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Also known as: Ethyl 4-hydroxybenzoate, 120-47-8, Ethyl paraben, Ethyl p-hydroxybenzoate, Ethyl parahydroxybenzoate, Tegosept e
Molecular Formula
C9H10O3
Molecular Weight
166.17  g/mol
InChI Key
NUVBSKCKDOMJSU-UHFFFAOYSA-N
FDA UNII
14255EXE39

Catalase
Ethyl-4-hydroxybenzoate is a metabolite found in or produced by Saccharomyces cerevisiae.
Ethylparaben is a Standardized Chemical Allergen. The physiologic effect of ethylparaben is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

Catalase

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl 4-hydroxybenzoate
2.1.2 InChI
InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
2.1.3 InChI Key
NUVBSKCKDOMJSU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC(=O)C1=CC=C(C=C1)O
2.2 Other Identifiers
2.2.1 UNII
14255EXE39
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ethyl Paraben

2. Ethyl-p-hydroxybenzoate

3. P-hydroxybenzoic Acid Ethyl Ester

2.3.2 Depositor-Supplied Synonyms

1. Ethyl 4-hydroxybenzoate

2. 120-47-8

3. Ethyl Paraben

4. Ethyl P-hydroxybenzoate

5. Ethyl Parahydroxybenzoate

6. Tegosept E

7. Mycocten

8. Ethyl Parasept

9. Aseptoform E

10. Nipagin A

11. 4-hydroxybenzoic Acid Ethyl Ester

12. Sobrol A

13. Easeptol

14. Ethyl P-oxybenzoate

15. Ethyl Butex

16. P-hydroxybenzoic Acid Ethyl Ester

17. Napagin A

18. Nipazin A

19. Solbrol A

20. Benzoic Acid, 4-hydroxy-, Ethyl Ester

21. P-carbethoxyphenol

22. Ethyl-p-hydroxybenzoate

23. Mekkings E

24. Aseptin A

25. Bonomold Oe

26. Ethyl-4-hydroxybenzoate

27. Ethyl Para-hydroxybenzoate

28. P-oxybenzoesaeureaethylester

29. 9001-05-2

30. 4-hydroxy-benzoic Acid Ethyl Ester

31. 4-carbethoxyphenol

32. Nsc 23514

33. P-hydroxybenzoate Ethyl Ester

34. Ethylparaben [nf]

35. Benzoic Acid, P-hydroxy-, Ethyl Ester

36. E214

37. 4-hydroxybenzoic Acid, Ethyl Ester

38. Ins No.214

39. 4-(ethoxycarbonyl)phenol

40. Para-hydroxybenzoic Acid Ethyl Ester

41. Ethylester Kyseliny P-hydroxybenzoove

42. Nsc-23514

43. Ins-214

44. Ester Etylowykwasu P-hydroksybenzoesowego

45. Ethyl Parahydroxybenzoate E214

46. E-214

47. 4-hydroxybenzoic Acid-ethyl Ester

48. Ethylparaben (nf)

49. 14255exe39

50. Ncgc00160654-01

51. Ethyl-paraben

52. Carbethoxyphenol

53. Dsstox_cid_2528

54. Wln: Qr Dvo2

55. Dsstox_rid_76615

56. Dsstox_gsid_22528

57. Caswell No. 447

58. P-hydroxybenzoic Acid, Ethyl Ester

59. 4-hydroxybenzoic Acid-ethyl Ester 1000 Microg/ml In Acetonitrile

60. Cas-120-47-8

61. Hsdb 938

62. Einecs 204-399-4

63. P-oxybenzoesaeureaethylester [german]

64. Epa Pesticide Chemical Code 061202

65. Brn 1101972

66. Ethyl Chemosept

67. Ai3-30960

68. Aseptine A

69. Nipagina A

70. Ethylester Kyseliny P-hydroxybenzoove [czech]

71. Unii-14255exe39

72. Ester Etylowykwasu P-hydroksybenzoesowego [polish]

73. Mfcd00002353

74. Ethylis Hydroxybenzoas

75. Ethyl 4-hydroxy-benzoate

76. Ethylparaben [ii]

77. Ethylparaben [mi]

78. Ethyl 4-hydroxyl-benzoate

79. Ethylparaben, Inn, Usan

80. Bmse010255

81. Ec 204-399-4

82. Ethylparaben [hsdb]

83. Ethylparaben [inci]

84. P-hydroxybenzoic Ethyl Ester

85. Schembl28368

86. 4-10-00-00367 (beilstein Handbook Reference)

87. Ethyl 4-hydroxybenzoate,(s)

88. Bidd:er0023

89. Chembl15841

90. Ethylparaben [usp-rs]

91. Ethyl Parahydroxybenzoate (tn)

92. Zinc1392

93. Dtxsid9022528

94. Ethyl 4-hydroxybenzenecarboxylate

95. Chebi:31575

96. Amy5118

97. Nsc8510

98. Ethyl Parahydroxybenzoate (jp17)

99. Ethyl Para Hydroxy Benzoate

100. Hms2091e17

101. Parahydroxybenzoic Acid Ethyl Ester

102. Pharmakon1600-01400151

103. 4-hydroxy Benzoic Acid Ethyl Ester

104. Hy-b0934

105. Nsc-8510

106. Nsc23514

107. Tox21_111961

108. Tox21_300335

109. Bbl012166

110. Bdbm50428380

111. Nsc755851

112. S4525

113. Stk070911

114. Ethyl Hydroxybenzoate [mart.]

115. Akos000120512

116. Ethyl Hydroxybenzoate [who-dd]

117. Ethyl Hydroxybenzoate [who-ip]

118. Tox21_111961_1

119. Ccg-213682

120. Cs-4403

121. Db13628

122. Ethyl Parahydroxybenzoate [jan]

123. Nsc-755851

124. Ncgc00160654-02

125. Ncgc00160654-03

126. Ncgc00160654-04

127. Ncgc00160654-06

128. Ncgc00254462-01

129. Ac-11586

130. Ac-34532

131. As-11988

132. Nci60_041866

133. Sbi-0206674.p002

134. Ethyl Ester Of P-hydroxybenzoic Acid

135. E0884

136. Ethylis Hydroxybenzoas [who-ip Latin]

137. Ft-0623514

138. Ft-0626357

139. Ft-0668364

140. H0211

141. 4-fluoro-3-methylphenylmagnesiumbromide

142. A16012

143. D01647

144. Ethyl 4-hydroxybenzoate, Reagentplus(r), 99%

145. Ethyl Parahydroxybenzoate [ep Impurity]

146. Ethyl Parahydroxybenzoate [ep Monograph]

147. W18471

148. Ab00375765_03

149. A804518

150. Q229976

151. Sr-05000001552

152. Sr-05000001552-1

153. W-108475

154. Brd-k02464583-001-01-4

155. Ethyl 4-hydroxybenzoate, Saj First Grade, >=99.0%

156. Propyl Hydroxybenzoate Impurity C [ep Impurity]

157. Ethyl 4-hydroxybenzoate, Vetec(tm) Reagent Grade, 99%

158. Ethylparaben, Certified Reference Material, Tracecert(r)

159. F0728-0009

160. Methyl Parahydroxybenzoate Impurity B [ep Impurity]

161. 4-hydroxybenzoic Acid-ethyl Ester 1000 Microg/ml In Methanol

162. 4-hydroxybenzoic Acid-ethyl Ester 100 Microg/ml In Acetonitrile

163. Ethylparaben, United States Pharmacopeia (usp) Reference Standard

164. Ethyl Parahydroxybenzoate, European Pharmacopoeia (ep) Reference Standard

165. Ethylparaben, Pharmaceutical Secondary Standard; Certified Reference Material

166. E4b

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 166.17 g/mol
Molecular Formula C9H10O3
XLogP32.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass166.062994177 g/mol
Monoisotopic Mass166.062994177 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count12
Formal Charge0
Complexity148
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 FDA Pharmacological Classification
4.1.1 Active Moiety
ETHYLPARABEN
4.1.2 FDA UNII
14255EXE39
4.1.3 Pharmacological Classes
Chemical Structure [CS] - Allergens
4.2 Absorption, Distribution and Excretion

By the oral route, parabens are rapidly absorbed, metabolized, and excreted. The metabolic reactions and conversions in mammals vary with the chain length of the ester, the animal species, route of administration, and quantity tested. The metabolism of parabens in humans appears to be most closely related to that of dogs. The rate of metabolite excretion appears to decrease with increasing molecular weight of the ester. /4-Hydroxybenzoates (Parabens)/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 639


... Deposition of parabens in dogs. Urine recoveries ranged from 50-95% except for butyl ester for which recoveries were 40%. /It/... was concluded that esters are well absorbed and that hydrolysis of ester linkage and metabolic conjugation constitute chief route of elimination. Similar metabolic scheme ... in man. /Parabens/

Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 126


The permeation of methylparaben, ethylparaben, propylparaben, and butylparaben through untreated and lipid-depleted excised guinea pig dorsal skin, and the effects of 3 penetration enhancers, N-dodecyl-2-pyrrolidone (lauryl pyrrolidone), ethyl alcohol (ethanol), and a mixture of menthol (l-menthol) and ethyl alcohol, on the permeation of the parabens were studied; the relationship between the permeability and octyl alcohol (n-octanol)/water partition coefficients of the parabens, and the effect of the penetration enhancers on the fluidity of the lipid bilayer of liposomes containing stratum corneum lipids were also examined. Permeability coefficients of the parabens correlated with their octyl alcohol/water partition coefficients in untreated guinea pig skin. In lipid-depleted guinea pig skin, permeability coefficients of the parabens increased and did not correlate with their octyl alcohol/water partition coefficients. The effect of the penetration enhancers on the permeation of the parabens was variable. The penetration enhancers increased the fluidity of liposome lipid bilayers.

PMID:9301035 Kitagawa S et al; Chem Pharm Bull 45 (Aug): 1354-7 (1997)


After ethyl paraben is intravenously infused into the dog, unhydrolyzed ethyl paraben is found only in the brain. In liver, kidney, and muscle, it is immediately hydrolyzed to p-hydroxybenzoic acid. Six hours after oral administration of 1.0 g/kg to dogs, the peak plasma concentration of free and total ethyl paraben (427 and 648 ug/cu cm, respectively) is reached. After 48 hr, all ethyl paraben is completely eliminated.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 668


4.3 Metabolism/Metabolites

Yields p-hydroxybenzoic acid in pig and in Aspergillus. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. E-11


/Paraben/ ... esters are well absorbed and hydrolysis of ester linkage and metabolic conjugation constitute chief route of elimination /in dogs/. Similar metabolic scheme was observed in man. /Paraben esters/

Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 126


Urine from cats who had received (14)C-labeled ethyl-p-hydroxybenzoate, orally contained 2 major metabolites, p-hydroxyhippuric acid and free p-hydroxybenzoic acid.

Phillips S et al; Toxicol Lett 2 (4): 237-242 (1978)


In mice, rats, rabbits, pigs, or dogs, ethyl paraben is excreted in the urine as unchanged benzoate, p-hydroxybenzoic acid, p-hydroxyhippuric acid (p-hydroxybenzoylglycine), ester glucuronides, ether glucuronides, or ether sulfates.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 668


For more Metabolism/Metabolites (Complete) data for ETHYLPARABEN (7 total), please visit the HSDB record page.


Ethyl-4-hydroxybenzoate has known human metabolites that include (2S,3S,4S,5R)-6-(4-ethoxycarbonylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.

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


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