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Chemistry

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Also known as: 75-91-2, Tbhp, T-butyl hydroperoxide, Tert-butylhydroperoxide, 2-hydroperoxy-2-methylpropane, Perbutyl h
Molecular Formula
C4H10O2
Molecular Weight
90.12  g/mol
InChI Key
CIHOLLKRGTVIJN-UHFFFAOYSA-N
FDA UNII
955VYL842B

Tert-Butyl Hydroperoxide
A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.
1 2D Structure

Tert-Butyl Hydroperoxide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroperoxy-2-methylpropane
2.1.2 InChI
InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
2.1.3 InChI Key
CIHOLLKRGTVIJN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)(C)OO
2.2 Other Identifiers
2.2.1 UNII
955VYL842B
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hydroperoxide, T-butyl

2. Hydroperoxide, Tert-butyl

3. T Butyl Hydroperoxide

4. T Butylhydroperoxide

5. T-butyl Hydroperoxide

6. T-butylhydroperoxide

7. Tert Butyl Hydroperoxide

8. Tert Butylhydroperoxide

9. Tert-butylhydroperoxide

10. Tertiary Butylhydroperoxide

11. Tertiary-butylhydroperoxide

2.3.2 Depositor-Supplied Synonyms

1. 75-91-2

2. Tbhp

3. T-butyl Hydroperoxide

4. Tert-butylhydroperoxide

5. 2-hydroperoxy-2-methylpropane

6. Perbutyl H

7. T-butylhydroperoxide

8. 1,1-dimethylethyl Hydroperoxide

9. Cadox Tbh

10. Hydroperoxide, 1,1-dimethylethyl

11. Tert-butyl Hydrogen Peroxide

12. Terc. Butylhydroperoxid

13. Hydroperoxyde De Butyle Tertiaire

14. Hydroperoxide, Tert-butyl

15. Slimicide De-488

16. Tertiary Butyl Hydroperoxide

17. Trigonox A-75

18. Trigonox A-w70

19. Tbhp-70

20. 1,1-dimethylethylhydroperoxide

21. Nsc 672

22. T-buooh

23. Tertiary-butyl Hydroperoxide

24. Tert-butyl-hydroperoxide

25. Dimethylethyl Hydroperoxide

26. T-hydro

27. Perbutyl H 69t

28. Luperox Tbh 70x

29. Trigonox A-w 70

30. Tert-butyl Hydroperoxide Solution

31. Chebi:64090

32. Nsc-672

33. 955vyl842b

34. Tert-butyl Hydroperoxide (70% Solution In Water)

35. Caswell No. 130bb

36. Trigonox A-75 [czech]

37. Tbooh

38. Terc.butylhydroperoxid [czech]

39. Ccris 5892

40. Hsdb 837

41. Terc.butylhydroperoxid

42. Terc. Butylhydroperoxid [czech]

43. Tert Butylhydroperoxide

44. Einecs 200-915-7

45. De 488

46. De-488

47. Brn 1098280

48. Hydroperoxyde De Butyle Tertiaire [french]

49. Unii-955vyl842b

50. Ai3-50541

51. Kayabutyl H

52. Tbuooh

53. Tert-buooh

54. Hydroperoxide, 1,1-dimethylethyl-

55. Perbutyl H 69

56. Perbutyl H 80

57. T-butyl-hydroperoxide

58. Terbutyl Hydroperoxide

59. Tert-butyhydroperoxide

60. Tert-c4h9ooh

61. T-butyl Hydrogenperoxide

62. T-butyl-hydrogenperoxide

63. Tert.-butylhydroperoxide

64. Tert.butyl Hydroperoxide

65. Tertiarybutylhydroperoxide

66. Tertbutylhydrogen Peroxide

67. T-butyl Hydrogen Peroxide

68. Tert.-butyl Hydroperoxide

69. Kayabutyl H 70

70. Dsstox_cid_4693

71. Tert-butylhydrogen Peroxide

72. Ec 200-915-7

73. Dsstox_rid_78866

74. Dsstox_gsid_31209

75. Tertiary Butyl Hydro Peroxide

76. Hydroperoxide,1-dimethylethyl

77. Trigonox A-80 (salt/mix)

78. Un 2093 (salt/mix)

79. Un 2094 (salt/mix)

80. Usp -800 (salt/mix)

81. Chembl348399

82. Nsc672

83. Dtxsid9024693

84. Tert-butyl Hydroperoxide (8ci)

85. Tert-butyl Hydroperoxide, >90% With Water [forbidden]

86. Wln: Qox1&1&1

87. Tert-butyl-hydroperoxide Solution

88. 2-methyl-prop-2-yl-hydroperoxide

89. Zinc8585869

90. Tox21_200838

91. Aztec T-butyl Hydroperoxide-70, Aq

92. Mfcd00002130

93. Tert-butyl Hydroperoxide [ii]

94. Tert-butyl Hydroperoxide [mi]

95. Tert-butyl Hydroperoxide Solution, Cp

96. Akos000121070

97. Tert-butyl Hydroperoxide [hsdb]

98. Ncgc00090725-01

99. Ncgc00090725-02

100. Ncgc00090725-03

101. Ncgc00258392-01

102. Tert-butyl Hydroperoxide Aqueous Solution

103. Hydroperoxide, 1,1-dimethylethyl (9ci)

104. Tert-butyl Hydroperoxide (70% In Water)

105. Tert-butyl Hydroperoxide, >90% With Water

106. B3153

107. Ft-0657109

108. Tert-butyl Hydroperoxide, 70% Solution In Water

109. Q286326

110. J-509597

111. Tert-butyl Hydroperoxide Solution, ~5.5 M In Decane

112. F1905-8242

113. Tert-butyl Hydroperoxide Solution (tbhp), 70% In H2o

114. Tert-butyl Hydroperoxide Solution, 5.0-6.0 M In Decane

115. Tert-butyl Hydroperoxide Solution, 5.0-6.0 M In Nonane

116. Luperox(r) Tbh70x, Tert-butyl Hydroperoxide Solution, 70 Wt. % In H2o

117. Tert-butyl Hydroperoxide Solution, ~80% In Di-tert-butyl Peroxide/water 3:2

118. Tert-butyl Hydroperoxide Solution, Packed In Fep Bottles, ~5.5 M In Decane (over Molecular Sieve 4??)

119. Tert-butyl Hydroperoxide Solution, Packed In Fep Bottles, ~5.5 M In Nonane (over Molecular Sieve 4 ??)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 90.12 g/mol
Molecular Formula C4H10O2
XLogP30.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass90.068079557 g/mol
Monoisotopic Mass90.068079557 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count6
Formal Charge0
Complexity35.3
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 Metabolism/Metabolites

t-Butyl hydroperoxide and cumene hydroperoxide, both known to be substrates for glutathione peroxidase, were used to oxidize erythrocyte GSH. Addition of concentrations of hydroperoxides equimolar with respect to GSH in the erythrocytes or whole blood quantitatively oxidizes GSH in the erythrocytes with a half-time of 4.5 s at 37 C and about three times as long at 4 C. In the presence of glucose, normal erythrocytes regenerate all the GSH in about 25 min. However, glucose 6-phosphate dehydrogenase-deficient erythrocytes failed to regenerate GSH. Treatment of erythrocytes with hydroperoxides does not affect erythrocyte survival in rabbits. Oxidation of erythrocyte GSH with equimolar concentrations of hydroperoxides does not lead to formation of mixed disulfides of hemoglobin and GSH. The hydroperoxides do not affect erythrocyte glycolytic and hexose monophosphate-shunt-pathway enzymes. Previous studies on transport of GSSG from erythrocytes were confirmed by using t-butyl hydroperoxide to oxidize erythrocyte GSH.

PMID:4447610 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1166284 Srivastava SK et al; Biochem J 139 (2): 289 (1974)


Metabolic activation of peroxides and hydroperoxides to free radicals is associated with the tumor promoting activity of these compounds. tert-Butyl hydroperoxide (t-BOOH) metabolism has been extensively studied as a model of peroxide biotransformation. In vivo studies are limited, and the hemoglobin-thiyl radical was the only species thus far identified in the blood of treated rats. Here we further examine t-BOOH metabolism in vivo with regard to free radical and DNA adduct production. Spin-trapping experiments with phenyl-N-tert-butylnitrone (PBN) led to the detection of electron paramagnetic resonance (EPR) signals in the blood, bile, and organic extracts of the liver and stomach of rats treated with t-BOOH. Analysis of these signals demonstrated that t-BOOH metabolism in vivo produces alkyl radicals, detected in the bile and organic extracts of liver and stomach, in addition to the previously identified hemoglobin-thiyl radical. To characterize the produced alkyl radicals, experiments were performed with (13)C-labeled t-BOOH and two spin traps, PBN and alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone (POBN). The latter was used because the EPR signals obtained with PBN were too weak to be unambiguous. Nevertheless, the EPR signals present in the bile of animals treated with (13)C-labeled t-BOOH and PBN or POBN were consistent with adducts of (13)C-labeled methyl radical and an unidentified alkyl radical. The latter is probably derived from lipids oxidized by the metabolically produced primary radicals, methyl and its precursor, tert-butoxyl. The presence of 8-methylguanine and 7-methylguanine in hydrolysates of DNA from liver and stomach of rats treated with t-BOOH was also examined. 8-Methylguanine, a typical product of methyl radical attack on DNA, was detectable in both the liver and stomach of treated rats. The results may be relevant to the understanding of the genotoxic properties of other peroxides, particularly of cumene hydroperoxide.

PMID:11080055 Hix S et al; Chem Res Toxicol 13 (10): 1056-64 (2000)


4.2 Mechanism of Action

A short-term exposure of PC12 cells to tert-butylhydroperoxide, followed by recovery in fresh culture medium, causes cell death and the extent of this response progressively increases during the 120 min of post-treatment incubation. Morphological and biochemical analyses of these cells revealed that the mode of cell death was necrosis. Cell killing induced by the hydroperoxide seems to be in part mediated by peroxynitrite because the lethal response was markedly and similarly reduced by the nitric oxide synthase inhibitor N omega-nitro-L-arginine methylester and by scavengers of nitric oxide or peroxynitrite. This peroxynitrite-dependent mechanism of cytotoxicity was blunted by antioxidants and inhibitors of mitochondrial permeability transition and the onset of cell death was preceded by mitochondrial depolarization and loss of cellular ATP. We conclude that tert-butylhydroperoxide promotes peroxynitrite-dependent PC12 cell necrosis causally linked to peroxidation of membrane lipids and mitochondrial permeability transition.

PMID:11536321 Palomba L et al; J Neurosci Res 65 (5): 387-95 (2001)


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