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Tox21_300044
Also known as: Phenylmethanol, Benzenemethanol, 100-51-6, Phenylcarbinol, Benzylalcohol, Benzoyl alcohol
Molecular Formula
C7H8O
Molecular Weight
108.14  g/mol
InChI Key
WVDDGKGOMKODPV-UHFFFAOYSA-N
FDA UNII
LKG8494WBH

A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.
Benzyl alcohol is a Pediculicide.
1 2D Structure

Tox21_300044

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
phenylmethanol
2.1.2 InChI
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
2.1.3 InChI Key
WVDDGKGOMKODPV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CO
2.2 Other Identifiers
2.2.1 UNII
LKG8494WBH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alcohol, Benzyl

2. Benzenemethanol

2.3.2 Depositor-Supplied Synonyms

1. Phenylmethanol

2. Benzenemethanol

3. 100-51-6

4. Phenylcarbinol

5. Benzylalcohol

6. Benzoyl Alcohol

7. Benzenecarbinol

8. Hydroxytoluene

9. Phenylmethyl Alcohol

10. Alpha-toluenol

11. (hydroxymethyl)benzene

12. Phenolcarbinol

13. Benzal Alcohol

14. Alpha-hydroxytoluene

15. Benzylic Alcohol

16. Alcool Benzylique

17. Benzylicum

18. Methanol, Phenyl-

19. Phenylcarbinolum

20. Hydroxymethylbenzene

21. Phenyl-methanol

22. Benzyl-alcohol

23. Euxyl K 100

24. 66072-40-0

25. Bentalol

26. Ulesfia

27. .alpha.-hydroxytoluene

28. Aromatic Alcohol

29. Caswell No. 081f

30. Fema No. 2137

31. .alpha.-toluenol

32. Benzyl Alcohol (natural)

33. Alcool Benzilico [dcit]

34. Itch-x

35. Alcoholum Benzylicum

36. Nci-c06111

37. Benzenmethanol

38. Benzylalkohol

39. Aromatic Primary Alcohol

40. Alcohol,benzyl

41. Alcool Benzylique [inn-french]

42. Benzyl Alkohol

43. Alcohol Bencilico [inn-spanish]

44. Methanol Benzene

45. Alcoholum Benzylicum [inn-latin]

46. Nsc 8044

47. Hoch-ph-polymer

48. Bnoh

49. Benzyl Alcohol, Polymer-bound

50. Nsc-8044

51. Mfcd00004599

52. Hydroxymethyl Resin (100-200 Mesh)

53. Toluene,alpha-hydroxy

54. Lkg8494wbh

55. Chebi:17987

56. Ins No.1519

57. Ins-1519

58. Hydroxymethyl Resin (200-400 Mesh)

59. Ncgc00091865-01

60. Phenyl Methanol

61. Dsstox_cid_152

62. E-1519

63. Dsstox_rid_75404

64. Dsstox_gsid_20152

65. 185532-71-2

66. Mbn

67. Alcool Benzilico

68. Alcohol, Benzyl

69. Alcohol Bencilico

70. Phenylmethan-1-ol

71. Cas-100-51-6

72. Hsdb 46

73. Ulesfia (tn)

74. Ccris 2081

75. Benzyl Alcohol Natural

76. Benzyl Alcohol [usan:inn:jan]

77. Einecs 202-859-9

78. Unii-lkg8494wbh

79. Epa Pesticide Chemical Code 009502

80. Brn 0878307

81. Enzylalcohol

82. Benzalalcohol

83. Benzalcohol

84. Bentanol

85. Alcoolbenzylique

86. Benzene-methanol

87. Benzyl Alcohole

88. A-hydroxytoluene

89. A-toluenol

90. Ai3-01680

91. Benzyl Alcohol [inn:jan:nf]

92. Alcohol Benzylicus

93. Hoch2-ph-polymer

94. Sunmorl Bk 20

95. Nat. Benzyl Alcohol

96. Phch2oh

97. 201740-95-6

98. Bn-oh

99. Benzyl Alcohol-13c6

100. Schembl147

101. Benzyl Alcohol, Acs Grade

102. Bmse000407

103. C6h5ch2oh

104. Chembl720

105. Ec 202-859-9

106. Wln: Q1r

107. Benzyl Alcohol [ii]

108. Benzyl Alcohol [mi]

109. Pinapur™ 9 Ba-r

110. Benzyl Alcohol (jp15/nf)

111. Benzyl Alcohol [fcc]

112. Benzyl Alcohol [inn]

113. Benzyl Alcohol [jan]

114. 4-06-00-02222 (beilstein Handbook Reference)

115. Benzyl Alcohol [fhfi]

116. Benzyl Alcohol [hsdb]

117. Benzyl Alcohol [inci]

118. Bidd:er0248

119. Alcohol,benzyl [vandf]

120. Benzyl Alcohol [vandf]

121. Tb 13g

122. Benzyl Alcohol [mart.]

123. Benzyl Alcohol, Lr, >=99%

124. Benzyl Alcohol (benzenemethanol)

125. Benzyl Alcohol [usp-rs]

126. Benzyl Alcohol [who-dd]

127. Benzyl Alcohol [who-ip]

128. Dtxsid5020152

129. Bdbm16418

130. Nsc8044

131. Benzyl Alcohol (jp17/nf/inn)

132. Benzyl Alcohol Reagent Acs Grade

133. Hms3264b16

134. Hms3885f10

135. Pharmakon1600-01502555

136. Zinc895302

137. Benzyl Alcohol, Analytical Standard

138. Benzyl Alcohol, Ar, >=99.5%

139. Hy-b0892

140. Benzyl Alcohol, Anhydrous, 99.8%

141. Tox21_111172

142. Tox21_202447

143. Tox21_300044

144. Bbl011938

145. Benzyl Alcohol [orange Book]

146. Mfcd03792087

147. Nsc760098

148. S4600

149. Stl163453

150. Benzyl Alcohol [ep Monograph]

151. Benzyl Alcohol, >=99%, Fcc, Fg

152. Akos000119907

153. Benzyl Alcohol, Natural, >=98%, Fg

154. Ccg-213843

155. Db06770

156. Nsc-760098

157. Benzylalcohol 100 Microg/ml In Methanol

158. Ncgc00091865-02

159. Ncgc00091865-03

160. Ncgc00091865-04

161. Ncgc00254154-01

162. Ncgc00259996-01

163. Alcohol Benzylicus [who-ip Latin]

164. Benzyl Alcohol, Acs Reagent, >=99.0%

165. Benzyl Alcohol, Reagentplus(r), >=99%

166. Benzyl Alcohol, Usp, 98.0-100.5%

167. Benzylalcohol 1000 Microg/ml In Ethanol

168. Benzyl Alcohol On Polystyrene, 3.5 Mmol/g

169. B2378

170. Benzyl Alcohol, Tested According To Ph.eur.

171. Benzylalcohol 100 Microg/ml In Acetonitrile

172. E1519

173. Ft-0622812

174. Benzyl Alcohol, P.a., Acs Reagent, 99.0%

175. Benzyl Alcohol, Saj First Grade, >=98.5%

176. A14564

177. Benzyl Alcohol, Saj Special Grade, >=99.0%

178. Benzyl Alcohol, Vetec(tm) Reagent Grade, 98%

179. C00556

180. C03485

181. D00077

182. D70182

183. Q52353

184. Ab01563201_01

185. A800221

186. Sr-01000872610

187. J-000153

188. Sr-01000872610-3

189. Benzalkonium Chloride Impurity A [ep Impurity]

190. F0001-0019

191. Z955123784

192. 3762963d-6c2a-4bff-ad94-3180e51bca68

193. Benzyl Alcohol, Certified Reference Material, Tracecert(r)

194. Benzyl Alcohol, European Pharmacopoeia (ep) Reference Standard

195. Benzyl Alcohol, Puriss. P.a., Acs Reagent, >=99.0% (gc)

196. Benzyl Alcohol, United States Pharmacopeia (usp) Reference Standard

197. (hydroxymethyl)polystyrene, 200-400 Mesh, Extent Of Labeling: ~1.7 Mmol/g Loading

198. (hydroxymethyl)polystyrene, 200-500 Mesh, Extent Of Labeling: ~1.1 Mmol/g Loading

199. Benzyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

200. Benzyl Alcohol, Pharmagrade, Usp/nf, Ph Eur, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production.

201. Benzyl Alcohol, Polymer-bound, 100-200 Mesh, Extent Of Labeling: 0.5-1.0 Mmol/g Loading, 1 % Cross-linked

202. Benzyl Alcohol, Polymer-bound, 100-200 Mesh, Extent Of Labeling: 1.0-2.0 Mmol/g Loading, 1 % Cross-linked With Divinylbenzene

203. Benzyl Alcohol, Polymer-bound, 70-90 Mesh, Extent Of Labeling: 0.5-1.0 Mmol/g Loading, 1 % Cross-linked With Divinylbenzene

204. Benzyl Alcohol, Polymer-bound, 70-90 Mesh, Extent Of Labeling: 1.0-1.5 Mmol/g Loading, 1 % Cross-linked

205. Benzyl Alcohol, Polymer-bound, 70-90 Mesh, Extent Of Labeling: 2.0-3.0 Mmol Loading, 1 % Cross-linked

206. Benzyl Alcohol, Puriss., Meets Analytical Specification Of Ph.??eur., Bp, Nf, 99-100.5% (gc)

207. Stratospheres(tm) Pl-hms (hydroxymethylstyrene) Resin, 50-100 Mesh, Extent Of Labeling: 2.0 Mmol Loading, 1 % Cross-linked

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 108.14 g/mol
Molecular Formula C7H8O
XLogP31.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass108.057514874 g/mol
Monoisotopic Mass108.057514874 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count8
Formal Charge0
Complexity55.4
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 Drug Information
1 of 2  
Drug NameUlesfia
Drug Label ULESFIA(benzyl alcohol) Lotion is supplied as a white topical lotion containing benzyl alcohol, 5%. Inactive ingredients in this formulation are water, mineral oil, sorbitan monooleate, polysorbate 80, carbomer 934P and trolamine....
Active IngredientBenzyl alcohol
Dosage FormLotion
RouteTopical
Strength5%
Market StatusPrescription
CompanyShionogi

2 of 2  
Drug NameUlesfia
Drug Label ULESFIA(benzyl alcohol) Lotion is supplied as a white topical lotion containing benzyl alcohol, 5%. Inactive ingredients in this formulation are water, mineral oil, sorbitan monooleate, polysorbate 80, carbomer 934P and trolamine....
Active IngredientBenzyl alcohol
Dosage FormLotion
RouteTopical
Strength5%
Market StatusPrescription
CompanyShionogi

4.2 Therapeutic Uses

Anesthetics, Local; Pharmaceutic Aids

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


/On April 9, 2009, the U.S. Food and Drug Administration approved a new prescription medication for the treatment of head lice ( Pediculosis capitis ) infestation. Benzyl Alcohol Lotion, 5%, received full market approval as a prescription medication, for use in patients 6 months of age and older. Benzyl Alcohol Lotion, 5%, is the first head lice product approved by the FDA with benzyl alcohol as the active pharmaceutical ingredient.

FDA; FDA Approves Benzyl Alcohol Lotion for the Treatment of Head Lice, FDA News (April 9, 2009) Available from, as of April 20, 2009: https://www.fda.gov/bbs/topics/NEWS/2009/NEW01993.html


The safety and effectiveness of Benzyl Alcohol Lotion, 5%, was demonstrated in two studies of 628 people, 6 months of age and older, with active head lice infestation. The subjects received two, 10-minute treatments of either Benzyl Alcohol Lotion or a topical placebo, one week apart. Fourteen days after the final treatment, more than 75 percent of the subjects treated with Benzyl Alcohol Lotion, 5%, were lice free.

FDA; FDA Approves Benzyl Alcohol Lotion for the Treatment of Head Lice, FDA News (April 9, 2009) Available from, as of April 20, 2009: https://www.fda.gov/bbs/topics/NEWS/2009/NEW01993.html


In each of two double-blind studies, 25 patients suffering from early progressive idiopathic cataracts, subcapsular or cortical in site, received one drop of saline containing 0.07% benzyl alcohol every 8 hours. The eyelid was held open for at least 2 minutes. Treatment continued for 22 months. In one study, a control group received placebo, whereas in the other study, the control group received an anticataract medication. Clinical findings were recorded every 30 days for the first 14 months, then patients were followed for up to 18 and 22 months. A significant (p < .01) increase in visual acuity (VA) was observed in patients treated with benzyl alcohol after 30 and 60 days as compared to those receiving either placebo or the medication. Compared to those placebo or medication treated, a significant (p < .01) decrease in lens opacity was noted in 19 and 17 patients treated with benzyl alcohol, respectively. In the course of the studies, a significant increase in the number of surgeries for cataracts was noted in patients not receiving benzyl alcohol. One patient treated with benzyl alcohol required surgery after 22 months compared to 38 total who had received either placebo or medication. benzyl alcohol was well tolerated except in two patients (4%) where tolerance was fair in one and poor in the other.

PMID:11766131 Nair B; Int J Toxicol 20 Suppl 3: 23-50 (2001)


For more Therapeutic Uses (Complete) data for BENZYL ALCOHOL (12 total), please visit the HSDB record page.


4.3 Drug Warning

Common side effects of /Benzyl Alcohol Lotion, 5%/ include irritations of the skin, scalp, and eyes, and numbness at the site of application. As with all medications, it is important to use benzyl alcohol, 5%, as labeled to maximize benefits and minimize risks. The product should be applied only to the scalp or the hair attached to the scalp. It is not approved for use in children younger than six months. Use in premature infants could lead to serious respiratory, heart- or brain-related adverse events such as seizure, coma, or death.

FDA; FDA Approves Benzyl Alcohol Lotion for the Treatment of Head Lice, FDA News (April 9, 2009) Available from, as of April 20, 2009: https://www.fda.gov/bbs/topics/NEWS/2009/NEW01993.html


It also seems prudent to avoid the use of products containing benzyl alcohol to pregnant patients within whom the benzyl alcohol molecule, given its small size, presumably crosses the placental barrier into immature fetal tissues as readily as it crosses the blood-brain barrier.

Organization for Economic Cooperation and Development; Screening Information Data Set for Benzoates, CAS #s 65-85-0, 532-32-1, 582-25-2, 100-51-6 p.294 (2001). Available from, as of July 9 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


Premature neonates may receive multiple drugs in the neonatal intensive care unit, some of which may contain benzyl alcohol. As there may be no safe lower dose of benzyl alcohol in these patients, it would seem prudent to avoid the use of multiple dose vials containing benzyl alcohol whenever alternatives exist.

Organization for Economic Cooperation and Development; Screening Information Data Set for Benzoates, CAS #s 65-85-0, 532-32-1, 582-25-2, 100-51-6 p.294 (2001). Available from, as of July 9, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


Benzyl alcohol is believe to have a role in the increased frequency of cerebral intraventricular hemorrhages and mortality reported in very-low-birth-weight (VLBW) infants (weight < 1000 g) who received flush solutions preserved with benzyl alcohol. An increased incidence of developmental delay and cerebral palsy is also noted in the same VLBW patient population, suggesting a secondary damaging effect of benzyl alcohol.

Goldfrank, L.R., Goldfrank's Toxicologic Emergencies 8th Ed. 2006., McGraw-Hill, New York, N.Y., p. 831


For more Drug Warnings (Complete) data for BENZYL ALCOHOL (6 total), please visit the HSDB record page.


4.4 Drug Indication

Ulesfia (benzyl alcohol) lotion is indicated for the topical treatment of head lice infestation in patients 6 months of age and older. Ulesfia Lotion does not have ovicidal activity.


FDA Label


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics, Local

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
BENZYL ALCOHOL
5.2.2 FDA UNII
LKG8494WBH
5.2.3 Pharmacological Classes
Pediculicide [EPC]
5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AX - Other ectoparasiticides, incl. scabicides

P03AX06 - Benzyl alcohol


5.4 Absorption, Distribution and Excretion

The percutaneous absorption was determined in vivo in rhesus monkeys. Absorption through occluded skin was high (56-80 %) in 24 hr. No correlation was seen between skin penetration and the octanol-water partition coefficient. Under unoccluded conditions skin penetration was reduced (32 %), because of evaporation of the compound.

OECD; SIDS Initial Assessment Report for SIAM 13. Report on Benzoates: Benzoic acid, Sodium benzoate, Potassium benzoate, Benzyl alcohol (CAS No: 65-85-0, 532-32-1, 582-25-2, 100-51-6) p.298 UNEP Publications (November 2001). Available from, as of November 18, 2014: https://www.inchem.org/pages/sids.html


High levels of benzyl alcohol (5-500 ug/10 mL plasma) were found in uremic patients on hemodialysis; benzyl alcohol was not detected in normal controls.

OECD; SIDS Initial Assessment Report for SIAM 13. Report on Benzoates: Benzoic acid, Sodium benzoate, Potassium benzoate, Benzyl alcohol (CAS No: 65-85-0, 532-32-1, 582-25-2, 100-51-6) p.294 UNEP Publications (November 2001). Available from, as of November 18, 2014: https://www.inchem.org/pages/sids.html


Rabbits given 1 g of benzyl alcohol sc eliminated 300-400 mg of hippuric acid within the following 24 hr. Within 6 hr after oral administration of 0.40 g benzyl alcohol/kg bw, rabbits eliminated 65.7% of dose as hippuric acid in the urine.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 2704


In humans and animals, benzyl alcohol was readily absorbed from the gastrointestinal tract. Percutaneous absorption was high following topical use. Rhesus monkeys absorbed 56-80% of a topical dose administered under occlusive conditions in 24 hours; absorption was less under unoccluded conditions due to evaporation. Benzyl alcohol rapidly disappeared from the injection site following intramuscular administration in rats; the disappearance half-life was estimated to be less than 10 minutes. ...

European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Benzyl Alcohol, Summary Report (1997). Available from, as of July 8, 2008: https://www.emea.europa.eu/pdfs/vet/mrls/Benzylalcohol.pdf


For more Absorption, Distribution and Excretion (Complete) data for BENZYL ALCOHOL (6 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Benzyl alcohol is normally oxidized rapidly to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. However, this metabolic pathway may not be well developed in premature infants. The benzyl alcohol may therefore have been metabolized to benzoic acid, which could not be conjugated by the immature liver but accumulated, causing metabolic acidosis ... .

CDC/MMWR; Neonatal Deaths Associated With Use Of Benzyl Alcohol -- United States. Morbidity and Mortality Weekly Repost 31(22);290-1 (June 11, 1982). Available from, as of July 23, 2008: https://www.cdc.gov/mmwr/preview/mmwrhtml/00001109.htm


When metabolized, benzyl alcohol is converted to benzoic acid by simple oxidation. The relevant data, therefore, relate to benzoic acid and sodium benzoate.

PMID:11766131 Nair B; Int J Toxicol 20 Suppl 3: 23-50 (2001)


Benzyl alcohol was an intermediate product in the metabolic pathway of benzyl acetate; the subsequent metabolism was identical to that of benzyl alcohol.

European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Benzyl Alcohol, Summary Report (1997). Available from, as of July 8, 2008: https://www.emea.europa.eu/pdfs/vet/mrls/Benzylalcohol.pdf


In adults, benzyl alcohol is oxidized to benzoic acid, conjugated in the liver with glycine, and excreted in the urine as hippuric acid. The immature metabolic capacities of infants diminish their ability to metabolize and excrete benzyl alcohol. Preterm babies have a greater ability to metabolize benzyl alcohol to benzoic acid than do term babies, but are unable to convert benzoic acid to hippuric acid, possibly because of glycine deficiency. This results in the accumulation of benzoic acid.

Goldfrank, L.R., Goldfrank's Toxicologic Emergencies 8th Ed. 2006., McGraw-Hill, New York, N.Y., p. 831


For more Metabolism/Metabolites (Complete) data for BENZYL ALCOHOL (8 total), please visit the HSDB record page.


Benzyl alcohol is a known human metabolite of toluene.

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


5.6 Biological Half-Life

The plasma half-life of benzyl alcohol administered as 2.5% solution in saline was found to be approximately 1.5 hr in dogs injected iv at doses of 52 and 105 mg/kg.

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. 4640


Benzyl alcohol rapidly disappeared from the injection site following intramuscular administration in rats; the disappearance half-life was estimated to be less than 10 minutes. ...

European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Benzyl Alcohol, Summary Report (1997). Available from, as of July 8, 2008: https://www.emea.europa.eu/pdfs/vet/mrls/Benzylalcohol.pdf


5.7 Mechanism of Action

Benzyl alcohol inhibits lice from closing their respiratory spiracles, allowing the vehicle to obstruct the spiracles and causing the lice to asphyxiate.


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