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Chemistry

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Also known as: 108-95-2, Carbolic acid, Hydroxybenzene, Phenic acid, Oxybenzene, Phenylic acid
Molecular Formula
C6H6O
Molecular Weight
94.11  g/mol
InChI Key
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
FDA UNII
339NCG44TV

Phenol
An antiseptic and disinfectant aromatic alcohol.
1 2D Structure

Phenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
phenol
2.1.2 InChI
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
2.1.3 InChI Key
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)O
2.2 Other Identifiers
2.2.1 UNII
339NCG44TV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Carbol

2. Carbolic Acid

3. Hydroxybenzene

4. Phenol, Sodium Salt

5. Phenolate Sodium

6. Phenolate, Sodium

7. Sodium Phenolate

2.3.2 Depositor-Supplied Synonyms

1. 108-95-2

2. Carbolic Acid

3. Hydroxybenzene

4. Phenic Acid

5. Oxybenzene

6. Phenylic Acid

7. Phenylic Alcohol

8. Benzenol

9. Monophenol

10. Phenyl Hydrate

11. Phenyl Hydroxide

12. Phoh

13. Monohydroxybenzene

14. Phenyl Alcohol

15. Paoscle

16. Phenole

17. Izal

18. Phenol Alcohol

19. Phenol, Liquefied

20. Acide Carbolique

21. Phenosmolin

22. Fenolo

23. Phenol Homopolymer

24. Benzene, Hydroxy-

25. Carbolsaure

26. Fenosmolin

27. Fenosmoline

28. Fenol

29. Liquid Phenol

30. Carbolic Oil

31. Liquefied Phenol

32. Phenol, Pure

33. Fenolo [italian]

34. Phenole [german]

35. Rcra Waste Number U188

36. Campho-phenique Gel

37. Phenol [jan]

38. Phenic

39. Carbolsaure [german]

40. Campho-phenique Liquid

41. Nci-c50124

42. Liquified Phenol

43. Phenol, Molten

44. Baker's P & S Liquid & Ointment

45. Carbolicum Acidum

46. Fenol [dutch, Polish]

47. Baker's P And S Liquid And Ointment

48. Monohydroxy Benzene

49. Phenol, Sulfurated

50. Un 2812 (solution)

51. Un 2312 (molten)

52. Acide Carbolique [french]

53. Un 1671 (solid)

54. Nsc 36808

55. Campho-phenique Cold Sore Gel

56. Anbesol

57. Phenic Alcohol

58. Synthetic Phenol

59. 2-allphenol

60. Phenol, Dimer

61. Rcra Waste No. U188

62. Phenol, Liquified

63. Mfcd00002143

64. Un1671

65. Un2312

66. Un2821

67. Ai3-01814

68. Nsc-36808

69. Chembl14060

70. 339ncg44tv

71. Dtxsid5021124

72. Chebi:15882

73. Phenol (or Solutions With 5% Or More Phenol)

74. Ent-1814

75. 27073-41-2

76. Phenol, Solid [un1671] [poison]

77. Phenol, Molten [un2312] [poison]

78. Ncgc00091454-04

79. Phenol Solutions [un2821] [poison]

80. Dsstox_cid_1124

81. Phenol, >=99.0%

82. Dsstox_rid_75955

83. Dsstox_gsid_21124

84. 17442-59-0

85. 61788-41-8

86. Caswell No. 649

87. Phenylalcohol

88. Hydroxy Benzene

89. Phenol 100 Microg/ml In Methanol

90. Phenol, Liquid

91. Phenol, Solid

92. Baker's P And S

93. Cas-108-95-2

94. Ccris 504

95. Fema No. 3223

96. Hsdb 113

97. (14c)phenol

98. Phenol [usp:jan]

99. Phenol (2,3,4,5,6-d5)

100. Einecs 203-632-7

101. Epa Pesticide Chemical Code 064001

102. Arenols

103. Unii-339ncg44tv

104. Benzophenol

105. Carbolsaeure

106. Karbolsaeure

107. Extracts, Coal Tar Oil Alk.

108. Acide Phenique

109. Hydroxy-benzene

110. Phenol Solution

111. Phenol Liquid

112. Phenol Molten

113. Phenol Solutions

114. Phenol Synthetic

115. Phenol,liquified

116. Phenolated Water

117. Pandy's Reagent

118. Cepastat Lozenges

119. Phenol, Labeled With Carbon-14

120. Phenol (liquid)

121. 2-phenyl Alcohol

122. Phenol, Synthetic

123. Phenol, Ultrapure

124. Phenol Acs Grade

125. Einecs 262-972-4

126. Paoscle (tn)

127. Carbolic Acid Liquid

128. Phenol Polymer-bound

129. Phenol (granulated)

130. Phenol (tn)

131. Phenol,(s)

132. Phenol, Acs Reagent

133. Carbolic Acid, Liquid

134. 1ai7

135. 1li2

136. 4i7l

137. Liquefied Phenol (tn)

138. Phenol [vandf]

139. Phenol [fhfi]

140. Phenol [hsdb]

141. Phenol [iarc]

142. Phenol [inci]

143. Phenol (jp17/usp)

144. Phenol [usp-rs]

145. Phenol [who-dd]

146. Phenol, Detached Crystals

147. Phenol [ii]

148. Phenol [mi]

149. Phenol, >=99%

150. Phenol [mart.]

151. Wln: Qr

152. Liquefied Phenol (jp17)

153. Bmse000290

154. Bmse010026

155. C6h5oh

156. Fenol(dutch, Polish)

157. Ec 203-632-7

158. Phenol, 80% In Ethanol

159. Phenol, Lr, >=99%

160. 63496-48-0

161. 65996-83-0

162. Mls001065591

163. Phenol, For Molecular Biology

164. Bidd:er0293

165. Phenol [ep Monograph]

166. Phenol For Disinfection (tn)

167. Phenol, Natural, 97%, Fg

168. Phenol [usp Monograph]

169. Cuticura Pain Relieving Ointment

170. Carbolicum Acidum [hpus]

171. Phenol, Ar, >=99.5%

172. Phenol,liquified [vandf]

173. Bdbm26187

174. Chebi:33853

175. Phenol For Disinfection (jp17)

176. Phenolated Water For Disinfection

177. Salicylic Acid Related Compound C

178. 3f39

179. Phenol 10 Microg/ml In Methanol

180. Phenol Solution, 1.0 M In Thf

181. Nsc36808

182. Zinc5133329

183. Phenol, Glass Distilled Under Argon

184. Tox21_113463

185. Tox21_201639

186. Tox21_300042

187. Phenol 1000 Microg/ml In Methanol

188. Phenol 5000 Microg/ml In Methanol

189. Phenol;phenol [jan];phenol, Pure;phenol Phenol [jan] Phenol, Pure

190. Stl194294

191. Akos000119025

192. Tox21_113463_1

193. Db03255

194. Na 2821

195. Phenol, Bioxtra, >=99.5% (gc)

196. Phenol, Saj First Grade, >=98.0%

197. Un 1671

198. Un 2312

199. Un 2821

200. Ncgc00091454-01

201. Ncgc00091454-02

202. Ncgc00091454-03

203. Ncgc00091454-05

204. Ncgc00091454-06

205. Ncgc00091454-07

206. Ncgc00254019-01

207. Ncgc00259188-01

208. Phenol Solution, 1 M In Dichloromethane

209. Phenol, Jis Special Grade, >=99.0%

210. 73607-76-8

211. Am802906

212. Bp-30160

213. Methyl Salicylate Impurity B [ep]

214. Smr000568492

215. Phenol 1000 Microg/ml In Dichloromethane

216. Phenol, Pestanal(r), Analytical Standard

217. Liquified Phenol (contains 7-10 % Water)

218. Metacresol Impurity A [ep Impurity]

219. Ft-0645154

220. Ft-0673707

221. Ft-0693833

222. P1610

223. P2771

224. Phenol Stock Solution, 100 Mg/dl, Standard

225. C00146

226. D00033

227. Phenol, Unstabilized, Reagentplus(r), >=99%

228. Salicylic Acid Impurity C [ep Impurity]

229. Hexylresorcinol Impurity A [ep Impurity]

230. Phenol, P.a., Acs Reagent, 99.5-100.5%

231. Phenol, >=96.0% (calc. On Dry Substance, T)

232. Q130336

233. J-610001

234. Phenol, For Molecular Biology, ~90% (t), Liquid

235. F1908-0106

236. Phenol, Unstabilized, Purified By Redistillation, >=99%

237. Salicylic Acid Related Compound C [usp Impurity]

238. Phenol, Bioultra, For Molecular Biology, >=99.5% (gc)

239. Phenol, United States Pharmacopeia (usp) Reference Standard

240. Liquified Phenol, Meets Usp Testing Specifications, >=89.0%

241. Phenol, Bioultra, For Molecular Biology, Te-saturated, ~73% (t)

242. Phenol Solution, 5000 Mug/ml In Methanol, Certified Reference Material

243. Phenol Solution, Certified Reference Material, 500 Mug/ml In Methanol

244. Phenol, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., 99.0-100.5%

245. P-hydroxy Polystyrene (100-200 Mesh, 0.5-1.5 Mmol/g)@crlfmfcd03703209

246. Phenol Solution, 100 Mug/ml In Acetonitrile, Pestanal(r), Analytical Standard

247. Phenol, Contains Hypophosphorous As Stabilizer, Loose Crystals, Acs Reagent, >=99.0%

248. Phenol, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Usp, 99.5-100.5% (gc)

249. Phenol Solution, Bioreagent, Equilibrated With 10??mm Tris Hcl, Ph??8.0, 1??mm Edta, For Molecular Biology

250. Phenol Solution, Bioreagent, Saturated With 0.1 M Citrate Buffer, Ph??4.3 +/- 0.2, For Molecular Biology

251. Phenol, Polymer-bound, 100-200 Mesh, Extent Of Labeling: 0.5-1.5 Mmol/g Loading, 1 % Cross-linked With Divinylbenzene

252. Phenol, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Usp, >=99.5% (gc), Crystalline (detached)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 94.11 g/mol
Molecular Formula C6H6O
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass94.041864811 g/mol
Monoisotopic Mass94.041864811 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count7
Formal Charge0
Complexity46.1
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

Anti-Infective Agents, Local; Disinfectants; Sclerosing Solutions; Sympatholytics

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


Medication (Vet): Antiseptic caustic. Topical anesthetic in pruritic skin conditions. Has been used internally and externally as an antiseptic.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1300


MEDICATION (VET): PHENOL HAS BEEN USED INTERNALLY AS ANTISEPTIC & GASTRIC ANESTHETIC ...

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 443


DISINFECTANT & ANTISEPTIC (PRIMARILY FORMER USE)

SRI


For more Therapeutic Uses (Complete) data for PHENOL (14 total), please visit the HSDB record page.


4.2 Drug Warning

Dil phenol solutions (1 to 2%) are used medicinally as antipruritic preparations for the skin. Their repeated use over large skin areas or on particularly moist areas (axillary region, groin, feet) should be avoided.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-344


Soln of phenol (6%) in glycerine are sometimes employed in medical practice to produce nerve blocks. The spread of phenol beyond the intended site (stellate ganglion) resulted in infarction on the cervical cord with extensive paralysis in one patient and neurolosis of the cervical posterior roots with respiratory arrest in another.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-344


... Phenol ... should be applied only on small areas of skin and occlusive dressings, bandages, or diapers should not be used.

American Medical Association, Department of Drugs. Drug Evaluations. 6th ed. Chicago, Ill: American Medical Association, 1986., p. 1527


Phenol should never be used in pregnant women, in infants under 6 mo, or for diaper rash.

American Medical Association, Department of Drugs. Drug Evaluations. 6th ed. Chicago, Ill: American Medical Association, 1986., p. 1527


For more Drug Warnings (Complete) data for PHENOL (8 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

Ingestion of as little as 4.8 g of pure phenol caused death in 10 min.

NIOSH; Criteria Document: Phenol p.65 (1976) DHEW Pub NIOSH 76-196


4.4 Drug Indication

Phenol is primarily indicated for minor sore throat pain, sore mouth, minor mouth irritation, and pain associated with canker sores. Additionally, phenol is indicated in the treatment of focal spasticity.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Sclerosing Solutions

Chemical agents injected into blood vessels and lymphatic sinuses to shrink or cause localized THROMBOSIS; FIBROSIS, and obliteration of the vessels. This treatment is applied in a number of conditions such as VARICOSE VEINS; HEMORRHOIDS; GASTRIC VARICES; ESOPHAGEAL VARICES; PEPTIC ULCER HEMORRHAGE. (See all compounds classified as Sclerosing Solutions.)


Disinfectants

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)


Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


5.2 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05B - Antivaricose therapy

C05BB - Sclerosing agents for local injection

C05BB05 - Phenol


D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AE - Phenol and derivatives

D08AE03 - Phenol


N - Nervous system

N01 - Anesthetics

N01B - Anesthetics, local

N01BX - Other local anesthetics

N01BX03 - Phenol


R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA19 - Phenol


5.3 Absorption, Distribution and Excretion

Absorption

Phenol is rapidly absorbed through the skin and into the lungs.


Route of Elimination

The kidney is the primary route of elimination of phenol.


Volume of Distribution

At I5 min after exposure, the liver contained the highest level of phenol, consisting mainly of free phenol. After 82 minutes post administration, phenol is uniformly distributed in the liver, blood, kidneys, lungs, along with the heart, testes, thymus and the spleen. With the passage of time, the proportion of free to conjugated phenol changed. By 360 minutes most phenol appears in conjugated forms.


Clearance

In rabbits, 72% is excreted in the urine, 1% in the feces, 4% in the carcass following sacrifice, and trace amounts were exhaled.


Phenol is absorbed by all routes of administration and can reach circulation even when applied to intact skin.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 967


Absorption of 2 g of phenol could result from 8 hr inhalation at about 50 ppm.

American Conference of Governmental Industrial Hygienists, Inc. Documentation of the Threshold Limit Values, 4th ed., 1980. Cincinnati, Ohio: American Conference of Governmmental Industrial Hygienists, Inc., 1980., p. 328


The extent of absorption of phenol through rabbit skin is more strongly influenced by the area of the skin exposed than by the concentration of the applied solution in water.

WHO; Environ Health Criteria 161: Phenol (1994). Available from, as of April 1, 2003: https://www.inchem.org/documents/ehc/ehc/ehc161.htm#PartNumber:6


Renal excretion is principal route of elimination. ... In man 90% of non-toxic oral dose (0.01 mg/kg) of (14)C-labeled phenol was excreted in 24 hr, principally as sulfate (77% of the excreted label) and as glucuronide (16%), with small amt of sulfate and glucuronide conjugates of ... hydroquinone. With larger doses, free (unmetabolized) phenol can presumably be found in urine.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-346


For more Absorption, Distribution and Excretion (Complete) data for PHENOL (23 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Phenyl sulfate, phenyl glucuronide, quinol sulfate, and quinol glucuronide were detected in human beings as phenol metabolites.


Phenols are subjected to oxidative metabolism leading to ortho- and para-hydroxylated products. These metabolites are then transformed into equimolar amounts of two conjugates, sulfates and glucuronides.

Britt DL, Hushon JM; Biol Effects, Crit and Stand Haz Pollut Assoc Energy Technol p.29 (1976)


Metabolism in rabbits given a lethal dose of phenol (0.5 g/kg) resulted in: 47% oxidation to carbon dioxide and water plus traces of 1,4-dihydroxybenzene and ortho-dihydroxybenzene, 3% excreted in urine, 50% remaining in the carcass. Amounts were exhaled in air and excreted in in the feces. Metabolism in rabbits given a sublethal dose of phenol (0.3 g/kg) resulted in: 23% oxidation to carbon dioxide and water plus traces of 1,4-dihydroxybenzene and ortho-dihydroxybenzene, 72% excreted in the urine, 4% remaining in the carcass, 1% excreted in the feces, and trace amounts exhaled in air. Urinary route resulted in either excretion as free phenol or as conjugate. (Conjugation with sulfuric acid, glucuronic acid or other acids). /From figure/

USEPA; Ambient Water Quality Criteria Doc: Phenol p.C-16-19 (1980) EPA 440/5-80-066


The cat was shown to be sensitive to phenol. In addition to sulfate conjugates, free 1,4-dihydroxybenzene was found as a major metabolite which may account for the toxicity observed in the cat.

USEPA; Ambient Water Quality Criteria Doc: Phenol p.C-19 (1980) EPA 440/5-80-066


Some species differences have been noted in the metabolism of phenol. Man, rat, mouse, jerboa, gerbil, hamster, lemming, and guinea pig excreted four metabolites: sulfate and glucuronic acid conjugates of phenol and of 1,4-dihydroxybenzene. The squirrel and capuchin monkeys excreted phenol glucuronide, 1,4-dihydroxybenzene glucuronide, and phenol sulfate. The ferret, dog, hedgehog, and rabbit excreted phenol sulfate, 1,4-dihydroxybenzene sulfate, and phenyl glucuronide. The Rhesus monkey, fruit bat, and chicken excreted phenyl sulfate and phenyl glucuronide but not 1,4-dihydroxybenzene conjugates. The cat excreted only phenyl sulfate and 1,4-dihydroxybenzene sulfate, and the pig excreted phenyl glucuronide as its major phenol metabolite. Relatively low doses were utilized in this study.

USEPA; Ambient Water Quality Criteria Doc: Phenol p.C-16-19 (1980) EPA 440/5-80-066


For more Metabolism/Metabolites (Complete) data for PHENOL (16 total), please visit the HSDB record page.


Phenol has known human metabolites that include Catechol and Hydroquinone.

Phenol is a known human metabolite of benzene.

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


5.5 Biological Half-Life

Urine: 3.5 hours; [TDR, p. 1020]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 1020


Elimination half-life was 13.86 hours, considerably longer than previously reported /in a 47 yr old male with accidental dermal exposure to his left foot (3% of body surface area)/.

PMID:9865239 Bentur Y et al; J Toxicol Clin Toxicol 36 (7): 707-11 (1998)


The excretion of phenol was studied in human volunteers exposed to phenol by inhalation or skin absorption. The human body behaved almost like a single compartment with respect to phenol absorption and clearance with an excretion rate constant of K= 0.2/hr This corresponds to a half-life of approximately 3.5 hours.

USEPA; Ambient Water Quality Criteria Doc: Phenol p.C-20 (1980) EPA 440/5-80-066


5.6 Mechanism of Action

Phenol is a potent proteolytic agent. Concentrations in the 5% to 7% range dissolve tissue on contact via proteolysis. In high concentrations when injected next to a nerve, phenol produces a chemical neurolysis which is nonselective across nerve fiber size and most prominent on its outer aspect. Local anesthetic effects occur within 5-10 minutes.


The effects of monoamine depletors and monoamine denervators on phenol induced tremor were studied in mice. The tremor induced by phenol was enhanced by pretreatment with reserpine or tetrabenazine, but not with syrosingopine. However, alpha-methyl-p-tyrosine, p-chlorophenylalanine or 6-hydroxydopamine did not affect the tremor. These results suggest that the depletion of central monoamines as a whole contribute to the enhancement of the tremor induced by phenol.

PMID:3975240 Suzuki T, Kisara K; Pharmacol Biochem Behav 22 (1): 153-5 (1985)


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PHENOL

NDC Package Code : 50335-0010

Start Marketing Date : 2021-06-19

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (1g/g)

Marketing Category : BULK INGREDIENT

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