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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
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 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

... 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.

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


... /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.

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


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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18-Jan-2021
17-Dec-2024
KGS
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ABOUT THIS PAGE

Looking for 108-39-4 / M-Cresol API manufacturers, exporters & distributors?

M-Cresol manufacturers, exporters & distributors 1

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PharmaCompass offers a list of M-Cresol 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 M-Cresol manufacturer or M-Cresol supplier for your needs.

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

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

API | Excipient name

M-Cresol

Synonyms

3-methylphenol, 108-39-4, Metacresol, Phenol, 3-methyl-, Meta-cresol, 3-cresol

Cas Number

108-39-4

Unique Ingredient Identifier (UNII)

GGO4Y809LO

About M-Cresol

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

M-Cresol Manufacturers

A M-Cresol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of M-Cresol, including repackagers and relabelers. The FDA regulates M-Cresol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. M-Cresol 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 M-Cresol manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

M-Cresol Suppliers

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

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

M-Cresol USDMF

A M-Cresol DMF (Drug Master File) is a document detailing the whole manufacturing process of M-Cresol active pharmaceutical ingredient (API) in detail. Different forms of M-Cresol DMFs exist exist since differing nations have different regulations, such as M-Cresol USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A M-Cresol DMF submitted to regulatory agencies in the US is known as a USDMF. M-Cresol USDMF includes data on M-Cresol's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The M-Cresol USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of M-Cresol suppliers with USDMF on PharmaCompass.

M-Cresol GMP

M-Cresol 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 M-Cresol 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 M-Cresol GMP manufacturer or M-Cresol GMP API supplier for your needs.

M-Cresol CoA

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

M-Cresol CoA mostly includes findings from lab analyses of a specific batch. For each M-Cresol 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.

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