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2D Structure
Also known as: 141-78-6, Ethyl ethanoate, Acetic acid ethyl ester, Acetoxyethane, Vinegar naphtha, Acetic ether
Molecular Formula
C4H8O2
Molecular Weight
88.11  g/mol
InChI Key
XEKOWRVHYACXOJ-UHFFFAOYSA-N
FDA UNII
76845O8NMZ

Ethyl acetate is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl acetate
2.1.2 InChI
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
2.1.3 InChI Key
XEKOWRVHYACXOJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC(=O)C
2.2 Other Identifiers
2.2.1 UNII
76845O8NMZ
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 141-78-6

2. Ethyl Ethanoate

3. Acetic Acid Ethyl Ester

4. Acetoxyethane

5. Vinegar Naphtha

6. Acetic Ether

7. Ethyl Acetic Ester

8. Acetic Acid, Ethyl Ester

9. Acetidin

10. Ethylacetate

11. Essigester

12. Acetic Ester

13. Etoac

14. Aethylacetat

15. Ethylacetat

16. 1-acetoxyethane

17. Rcra Waste Number U112

18. Acoet

19. Ethylacetaat

20. Octan Etylu

21. Fema No. 2414

22. Etile (acetato Di)

23. Ethyle (acetate D')

24. Ethylazetat

25. Ethyl-acetate

26. Chebi:27750

27. Ethylester Kyseliny Octove

28. Acetic Acid Ethyl

29. Ethyl Ester Of Acetic Acid

30. Mfcd00009171

31. Nsc 70930

32. Essigsaeureethylester

33. Ethyl Acetate [nf]

34. Acetic-acid-ethylester

35. Ethyl Acetate Solution

36. Ethyl Acetate, Hplc

37. Nsc-70930

38. Ch3-co-o-ch3

39. 76845o8nmz

40. Ethyl Acetate (nf)

41. Ncgc00091766-01

42. E1504

43. Dsstox_cid_2001

44. Ethyl Acetate, Acs Reagent

45. Dsstox_rid_76453

46. Dsstox_gsid_22001

47. Essigester [german]

48. Ethylacetaat [dutch]

49. Aethylacetat [german]

50. Caswell No. 429

51. Octan Etylu [polish]

52. Ethyl Acetate (natural)

53. Acetate D'ethyle

54. Acetato De Etilo

55. Acetate D'ethyle [french]

56. Acetato De Etilo [spanish]

57. Ethyl Acetate, Acs Reagent, >=99.5%

58. Cas-141-78-6

59. Hsdb 83

60. Etile (acetato Di) [italian]

61. Ccris 6036

62. Ethyle (acetate D') [french]

63. Ethylester Kyseliny Octove [czech]

64. Einecs 205-500-4

65. Un1173

66. Ch3cooc2h5

67. Rcra Waste No. U112

68. Epa Pesticide Chemical Code 044003

69. Ethylaceate

70. Ethylactate

71. Ethylacteate

72. Etylacetate

73. Acet-ethylester

74. Ehtyl Acetate

75. Ethanol Acetate

76. Ethly Acetate

77. Ethyl Acteate

78. Ethyl_acetate

79. Ehyl Acetate

80. Ethl Acetate

81. Ethy Acetate

82. Ethyl Aceate

83. Ethyl Actate

84. Etyl Acetate

85. Unii-76845o8nmz

86. Acetyl Ester

87. Acet-eth-ester

88. Ai3-00404

89. 1-ethyl Acetate

90. 2~ethyl Acetate

91. Acetic Ethyl Ester

92. Etile(acetato Di)

93. Nat.ethyl Acetate

94. Et-oac

95. Ethyle(acetate D')

96. Acetic Acid Ethylester

97. Ethyl Acetate Natural

98. Ch3co2et

99. Ethyl Acetate Hplc Grade

100. Ethyl Acetate, For Hplc

101. Ethyl Acetate, 99.9%

102. Ethyl Acetate, Acs Grade

103. Ch3co2ch2ch3

104. Epitope Id:116868

105. Ec 205-500-4

106. Ethyl Acetate [ii]

107. Ethyl Acetate [mi]

108. Ethyl Acetate, Hplc Grade

109. Ch3co2c2h5

110. Ethyl Acetate [fcc]

111. Ethyl Acetate [fhfi]

112. Ethyl Acetate [hsdb]

113. Ethyl Acetate [inci]

114. Ethyl Acetate 100ml

115. Ethyl Acetate, >=99.5%

116. Wln: 2ov1

117. Chembl14152

118. Acetic Acid,ethyl Ester

119. Ethyl Acetate [mart.]

120. Ethyl Acetate, Ar, >=99%

121. Ethyl Acetate, Lr, >=99%

122. Ethyl Acetate [usp-rs]

123. Ethyl Acetate [who-dd]

124. Dtxsid1022001

125. Ethyl Acetate Reagent Grade Acs

126. 2-oxo-2-ethoxyethylidyne Radical

127. Ethyl Acetate, Analytical Standard

128. Ethyl Acetate, Environmental Grade

129. Zinc895412

130. Ethyl Acetate, Anhydrous, 99.8%

131. Nsc70930

132. Ethyl Acetate, 99.9% Low Benzene

133. Tox21_111166

134. Tox21_202512

135. Bdbm50128823

136. C0036

137. Ethyl Acetate [ep Monograph]

138. Stl282717

139. Ethyl Acetate, >=99%, Fcc, Fg

140. Ethyl Acetate, Hplc Grade, 99.8%

141. Akos000121947

142. Ethyl Acetate Ethanol Solution (3:1)

143. Ethyl Acetate Gc, For Residue Analysis

144. Ethyl Acetate, Spectrophotometric Grade

145. Un 1173

146. Ethyl Acetate, For Hplc, >=99.5%

147. Ethyl Acetate, For Hplc, >=99.7%

148. Ethyl Acetate, For Hplc, >=99.8%

149. Ethyl Acetate, Pra Grade, >=99.5%

150. Ncgc00260061-01

151. Ethyl Acetate 100 Microg/ml In N-hexane

152. Ethyl Acetate 1000 Microg/ml In Methanol

153. Ethyl Acetate, Biotech. Grade, >=99.8%

154. Ethyl Acetate, Reagentplus(r), >=99.5%

155. Ethyl Acetate, Reagentplus(r), >=99.8%

156. Ethyl Acetate, Tested According To Ph.eur.

157. A0030

158. Ethyl Acetate 100 Microg/ml In Acetonitrile

159. Ethyl Acetate, Natural, >=99%, Fcc, Fg

160. Ethyl Acetate, Saj First Grade, >=99.0%

161. Ft-0621744

162. Ft-0693343

163. Q0040

164. Ethyl Acetate [un1173] [flammable Liquid]

165. Ethyl Acetate, For Hplc, >=99.8% (gc)

166. Ethyl Acetate, Jis Special Grade, >=99.5%

167. J3.639.860d

168. C00849

169. D02319

170. Ethyl Acetate, Capillary Gc Grade, >=99.5%

171. A807811

172. Q407153

173. Ethyl Acetate, Laboratory Reagent, >=99.0% (gc)

174. Ethyl Acetate, Uv-ir Min. 99.8%, Isocratic Grade

175. J-007556

176. J-521240

177. F0001-0489

178. Ethyl Acetate, Puriss. P.a., Acs Reagent, >=99.5% (gc)

179. Ethyl Acetate, For Residue Analysis, Suitable For 5000 Per Jis

180. Ethyl Acetate, United States Pharmacopeia (usp) Reference Standard

181. Ethylacetate, Pure, Meets The Analytical Specifications Of Ph. Eur.

182. Ethyl Acetate, Hplc Plus, For Hplc, Gc, And Residue Analysis, 99.9%

183. Ethyl Acetate, Suitable For 1000 Per Jis, >=99.5%, For Residue Analysis

184. Ethyl Acetate, Suitable For 300 Per Jis, >=99.5%, For Residue Analysis

185. Ethyl Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

186. Ethyl Acetate, Puriss. P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., >=99.5% (gc)

187. Ethyl Acetate, Puriss. P.a., Free Of Higher Boiling Impurities, >=99.9% (gc)

188. Ethyl Acetate, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Nf, >=99.5% (gc)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 88.11 g/mol
Molecular Formula C4H8O2
XLogP30.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass88.052429494 g/mol
Monoisotopic Mass88.052429494 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count6
Formal Charge0
Complexity49.5
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-Arrhythmia Agents

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


... It has been used internally in a dose of 1 to 2 cc as carminative & antispasmodic, also externally as counterirritant ... .

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 412


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

... The primary route of absorption responsible for the toxicity of ethyl acetate is inhalation.

Ryan, R.P., C.E. Terry (eds.). Toxicology Desk Reference 4th ed. Volumes 1-3. Taylor & Francis, Washington, D.C. 1997., p. 1253


5.2 Metabolism/Metabolites

... The current study was aimed at quantitating the extent of metabolism of inspired ethyl acetate in the upper respiratory tract (URT) of the F344 rat and Syrian hamster. Ethyl acetate deposition was measured in the surgically isolated URT of these species under constant velocity unidirectional flow conditions. The degree of metabolism was estimated by mathematic modeling based on a simple venous-equilibration approach and by direct comparison of deposition efficiencies in naive and carboxylesterase-inhibited animals. Ethyl acetate deposition efficiencies averaged between 10 and 35% in the rat URT and 36 and 72% in the hamster. Carboxylesterase inhibition decreased deposition in both species. Both the modeling efforts and the direct comparisons between naive and inhibited animals indicated that significant amounts of the deposited ethyl acetate were metabolized in the URT of both species with the extent of metabolism being more pronounced in the hamster. Specifically, 40-65% of the deposited ethyl acetate was metabolized in the URT of the rat compared to 63-90% in the hamster. This first-pass metabolism (i) increased URT deposition efficiencies; (ii) led to production of high metabolite levels in URT tissues; and (iii) decreased the amount of parent ethyl acetate available for absorption into the bloodstream in the URT.

PMID:2300973 Morris JB; Toxicol Appl Pharmacol 102 (2): 331-345 (1990)


Because of the abundance of nonspecific esterases, one might expect the common solvent ethyl acetate (EtAc) to be hydrolyzed to ethyl alcohol (EtOH) in vivo. It would then be possible to demonstrate EtOH accumulation following exposure to EtAc vapor. Preliminary studies showed that rat blood incubated at 37 C does hydrolyze EtAc to EtOH, with a half-time of approximately 65 min. Analyses were done by gas chromatography. To study this reaction in vivo, rats were anesthetized with pentobarbital, and cannulae were inserted into the femoral arteries. EtAc was injected ip as a 25% () solution in corn oil (1.6 g/kg) and blood samples were drawn periodically. Hydrolysis was very rapid in vivo, with a half-time estimated at 5-10 min. Inhalation studies were then carried out by exposing anesthetized rats to several concentrations of EtAc vapor via an endotracheal tube. When EtAc concentrations were increased above 2000 ppm, EtAc absorption exceeded EtOH oxidation, leading to an accumulation of EtOH in the blood. Although blood EtOH concentrations increased steadily to over 0.10 g/100 mL in 5 hr, EtAc remained consistently below 0.01 g/100 mL and did not change throughout the course of the experiment, again indicating rapid hydrolysis. The data indicate that EtOH will accumulate during exposure to EtAc if the ambient concentration of EtAc is sufficiently high.

Gallaher EJ, Loomis TA; Toxicol Appl Pharmacol 34 (2): 309-313 (1975)


... Ethyl acetate ... metabolism produces corresponding ethyl alcohol & is partly excreted in exhaled air & urine & partly metabolized.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. Second Edition. Volume 3 Alcohols and Esters. New York, NY: Elsevier, 1992., p. 237


Metabolic studies in the rat have revealed an approximate 2000 ppm no-effect level. At higher levels, the rate of hydrolysis of ethyl acetate appeared to exceed ethanol oxidation, leading to its accumulation in the vascular system. Also, when it was injected intraperitoneally at 1.6 g/kg, hydrolysis to acetic acid and ethanol occurred rapidly. Intraperitoneal injections of 1 mL/kg to male rats for 8 days increased the blood pyruvic and lactic acid content considerably and also elevated the glycolytic enzymatic activity.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 567


5.3 Biological Half-Life

No reports found; [TDR, p. 625]

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. 625