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Chemistry

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Also known as: Pyrocatechol, 120-80-9, 1,2-benzenediol, 1,2-dihydroxybenzene, Benzene-1,2-diol, Pyrocatechin
Molecular Formula
C6H6O2
Molecular Weight
110.11  g/mol
InChI Key
YCIMNLLNPGFGHC-UHFFFAOYSA-N
FDA UNII
LF3AJ089DQ

Catechol
catechol is a natural product found in Populus tremula, Aloe ferox, and other organisms with data available.
1 2D Structure

Catechol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
benzene-1,2-diol
2.1.2 InChI
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
2.1.3 InChI Key
YCIMNLLNPGFGHC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C(=C1)O)O
2.2 Other Identifiers
2.2.1 UNII
LF3AJ089DQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2-benzenediol

2. 1,2-dihydroxybenzene

3. 1,3-dihydroxybenzene

4. 2-hydroxyphenol

5. Catechol Dipotassium Salt

6. Catechol Sodium Salt

7. Catechol, 14c-labeled Cpd

8. Pyrocatechol

2.3.2 Depositor-Supplied Synonyms

1. Pyrocatechol

2. 120-80-9

3. 1,2-benzenediol

4. 1,2-dihydroxybenzene

5. Benzene-1,2-diol

6. Pyrocatechin

7. 2-hydroxyphenol

8. O-benzenediol

9. O-dihydroxybenzene

10. O-dioxybenzene

11. O-hydroquinone

12. O-hydroxyphenol

13. Phthalhydroquinone

14. Pyrocatechine

15. O-phenylenediol

16. Oxyphenic Acid

17. Fouramine Pch

18. Benzenediol

19. Durafur Developer C

20. Pelagol Grey C

21. Catechin (phenol)

22. Fourrine 68

23. Benzene, O-dihydroxy-

24. Catechol (phenol)

25. O-diphenol

26. C.i. Oxidation Base 26

27. Pyrokatechin

28. Pyrokatechol

29. Katechol

30. Ortho-dihydroxybenzene

31. Nci-c55856

32. Nsc 1573

33. C.i. 76500

34. Catechol-pyrocatechol

35. 12385-08-9

36. Mfcd00002188

37. Lf3aj089dq

38. 1,2-benzenediol, Homopolymer

39. Chembl280998

40. Dtxsid3020257

41. Chebi:18135

42. Nsc-1573

43. Ortho-hydroxyphenol

44. 26982-53-6

45. Caq

46. Dsstox_cid_257

47. Ortho-benzenediol

48. Ortho-dioxybenzene

49. Ortho-hydroquinone

50. Dsstox_rid_75468

51. Katechol [czech]

52. Ortho-phenylenediol

53. Pyrocatechinic Acid

54. Dsstox_gsid_20257

55. Pyrokatechin [czech]

56. Pyrokatechol [czech]

57. Benzene-1,2-diol (pyrocatechol)

58. Ci Oxidation Base 26

59. Phthalic Alcohol

60. Cas-120-80-9

61. Smr000326660

62. Ccris 741

63. Hsdb 1436

64. Einecs 204-427-5

65. Unii-lf3aj089dq

66. Brn 0471401

67. Oxyphenate

68. Ci 76500

69. Kachin

70. Ortho-diphenol

71. Benzene Diol

72. Ortho-quinol

73. Ai3-03995

74. 4oow

75. Alpha-hydroxyphenol

76. 1,2-benzenedio

77. O-dihydroxy-benzene

78. Phenol Derivative, 2

79. 3fw4

80. 4k7i

81. Catechol [hsdb]

82. Catechol [iarc]

83. Pyrocatechol, >=99%

84. Catechol [vandf]

85. Lopac-c-9510

86. Pyrocatechol [mi]

87. Wln: Qr Bq

88. Bmse000385

89. Ec 204-427-5

90. Pyrocatechol [inci]

91. 1,2-dihydroxybenzene, Xi

92. 1,2-benzenediol; Catechol

93. Lopac0_000280

94. Schembl18351

95. Mls002153385

96. Mls002303022

97. Bidd:er0327

98. Pyrocatechinic Acidpyrocatechol

99. Pyrocatechol, P.a., 99.0%

100. Bdbm26188

101. Durafur Developer Cfouramine Pch

102. Nsc1573

103. Hms2233a17

104. Hms3260h22

105. Hms3373k16

106. Tox21_202317

107. Tox21_300153

108. Tox21_500280

109. S6305

110. Stk398651

111. Zinc13512214

112. Akos000119002

113. Ccg-204375

114. Db02232

115. Lp00280

116. Sdccgsbi-0050268.p002

117. Catechol 100 Microg/ml In Acetonitrile

118. Ncgc00015283-01

119. Ncgc00015283-02

120. Ncgc00015283-03

121. Ncgc00015283-04

122. Ncgc00015283-05

123. Ncgc00015283-06

124. Ncgc00015283-07

125. Ncgc00015283-08

126. Ncgc00015283-10

127. Ncgc00091262-01

128. Ncgc00091262-02

129. Ncgc00091262-03

130. Ncgc00253952-01

131. Ncgc00259866-01

132. Ncgc00260965-01

133. Ac-34196

134. Bp-21156

135. Bs-20054

136. Catechol (pyrocatechol; Benzene-1,2-diol)

137. Db-003770

138. C.i.-76500

139. Eu-0100280

140. Ft-0606411

141. P0317

142. P0567

143. C 9510

144. C00090

145. C01785

146. D91943

147. 1,2-dihydroxybenzene, Reagentplus(r), >=99%

148. Pyrocatechol, Purified By Sublimation, >=99.5%

149. A804599

150. Ab-131/40235236

151. Q282440

152. Sr-01000075791

153. Sr-01000075791-1

154. W-109068

155. F0001-0332

156. Pyrocatechol, Certified Reference Material, Tracecert(r)

157. Z1262246103

158. Pyrocatechol, Plant Cell Culture Tested, Bioreagent, >=99%, Powder

159. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2r-trans)-

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 110.11 g/mol
Molecular Formula C6H6O2
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass110.036779430 g/mol
Monoisotopic Mass110.036779430 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count8
Formal Charge0
Complexity62.9
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 Minimum/Potential Fatal Human Dose

4. =very toxic: Probable oral lethal dose (human) 50 to 500 mg/kg, between 1 teaspoon and 1 ounce for 70 kg person (150 lbs)

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-190


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Pyrocatechol is readily absorbed from the GI tract and through the intact skin of mice, and probably through the lungs ... Part of the catechol ... conjugates in the body with glucuronic, sulfuric, and other acids and is excreted in the urine, with a little "free" pyrocatechol. The conjugates hydrolyze easily in the urine with the liberation of the "free" catechol, which is oxidized by air with the formation of dark-colored substances that impart to the urine a "smokey" appearance.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:400


When mice were exposed to cigarette smoke containing radiolabeled pyrocatechol, pyrocatechol was distributed readily into the blood and tissues; 90% of the radioactivity was excreted in the urine within 24 hr.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:400


Catechol... is absorbed in the respiratory tract. ...Very little is excreted in the urine as free catechol.

Sullivan, J.B., Krieger G.R. (eds). Clinical Environmental Health and Toxic Exposures. Second edition. Lippincott Williams and Wilkins, Philadelphia, Pennsylvania 1999., p. 1262


The "'S" skin notation in the listing /of the American Conference of Industrial Hygienists (ACGIH)/ refers to the "potential significant contribution to the overall exposure by the cutaneous route, including mucous membrane and the eyes, either by contact with vapors or, of probable greater significance, by direct skin contact with the substance."

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:402


5.2 Metabolism/Metabolites

Part of the catechol is oxidized with polyphenol oxidase to benzoquinone. Another fraction conjugates in the body with glucuronic, sulfuric, and other acids ... The conjugates hydrolyze easily in the urine with the liberation of the free catechol ...

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:400


Catechol yields guaiacol in rat. ... In the rabbit /catechol/ ... yields o-hydroxyphenyl-beta-d-glucuronide, o-hydroxyphenyl sulfate, and hydroxyquinol ... .

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-11


Structure-reactivity studies ... undertaken in rat ... results obtained with ... catechol ... show that 2 vicinal hydroxyl groups are a necessary condition for the /methylation/ reaction to take place, providing evidence for mode of action of catechol o-methyl transferase.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 174


Rabbits administered pyrocatechol orally excreted in the urine 18% as sulfate, 70% as monoglucuronide, and 2% as free pyrocatechol.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:400


For more Metabolism/Metabolites (Complete) data for CATECHOL (9 total), please visit the HSDB record page.


Catechol has known human metabolites that include Diphenol glucuronide, catechol sulfate, and o-Methoxyphenyl sulfate.

Catechol is a known human metabolite of phenol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.3 Biological Half-Life

The calculated biological half-life of pyrocatechol in humans was 3-7 hr.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:401


5.4 Mechanism of Action

The effects of catechol on various ionic channels of isolated primary afferent neurons of the bull frog were examined by a single suction electrode clamp system, which combined internal perfusion and current or voltage clamp using an electronic switching circuit. Catechol was found to inhibit rather specifically the fast potassium(+) current as does 4-aminopyridine. Calcium(2+), sodium(+) and slow potassium(+) currents were not affected. Although both 4-aminopyridine and catechol were inhibitors of the fast potassium(+) channels, their sites of action were quite different. Catechol was effective when applied on the external surface of the cell membrane whereas 4-aminopyridine acted preferably internally. We assumed that a single fast potassium(+) channel has two distinct sites for blockers: the catechol site is exposed to the external medium or situated at the outer orifice of the pore, and the 4-aminopyridine site is located within the same channel but is more easily accessible from inside the nerve cell than outside. The 4-aminopyridine and catechol sites were not, however, completely separate and independent of each other since a synergistic interaction was observed between catechol and 4-aminopyridine.

PMID:2427692 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1182528 Ito I, Maeno T; J Physiol 373: 115-27 (1986)


Catechol, a naturally occurring and an important industrial chemical, has been shown to have strong promotion activity and induce glandular stomach tumors in rodents. In addition, catechol is a major metabolite of carcinogenic benzene. To clarify the carcinogenic mechanism of catechol, we investigated DNA damage using human cultured cell lines and 32P-labeled DNA fragments obtained from the human p53 and p16 tumor suppressor genes and the c-Ha-ras-1 proto-oncogene. Catechol increased the amount of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG), which is known to be correlated with the incidence of cancer, in a human leukemia cell line HL-60, whereas the amount of 8-oxodG in its hydrogen peroxide (H2O2)-resistant clone HP100 was not increased. The formation of 8-oxodG in calf thymus DNA was increased by catechol in the presence of Cu(2+). Catechol caused damage to 32P-labeled DNA fragments in the presence of Cu(2+). When NADH was added, DNA damage was markedly enhanced and clearly observed at relatively low concentrations of catechol (<1 microM). DNA cleavage was enhanced by piperidine treatment, suggesting that catechol plus NADH caused not only deoxyribose phosphate backbone breakage but also base modification. Catechol plus NADH frequently modified thymine residues. Bathocuproine, a specific Cu(+) chelator and catalase inhibited the DNA damage, indicating the participation of Cu(+) and H2O2 in DNA damage. Typical hydroxyl radical scavengers did not inhibit catechol plus Cu(2+)-induced DNA damage, whereas methional completely inhibited it. These results suggest that reactive species derived from the reaction of H2O2 with Cu(+) participates in catechol-induced DNA damage. Therefore, /the authors/ conclude that oxidative DNA damage by catechol through the generation of H2O2 plays an important role in the carcinogenic process of catechol and benzene.

PMID:11470755 Oikawa S et al; Carcinogenesis 22 (8): 1239-45 (2001)


We examined the redox properties of the "carcinogenic" catechol and the "noncarcinogenic" hydroquinone in relation to different DNA damaging activities and carcinogenicity using 32P-labeled DNA fragments obtained from the human genes. In the presence of endogenous NADH and Cu2+, catechol induces stronger DNA damage than hydroquinone, although the magnitudes of their DNA damaging activities were reversed in the absence of NADH. In both cases, DNA damage resulted from base modification at guanine and thymine residues in addition to strand breakage induced by Cu+ and H2O2, generated during the oxidation of catechol and hydroquinone into 1,2-benzoquinone and 1,4-benzoquinone, respectively. EPR and 1H NMR studies indicated that 1,2-benzoquinone is converted directly into catechol through a nonenzymatic two-electron reduction by NADH whereas 1,4-benzoquinone is reduced into hydroquinone through a semiquinone radical intermediate through two cycles of one-electron reduction. The reduction of 1,2-benzoquinone by NADH proceeds more rapidly than that of 1,4-benzoquinone. This study demonstrates that the rapid 1,2-benzoquinone two-electron reduction accelerates the redox reaction turnover between catechol and 1,2-benzoquinone, resulting in the enhancement of DNA damage. These results suggest that the differences in NADH-mediated redox properties of catechol and hydroquinone contribute to their different carcinogenicities

PMID:11800599 Hirakawa K et al; Chem Res Toxicol 15 (1): 76-82 (2002)


Catechol is possibly carcinogenic to humans (International Agency for Research on Cancer, IARC). The key mechanism could include its oxidative DNA-damaging effect in combination with reductive-oxidative metals like Cu. We found that DNA damage was suppressed by introducing an alpha-carbonyl group to catechol at C4-position to produce carbonyl catechols. During the oxidative DNA-damaging process, catechols but not carbonyl catechols were oxidized to o-quinone; however, coexisting Cu(II) was reduced to Cu(I). Carbonyl catechols were possibly arrested at the oxidation step of semiquinones in the presence of Cu(II). Cu(I)-binding to DNA was stronger than Cu(II)-binding, on the basis of the circular dichroism spectral change. None of the carbonyl catechols induced such change, suggesting sequestration of Cu(I) from DNA. Solid-phase extraction experiments and spectrophotometric analyses showed the formation of semiquinone chelates with Cu(I). Thus, chelate formation could explain the suppression mechanism of the Cu-catechol-dependent DNA damage by terminating the reduction-oxidation cycle. Structural modifications such as introducing an alpha-carbonyl group to catechol at C4-position would contribute to reducing the risk and improving industrial and medical potentials of aromatic/phenolic compounds ... .

PMID:20832456 Ando M et al; Toxicol Lett. 199 (3): 213-7 (2010)


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02-Jan-2022
31-May-2025
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Looking for 120-80-9 / Catechol API manufacturers, exporters & distributors?

Catechol manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Catechol API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Catechol manufacturer or Catechol supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Catechol manufacturer or Catechol supplier.

PharmaCompass also assists you with knowing the Catechol API Price utilized in the formulation of products. Catechol API Price is not always fixed or binding as the Catechol Price is obtained through a variety of data sources. The Catechol Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Catechol

Synonyms

Pyrocatechol, 120-80-9, 1,2-benzenediol, 1,2-dihydroxybenzene, Benzene-1,2-diol, Pyrocatechin

Cas Number

120-80-9

Unique Ingredient Identifier (UNII)

LF3AJ089DQ

About Catechol

catechol is a natural product found in Populus tremula, Aloe ferox, and other organisms with data available.

Catechol Manufacturers

A Catechol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Catechol, including repackagers and relabelers. The FDA regulates Catechol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Catechol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Catechol manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Catechol Suppliers

A Catechol supplier is an individual or a company that provides Catechol active pharmaceutical ingredient (API) or Catechol finished formulations upon request. The Catechol suppliers may include Catechol API manufacturers, exporters, distributors and traders.

click here to find a list of Catechol suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Catechol GMP

Catechol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Catechol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Catechol GMP manufacturer or Catechol GMP API supplier for your needs.

Catechol CoA

A Catechol CoA (Certificate of Analysis) is a formal document that attests to Catechol's compliance with Catechol specifications and serves as a tool for batch-level quality control.

Catechol CoA mostly includes findings from lab analyses of a specific batch. For each Catechol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Catechol may be tested according to a variety of international standards, such as European Pharmacopoeia (Catechol EP), Catechol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Catechol USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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