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Chemistry

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Also known as: Benzene-1,2,3-triol, 87-66-1, 1,2,3-trihydroxybenzene, Pyrogallic acid, 1,2,3-benzenetriol, Fourrine pg
Molecular Formula
C6H6O3
Molecular Weight
126.11  g/mol
InChI Key
WQGWDDDVZFFDIG-UHFFFAOYSA-N
FDA UNII
01Y4A2QXY0

Pyrogallol
A trihydroxybenzene or dihydroxy phenol that can be prepared by heating GALLIC ACID.
1 2D Structure

Pyrogallol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
benzene-1,2,3-triol
2.1.2 InChI
InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
2.1.3 InChI Key
WQGWDDDVZFFDIG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C(=C1)O)O)O
2.2 Other Identifiers
2.2.1 UNII
01Y4A2QXY0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2,3-trihydroxybenzene

2. Acid, Pyrogallic

3. Pyrogallic Acid

2.3.2 Depositor-Supplied Synonyms

1. Benzene-1,2,3-triol

2. 87-66-1

3. 1,2,3-trihydroxybenzene

4. Pyrogallic Acid

5. 1,2,3-benzenetriol

6. Fourrine Pg

7. Fouramine Brown Ap

8. Fourrine 85

9. Pyro

10. Piral

11. C.i. Oxidation Base 32

12. Benzenetriol

13. Fouramine Base Ap

14. C.i. 76515

15. 1,2,3-trihydroxybenzen

16. Benzene, 1,2,3-trihydroxy-

17. Nsc 5035

18. 2,3-dihydroxyphenol

19. 1,2,3-trihydroxybenzen [czech]

20. 1,2,3-trihydroxy-benzene

21. Nsc-5035

22. 01y4a2qxy0

23. Chembl307145

24. 35296-77-6

25. Chebi:16164

26. 1,2,3-benzenetriol, Homopolymer

27. Benzene-1,2,3-triol (pyrogallol)

28. Mfcd00002192

29. Ncgc00091507-01

30. 1, 2, 3-benzenetriol

31. Dsstox_cid_5983

32. Dsstox_rid_77980

33. Dsstox_gsid_25983

34. 30813-84-4

35. 1,2,3-trihydroxybenzen (czech)

36. Ci Oxidation Base 32

37. Cas-87-66-1

38. Pyrogallol [nf]

39. Pyg

40. Ccris 1940

41. Hsdb 794

42. Pyrogallol, Acs

43. Einecs 201-762-9

44. Brn 0907431

45. Unii-01y4a2qxy0

46. Ci 76515

47. Pyrogallol;

48. Trihydroxybenzene

49. Ai3-00709

50. Pyrogallol Polymer

51. Pyrogallol Solution

52. Pyrogallol-[d6]

53. 1,3-benzenetriol

54. Pyrogallol, 98%

55. Pyrop

56. Pyrogallol Acs Grade

57. 1,3-trihydroxybenzen

58. 1216684-97-7

59. Pyrogallic Acid,(s)

60. 1,3-trihydroxybenzene

61. Benzene-1,2-3-triol

62. Pyrogallol [mi]

63. Pyrogallol, Acs Reagent

64. Pyrogallol [hsdb]

65. Pyrogallol [inci]

66. Benzene,2,3-trihydroxy-

67. Wln: Qr Bq Cq

68. Pyrogallol [vandf]

69. Pyrogallol [mart.]

70. Schembl3532

71. Pyrogallol [who-dd]

72. C.i. Oxidation Base 32

73. 4-06-00-07327 (beilstein Handbook Reference)

74. Mls001066376

75. Pyrogallol, Analytical Standard

76. 1,2,3-trihydroxybenzene, Xiv

77. Dtxsid6025983

78. Pyrogallol, >=98% (hplc)

79. Pyrogallol, P.a., Acs Reagent

80. Nsc5035

81. Zinc330141

82. Bcp15871

83. Hy-n1579

84. Pyrogallol, Acs Reagent, >=99%

85. Str08708

86. Tox21_111143

87. Tox21_202373

88. Bbl011607

89. Bdbm50031472

90. Pyrogallol, Vetec(tm) Reagent Grade

91. S3885

92. Stl163335

93. Akos000120163

94. Am10660

95. Ccg-266100

96. Cs-w019928

97. 1,2,3-benzenetriol (acd/name 4.0)

98. Ncgc00091507-02

99. Ncgc00091507-03

100. Ncgc00259922-01

101. Pyrogallol, Purum, >=98.0% (hplc)

102. Ac-11384

103. Bp-12538

104. Da-40956

105. Gmn

106. Pyrogallol, Saj First Grade, >=98.0%

107. Smr000471842

108. Pyrogallol, Jis Special Grade, >=99.0%

109. Ft-0606230

110. P0570

111. C01108

112. Ab-131/40221933

113. Q388692

114. W-104009

115. 2,3-dihydroxyphenol; Benzene-1,2,3-triol; Nsc 5035

116. F0001-2163

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 126.11 g/mol
Molecular Formula C6H6O3
XLogP30.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass126.031694049 g/mol
Monoisotopic Mass126.031694049 g/mol
Topological Polar Surface Area60.7 Ų
Heavy Atom Count9
Formal Charge0
Complexity84.3
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

/Experimental Therapy/ ... Pyrogallol had highly cytotoxic effect on human lung cancer cell lines and less effect on human bronchial epithelium cell line. This study was performed to investigate the beneficial effect of pyrogallol on human lung cancer cell lines - H441 (lung adenocarcinoma) and H520 (lung squamous cell carcinoma). The MTT (cytotoxic) data showed the inhibition growth of lung cancer cells followed pyrogallol treatment. The cell cycle of lung cancer cells was arrested in G2/M phase using flow cytometry. Using Western blot analysis, the cell cycle related proteins - cyclin B1 and Cdc25c were decreased in a time-dependent manner and the phosphorylated Cdc2 (Thr14) was increased within 4h pyrogallol treatment. Moreover, the higher cleavage of poly (ADP)-ribose polymerase (PARP), the increased of Bax concurrent with the decreased of Bcl-2 indicated that pyrogallol treatment resulted in apoptosis of lung cancer cells. The cell apoptosis was also directly demonstrated using Annexin V-FITC and TUNEL stain. Additionally, the tumoricidal effect of pyrogallol was measured using a xenograft nude mice model. After 5 weeks of pyrogallol treatment could cause the regression of tumor. Taking in vitro and in vivo studies together, these results suggest that pyrogallol can be developed as a promising anti-lung cancer drug particular for the non-small cell lung cancer (NSCLC).

PMID:19233505 Yang CJ et al; Lung Cancer 66 (2): 162-8 (2009)


4.2 Minimum/Potential Fatal Human Dose

4. 4 = Very toxic: Probable oral lethal dose (human) 50-500 mg/kg, between 1 teaspoon and 1 ounce for 80 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-128


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


5.2 Absorption, Distribution and Excretion

The substance can be absorbed into the body by ingestion.

International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Pyrogallic acid (April 2006). Available from, as of May 20, 2010: https://www.inchem.org/pages/icsc.html


Readily absorbed via skin.

Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2842


...Readily absorbed from gastroenteric tract & from parenteral sites of injection. Little is absorbed through intact skin. ...readily conjugated with hexuronic, sulfuric, or other acids & excreted within 24 hr via kidneys. A fraction is excreted unchanged.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 1596


5.3 Metabolism/Metabolites

...Pyrogallol /is a metabolite of tannic acid...

Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 123


With pyrogallol derivatives...the middle phenolic group is methylated, with catechol derivatives methylation may be meta or para, dependent on the other substituents present. Pyrogallol /is methylated by catechol o-methyl transferase to form/ 2-methyl pyrogallol.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 86


Pyrogallol in rats yields 3-methoxycatechol & 2-methoxyresorcinol. In grass yields 2-methoxyresorcinol. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. 46


Pyrogallol in beef yields purpurogallin. In tea yields purpurogallin. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. 46


For more Metabolism/Metabolites (Complete) data for Pyrogallic acid (7 total), please visit the HSDB record page.


5.4 Mechanism of Action

Pyrogallol (PG) as a polyphenol induces apoptosis in cells. The effects of PG on the growth and death of endothelial cells (ECs) /were examined/. PG dose-dependently inhibited the growth of calf pulmonary artery endothelial cells (CPAEC) and human umbilical vein endothelial cells (HUVEC). PG also induced apoptosis in both cells accompanied by the loss of mitochondrial membrane potential (DeltaPsi(m)). CPAEC were more sensitive to PG than HUVEC concerning cell growth and death. Caspase inhibitors (pan-caspase, caspase-3, -8 or -9 inhibitor) did not affect the growth inhibition of CPAEC by PG. However, pan-caspase inhibitor (Z-VAD) significantly reduced apoptosis and the loss of DeltaPsi(m) in PG-treated CPAEC. PG reduced ROS level and increased GSH depleted cell numbers in CPAEC. While Z-VAD increased ROS levels in PG-treated CPAEC, it decreased GSH depleted cell numbers. In conclusion, PG inhibited the growth of ECs, especially CPAEC via caspase-dependent apoptosis and GSH depletion.

PMID:19913593 Han YH et al; Food Chem Toxicol 48 (2): 558-63 (2010)


Pyrogallol (PG) as a polyphenol compound induces apoptosis in several types of cells. Here, we evaluated the effects of PG on endothelial cells (ECs), especially calf pulmonary artery endothelial cells (CPAEC) in relation to the cell growth, ROS and glutathione (GSH) levels. PG dose-dependently inhibited the growth of CPAEC and human umbilical vein endothelial cells (HUVEC) at 24 h. PG also induced apoptosis in CPAEC, which was accompanied by the loss of mitochondrial membrane potential (MMP; DeltaPsim). PG decreased ROS level including O2*- and PG dose-dependently increased GSH depleted cell number in both EC types. N-acetyl-cysteine (NAC; a well-known antioxidant) increased ROS levels in PG-treated CPAEC with the prevention of cell death and GSH depletion. In conclusion, PG inhibited the growth of ECs, especially CPAEC via apoptosis. PG-induced EC death was related to GSH depletion rather than ROS level changes.

PMID:19956894 Han YH et al; Oncol Rep 23 (1): 287-92 (2010)


Treatment with 50 or 100 uM pyrogallol (PG) significantly inhibited the cell growth of human pulmonary A549 cells for 72 hr. DNA flow cytometric analysis indicated that PG slightly induced a G1 phase arrest of the cell cycle at 24 or 48 hr, but did not induce the specific cell cycle arrest at 72 hr. Intracellular GSH depletion was observed in PG-treated cells. PG induced apoptosis in A549 cells, as evidenced by sub-G1 cells, annexin V staining cells, and the loss of mitochondrial membrane potential (DeltaPsi(m)). The intracellular ROS (reactive oxygen species) level including O(2)(*-) increased in PG-treated A549 cells at 24 and 48 hr, and persisted at 72 hr. The changes in GSH as well as ROS levels by PG affected the cell viability in A549 cells. In conclusion, PG inhibited the growth of human pulmonary A549 cells by inducing cell cycle arrest as well as triggering apoptosis.

PMID:19202562 Han YH et al; J Biochem Mol Toxicol 23 (1): 36-42 (2009)


Pyrogallol (PG) decreased the viability of human pulmonary adenocarcinoma Calu-6 cells in a dose- and time-dependent manner. The induction of apoptosis by PG was accompanied by the loss of mitochondrial membrane potential (DeltaPsi(m)), cytochrome c release from mitochondria and activation of caspase-3 and caspase-8. All tested caspase inhibitors, especially the pan-caspase inhibitor (Z-VAD), markedly rescued Calu-6 cells from PG-induced cell death. Rescue was accompanied by inhibition of caspase-3 activation and PARP cleavage. Treatment with Z-VAD also prevented the loss of mitochondrial membrane potential (DeltaPsi(m)). In conclusion, PG inhibits the growth of Calu-6 cells via caspase-dependent apoptosis.

PMID:19000662 Han YH et al; Chem Biol Interact 177 (2): 107-14 (2009)


For more Mechanism of Action (Complete) data for Pyrogallic acid (7 total), please visit the HSDB record page.


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08-Jan-2021
25-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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