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Chemistry

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Also known as: 552-30-7, 1,2,4-benzenetricarboxylic anhydride, Anhydrotrimellic acid, 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid, Trimellitic acid anhydride, 4-carboxyphthalic anhydride
Molecular Formula
C9H4O5
Molecular Weight
192.12  g/mol
InChI Key
SRPWOOOHEPICQU-UHFFFAOYSA-N
FDA UNII
80T61EUU7H

Trimellitic Anhydride
1 2D Structure

Trimellitic Anhydride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,3-dioxo-2-benzofuran-5-carboxylic acid
2.1.2 InChI
InChI=1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
2.1.3 InChI Key
SRPWOOOHEPICQU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC2=C(C=C1C(=O)O)C(=O)OC2=O
2.2 Other Identifiers
2.2.1 UNII
80T61EUU7H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Tri-mellitic Anhydride

2.3.2 Depositor-Supplied Synonyms

1. 552-30-7

2. 1,2,4-benzenetricarboxylic Anhydride

3. Anhydrotrimellic Acid

4. 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic Acid

5. Trimellitic Acid Anhydride

6. 4-carboxyphthalic Anhydride

7. Tman

8. Trimellitic Acid 1,2-anhydride

9. Anhydrotrimellitic Acid

10. Trimellic Acid Anhydride

11. Trimellic Acid 1,2-anhydride

12. 1,3-dioxo-5-phthalancarboxylic Acid

13. Trimellitic Acid Cyclic 1,2-anhydride

14. 5-isobenzofurancarboxylic Acid, 1,3-dihydro-1,3-dioxo-

15. 1,3-dihydro-1,3-dioxo-5-isobenzofurancarboxylic Acid

16. 1,2,4-benzenetricarboxylic Acid Anhydride

17. Epon 9150

18. 1,2,4-benzenetricarboxylic Acid 1,2-anhydride

19. Nci-c56633

20. 1,3-dioxo-2-benzofuran-5-carboxylic Acid

21. 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylic Acid

22. Nsc 60252

23. 1,2,4-benzenetricarboxylic Acid, Cyclic 1,2-anhydride

24. 5-phthalanacarboxylic Acid, 1,3-dioxo-

25. Chebi:53050

26. Benzene-1,2,4-tricarboxylic-1,2-anhydride

27. Mfcd00005925

28. 1,3-dioxoisobenzofuran-5-carboxylic Acid

29. 1,2,4-benzenetricarboxylic 1,2-anhydride

30. 80t61euu7h

31. Diphenylmethane-4,4'-diisocyanate-trimellic Anhydride-ethomid Ht Polymer

32. Nsc-60252

33. 1,2,4-benzene Tricarboxylic Anhydride

34. Benzene-1,2,4-tricarboxylic Anhydride

35. Benzene-1,2,4-tricarboxylic Acidanhydride

36. Dsstox_cid_6235

37. Dsstox_rid_78070

38. Dsstox_gsid_26235

39. 1,3-dioxo-1,3-dihydro-isobenzofuran-5-carboxylic Acid

40. Anhydride-ethomid Ht Polymer

41. Cas-552-30-7

42. Ccris 6282

43. Hsdb 4299

44. 1,2,4-benzenetricarboxylicanhydride

45. Einecs 209-008-0

46. Benzene-1,2,4-tricarboxylic Acid 1,2-anhydride

47. Brn 0009394

48. Unii-80t61euu7h

49. Cyclic 1,2-anhydride

50. Epitope Id:113235

51. Ec 209-008-0

52. Schembl22458

53. Trimellitic Acid,2-anhydride

54. 5-18-08-00562 (beilstein Handbook Reference)

55. Trimellic Acid-1,2-anhydride

56. Wln: T56 Bvovj Gvq

57. Trimellitic Anhydride-dendrimers

58. Chembl2137687

59. Dtxsid7026235

60. Trimellitic Anhydride Treated Bsa

61. Trimellitic Anhydride Treated Hsa

62. Trimellitic Anhydride Treated Igg

63. 1,4-benzenetricarboxylic Anhydride

64. Trimellitic Anhydride [mi]

65. Nsc60252

66. Trimellitic Anhydride Treated Casein

67. Tox21_202066

68. Tox21_303117

69. Trimellitic Anhydride [hsdb]

70. Trimellitic Anhydride [inci]

71. 5-phthalanacarboxylic Acid,3-dioxo-

72. Ac-811

73. Ac8872

74. Bbl010496

75. Stl146149

76. Zinc22346496

77. 1,2,4 Benzenetricarboxylic Anhydride

78. Akos000120069

79. Cs-w015822

80. Trimellitic Anhydride Treated Hemoglobin

81. 1,4-benzenetricarboxylic Acid Anhydride

82. Benzene-1,2,4-tricarboxylicacidanhydride

83. Ncgc00164022-01

84. Ncgc00164022-02

85. Ncgc00256953-01

86. Ncgc00259615-01

87. 1,3-dioxo-5-isobenzofurancarboxylic Acid

88. Bp-13468

89. Sy001151

90. Trimellitic Anhydride-trypsin Treated Bsa

91. Vs-02531

92. 1,2,4 Benzenetricarboxylic Acid Anhydride

93. 1,2,4-benzenetricarboxylic Anhydride, 97%

94. 1,4-benzenetricarboxylic Acid 1,2-anhydride

95. C0959

96. Ft-0689091

97. Trimellitic Anhydride Treated Human Transferrin

98. Trimellitic Anhydride, Purum, >=97.0% (t)

99. 1,2,4-benzenetricarboxylic Acid Anhydride-1,2

100. Trimellitic Anhydride Treated Human Serum Albumin

101. A830542

102. Trimellitic Anhydride Treated Bovine Serum Albumin

103. Q1675143

104. W-105576

105. 1,4-benzenetricarboxylic Acid, Cyclic 1,2-anhydride

106. 5-isobenzofurancarboxylic Acid,3-dihydro-1,3-dioxo-

107. Trimellitic Anhydride Treated Non-fat Dry Milk Powder

108. 1,2,4-benzenetricarboxylic Anhydride Treated Hemoglobin

109. F0001-1448

110. 1,3-dioxo-1,3-dihydro-isobenzofuran-5-carboxylic Acid #

111. Trimellitic Anhydride-trypsin Treated Bovine Serum Albumin

112. 1,2,4-benzenetricarboxylic Anhydride Trimellitic Anhydride Tma

113. 1,3-dioxoisobenzofuran-5-carboxylic Acid;trimellitic Anhydride

114. Trimellitic Anhydride Treated .beta.-lactoglobulin From Bovine Whey

115. 1,2,4-benzenetricarboxylic Anhydride Treated .beta.-lactoglobulin From Bovine Whey

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 192.12 g/mol
Molecular Formula C9H4O5
XLogP30.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass192.00587322 g/mol
Monoisotopic Mass192.00587322 g/mol
Topological Polar Surface Area80.7 Ų
Heavy Atom Count14
Formal Charge0
Complexity308
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 Absorption, Distribution and Excretion

Tissue concentration time-course data were collected for rats exposed to 0.95 mg/cu m trimellitic anhydride (TMA) for 45 min ... Animals were sacrificed 3 hr, 1, 2, 4, 8, 16, and 32 days following exposure. In general, the highest tissue concentrations were obtained at the first time point (T-max<3 hr). A second T-max of eight days was reported for lung lymph nodes in male rats, suggesting a possible role in the gender differences observed for lung toxicity ...

OECD; Screening Information Data Set for Trimellitic anhydride & trimellitic acid, CAS #: 552-30-7; 528-44-9 (October 2002). Available from, as of August 28, 2006: https://www.inchem.org/documents/sids/sids/TLANA.pdf


4.2 Biological Half-Life

... Biological half-lives /in rats/ ranging from 3 to 46 days were estimated ... Specific half-lives for trimellitic anhydride in the lungs were estimated to be 21 days in male rats and 16 days in female rats ... In lung associated lymph nodes, half-lives of 13 and 33 days were estimated for male and female rats, respectively ...

OECD; Screening Information Data Set for Trimellitic anhydride & trimellitic acid, CAS #: 552-30-7; 528-44-9 (October 2002). Available from, as of August 28, 2006: https://www.inchem.org/documents/sids/sids/TLANA.pdf


4.3 Mechanism of Action

... Trimellitic anhydride (TMA) and trimellitic acid (TMLA) are structurally similar ... Studies on stability of TMA in water suggest complete hydrolysis occurs in less than ten minutes. Since TMA rapidly forms TMLA under the conditions used to test its toxicity, the toxicities of TMA and TMLA are believed to be the same with a few exceptions. Specifically, the alergic symptoms (both respiratory and dermal sensitization) of TMA are directly attributable to the reaction of TMA with free amines within proteins to form haptens, which when present at sufficiently high levels in tissues can produce sensitization. TMLA does not react with proteins to form haptens ... In addition to the immunological differences, there may be some slight quantitative differences in reactions at the site of contact. While both materials cause slight irritation of the skin and are severe eye irritants, there appears to be a difference in the magnitude of response. This difference in the magnitude of irritation may be attributable to the heat of hydrolysis of the anhydride. With the exception of the immunological and site of contact effects, all other endpoints are expected to be the same.

OECD; Screening Information Data Set for Trimellitic anhydride & trimellitic acid, CAS #: 552-30-7; 528-44-9 (October 2002). Available from, as of August 28, 2006: https://www.inchem.org/documents/sids/sids/TLANA.pdf


Occupational inhalation of trimellitic anhydride (TMA) apparently results in an antibody response with specificity for unique new antigenic determinants which arise from the coupling of TMA with autologous resp tract proteins.

ZEISS ET AL; INT ARCH ALLERGY APPL IMMUNOL 61(4) 380 (1980)


... Sensitization with trimellitic anhydride (TMA) led to decreased lung function parameters during and within 1 hr after challenge as compared to non-sensitized rats. Alveolar macrophages (AM) depletion alleviated the TMA-induced drop in lung function parameters and induced a faster recovery compared to sham-depleted TMA-sensitized rats. It also decreased the levels of serum IgE 24 hr after challenge, but did not affect the sensitization-dependent increase in lung lavage fluid IL-6 and tissue TNF-alpha levels. AM depletion augmented the TMA-induced tissue damage and inflammation 24 hr after challenge.

PMID:15992840 Valstar DL et al; Toxicol Appl Pharmacol 211 (1): 20-9 (2006)


... In the TNF-alpha knockout TNF-alpha-/- (B6;129S-Tnftm1Gk1) mice, the repetition of the trimellitic anhydride (TMA) challenges enlarged the extent of the late phase of contact hypersensitivity (CHS), but less than those in TNF-alpha+/+ mice. Injection of anti-TNF-alpha antibody into the peritoneal cavity of Balb/c mice significantly decreased the extent of the late phase of CHS. Subcutaneous injection of anti-IgE antibody into Balb/c mice also decreased the extent of the late phase of CHS in dose-dependent manner. Histologically, infiltration of polymorphonuclear leukocytes and eosinophils was more pronounced in repeatedly TMA-challenged TNF-alpha+/+ and Balb/c mice than in the TNF-alpha-/- mice and anti-TNF-alpha or anti-IgE antibodies treated Balb/c mice.

PMID:16264265 Chai OH et al; Exp Mol Med 37 (5): 408-17 (2005)


For more Mechanism of Action (Complete) data for TRIMELLITIC ANHYDRIDE (6 total), please visit the HSDB record page.


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