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2D Structure
Also known as: 4-methylphenol, 106-44-5, 4-cresol, 4-hydroxytoluene, Phenol, 4-methyl-, P-methylphenol
Molecular Formula
C7H8O
Molecular Weight
108.14  g/mol
InChI Key
IWDCLRJOBJJRNH-UHFFFAOYSA-N
FDA UNII
1MXY2UM8NV

P-cresol is a natural product found in Podocarpus fasciculus, Artemisia macrocephala, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-methylphenol
2.1.2 InChI
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
2.1.3 InChI Key
IWDCLRJOBJJRNH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=C(C=C1)O
2.2 Other Identifiers
2.2.1 UNII
1MXY2UM8NV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-cresol

2. 4-cresol, Aluminum Salt

3. 4-cresol, Potassium Salt

4. 4-cresol, Sodium Salt

5. 4-methylphenol

6. Para-cresol

2.3.2 Depositor-Supplied Synonyms

1. 4-methylphenol

2. 106-44-5

3. 4-cresol

4. 4-hydroxytoluene

5. Phenol, 4-methyl-

6. P-methylphenol

7. Para-cresol

8. P-hydroxytoluene

9. P-tolyl Alcohol

10. P-kresol

11. P-oxytoluene

12. P-toluol

13. P-cresylic Acid

14. 1-hydroxy-4-methylbenzene

15. Paracresol

16. P-methylhydroxybenzene

17. 1-methyl-4-hydroxybenzene

18. Paramethyl Phenol

19. Para-cresylic Acid

20. 4-methyl Phenol

21. Cresol, Para-

22. Cresol, P-

23. P-kresol [german]

24. Cresol, P-isomer

25. Fema No. 2337

26. Cresol, Para

27. P-methyl Phenol

28. 4-methyl-phenol

29. 4-methylphenol (p-cresol)

30. Nsc 3696

31. Mfcd00002376

32. 1mxy2um8nv

33. Chembl16645

34. Phenol, 4-methyl-, Homopolymer

35. Chebi:17847

36. Nsc-3696

37. Ncgc00091519-04

38. Toluene,4-hydroxy (para-cresol)

39. P-cresol [un2076] [poison, Corrosive]

40. Dsstox_cid_1869

41. Dsstox_rid_76375

42. Dsstox_gsid_21869

43. 27289-34-5

44. Cas-106-44-5

45. Ccris 647

46. Hsdb 1814

47. Einecs 203-398-6

48. Unii-1mxy2um8nv

49. Para Cresol

50. P-cresylate

51. P-methyl-phenol

52. Ai3-00150

53. 4 -methylphenol

54. Cresol,p-

55. Para-cresyl Alcohol

56. Phenol, 4-methyi

57. P-cresol, 99%

58. Spectrum_000850

59. P-cresol, High Purity

60. 4-methyl Phenol 99%

61. P-cresol [fhfi]

62. P-cresol [hsdb]

63. P-cresol [inci]

64. Spectrum2_000765

65. Spectrum4_001740

66. Spectrum5_000540

67. P-cresol [mi]

68. Schembl375

69. Bmse000458

70. Ec 203-398-6

71. Dsstox_rid_77380

72. Dsstox_rid_77554

73. Nciopen2_001516

74. Wln: Qr D1

75. Dsstox_gsid_24364

76. Dsstox_gsid_24858

77. Kbiogr_002160

78. Kbioss_001330

79. 1-hydroxyl 4-methyl Benzene

80. P-cresol, Analytical Standard

81. Bidd:er0010

82. Divk1c_000381

83. Spectrum1500209

84. P-cresol, >=99%, Fg

85. Spbio_000810

86. Schembl7812506

87. Sgcut00097

88. Dtxsid7021869

89. Hms501d03

90. Kbio1_000381

91. Kbio2_001330

92. Kbio2_003898

93. Kbio2_006466

94. Nsc3696

95. Paracresol [usp Impurity]

96. Ninds_000381

97. Hms1920a16

98. Hms2091i04

99. Pharmakon1600-01500209

100. Zinc897142

101. P-cresol, For Synthesis, 98.0%

102. 4-methylphenol, Analytical Standard

103. Nsc95259

104. To_000033

105. Tox21_113240

106. Tox21_113445

107. Tox21_200402

108. Tox21_201115

109. Tox21_300029

110. Bdbm50008543

111. Ccg-38990

112. Nsc-95259

113. Nsc756709

114. Stl183323

115. Akos000119005

116. Tox21_113445_1

117. Db01688

118. Idi1_000381

119. Ncgc00013272-01

120. Ncgc00091519-01

121. Ncgc00091519-02

122. Ncgc00091519-03

123. Ncgc00091519-05

124. Ncgc00091519-06

125. Ncgc00091519-07

126. Ncgc00091519-09

127. Ncgc00253980-01

128. Ncgc00257956-01

129. Ncgc00258667-01

130. 4-methylphenol 10 Microg/ml In Methanol

131. Ps-11958

132. 4-methylphenol 100 Microg/ml In Methanol

133. Cas-1319-77-3

134. P-cresol, Jis Special Grade, >=99.0%

135. Sbi-0051322.p003

136. Metacresol Impurity C [ep Impurity]

137. Ft-0660000

138. 4-methylphenol 100 Microg/ml In Cyclohexane

139. P-cresol, Puriss. P.a., >=99.0% (gc)

140. Amylmetacresol Impurity D [ep Impurity]

141. C01468

142. Ab00051955_02

143. Q312251

144. Sr-05000002037

145. J-001591

146. J-515803

147. Sr-05000002037-1

148. F1908-0066

149. 2876-02-0

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 108.14 g/mol
Molecular Formula C7H8O
XLogP31.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass108.057514874 g/mol
Monoisotopic Mass108.057514874 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count8
Formal Charge0
Complexity62.8
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): 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


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Humans normally excrete approximately 50 mg of p-cresol in the urine daily. p-Cresol is produced endogenously from tyrosine by anaerobic bacteria in the gastrointestinal tract.

Sullivan, J.B., Krieger G.R. (eds). Clinical Environmental Health and Toxic Exposures. Second edition. Lippincott Williams and Wilkins, Philadelphia, Pennsylvania 1999., p. 1259


The normal human excretes 16 to 39 mg p-cresol/day.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 446


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


Healthy humans excrete an average of about 50 mg (range 16-74 mg) of p-cresol in the urine daily. Endogenous p-cresol is produced from tyrosine, an amino acid present in most proteins, by anaerobic bacteria in the intestine. Free p-cresol formed in this way is absorbed from the intestine and eliminated in the urine as conjugates.

WHO; Environ Health Criteria 168: Cresols (1995). Available from, as of December 22, 2014: https://www.inchem.org/pages/ehc.html


For more Absorption, Distribution and Excretion (Complete) data for p-CRESOL (9 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

p-Cresol fed to rabbits is excreted in the urine as the glucuronide (60%) and sulfate (15%) conjugates, some 10% is oxidized to p-hydroxybenzoic acid and a trace is hydroxylated to 3,4-dihydroxytoluene.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 147


p-Cresol yields p-cresyl-beta-d-glucuronide, p-cresyl sulfate, p-hydroxybenzyl alcohol, 4-methylcatechol, and p-methylanisole in rabbits.

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


p-Cresol yields p-cresyl sulfate in man.

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


p-Cresol yields p-cresyl sulfate and p-methylanisole in rats.

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


For more Metabolism/Metabolites (Complete) data for p-CRESOL (18 total), please visit the HSDB record page.


4-Methylphenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid, 4-Hydroxybenzyl alcohol, 4-Methyl-2,5-cyclohexadien-1-one, and 4-methyl-hydroquinone.

4-Methylphenol is a known human metabolite of toluene.

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