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Chemistry

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Also known as: 3-methylphenol, 108-39-4, Metacresol, Phenol, 3-methyl-, Meta-cresol, 3-cresol

Molecular Formula

C₇H₈O

Molecular Weight

108.14 g/mol

InChI Key

RLSSMJSEOOYNOY-UHFFFAOYSA-N

FDA UNII

GGO4Y809LO

m-Cresol is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

M-Cresol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-methylphenol

2.1.2 InChI

InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3

2.1.3 InChI Key

RLSSMJSEOOYNOY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=CC=C1)O

2.2 Other Identifiers

2.2.1 UNII

GGO4Y809LO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-cresol

2. 3-cresol, Calcium Salt(1:2)

3. 3-cresol, Sodium Salt

4. 3-methylphenol

5. Meta-cresol

6. Metacresol

2.3.2 Depositor-Supplied Synonyms

1. 3-methylphenol

2. 108-39-4

3. Metacresol

4. Phenol, 3-methyl-

5. Meta-cresol

6. 3-cresol

7. 3-hydroxytoluene

8. M-methylphenol

9. M-kresol

10. M-cresylic Acid

11. 1-hydroxy-3-methylbenzene

12. M-oxytoluene

13. M-toluol

14. M-hydroxytoluene

15. Meta-cresylic Acid

16. 1-methyl-3-hydroxybenzene

17. Cresol, M-

18. Fema No. 3530

19. Hydroxy-3-methylbenzene

20. Cresol, Meta

21. M-cresylic

22. M-cresole

23. 3-methyl-1-hydroxybenzene

24. Nsc 8768

25. Ggo4y809lo

26. Chembl298312

27. Phenol, 3-methyl-, Homopolymer

28. Chebi:17231

29. Nsc-8768

30. M-cresol, 99%

31. Toluene,3-hydroxy (meta-cresol)

32. Dsstox_cid_4200

33. Franklin Cresolis

34. Dsstox_rid_77325

35. Dsstox_gsid_24200

36. Metacresol (3-methylphenol)

37. Crs

38. M-kresol [german]

39. Rover's Dog Shampoo

40. Caswell No. 261a

41. Meta Cresol

42. Mfcd00002302

43. 3-methyl Phenol

44. Cresol, M-isomer

45. 27289-33-4

46. Cas-108-39-4

47. Ccris 645

48. Hsdb 1815

49. Metacresol [usp:ban]

50. Einecs 203-577-9

51. Unii-ggo4y809lo

52. Epa Pesticide Chemical Code 022102

53. 3methylphenol

54. Ai3-00136

55. 3-methyl-phenol

56. Cresol,m-

57. M-cresol;

58. Celcure Dry Mix (chemicals For Wood Preserving)

59. Metacresol (usp)

60. Metacresol [ii]

61. M-cresol [inci]

62. Metacresol [hsdb]

63. Bmse000350

64. Ec 203-577-9

65. M-cresol [who-dd]

66. Metacresol [usp-rs]

67. Wln: Qr C1

68. Schembl10736

69. M-cresol, Analytical Standard

70. M-cresol, >=98%, Fg

71. Schembl7410931

72. Dtxsid6024200

73. M-cresol, For Synthesis, 99%

74. M-cresol, Reagent Grade, 97%

75. Metacresol [ep Impurity]

76. Metacresol [ep Monograph]

77. Metacresol [usp Impurity]

78. Nsc8768

79. M-cresol, Ph.eur., 99.5%

80. Metacresol [usp Monograph]

81. Zinc897141

82. 3-methylphenol, Analytical Standard

83. Tox21_201941

84. Tox21_302645

85. Bdbm50008548

86. Stl185666

87. Akos000119006

88. Am62795

89. Ccg-230271

90. Db01776

91. Ncgc00159366-02

92. Ncgc00159366-03

93. Ncgc00159366-04

94. Ncgc00159366-05

95. Ncgc00159366-06

96. Ncgc00256824-01

97. Ncgc00259490-01

98. Ac-14350

99. Bs-23591

100. M-cresol, Saj First Grade, >=97.0%

101. 3-methylphenol 100 Microg/ml In Methanol

102. Ft-0628174

103. M-cresol [un2076] [poison, Corrosive]

104. 3-methylphenol 100 Microg/ml In Isopropanol

105. Amylmetacresol Impurity B [ep Impurity]

106. C01467

107. D04951

108. A801870

109. Q312240

110. J-002137

111. J-521679

112. F0001-0167

113. Z955123620

114. Metacresol, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₇H₈O
Molecular Weight	108.14 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	108.057514874 g/mol
Monoisotopic Mass	108.057514874 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	70.8
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Therapeutic Uses

MEDICATION (VET): Local antiseptic, parasiticide, disinfectant; has been used as an intestinal antiseptic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 460

Disinfectant

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 460

Cresol is a well-known environmental pollutant, toluene metabolite, uremic toxicant and accidental poisoning product. Formocresol, a preparation of formalin and cresol, is also used as a root canal medicament and for pulpotomy of primary teeth. However, little is known about its effect on cardiovascular system. In this study, m-cresol inhibited the AA-induced platelet aggregation by 43-97% at concentrations ranging from 0.25 to 1 mM. Collagen-induced platelet aggregation was also inhibited by 0.25-1 mM of m-cresol by 47-98%. Accordingly, o-cresol (0.1-0.5 mM) also inhibited the AA-induced platelet aggregation by 46-96% and the collagen-induced platelet aggregation by 35-88% at concentrations of 0.1-1 mM. AA- and collagen-induced platelet thromboxane B(2) (TXB(2)) production was inhibited by even 0.1 mM of m-cresol with 88 and 54% of inhibition, respectively. The o-cresol (0.1 mM) also inhibited the AA- and collagen-induced platelet TXB(2) production with 91 and 97% respectively. Although m- and o-cresol (<1 mM) showed little effect on thrombin-induced platelet aggregation, they effectively inhibited the thrombin-induced platelet TXB(2) production. The m-cresol (2 and 5 mM) inhibited the COX-1 activity by 55-99%, but showed little effect on COX-2 enzyme activity. Moreover, o-cresol (0.5 and 1 mM) inhibited the COX-1 activity by 40-95%. COX-2 enzyme activity was inhibited by 68% at a concentration of 5 mM o-cresol. These results indicate that acute cresol-poisoning, direct root canal medication with formocresol or long-term occupational exposure to cresol and toluene may potentially suppress blood clot formation and lead to tissue hemorrhage via inhibition of platelet aggregation, TXB(2) production and COX enzyme activity.

PMID:15664436 Chan CP et al; Toxicology 208 (1): 95-104 (2005)

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

... m-Cresol (in NaHCO2) /was administered/ to rabbits by gavage. Urinary metabolites were evaluated after administration of 500 mg of m-Cresol. Ten percent of the dose was excreted as ethereal sulfate, 60% as ether glucuronide, 1% as the free cresol, about 3% as 2,5-dihydroxytoluene, and a trace amount as 3,4-dihydroxytoluene.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Sodium p-Chloro-m-Cresol, p-Chloro-m-Cresol, Chlorothymol, Mixed Cresols, m-Cresol, o-Cresol, p-Cresol, Isopropyl Cresols, Thymol, o-Cymen-5-ol, and Carvacrol; Int J Toxicol 25 Suppl 1: 29-127 (2006) https://www.cir-safety.org/ingredients

/It has been/ reported that 22% of the sulfate conjugate of m-Cresol (in water) was excreted after 290 mg/kg m-Cresol was administered to rabbits by gavage.

Cresols are slightly more corrosive /to the skin or eyes/ than phenol, but systemic effects may be a little milder because of slower absorption.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-192

... /It has been/ reported that 20% of a subcutaneous dose of 7.2 to 10.0 mg m-Cresol was excreted unchanged via urine in guinea pigs.

5.2 Metabolism/Metabolites

m-Cresol yields m-cresyl-beta-d-glucuronide, m-cresyl sulfate, 4-methylcatechol, methylquinol and m-methylanisole in rabbits. m-Cresol yields m-cresyl sulfate & m-methylanisole in rats. m-Cresol yields m-methylanisole in guinea pigs and mice. m-Cresol yields m-cresyl-beta-d-glucuronide in hens.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-59

The ... m-cresols /is/ ... ring-hydroxylated to a small extent ... 2,5-Dihydroxytoluene has been isolated from the urine of rabbits fed ... m-cresols ...

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:436

Ten healthy men were exposed to approximately 200 ppm toluene for 4 hr. Urinary m-cresol concentration was 0.570 mg/L at the end of the exposure, 0.599 mg/L 4 hr after exposure, and 0.527 mg/L 20 hr after exposure.

Fatiadi AJ; Environ Int 10: 175-205 (1984)

The urinary & biliary excretion of (14)C-labeled m-cresol was investigated in 12 species of freshwater fish when immersed in sublethal concn in the aquarium water for 48 hr. The oxidation product, m-hydroxybenzoic acid & the m-cresol sulfate conjugate were excreted into the aquarium water by all species except the guppy, which did not excrete m-hydroxybenzoic acid. In addition to these two metabolites, the m-cresol glucuronic acid conjugate was found in the bile of all species, except the guppy.

PMID:6880238 Layiwola PJ et al; Xenobiotica 13 (2): 107-13 (1983)

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

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