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2-Phenoxyethanol
Also known as: Phenoxyethanol, 122-99-6, Ethylene glycol monophenyl ether, Phenyl cellosolve, Phenoxethol, Phenoxytol
Molecular Formula
C8H10O2
Molecular Weight
138.16  g/mol
InChI Key
QCDWFXQBSFUVSP-UHFFFAOYSA-N
FDA UNII
HIE492ZZ3T

phenoxyethanol is a natural product found in Cichorium endivia and Allium cepa with data available.
1 2D Structure

2-Phenoxyethanol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-phenoxyethanol
2.1.2 InChI
InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
2.1.3 InChI Key
QCDWFXQBSFUVSP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)OCCO
2.2 Other Identifiers
2.2.1 UNII
HIE492ZZ3T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Emuclens

2. Erisept

3. Ethylene Glycol Monophenyl Ether

4. Phenoxethol

5. Phenoxyethanol

2.3.2 Depositor-Supplied Synonyms

1. Phenoxyethanol

2. 122-99-6

3. Ethylene Glycol Monophenyl Ether

4. Phenyl Cellosolve

5. Phenoxethol

6. Phenoxytol

7. Ethanol, 2-phenoxy-

8. 2-phenoxyethan-1-ol

9. Ethylene Glycol Phenyl Ether

10. Phenoxetol

11. Phenoxyethyl Alcohol

12. 1-hydroxy-2-phenoxyethane

13. Rose Ether

14. Phenylmonoglycol Ether

15. Arosol

16. Dowanol Ep

17. 2-phenoxyethyl Alcohol

18. Glycol Monophenyl Ether

19. 2-hydroxyethyl Phenyl Ether

20. Phenylglycol

21. Fenyl-cellosolve

22. 2-fenoxyethanol

23. Dowanol Eph

24. 2-phenoxy-ethanol

25. Emery 6705

26. Emeressence 1160

27. Fenylcelosolv

28. Beta-hydroxyethyl Phenyl Ether

29. Nsc 1864

30. Mfcd00002857

31. Phe-g

32. .beta.-hydroxyethyl Phenyl Ether

33. Nsc-1864

34. 2-phenoxy Ethanol

35. 9004-78-8

36. Phenoxyethanol [nf]

37. .beta.-phenoxyethyl Alcohol

38. Hie492zz3t

39. Poly(oxy-1,2-ethanediyl), Alpha-phenyl-omega-hydroxy-

40. Ethylene Glycol-monophenyl Ether

41. Fema No. 4620

42. Chebi:64275

43. Nsc1864

44. Phenoxyethanol (nf)

45. Ncgc00090731-01

46. Ncgc00090731-05

47. Dsstox_cid_1976

48. Dsstox_rid_76437

49. Dsstox_gsid_21976

50. Egmpe

51. Fenylcelosolv [czech]

52. 2-fenoxyethanol [czech]

53. Fenyl-cellosolve [czech]

54. Plastiazan-41 [russian]

55. Plastiazan-41

56. Beta-phenoxyethanol

57. Cas-122-99-6

58. Phenol, Ethoxylated

59. .beta.-phenoxyethanol

60. Hsdb 5595

61. Phe-s

62. Einecs 204-589-7

63. Unii-hie492zz3t

64. Brn 1364011

65. Ai3-00752()c

66. Phenylcellosolve

67. Ethyleneglycol Monophenyl Ether

68. Ccris 9481

69. Dalpad A

70. 2-phenyloxyethanol

71. Newpol Efp

72. 2-(phenoxy)ethanol

73. Beta-hydroxyphenetole

74. 2-phenoxy-1-ethanol

75. Beta-phenoxyethylalcohol

76. Starbld0047047

77. 2-phenoxyethanol, 9ci

78. 2-phenoxyethanol, 99%

79. Wln: Q2or

80. Ec 204-589-7

81. Phenoxyethanol [ii]

82. Schembl15708

83. 2-phenoxyethanol, >=99%

84. Phenoxyethanol [hsdb]

85. Phenoxyethanol [inci]

86. 4-06-00-00571 (beilstein Handbook Reference)

87. Mls002174254

88. Euxyl K 400 (salt/mix)

89. 2-phenoxyethanol [mi]

90. Phenoxyethanol [mart.]

91. Phenoxyethanol [usp-rs]

92. Phenoxyethanol [who-dd]

93. 2-phenoxyethanol 500ml

94. Chembl1229846

95. Dtxsid9021976

96. Amy9420

97. Hms2268a20

98. Nsc1864nsc 1864

99. Hy-b1729

100. Polyethylene Glycol Monophenyl Ether

101. Str04582

102. Zinc1577061

103. Tox21_111002

104. Tox21_113532

105. Tox21_202111

106. Tox21_300842

107. Bbl027410

108. Phenoxyethanol [ep Monograph]

109. Stk802556

110. 2-phenoxyethanol, Analytical Standard

111. Fungal Terminator [veterinary] (tn)

112. Akos000118741

113. Tox21_111002_1

114. Db11304

115. Ncgc00090731-02

116. Ncgc00090731-03

117. Ncgc00090731-04

118. Ncgc00090731-06

119. Ncgc00090731-07

120. Ncgc00090731-08

121. Ncgc00254745-01

122. Ncgc00259660-01

123. 56257-90-0

124. Ethylene Glycol Monophenyl Ether, >=90%

125. Smr000112131

126. Ethanol,2-phenoxy Mfc8 H10 O2

127. Cs-0013737

128. Ft-0613280

129. P0115

130. P1953

131. 2-phenoxyethanol, Tested According To Ph.eur.

132. D08359

133. A805003

134. Q418038

135. Sr-01000838345

136. J-510235

137. Sr-01000838345-2

138. F1905-6997

139. Z426194440

140. Ethyleneglycol-monophenyl Ether 100 Microg/ml In Methanol

141. Ethylene Glycol Monophenyl Ether, Saj First Grade, >=95.0%

142. Ethylene Glycol-monophenyl Ether 1000 Microg/ml In Methanol

143. Phenoxyethanol, European Pharmacopoeia (ep) Reference Standard

144. Phenoxyethanol, United States Pharmacopeia (usp) Reference Standard

145. 2-phenoxyethanol, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 138.16 g/mol
Molecular Formula C8H10O2
XLogP31.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass138.068079557 g/mol
Monoisotopic Mass138.068079557 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count10
Formal Charge0
Complexity77.3
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

Phenoxyethanol (PE) is a preservative added to cosmetics and pharmaceuticals such as antibiotic ointments and solutions, ear-drops, and vaccines.

Bohn S and Bircher AJ; Allergy 56: 922-923 (2001) https://onlinelibrary.wiley.com/doi/10.1034/j.1398-9995.2001.00218.x/full


Anti-Infective Agents, Local; Anesthetics

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


Phenoxyethanol has antibacterial properties and is effective against strains of Pseudomonas aeruginosa even in the presence of 20% serum. It is less effective against Proteus vulgaris, other Gram-negative organisms, and Gram-positive organisms. It has been used as a preservative at a concentration of 1%. A wider spectrum of antimicrobial activity is obtained with preservative mixtures of phenoxyethanol and hydroxybenzoates. Phenoxyethanol may be used as a 2.2% solution or a 2% cream for the treatment of superficial wounds, burns, or abscesses infected by Pseudomonas aeruginosa. In skin infection derivatives of phenoxyethanol are used with either cyclic acid or zinc undecenoate.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1288


TOPICAL ANTISEPTIC

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 1153


4.2 Drug Warning

Peritonitis is the established term for infective inflammation of the peritoneum, whereas serositis generally refers to aseptic inflammation of a serous cavity, including the peritoneum. Serositis may be metabolic, viral, autoimmune, drug induced, genetic, allergic or granulomatous, or due to chemical antiseptics. In ...gynecological department, 4 patients had peritonitis and ascites after laparotomy. Based on the investigation... the solution used for peritoneal lavage (0.1% octenidine dihydrochloride and 2% phenoxyethanol) played a role in the tissue toxicity that caused chemical serositis with effusion.

PMID:15863605 Hupuczi P, Papp Z; Obstet Gynecol 105 (5 Pt 2): 1267-8 (2005)


4.3 Drug Indication

Antimicrobial agent used as a preservative in cosmetics,,.


5 Pharmacology and Biochemistry
5.1 Pharmacology

This substance has broad-spectrum antimicrobial activity against bacteria, yeasts, and mold.


5.2 MeSH Pharmacological Classification

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.)


Anesthetics

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site. (See all compounds classified as Anesthetics.)


5.3 Absorption, Distribution and Excretion

Route of Elimination

The fate of phenoxyethanol in rats and humans has been investigated. More than 90% of an oral dose of 16, 27 or 160 mg/kg body weight of (2-(14)C)phenoxyethanol administered to male Colworth rats by was excreted in the urine within 24 hours of administration. A female rat also excreted about 90% of a dose of 27 mg/kg body weight in the urine within 24 hours. About 2% and 1.3% of the ingested dose was recovered from the exhaled air of female and male rats, respectively.


Volume of Distribution

A pharmacokinetic study of phenoxyethanol was performed using a mass spectrometry model for simultaneous analysis of phenoxyethanol (PE) and its major metabolite, phenoxyacetic acid (PAA), in rat plasma, urine, and 7 different tissues. The absolute topical bioavailability of PE was 75.4% and 76.0% for emulsion and lotion, respectively. Conversion of PE to PAA was extensive, with the average AUCPAA-to-AUCPE ratio being 4.4 and 5.3 for emulsion and lotion, respectively. The steady-state tissue-to-plasma PE concentration ratio (Kp) was higher than unity for kidney, spleen, heart, brain, and testis and was lower (0.6) for lung and liver, while the metabolite Kp ratio was higher than unity for kidney, liver, lung, and testis and was lower (0.3) for other tissues.


... An entire oral dose of 11 mg of unlabelled 2-phenoxyethanol was accounted for in the urine of one healthy male volunteer as 2-phenoxyacetic acid. Most of the acid was excreted unconjugated.

WHO/FAO: Expert Committee on food additives. FAO Nutrition Meetings Report Series for 2-phenoxyethanol (122-99-6) (2003). Available from, as of October 25, 2011: https://www.inchem.org/pages/jecfa.html


The fate of 2-phenoxyethanol in rats and humans has been investigated. More than 90% of an oral dose of 16, 27 or 160 mg/kg bw of (2-(14)C)phenoxyethanol given to male Colworth rats by gavage was excreted in the urine within 24 hr. A female rat also excreted about 90% of a dose of 27 mg/kg bw in the urine within 24 hr. Approximately 2 and 1.3% of the ingested dose was recovered from expired air of female and male rats, respectively. The rate of intestinal absorption was rapid, with 60-70% of the excreted (14)C detected at 3 hr and > 95% of the total 4-day urinary (14)C detected within the first 24 hr. Trace amounts of radioactivity were detected in feces. Four days after dosing, only trace amounts of radioactivity remained in the carcass, primarily in the liver (< 0.2% of the dose), fat and muscle. At 4 days, the (14)C concentration in blood was only 0.001.

WHO/FAO: Expert Committee on food additives. FAO Nutrition Meetings Report Series for 2-phenoxyethanol (122-99-6) (2003). Available from, as of October 25, 2011: https://www.inchem.org/pages/jecfa.html


... NOT READILY ABSORBED THROUGH THE SKIN IN ACUTELY TOXIC AMT.

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. 3944


2-PHENOXYETHANOL (0.1-0.5 ML/L) SEDATED OR ANESTHETIZED FISH WITHIN MINUTES WHEN THE ANIMALS WERE IMMERSED IN THE AGENT. WHEN ADMIN IN THIS WAY, THE ANESTHETIC WAS ABSORBED INTO THE BLOOD STREAM THROUGH THE GILL LAMELLAE.

PMID:4346046 JOLLY DW ET AL; VET REC 91 (18): 424 (1972)


5.4 Metabolism/Metabolites

The fate of phenoxyethanol in rats and humans has been investigated. The rate of intestinal absorption was rapid, with 60-70% of the excreted (14)C detected at 3 hours and > 95% of the total 4-day urinary (14)C detected within the first 24 hr. Trace amounts of radioactivity were detected in feces. Four days after dosing, only trace amounts of radioactivity remained in the carcass, primarily in the liver (< 0.2% of the dose), fat and muscle. At the 4 day point, the (14)C concentration in blood was measured to be only 0.001. The major metabolite of phenoxyethanol is phenoxyacetic acid.


Once hydrolyzed, 2-phenoxyethanol is rapidly absorbed and oxidized to phenoxyacetic acid ...

WHO/FAO: Expert Committee on food additives. FAO Nutrition Meetings Report Series for 2-phenoxyethanol (122-99-6) (2003). Available from, as of October 25, 2011: https://www.inchem.org/pages/jecfa.html


YIELDS PHENOL IN CONIOPHORA, IN PLEUROTUS, & IN POLYSTICTUS ... . /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. 10


The toxicity of glycol ethers is associated with their oxidation to the corresponding aldehyde and alkoxyacetic acid by cytosolic alcohol dehydrogenase (ADH; EC 1.1.1.1.) and aldehyde dehydrogenase (ALDH; 1.2.1.3). Dermal exposure to these compounds can result in localised or systemic toxicity including skin sensitisation and irritancy, reproductive, developmental and hematological effects. It has previously been shown that skin has the capacity for local metabolism of applied chemicals. Therefore, there is a requirement to consider metabolism during dermal absorption of these compounds in risk assessment for humans. Cytosolic fractions were prepared from rat liver, and whole and dermatomed skin by differential centrifugation. Rat skin cytosolic fractions were also prepared following multiple dermal exposure to dexamethasone, ethanol or 2-butoxyethanol (2-BE). The rate of ethanol, 2-ethoxyethanol (2-EE), ethylene glycol, 2-phenoxyethanol (2-PE) and 2-BE conversion to alkoxyacetic acid by ADH/ALDH in these fractions was continuously monitored by UV spectrophotometry via the conversion of NAD+ to NADH at 340 nm. Rates of ADH oxidation by rat liver cytosol were greatest for ethanol followed by 2-EE >ethylene glycol >2-PE >2-BE. However, the order of metabolism changed to 2-BE >2-PE >ethylene glycol >2-EE >ethanol using whole and dermatomed rat skin cytosolic fractions, with approximately twice the specific activity in dermatomed skin cytosol relative to whole rat skin. This suggests that ADH and ALDH are localised in the epidermis that constitutes more of the protein in dermatomed skin than whole skin cytosol. Inhibition of ADH oxidation in rat liver cytosol by pyrazole was greatest for ethanol followed by 2-EE >ethylene glycol >2-PE >2-BE, but it only inhibited ethanol metabolism by 40% in skin cytosol. Disulfiram completely inhibited alcohol and glycol ether metabolism in the liver and skin cytosolic fractions. Although ADH1, ADH2 and ADH3 are expressed at the protein level in rat liver, only ADH1 and ADH2 are selectively inhibited by pyrazole and they constitute the predominant isoforms that metabolise short-chain alcohols in preference to intermediate chain-length alcohols. However, ADH1, ADH3 and ADH4 predominate in rat skin, demonstrate different sensitivities to pyrazole, and are responsible for metabolising glycol ethers. ALDH1 is the predominant isoform in rat liver and skin cytosolic fractions that is selectively inhibited by disulfiram and responds to the amount of aldehyde formed by the ADH isoforms expressed in these tissues. Thus, the different affinity of ADH and ALDH for alcohols and glycol ethers of different carbon-chain length may reflect the relative isoform expression in rat liver and skin. Following multiple topical exposure, ethanol metabolism increased the most following ethanol treatment, and 2-BE metabolism increased the most following 2-BE treatment. Ethanol and 2-BE may induce specific ADH and ALDH isoforms that preferentially metabolise short-chain alcohols (i.e. ADH1, ALDH1) and longer chain alcohols (i.e. ADH3, ADH4, ALDH1), respectively. Treatment with a general inducing agent such as dexamethasone enhanced ethanol and 2-BE metabolism suggesting induction of multiple ADH isoforms.

PMID:15551062 Lockley DJ et al; Arch Toxicol 79 (3): 160-8 (2005)


Studies were conducted... to evaluate the in vitro hemolytic potential of / ethylene glycol phenyl ether/ EGPE and its major metabolite using rabbit red blood cells (RBC). Phenoxyacetic acid (PAA) was identified as a major blood metabolite of EGPE. In vitro exposure of female rabbit erythrocytes indicated EGPE to be considerably more hemolytic than PAA.

PMID:1794651 Breslin WJ et al; Fundam Appl Toxicol 17 (3): 466-81 (1991)


5.5 Mechanism of Action

Phenoxyethanol has antibacterial properties and is effective against strains of Pseudomonas aeruginosa even in the presence of 20% serum. It not as effective against Proteus vulgaris, other gram-negative organisms, and gram-positive organisms. Phenoxyethanol has been used as a preservative at a concentration of 1%. A wider spectrum of antimicrobial activity is achieved with preservative mixtures of phenoxyethanol and hydroxybenzoates. Phenoxyethanol may be used as a 2.2% solution or a 2% cream for the treatment of superficial wounds, burns, or abscesses infected by Pseudomonas aeruginosa. In skin infection, derivatives of phenoxyethanol are used in combination with either cyclic acid or zinc undecenoate.


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