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Chemistry

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Also known as: Phenethyl alcohol, Phenylethyl alcohol, 60-12-8, Benzeneethanol, Phenylethanol, Benzyl carbinol
Molecular Formula
C8H10O
Molecular Weight
122.16  g/mol
InChI Key
WRMNZCZEMHIOCP-UHFFFAOYSA-N
FDA UNII
ML9LGA7468

2-Phenylethanol
An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.
1 2D Structure

2-Phenylethanol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-phenylethanol
2.1.2 InChI
InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
2.1.3 InChI Key
WRMNZCZEMHIOCP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CCO
2.2 Other Identifiers
2.2.1 UNII
ML9LGA7468
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Phenylethanol

2. Alcohol, Phenethyl

3. Alcohol, Phenylethyl

4. Benzyl Carbinol

5. Beta Phenylethanol

6. Beta-phenylethanol

7. Carbinol, Benzyl

8. Phenethyl Alcohol

9. Phenylethanol

10. Phenylethyl Alcohol

2.3.2 Depositor-Supplied Synonyms

1. Phenethyl Alcohol

2. Phenylethyl Alcohol

3. 60-12-8

4. Benzeneethanol

5. Phenylethanol

6. Benzyl Carbinol

7. Phenethanol

8. 2-phenylethyl Alcohol

9. 2-phenyl-ethanol

10. 2-phenylethan-1-ol

11. Beta-phenylethanol

12. 2-phenethyl Alcohol

13. Benzylmethanol

14. Methanol, Benzyl-

15. Benzenethanol

16. Benzylcarbinol

17. Phenethylalcohol

18. 2-hydroxyethylbenzene

19. Fema No. 2858

20. 1-phenyl-2-ethanol

21. Ethanol, 2-phenyl-

22. 2-pea

23. Phenyl Ethyl Alcohol

24. 1321-27-3

25. Beta-phenylethyl Alcohol

26. Beta-pea

27. 2-phenethanol

28. .beta.-hydroxyethylbenzene

29. .beta.-phenylethyl Alcohol

30. Hydroxyethylbenzene

31. Mfcd00002886

32. .beta.-phenylethanol

33. .beta.-pea

34. Beta-phenethyl Alcohol

35. .beta.-phenethyl Alcohol

36. Phenylethyl Alcohol [usp]

37. Nsc-406252

38. .beta.-(hydroxyethyl)benzene

39. Ml9lga7468

40. Chebi:49000

41. Ncgc00166215-02

42. Dsstox_cid_6342

43. Phenylethyl Alcohol (usp)

44. Ethanol, Phenyl-

45. Dsstox_rid_78104

46. Dsstox_gsid_26342

47. Caswell No. 655c

48. Phenyl Ethanol(natural)

49. Fema Number 2858

50. Beta-fenylethanol

51. Beta-fenylethanol [czech]

52. 2-phenyl Ethanol

53. Cas-60-12-8

54. Phenethyl Alcohol (natural)

55. Beta-fenethylalkohol [czech]

56. Beta-fenethylalkohol

57. Pel

58. Smr000059156

59. Hsdb 5002

60. Einecs 200-456-2

61. Epa Pesticide Chemical Code 001503

62. Nsc 406252

63. Brn 1905732

64. Unii-ml9lga7468

65. Benzene-ethanol

66. Mellol

67. Phenyl-ethanol

68. Benzyl-methanol

69. Ai3-00744

70. 2-phenyiethanol

71. Phenylethyl-alcohol

72. .beta.-phenethanol

73. .beta.-fenylethanol

74. B-hydroxyethylbenzene

75. Benzyl Ethyl Alcohol

76. 2-phenyl-1-ethanol

77. Benzeneethanol, 9ci

78. Betaphenylethyl Alcohol

79. .beta.-fenethylalkohol

80. 2-phenylethanol, Usp

81. Rose Oil (salt/mix)

82. A-pea

83. (2-hydroxyethyl)benzene

84. Beta -hydroxyethylbenzene

85. 2-phenylethanol, 99%

86. .beta.-p.e.a.

87. Phenylethyl Alcohol, Usan

88. Bmse000659

89. Phenylethyl, Beta- Alcohol

90. Ec 200-456-2

91. 2-(2-hydroxyethyl)benzene

92. Schembl1838

93. Wln: Q2r

94. 4-06-00-03067 (beilstein Handbook Reference)

95. Mls001066349

96. Mls001336026

97. Phenethyl Alcohol [mi]

98. Phenethyl Alcohol, 8ci, Ban

99. Chembl448500

100. Phenethyl Alcohol [fcc]

101. Phenylethyl, B- Alcohol

102. Dtxsid9026342

103. Phenethyl Alcohol [inci]

104. Phenylethyl Alcohol [ii]

105. Bdbm85807

106. Fema 2858

107. Phenethyl Alcohol [mart.]

108. Hms2093h05

109. Hms2233h06

110. Hms3374p04

111. Pharmakon1600-01505398

112. Phenylethyl Alcohol [fhfi]

113. Phenylethyl Alcohol [hsdb]

114. Zinc895934

115. Phenethyl Alcohol [who-dd]

116. Bcp32115

117. Cs-b1821

118. Hy-b1290

119. Nsc_6054

120. Tox21_113544

121. Tox21_201322

122. Tox21_303383

123. Bbl036905

124. Nsc406252

125. Nsc759116

126. Phenylethyl Alcohol [usp-rs]

127. S3703

128. Stl281950

129. 2-phenylethanol, >=99.0% (gc)

130. Akos000249688

131. Tox21_113544_1

132. Ccg-213419

133. Db02192

134. Nsc-759116

135. Cas_60-12-8

136. Phenethyl Alcohol, >=99%, Fcc, Fg

137. Ncgc00166215-01

138. Ncgc00166215-03

139. Ncgc00166215-05

140. Ncgc00257347-01

141. Ncgc00258874-01

142. Ac-18484

143. Phenylethyl Alcohol [usp Monograph]

144. Sbi-0206858.p001

145. Ft-0613332

146. Ft-0673679

147. P0084

148. En300-19347

149. C05853

150. D00192

151. D70868

152. Phenethyl Alcohol, Natural, >=99%, Fcc, Fg

153. Ab00698274_05

154. A832606

155. Q209463

156. Sr-01000763553

157. Phenylethyl Alcohol;phenethyl Alcohol;benzeneethanol

158. Q-200318

159. Sr-01000763553-2

160. 0de4cadc-ab8a-4038-bd6f-ebd009885652

161. F0001-1575

162. Z234896351

163. 2-phenylethanol;2-phenylethyl Alcohol;benzeneethanol;phenylethanol

164. Phenylethyl Alcohol, United States Pharmacopeia (usp) Reference Standard

165. Phenylethyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

166. 19601-20-8

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 122.16 g/mol
Molecular Formula C8H10O
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass122.073164938 g/mol
Monoisotopic Mass122.073164938 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count9
Formal Charge0
Complexity65
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; Preservatives, Pharmaceutical

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


Phenylethyl alcohol ... has been used in 0.5% conc as an antibacterial agent in ophthalmic solutions. /Phenylethyl alcohol/

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 725


4.2 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG; BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-118


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Preservatives, Pharmaceutical

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants. (See all compounds classified as Preservatives, Pharmaceutical.)


5.2 Metabolism/Metabolites

2-PHENYLETHANOL YIELDS PHENYLACETYLALDEHYDE IN RABBITS: SMITH JM ET AL, BIOCHEM J, 56, 320, 1954. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. 24


Phenylethyl alcohol is oxidized almost entirely to the corresponding acid. Metabolites excreted in urine following oral doses of 0.2 to 0.3 g/kg to rabbits were phenaceturic acid, the glycine conjugate of phenylacetic acid, 42%; glucosidurinic acid, 5%; and an ether-soluble acid, probably phenylacetic acid, 19%. Only 66% of the original dose could be accounted for. /Phenylethyl alcohol/

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. 4643


... beta-Phenylethyl alcohol is a substrate for ADH, with an initial rate of oxidation nearly as high as that of allyl alcohol and appreciably greater than that of ethanol.

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. 4643


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