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Chemistry

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Also known as: 2-methoxyphenol, 90-05-1, O-methoxyphenol, 2-hydroxyanisole, Phenol, 2-methoxy-, Guaiastil
Molecular Formula
C7H8O2
Molecular Weight
124.14  g/mol
InChI Key
LHGVFZTZFXWLCP-UHFFFAOYSA-N
FDA UNII
6JKA7MAH9C

Guaiacol
An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747)
1 2D Structure

Guaiacol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methoxyphenol
2.1.2 InChI
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
2.1.3 InChI Key
LHGVFZTZFXWLCP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=CC=CC=C1O
2.2 Other Identifiers
2.2.1 UNII
6JKA7MAH9C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-hydroxy-anisole

2. 2-hydroxyanisole

3. 2-methoxy-phenol

4. 2-methoxyphenol

5. Catechol, Methyl

6. Guaicol

7. Methyl Catechol

2.3.2 Depositor-Supplied Synonyms

1. 2-methoxyphenol

2. 90-05-1

3. O-methoxyphenol

4. 2-hydroxyanisole

5. Phenol, 2-methoxy-

6. Guaiastil

7. Pyroguaiac Acid

8. O-guaiacol

9. O-hydroxyanisole

10. Pyrocatechol Monomethyl Ether

11. 1-hydroxy-2-methoxybenzene

12. Methylcatechol

13. Anastil

14. Guaicol

15. Phenol, O-methoxy-

16. Guaicolina

17. Guajol

18. Guasol

19. O-methyl Catechol

20. Catechol Monomethyl Ether

21. Creosote, Wood

22. Methoxyphenol

23. Guajakol

24. Creodon

25. 8021-39-4

26. Wood Creosote

27. 2-methoxy-phenol

28. Hydroxyanisole

29. Fema No. 2532

30. Guaiacol [jan]

31. Methylcatachol

32. Ortho-guaiacol

33. 2-methoxy Phenol

34. Nsc 3815

35. (mu)-methoxyphenol

36. Mfcd00002185

37. Guaiacol (jan)

38. Creodon (tn)

39. Nsc-3815

40. 2-methoxyl-4-vinylphenol

41. 6jka7mah9c

42. 9009-62-5

43. 2-methoxyphenol (guaiacol)

44. Chembl13766

45. Chebi:28591

46. Phenol, 2-methoxy-, Homopolymer

47. Phenol, Methoxy-

48. Ncgc00090827-02

49. Ncgc00090827-04

50. Guajacol

51. Dsstox_cid_3113

52. Dsstox_rid_76880

53. Guajakol [czech]

54. Dsstox_gsid_23113

55. Creosote, Beechwood

56. Guaiacol (natural)

57. Pyrocatechol Methyl Ester

58. Cas-90-05-1

59. 26247-00-7

60. Ccris 2943

61. Guaiacol [jan:nf]

62. Hsdb 4241

63. Sr-01000838056

64. Einecs 201-964-7

65. Unii-6jka7mah9c

66. Guiacol

67. Creasote

68. Methoxy Phenol

69. 6-methoxyphenol

70. Hydroxyl Anisole

71. Ai3-05615

72. Nat.guaiacol

73. O-methylcatechol

74. O-guiacol

75. O--methoxyphenol

76. Orthomethoxyphenol

77. O-methoxy-phenol

78. 2-methyloxyphenol

79. Ortho-methoxyphenol

80. Guaiacol,(s)

81. Jz3

82. 2-(methyloxy)phenol

83. Guaiacol [fhfi]

84. Guaiacol [hsdb]

85. Guaiacol [mi]

86. Guaiacol [vandf]

87. Catechol Mono Methyl Ether

88. Guaiacol [mart.]

89. Bmse000436

90. Bmse010027

91. Guaiacol [usp-rs]

92. Guaiacol [who-dd]

93. Ec 201-964-7

94. Guaiacol, Puriss., 99%

95. Wln: Qr Bo1

96. Dsstox_rid_77552

97. 1- Hydroxy-2-methoxybenzene

98. 3-methoxy-4-hydroxy Benzene

99. Dsstox_gsid_24853

100. Schembl21626

101. Ghl.pd_mitscher_leg0.900

102. Guaiacol (liquid) Extra Pure

103. Guaiacol, Oxidation Indicator

104. Mls001055375

105. Guaiacol [ep Monograph]

106. Guaiacol [usp Impurity]

107. Dtxsid0023113

108. Nsc3815

109. Guaiacol, Natural, >=99%, Fg

110. Hms2089d18

111. Hms2233p04

112. Hms3372n11

113. Hms3715e11

114. Pharmakon1600-01506165

115. A Hydroxlyated Aryl Lignin Fragment

116. Bcp27082

117. Cs-d1347

118. Hy-n1380

119. Str03604

120. Tox21_111031

121. Tox21_201136

122. Tox21_202990

123. Tox21_400004

124. Bdbm50240369

125. Nsc760376

126. S3872

127. Stl281868

128. Zinc13512224

129. Akos000118831

130. Ccg-214035

131. Db11359

132. Nsc-760376

133. Pb43791

134. Ps-3252

135. Guaiacol, Saj First Grade, >=98.0%

136. Ncgc00090827-01

137. Ncgc00090827-03

138. Ncgc00090827-05

139. Ncgc00090827-06

140. Ncgc00090827-07

141. Ncgc00258688-01

142. Ncgc00260535-01

143. Ac-34997

144. Guaiacol, Vetec(tm) Reagent Grade, 98%

145. Smr000059155

146. Sy048708

147. Cas-8021-39-4

148. Db-024854

149. Ft-0626815

150. Ft-0671312

151. Guaifenesin Impurity A [ep Impurity]

152. M0121

153. C01502

154. D00117

155. F70227

156. 2-methoxyphenol;o-methoxyphenol;2-hydroxyanisole

157. Ab00876226-06

158. Ab00876226_07

159. A843426

160. Q412403

161. Q-100002

162. Sr-01000838056-2

163. Sr-01000838056-3

164. F2173-0425

165. Guaiacol, European Pharmacopoeia (ep) Reference Standard

166. Guaiacol, United States Pharmacopeia (usp) Reference Standard

167. Guaiacol, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 124.14 g/mol
Molecular Formula C7H8O2
XLogP31.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass124.052429494 g/mol
Monoisotopic Mass124.052429494 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count9
Formal Charge0
Complexity83
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

IT IS USED EMPIRICALLY AS AN EXPECTORANT TO LESSEN AMT OF MUCOUS IN THE CHRONIC STAGES OF BRONCHITIS & BRONCHIECTASIS. IT IS FREQUENTLY PRESCRIBED FOR ITS STIMULANT EXPECTORANT ACTION AS A CONSTITUENT OF A STEAM INHALANT. THE ANTISEPTIC ACTION IS WEAK & NOT CLINICALLY USEFUL. ... IT HAS BEEN EMPLOYED AS A LOCAL ANESTHETIC IN DENTISTRY, IN A MANNER SIMILAR TO THYMOL. IT IS OCCASIONALLY EMPLOYED EXTERNALLY FOR ITS DISINFECTANT ACTION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1102


MEDICATION (VET): TOPICALLY (1.0-1.5%), IN UDDER AND WOUND TREATMENT OINTMENTS & IN POULTICES; WHEN ELIMINATED BY RESP MUCOUS MEMBRANES, SLIGHT ANTISEPTIC & LOCAL ANESTHETIC EFFECTS MAY OCCUR. INTERNALLY ... USED IN ANTIFERMENT & ANTIBLOAT MIXTURES.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 144


ANTIPYRETIC; STYPTIC; ASTRINGENT

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2601


MEDICATION (VET): PARASITICIDE, DEODORANT

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 403


Disinfectants; Expectorants

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Medication (Vet): ... Oral or parenteral mucolytic antiseptic antitussive in bronchopneumonias. ... Inhalant. In antiphlogistic, anodyne liquids on congested udders, in horse leg paints, and in poultices. Spray over tail biting swine to ... discourage cannibalism. Parenteral /dosage/ in camphorated oil. US mfr use 50 mg/mL concentration.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 249


For the symptomatic relief of coughs associated with colds, bronchial catarrh, influenza and upper respiratory tract infections such as laryngitis and pharyngitis. Codeine is a well-known centrally acting cough suppressant. Guaiacol acts as an expectorant, loosening bronchial secretions in the respiratory tract. /Guaiacol, codeine combination/

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Pulmo Bailly (Last updated February 2010). Available from, as of March 9, 2010: https://emc.medicines.org.uk/medicine/22147/SPC/Pulmo+Bailly/


4.2 Drug Warning

THE REPEATED ABSORPTION OF THERAPEUTIC DOSES FROM GASTROENTERIC TRACT MAY INDUCE SIGNS OF CHRONIC INTOXICATION, CHARACTERIZED BY DISTURBANCES OF VISION & DIGESTION (INCR PERISTALSIS & EXCRETION OF BODY FECES). IN ISOLATED CASES OF "SELF-MEDICATION", HYPERTENSION & ALSO GENERAL CARDIOVASCULAR COLLAPSE HAVE BEEN DESCRIBED.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2603


WHEREVER CREOSOTE IS INDICATED FOR INTERNAL MEDICATION CREOSOTE FROM WOOD TAR SHOULD BE DISPENSED & UNDER NO CIRCUMSTANCES SHOULD CREOSOTE FROM COAL TAR BE GIVEN, UNLESS EXPLICITLY SO DIRECTED.

The Merck Index. 10th ed. Rahway, New Jersey: Merck Co., Inc., 1983., p. 368


Do not use in Cats.

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 403


4.3 Drug Indication

It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation.


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Absorption

In rats, guaiacol is rapidly absorbed, being present in the blood 5 minutes after oral administration, and reaching its peak plasma concentration in about 10 minutes. Its elimination from the blood is usually as rapid.


Route of Elimination

Excreted by rabbits in combined form with sulfate (15%) and glucuronic acid (72%).


CREOSOTE IS RAPIDLY ABSORBED FROM THE GASTROENTERIC TRACT AND THROUGH THE SKIN. IT APPEARS TO BE EXCRETED IN THE URINE MAINLY IN CONJUGATION WITH SULFURIC, HEXURONIC, & OTHER ACIDS. OXIDATION ALSO OCCURS WITH THE FORMATION OF CMPD THAT IMPART A SMOKY APPEARANCE TO THE URINE. TRACES ARE EXCRETED BY WAY OF THE LUNGS.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2603


Medical experience indicates that toxic quantities can be absorbed through the skin quite readily.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2525


Methoxyphenol largely absorbed from digestive tract and stored in blood, kidneys, and respiratory organs. Excreted by rabbits in combined form with sulfate (15%) and glucuronic acid (72%).

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 740


In rats, guaiacol is rapidly absorbed, being present in the blood 5 minutes after oral administration, and reaching its peak plasma concentration in about 10 minutes. Its elimination from the blood is usually as rapid.

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Pulmo Bailly (Last updated February 2010). Available from, as of March 9, 2010: https://emc.medicines.org.uk/medicine/22147/SPC/Pulmo+Bailly/


5.2 Metabolism/Metabolites

.../IT APPEARS TO BE CONJUGATED/ WITH SULFURIC, HEXURONIC & OTHER ACIDS. OXIDATION...OCCURS WITH FORMATION OF COMPOUNDS THAT IMPART A SMOKY APPEARANCE TO THE URINE.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2603


Several strains of Aspergillus niger hydroxylated anisole to give o-hydroxyanisole as main product.

Bocks SM; Phytochemistry 6 (6): 785 (1967)


o-Methoxyphenol yields 3-methoxycatechol probably in rabbit; yields o-methoxyphenyl sulfate probably in rabbit. o-Methoxyphenol yields catechol in rat; yields 1,2-dimethoxybenzene in mouse, rabbit, guinea pig, and rat. /From table/

SRI


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01-Jan-2021
26-Oct-2024
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