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Chemistry

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Also known as: 2-methylphenol, 95-48-7, Orthocresol, 2-hydroxytoluene, 2-cresol, Phenol, 2-methyl-
Molecular Formula
C7H8O
Molecular Weight
108.14  g/mol
InChI Key
QWVGKYWNOKOFNN-UHFFFAOYSA-N
FDA UNII
YW84DH5I7U

O-Cresol
2-Methylphenol is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

O-Cresol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methylphenol
2.1.2 InChI
InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
2.1.3 InChI Key
QWVGKYWNOKOFNN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=CC=C1O
2.2 Other Identifiers
2.2.1 UNII
YW84DH5I7U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-cresol

2. 2-cresol, Ammonium Salt

3. 2-cresol, Potassium Salt

4. 2-cresol, Sodium Salt

5. 2-methylphenol

6. Ortho-cresol

2.3.2 Depositor-Supplied Synonyms

1. 2-methylphenol

2. 95-48-7

3. Orthocresol

4. 2-hydroxytoluene

5. 2-cresol

6. Phenol, 2-methyl-

7. O-methylphenol

8. O-cresylic Acid

9. O-oxytoluene

10. O-toluol

11. 1-hydroxy-2-methylbenzene

12. Ortho-cresol

13. O-hydroxytoluene

14. O-methylphenylol

15. O-kresol

16. Cresol, Ortho-

17. Cresol, O-

18. 2-hydroxy-1-methylbenzene

19. 2-methyl Phenol

20. O-kresol [german]

21. 2-methyl-phenol

22. Cresol, O-isomer

23. Fema No. 3480

24. 1-methyl-2-hydroxybenzene

25. Nsc 23076

26. Yw84dh5i7u

27. Chebi:28054

28. Mfcd00002226

29. Nsc-23076

30. Nsc-36809

31. Toluene,2-hydroxy (ortho-cresol)

32. O-cresol [un2076] [poison, Corrosive]

33. Dsstox_cid_1808

34. Cresol Mixture Of Isomers;methylphenol;tricresol

35. Dsstox_rid_76341

36. Wln: Qr B1

37. Dsstox_gsid_21808

38. Hydroxy Toluene

39. Cas-95-48-7

40. Orthocresol [nf]

41. Cresols Are Organic Compounds Which Are Methylphenols. They Are A Widely Occurring Natural And Manufactured Group Of Aromatic Organic Compounds, Which Are Categorized As Phenols.

42. Ccris 646

43. Hsdb 1813

44. Einecs 202-423-8

45. Unii-yw84dh5i7u

46. Ortho Cresol

47. Methyl Phenol

48. 2-methyiphenol

49. Ai3-00137

50. Jz0

51. O-cresol,(s)

52. Carvacrol Derivative, 9

53. O-cresol [fhfi]

54. O-cresol [inci]

55. O-cresol, >=99%

56. O-cresol [mi]

57. Orthocresol [hsdb]

58. Bmse000433

59. Un 2076 (related)

60. Ec 202-423-8

61. 2-methylphenol (o-cresol)

62. Ortho-cresol,2-methylphenol

63. Schembl16002

64. Mls002454426

65. O-cresol, Analytical Standard

66. Bidd:er0677

67. Chembl46931

68. Dtxsid8021808

69. Bdbm248166

70. Hms2268o24

71. Orthocresol [usp Impurity]

72. Zinc901022

73. O-cresol, For Synthesis, 99.3%

74. 2-methylphenol, Analytical Standard

75. Nsc23076

76. Nsc36809

77. Tox21_202305

78. Tox21_300021

79. Stl194295

80. O-cresol, Reagentplus(r), >=99%

81. Akos000119021

82. Ncgc00091534-01

83. Ncgc00091534-02

84. Ncgc00091534-03

85. Ncgc00091534-04

86. Ncgc00254140-01

87. Ncgc00259854-01

88. O-cresol, Saj First Grade, >=97.0%

89. Smr001252248

90. 2-methylphenol 100 Microg/ml In Methanol

91. Metacresol Impurity B [ep Impurity]

92. Ft-0656046

93. 2-methylphenol 100 Microg/ml In Isopropanol

94. C01542

95. 1-hydroxyl 2-methyl Benzene, 2-hydroxyl Toluene

96. Q312708

97. J-006098

98. J-523819

99. F0001-2271

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 108.14 g/mol
Molecular Formula C7H8O
XLogP32
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
Complexity70.8
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


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

... o-Cresol (in water) /was administered/ to rabbits by gavage. The extent of sulfate conjugation was determined before and after a 290 mg/kg o-Cresol dose. Twenty-two percent of the o-Cresol was excreted as the sulfate conjugate.

PMID:16835130 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


... o-Cresol (in NaHCO2) /was administered/ to rabbits by gavage. Urinary metabolites were evaluated after administration of 500 mg of o-Cresol. Fifteen percent of the dose was excreted as ethereal sulfate, 72% as ether glucuronide, 1% as free cresol, and about 3% as 2,5-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


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


A subcutaneous dose of 7.2 to 10.0 mg o-Cresol /was administered/ to guinea pigs. About 38% of the dose was excreted unchanged via urine.

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


... A cross-sectional study on 100 workers indicated that the biological threshold for o-cresol:creatinine ratio reference value of <1 mg/g could presently be used as a reference for non-industrial human exposure while the <2 mg/g rate is for worker exposure in an industrial environment at a coal combustion plant.

Kocks DJ, Smith CE; Occup Med (Oxf) 48 (3): 195-7 (1998)


5.2 Metabolism/Metabolites

The o- ... cresols are ring-hydroxylated to a small extent ... 2,5-Dihydroxytoluene has been isolated from the urine of rabbits fed o- ... cresol ...

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 436


o-Cresol yields o-cresyl-beta-d-glucuronide, o-cresyl sulfate, methylquinol, o-methylanisole, & 3-methylcatechol in rabbits. o-Cresol yields o-cresol sulfate and o-methylanisole in rats. o-Cresol yields o-methylanisole in guinea pigs & mice. /From Table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-58


Ten healthy men were exposed to approximately 200 ppm toluene for 4 hr. Urinary o-cresol concentration was 1.603 mg/L at the end of the exposure, 1.400 mg/L 4 hr after exposure, and 0.495 mg/l 20 hr after exposure.

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


In two workers admitted to hospital because of coma due to accidental occupational exposure to mixture of solvents, the level of toluene was respectively 823-1122 ug/L in blood & 53-38 ug/L in alveolar air on second day (36 hr after exposure). On fifth day (112 hr after exposure) the toluene level was 120-45 ug/L in blood & 3-1 ug/L in alveolar air. Urinary excretion of o-cresol, calculated as a toluene equivalent, was 0.8-0.9 mg on second day & 1.7 to 1.6 mg on third day. Urinary hippuric acid, as a toluene equivalent, was 1.7 to 1.4 g on second day & 1.3 to 0.7 g on third day.

Brugnone F et al; Int Arch Occp Environ Health 53 (2): 157-65 (1983)


For more Metabolism/Metabolites (Complete) data for o-CRESOL (15 total), please visit the HSDB record page.


O-Cresol is a known human metabolite of toluene.

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


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