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Chemistry

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Also known as: 131-11-3, Avolin, Dimethylphthalate, Fermine, Solvanom, Mipax
Molecular Formula
C10H10O4
Molecular Weight
194.18  g/mol
InChI Key
NIQCNGHVCWTJSM-UHFFFAOYSA-N
FDA UNII
08X7F5UDJM

Dimethyl Phthalate
dimethyl phthalate is a natural product found in Eleutherococcus sessiliflorus, Allium ampeloprasum, and Cryptotaenia canadensis with data available.
1 2D Structure

Dimethyl Phthalate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
dimethyl benzene-1,2-dicarboxylate
2.1.2 InChI
InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
2.1.3 InChI Key
NIQCNGHVCWTJSM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC(=O)C1=CC=CC=C1C(=O)OC
2.2 Other Identifiers
2.2.1 UNII
08X7F5UDJM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimethyl Phthalate, Conjugate Diacid

2. Dimethylphthalate

2.3.2 Depositor-Supplied Synonyms

1. 131-11-3

2. Avolin

3. Dimethylphthalate

4. Fermine

5. Solvanom

6. Mipax

7. Palatinol M

8. Solvarone

9. Dimethyl O-phthalate

10. Phthalic Acid Dimethyl Ester

11. Unimoll Dm

12. Repeftal

13. Methyl Phthalate

14. Dimethyl Benzene-1,2-dicarboxylate

15. Dimethyl 1,2-benzenedicarboxylate

16. 1,2-benzenedicarboxylic Acid, Dimethyl Ester

17. Phthalsaeuredimethylester

18. Phthalic Acid, Dimethyl Ester

19. Dimethyl Benzene-o-dicarboxylate

20. Ent 262

21. Dimethylphtalate

22. Dimethyl Benzeneorthodicarboxylate

23. Nsc 15398

24. 1,2-benzenedicarboxylic Acid, 1,2-dimethyl Ester

25. Dmf, Insect Repellent

26. Nsc-15398

27. Benzenedicarboxylic Acid, Dimethyl Ester

28. 08x7f5udjm

29. Chebi:4609

30. Chembl323348

31. Ntm

32. Phthalic Acid, Bis-methyl Ester

33. Ncgc00090692-02

34. Dsstox_cid_2455

35. Dimethyl Phthalate 5000 Microg/ml In Methanol

36. Dsstox_rid_76596

37. Dsstox_gsid_22455

38. Dimethyl Phthalate, >=99%

39. Caswell No. 380

40. Dmf (insect Repellant)

41. Rcra Waste Number U102

42. Cas-131-11-3

43. Dimethyl Phthalate [bsi:iso]

44. Ccris 2674

45. Phtalate De Dimethyle

46. Hsdb 1641

47. Phthalic Acid Dimethyl Ester (d6)

48. Phthalsaeuredimethylester [german]

49. Phtalate De Dimethyle [iso-french]

50. Einecs 205-011-6

51. Dimethyl Phthalate, Pestanal(r), Analytical Standard

52. Rcra Waste No. U102

53. Unii-08x7f5udjm

54. Dimethylester Kyseliny Ftalove [czech]

55. Epa Pesticide Chemical Code 028002

56. Dimethylester Kyseliny Ftalove

57. Ai3-00262

58. Density Standard 1191 Kg/m3

59. Dimethyl-phthalate

60. Kemester Dmp

61. Kodaflex Dmp

62. 1,dimethyl Ester

63. Uniplex 110

64. Dimethyl Orthophthalate

65. 1,2-dimethyl Benzene-1,2-dicarboxylate

66. 1,2-dimethyl Phthalate

67. Dimethyl Phthalate, 99%

68. Dimethyl Phthalate [usp]

69. Phthalic Acid Methyl Ester

70. Ec 205-011-6

71. Wln: 1ovr Bvo1

72. 1,2-benzenedicarboxylic Acid 1,2-dimethyl Ester

73. Schembl34630

74. Dimethyl Phthalate, Ar,99%

75. Dimethyl Phthalate, Cp,99%

76. Mls002177801

77. Bidd:er0349

78. Dimethyl Phthalate [ii]

79. Dimethyl Phthalate [mi]

80. Dimethyl Phthalate [iso]

81. Dtxsid3022455

82. Dimethyl 1,2-benzendicarboxylate

83. Dimethyl Phthalate [hsdb]

84. Dimethyl Phthalate [inci]

85. Zinc391885

86. Dimethyl Phthalate [mart.]

87. Amy40794

88. Dimethyl Phthalate [who-dd]

89. Hy-n7106

90. Nsc15398

91. Tox21_113536

92. Tox21_202145

93. Tox21_301045

94. Bdbm50090983

95. Mfcd00008425

96. S5378

97. Stl283931

98. Akos008969337

99. Ccg-266531

100. Db13336

101. Ncgc00090692-01

102. Ncgc00090692-03

103. Ncgc00090692-04

104. Ncgc00090692-05

105. Ncgc00090692-06

106. Ncgc00254947-01

107. Ncgc00259694-01

108. Bs-20466

109. Smr000777937

110. Db-062803

111. Benzene-1,2-dicarboxylic Acid Dimethyl Ester

112. Cs-0013572

113. Ft-0625095

114. P0302

115. En300-18366

116. Dimethyl Phthalate, Saj Special Grade, >=99.0%

117. Q423551

118. J-005938

119. Z57902306

120. Density Standard 1191 Kg/m3, H&d Fitzgerald Ltd. Quality

121. Phthalic Acid, Bis-methyl Ester 100 Microg/ml In Acetonitrile

122. Phthalic Acid, Bis-methyl Ester 1000 Microg/ml In Acetonitrile

123. Phthalic Acid, Bis-methyl Ester 1000 Microg/ml In N-hexane

124. Benzene,1,2-dicarboxylic Acid,dimethyl Ester (phthalic Acid,dimethyl Ester)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 194.18 g/mol
Molecular Formula C10H10O4
XLogP31.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass194.05790880 g/mol
Monoisotopic Mass194.05790880 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count14
Formal Charge0
Complexity200
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 MeSH Pharmacological Classification

Insect Repellents

Substances causing insects to turn away from them or reject them as food. (See all compounds classified as Insect Repellents.)


Fixatives

Agents employed in the preparation of histologic or pathologic specimens for the purpose of maintaining the existing form and structure of all of the constituent elements. Great numbers of different agents are used; some are also decalcifying and hardening agents. They must quickly kill and coagulate living tissue. (See all compounds classified as Fixatives.)


4.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03B - Insecticides and repellents

P03BX - Other insecticides and repellents

P03BX02 - Dimethylphthalate


4.3 Absorption, Distribution and Excretion

/After/ oral admin of (14)C dimethyl phthalate to rats or mice, radioactivity was found in the blood and various tissues. Maximum values for radioactivity were observed within 1 hr. Tissue radioactivity was highest in the kidneys, followed in decreasing order by the liver, fat, and spleen. After 24 hr, 91% of the admin dose had been excreted in the urine and 4.1% in the feces.

ITC/USEPA; Information Review #214 (Draft) Alkyl Phthalates p.4 (1980)


The percutaneous absorption of a series of phthalate esters, dimethylphthalate, diethylphthalate, dibutyl phthalate, and di-(2-ethylhexyl) phthalate, was measured through human and rat epidermal membranes mounted in glass diffusion cells. The esters were applied directly to the epidermal membranes. Following application to the membranes, a lag phase followed by a linear phase of absorption was detected for each phthalate diester. Human skin was less permeable than rat skin for all four diesters. There appeared to be a trend to an increasing lag time with increasing molecular weight, but this relationship did not always hold true. The phthalate diesters were determined to have a 300 fold range of aqueous solubility and a wide range of lipophilicity. Once the diesters had contacted the human epidermal membrane, a slight increase in the permeability of the skin was detected. Relatively large changes in permeability were detected in the membrane following exposure.

PMID:3691429 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1474516 Scott RC et al; Environ Health Perspect 74: 223-27 (1987)


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)


DMP is readily absorbed from the skin, intestinal tract, the peritoneal cavity, and lung.

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 819


For more Absorption, Distribution and Excretion (Complete) data for DIMETHYL PHTHALATE (6 total), please visit the HSDB record page.


4.4 Metabolism/Metabolites

Intestinal extracts from man, ferrets and the baboon, as well as liver extracts from the latter 2 species, break down dimethyl phthalate to the monoester.

European Chemicals Bureau; IUCLID Dataset, Dimethyl phthalate (131-11-3) p.129 (2000 CD-ROM edition). Available from, as of April 25, 2008: https://esis.jrc.ec.europa.eu/


In vitro studies on metabolism of dimethylphthalate, dibutyl phathalate, di-n-octyl phthalate ... and diethylhexyl phthalate by rat liver and kidney liver homogenates have demonstrated that the lower the molecular weight of phthalate ester the faster the rate of metabolism. Rate of degradation of esters by rat kidney homogenates was relatively slow when compared with that by liver homogenates.

The Royal Society of Chemistry. Foreign Compound Metabolism in Mammals. Volume 6: A Review of the Literature Published during 1978 and 1979. London: The Royal Society of Chemistry, 1981., p. 340


Of a single dose of 120 mg dimethyl phthalate admin to rats by stomach tube, 44.6% was detected in the urine, consisting of 77.5% as the monomethyl ester with 14.4% as 0-phthalate acid and 8.1% as intact dimethyl phthalate.

European Chemicals Bureau; IUCLID Dataset, Dimethyl phthalate (131-11-3) p.129 (2000 CD-ROM edition). Available from, as of April 25, 2008: https://esis.jrc.ec.europa.eu/


... In a host-mediated mutagenesis assay, rats were injected ip with dimethyl phthalate (DMP) (2 g/kg body weight); urine was collected for 24 hr, extracted, and analyzed for ... phthalic acid-containing derivatives. The extracted urine ... contained an equivalent of 1.96 mg phthalate/mL urine. More than 97% of the phthalic acid-containing derivatives present in the extracted urine consisted of the nonmutagenic metabolite of DMP, monomethyl phthalate (MMP). In vitro experiments showed that rat liver homogenates hydrolyzed 93% of carbonyl-labeled (14)C-DMP (7.7 mM) to MMP in 2 hr and bound 0.07 nmol of ((14)C)phthalate/mg liver macromolecules. By contrast, rat epidermal homogenates metabolized only 5% and bound 38-fold higher levels of carbonyl-labeled (14)C-DMP (2.66 nmol/mg of macromolecules), with no detectable binding to nucleic acids. Compared to epidermis and plasma, liver had a fivefold higher rate of DMP monoesterase activity (1240 nmol/hr/mg protein), which, when inhibited by 67%, resulted in a 4.4-fold increase in phthalate-bound hepatic macromolecules (0.31 vs. 0.07 nmol of carbonyl-labeled (14)C-DMP/mg macromolecules). In addition to MMP, formaldehyde was produced during the metabolism of DMP by liver. When ethanol was used to inhibit the oxidation of DMP-derived methanol by hepatic homogenates, there resulted a 74% reduction in the accumulation of formaldehyde and similar reductions of 71 and 73% in the binding of methyl-labeled (14)C-DMP to nucleic acids and macromolecules. (Methyl-labeled, unlike carbonyl-labeled, (14)C-DMP yields a (14)C-labeled methanol when hydrolyzed.) These results indicate that the DMP diester ... binds to epidermal and hepatic macromolecules other than nucleic acids, and that although the rapid hepatic metabolism of DMP to its monoester (MMP) and methanol affords protection against higher levels of phthalate binding as well as against DMP-induced bacterial mutagenesis, it also oxidizes DMP-derived methanol to formaldehyde, a metabolite that binds macromolecules, including nucleic acids.

PMID:1709688 Kozumbo WJ, Rubin RJ; J Toxicol Environ Health 33 (1): 29-46 (1991)


For more Metabolism/Metabolites (Complete) data for DIMETHYL PHTHALATE (12 total), please visit the HSDB record page.


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