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Chemistry

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Also known as: 84-66-2, Ethyl phthalate, Phthalic acid diethyl ester, Anozol, Diethylphthalate, Diethyl benzene-1,2-dicarboxylate

Molecular Formula

C₁₂H₁₄O₄

Molecular Weight

222.24 g/mol

InChI Key

FLKPEMZONWLCSK-UHFFFAOYSA-N

FDA UNII

UF064M00AF

Diethyl Phthalate is a clear, colorless liquid used as a plasticizer for fabricating flexible materials for many household products. It is also used in cosmetics, insecticides and aspirin.

1 2D Structure

Diethyl Phthalate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

diethyl benzene-1,2-dicarboxylate

2.1.2 InChI

InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3

2.1.3 InChI Key

FLKPEMZONWLCSK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOC(=O)C1=CC=CC=C1C(=O)OCC

2.2 Other Identifiers

2.2.1 UNII

UF064M00AF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Phthalic Acid Diethyl Ester

2.3.2 Depositor-Supplied Synonyms

1. 84-66-2

2. Ethyl Phthalate

3. Phthalic Acid Diethyl Ester

4. Anozol

5. Diethylphthalate

6. Diethyl Benzene-1,2-dicarboxylate

7. Neantine

8. Phthalol

9. Solvanol

10. Diethyl O-phthalate

11. Palatinol A

12. Placidol E

13. Unimoll Da

14. Phthalsaeurediaethylester

15. O-bis(ethoxycarbonyl)benzene

16. Diethyl 1,2-benzenedicarboxylate

17. 1,2-diethyl Phthalate

18. 1,2-benzenedicarboxylic Acid, Diethyl Ester

19. Estol 1550

20. O-benzenedicarboxylic Acid Diethyl Ester

21. Di-n-ethyl Phthalate

22. Diethyl O-phenylenediacetate

23. Diethyl Phtalate

24. Phthalic Acid, Diethyl Ester

25. Rcra Waste Number U088

26. Diethylester Kyseliny Ftalove

27. Nci-c60048

28. 1,2-benzenedicarboxylic Acid Diethyl Ester

29. Nsc 8905

30. Chebi:34698

31. Diethyl Phthalate (nf)

32. Diethyl Phthalate [nf]

33. Nsc-8905

34. 1,2-benzenedicarboxylic Acid, 1,2-diethyl Ester

35. O-phthalic Acid, Diethyl Ester

36. Uf064m00af

37. 1,2-benzenedicarboxylic Acid, Di-c4-13-alkyl Esters

38. Ncgc00090974-03

39. O-benzenedicarboxylic Acid, Diethyl Ester

40. Diethyl Phthalate, 99%

41. Dsstox_cid_1780

42. Dsstox_rid_76323

43. Dsstox_gsid_21780

44. Phthalic Acid, Bis-iso-nonyl Ester

45. Diethyl-phthalate

46. Cas-84-66-2

47. Smr000857334

48. Ccris 2675

49. Hsdb 926

50. Dpx-f5384

51. Phthalsaeurediaethylester [german]

52. Einecs 201-550-6

53. Diethyl Phthalate, Pestanal(r), Analytical Standard

54. Diethylester Kyseliny Ftalove [czech]

55. Rcra Waste No. U088

56. Brn 1912500

57. Unii-uf064m00af

58. Ai3-00329

59. Kodaflex Dep

60. Diethyl-o-phthalate

61. Diethyl Phthalic Acid

62. Phthalic Acid Diethyl

63. Diethyl Phthalate, Nf

64. Diethyl 1,2-benzenedioate

65. Bmse000846

66. Epitope Id:140105

67. Ec 201-550-6

68. Wln: 2ovr Bvo2

69. Diethyl Phthalate, >=99%

70. Diethyl Phthalate, 99.5%

71. Schembl22296

72. Dimethyphalate ,ethylphthalate

73. 4-09-00-03172 (beilstein Handbook Reference)

74. Mls001336021

75. Mls001336022

76. Mls002152901

77. Mls002177800

78. Bidd:er0639

79. Diethyl Phthalate [ii]

80. Phthalic Acid, Bis-ethyl Ester

81. Chembl388558

82. Zinc1287

83. Diethyl Phthalate, >=99.5%

84. Diethyl Phthalate [hsdb]

85. Diethyl Phthalate [inci]

86. Dtxsid7021780

87. Diethyl-1,2-benzenedicarboxylate

88. Phthalic Acid Ethyl Ester

89. Diethyl Phthalate [vandf]

90. Ethyl Phthalate [who-dd]

91. Nsc8905

92. Diethyl Phthalate [mart.]

93. Diethyl Phthalate, Lr, >=99%

94. Hms2233j05

95. Hms3369g01

96. Phthalic Acid,diethyl Ester

97. Diethyl Phthalate [usp-rs]

98. Diethyl Phthalate/dimethyl Phthalate

99. Str04116

100. Tox21_111050

101. Tox21_201874

102. Tox21_300183

103. Bbl011577

104. Mfcd00009111

105. Stl163320

106. Akos000119867

107. Phthalic Acid Ethyl Ester [mi]

108. 1,2-diethyl Benzene-1,2-dicarboxylate

109. Diethyl Phthalate [ep Monograph]

110. Diethyl Phthalate Mil-d-242 Mil Spec

111. Ncgc00090974-01

112. Ncgc00090974-02

113. Ncgc00090974-04

114. Ncgc00090974-05

115. Ncgc00090974-06

116. Ncgc00254098-01

117. Ncgc00259423-01

118. 68988-18-1

119. Diethyl Phthalate Metal Plastic Ibc/tote

120. Benzene-1,2-dicarboxylic Acid Diethyl Ester

121. Cs-0013981

122. Ft-0624802

123. Ft-0666787

124. P0296

125. Diethyl Ester Of 1,2-benzenedicarboxylic Acid

126. Diethylphthalate, A-a-59314, Jan-d-242

127. D03804

128. Diethyl Phthalate, Saj Special Grade, >=98.0%

129. Q419811

130. Q-200982

131. F1908-0104

132. Phthalic Acid, Bis-ethyl Ester 100 Microg/ml In Methanol

133. Phthalic Acid, Bis-ethyl Ester 1000 Microg/ml In Methanol

134. Phthalic Acid, Bis-ethyl Ester 100 Microg/ml In Acetonitrile

135. Diethyl Phthalate, European Pharmacopoeia (ep) Reference Standard

136. Diethyl Phthalate, United States Pharmacopeia (usp) Reference Standard

137. Diethyl Phthalate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₄O₄
Molecular Weight	222.24 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	222.08920892 g/mol
Monoisotopic Mass	222.08920892 g/mol
Topological Polar Surface Area	52.6 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	223
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

Absorption of diethyl phthalate and three other phthalates (dimethyl, dibutyl, and di(2-ethylhexyl)) was measured using human epidermal skin obtained from the abdominal skin of 11 cadavers (mostly females 55 years of age or older) and subcutaneous fat removed in vitro. Epidermal membranes were set up in glass diffusion cells, and their permeability to tritiated water was measured to establish the integrity of the skin. Lag time for absorption of diethyl phthalate was 6 hr, and the steady-state absorption rate was 12.8 ug/sq cm per hour.

International Programme on Chemical Safety (IPCS); Concise International Chemical Assessment Document (CICADS) 52: Diethyl Phthalate (2003) Available from, as of April 17, 2008: https://www.inchem.org/documents/cicads/cicads/cicad52.htm

Percutaneous absorption of diethyl phthalate was evaluated in vitro in flow-through diffusion cells using human breast skin. Neat chemical (16-21 mg/sq cm) was applied over 72 hr to the epidermal surface of the skin, which was either uncovered or covered. The absorption of diethyl phthalate through skin was 3.9% and 4.8% of the applied doses for covered and uncovered conditions, respectively. The interindividual variation was 4-fold, ranging from 1.6% (SD 1.2) (n = 3) to 8.7% (SD 3.9) (n = 6) among skin donors.

This study examined the extent of dermal absorption of a series of phthalate diesters in the rat. Those tested were dimethyl, diethyl, dibutyl, diisobutyl, dihexyl, di(2-ethylhexyl), diisodecyl, and benzyl butyl phthalate. Hair from a skin area (1.3 cm in diameter) on the back of male F344 rats was clipped, the 14(C)phthalate diester was applied in a dose of 157 mumol/kg, and the area of application was covered with a perforated cap. The rat was restrained and housed for 7 days in a metabolic cage that allowed separate collection of urine and feces. Urine and feces were collected every 24 hr, and the amount of (14)C excreted was taken as an index of the percutaneous absorption. At 24 hr, diethyl phthalate showed the greatest excretion (26%). As the length of the alkyl side chain increased, the amount of (14)C excreted in the first 24 hr decreased signficantly. The cumulative percentage dose excreted in 7 days was greatest for diethyl, dibutyl, and diisobutyl phthalate, about 50-60% of the applied (14)C; and intermediate (20-40%) for dimethyl, benzyl butyl, and dihexyl phthalate. Urine was the major route of excretion of all phthalate diesters except for diisodecyl phthalate. This compound was poorly absorbed and showed almost no urinary excretion. After 7 days, the percentage dose for each phthalate that remained in the body was minimal showed no specific tissue distribution. Most of the unexcreted dose remained in the area of application. These data show that the structure of the phthalate diester determines the degree of dermal absorption. Absorption maximized with diethyl phthalate and then decreased significantly as the alkyl side chain length increased.

PMID:2925020 Elsisi AE et al; Fundam Appl Toxicol 12 (1): 70-7 (1989)

(14)C-Carboxy-labelled diethyl phthalate (2850 mg/kg body weight) was administered intraperitoneally to a group of 13 pregnant rats on either day 5 or day 10 of gestation. The results showed that radioactivity in the maternal blood peaked during the first 24 hr, then diminished quickly. A similar pattern was observed in amniotic fluid and fetal tissues. The reduction in concentration of (14)C from these tissues as a function of time was found to fit a first-order excretion curve. From this model curve, the half-life was calculated to be 2.22 days for diethyl phthalate. Radioactivity from (14)C-diethyl phthalate is transmitted across the placenta from mother to fetus for at least 15 days post-injection. (14)C radioactivity was widely distributed and was detected (<1%) in maternal blood, placenta, amniotic fluid, and developing fetuses at all gestational stages investigated.

For more Absorption, Distribution and Excretion (Complete) data for DIETHYL PHTHALATE (12 total), please visit the HSDB record page.

4.2 Metabolism/Metabolites

Diethyl phthalate (10 or 100 mg) was administered to each of three Wistar rats by stomach intubation. Daily urine collections were analyzed for 10 days by GC-MS. For both doses, 77-78% of the administered dose was excreted in urine within 24 hr as monoester derivative (67-70% of the dose), phthalic acid (8-9% of the dose), or parent compound (0.1-0.4%), and about 85-93% was excreted within 1 week after administration.

Using in vitro preparations of rat, baboon, and human tissues, /investigators/ demonstrated that DEP was hydrolyzed to the monoester. Further hydrolysis of the monoester and its conjugation with glucuronic acid are consistent with the biotransformation pathways for related phthalates.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's with Other World Wide Occupational Exposure Values. CD-ROM Cincinnati, OH 45240-1634 2007.

The first step of metabolism involves hydrolysis to a monoester derivative. This was seen in the in vitro metabolism of (14)C-diethyl phthalate (5-mmol/L solution) by hepatic and small intestine preparations from a rodent (rat), a nonrodent (ferret), and a nonhuman primate (baboon). Hepatic postmitochondrial supematant and intestinal preparations from the rat, baboon, and ferret were able to catalyze the hydrolysis of diethyl phthalate to its monoester derivative. Enzyme activity was expressed as micromoles of product formed per hour per gram of liver (umol/hour/g) or per milligram of intestinal mucosal cell protein (umol/hour/mg). Quantitative species differences were observed in the hepatic and intestinal studies. In the hepatic studies, diethyl phthalate hydrolase activity decreased in the following order: baboon (516 umol/hour/g) > rat (231 umol/hour/g) > ferret (45.9 umol/hour/g). In the intestinal preparation, diethyl phthalate hydrolase activity decreased in the same order: baboon (4.33 umol/hour/mg) > rat (0.648 umol/hour/mg) > ferret (0.053 umol/hour/mg). Studies were also performed with samples of human duodenum and jejunum tissues. As with the three animal species, human intestinal preparations were also active in the metabolism of diethyl phthalate. The results obtained with human intestinal preparations were expressed as nanomoles of product formed per hour per milligram of intestinal protein (nmol/hour/mg). In the human intestinal preparation, the diethyl phthalate hydrolase activity was 31.2-153 nmol/hour/mg in the duodenum and 129 nmol/hour/mg in the jejunum. Similarly, of the tissues from three rat and one human studied in vitro, the rat small intestine hydrolyzed the greatest amount (36.4%) of diethyl phthalate in a 16-hour period. These results show a qualitative species similarity in the hydrolytic metabolism of diethyl phthalate in humans, a rodent, a nonrodent, and a nonhuman primate.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Diethylphthalate p.34-5 (1995) PB/95/264214/AS. Available from, as of April 23, 2008: https://www.atsdr.cdc.gov/toxpro2.html#

Once formed, the monoester derivative can be further hydrolysed in vivo to phthalic acid and excreted or conjugated to glucuronide and excreted; the terminal or next-to-last carbon atom in the monoester can be oxidized to an alcohol and excreted; or the alcohol can be successively oxidized to an aldehyde, ketone, or carboxylic acid and excreted.

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

4.3 Biological Half-Life

(14)C-Carboxy-labelled diethyl phthalate (2850 mg/kg body weight) was administered intraperitoneally to a group of 13 pregnant rats on either day 5 or day 10 of gestation. ... The half-life was calculated to be 2.22 days for diethyl phthalate.

In fish, the half-life may be as short as 1.5 hr, yielding 99% clearance in 24 hr. /Phthalate esters/

Nat'l Research Council Canada; Phthalate Esters p.20 (1980) NRCC No. 17583

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