210369

89. Bcp18127

90. Hy-n0523

91. Nsc36997

92. Tox21_111089

93. Tox21_202515

94. Bbl009937

95. Bdbm50085536

96. Ccg-38670

97. Nsc-36997

98. Nsc755825

99. S4603

100. Stk298718

101. Akos000119625

102. Tox21_111089_1

103. Ac-1206

104. Cs-8191

105. Nsc-755825

106. Ps-8710

107. Sdccgmls-0066503.p001

108. Ncgc00091125-02

109. Ncgc00091125-03

110. Ncgc00091125-04

111. Ncgc00091125-05

112. Ncgc00091125-07

113. Ncgc00260064-01

114. Da-33612

115. Sy038078

116. Sbi-0052184.p002

117. Gallic Acid 100 Microg/ml In Acetonitrile

118. Gallic Acid, 97.5-102.5% (titration)

119. Ft-0626592

120. G0011

121. N1830

122. C01424

123. D85056

124. 3,4,5-trihydroxybenzoic Acid (acd/name 4.0)

125. Ab00052697_03

126. Q375837

127. Q-201146

128. Sr-05000001537-1

129. Sr-05000001537-2

130. Sr-05000001537-3

131. Brd-k77345217-001-01-9

132. F1908-0156

133. Gallic Acid, Certified Reference Material, Tracecert(r)

134. Z966690556

135. 78563c7d-0e2d-4766-a8ea-670a03c78fcf

136. Gallic Acid (constituent Of Grape Seeds Oligomeric Proanthocyanidins) [dsc]

137. 137657-43-3

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 170.12 g/mol
Molecular Formula C7H6O5
XLogP30.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass170.02152329 g/mol
Monoisotopic Mass170.02152329 g/mol
Topological Polar Surface Area98 Ų
Heavy Atom Count12
Formal Charge0
Complexity169
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

MEDICATION (VET): HAS BEEN USED AS INTESTINAL ASTRINGENT.

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 737


MEDICATION (VET): ANTIDIARRHEAL

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 236


4.2 Minimum/Potential Fatal Human Dose

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 500 MG-5 G/KG; BETWEEN 1 OUNCE AND 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-127


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

READILY ABSORBED FROM THE GASTROINTESTINAL TRACT.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-127


ADMIN TO RABBITS IT IS LARGELY EXCRETED UNCHANGED IN URINE, BUT SMALL AMT ARE ALSO EXCRETED AS PYROGALLOL & 4-METHOXY-3,5-DIHYDROXYBENZOIC ACID.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 167


5.2 Metabolism/Metabolites

... GALLIC ACID...METHYLATED BY CATECHOL O-METHYL TRANSFERASE /TO 3,5-DIHYDROXY-4-METHOXY-BENZOIC ACID/. THIS ENZYME IS LOCALIZED IN SOL FRACTION & IS FOUND IN LIVER, KIDNEYS, SKIN, BLOOD CELLS, GLANDULAR TISSUES & NERVE FIBERS. IT REQUIRES S-ADENOSYLMETHIONINE AS METHYL DONOR &...MG++ OR OTHER DIVALENT IONS.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 85


ADMIN TO RABBITS IT IS LARGELY EXCRETED UNCHANGED IN URINE, BUT SMALL AMT ARE ALSO EXCRETED AS PYROGALLOL & 4-METHOXY-3,5-DIHYDROXYBENZOIC ACID. DECARBOXYLATION TO PYROGALLOL IS RESULT OF METAB BY INTESTINAL MICROFLORA.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 167


GALLIC ACID YIELDS GALLIC ACID-BETA-D-GLUCURONIDE IN RABBIT. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. G-1


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