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Cumene Hydroperoxide

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Also known as: Cumyl hydroperoxide, 80-15-9, Hydroperoxide, 1-methyl-1-phenylethyl, Cumenyl hydroperoxide, Alpha,alpha-dimethylbenzyl hydroperoxide, Cumolhydroperoxid

Molecular Formula

C₉H₁₂O₂

Molecular Weight

152.19 g/mol

InChI Key

YQHLDYVWEZKEOX-UHFFFAOYSA-N

FDA UNII

PG7JD54X4I

1 2D Structure

Cumene hydroperoxide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroperoxypropan-2-ylbenzene

2.1.2 InChI

InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

2.1.3 InChI Key

YQHLDYVWEZKEOX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C1=CC=CC=C1)OO

2.2 Other Identifiers

2.2.1 UNII

PG7JD54X4I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cumene Hydroperoxide, Sodium Salt

2. Cumyl Hydroperoxide

3. Cumylhydroperoxide

4. Isopropyl Benzene Hydroperoxide

2.3.2 Depositor-Supplied Synonyms

1. Cumyl Hydroperoxide

2. 80-15-9

3. Hydroperoxide, 1-methyl-1-phenylethyl

4. Cumenyl Hydroperoxide

5. Alpha,alpha-dimethylbenzyl Hydroperoxide

6. Cumolhydroperoxid

7. 7-cumyl Hydroperoxide

8. Cument Hydroperoxide

9. Hydroperoxyde De Cumene

10. Hydroperoxyde De Cumyle

11. Isopropylbenzene Hydroperoxide

12. Cumeenhydroperoxyde

13. Kumenylhydroperoxid

14. 2-hydroperoxypropan-2-ylbenzene

15. 7-hydroperoxykumen

16. Rcra Waste Number U096

17. 1-methyl-1-phenylethyl Hydroperoxide

18. Idroperossido Di Cumene

19. Idroperossido Di Cumolo

20. Percumyl H

21. Pg7jd54x4i

22. Dtxsid3024869

23. Chebi:78673

24. Cumolhydroperoxide

25. .alpha.,.alpha.-dimethylbenzyl Hydroperoxide

26. Hydroperoxide, .alpha.,.alpha.-dimethylbenzyl

27. Cumene Hydroperoxide (80per Cent, Technical Grade)

28. Hydroperoxide De Cumene

29. Cumolhydroperoxid [german]

30. Cumeenhydroperoxyde [dutch]

31. Kumenylhydroperoxid [czech]

32. 7-hydroperoxykumen [czech]

33. Ccris 3801

34. Hsdb 254

35. Hydroperoxyde De Cumene [french]

36. Hydroperoxyde De Cumyle [french]

37. Idroperossido Di Cumene [italian]

38. Idroperossido Di Cumolo [italian]

39. Einecs 201-254-7

40. Rcra Waste No. U096

41. Alpha,alpha-dimethylbenzylhydroperoxide

42. Unii-pg7jd54x4i

43. Brn 1908117

44. Hydroperoxide, 1-methyl-1-phenylethyl-

45. Hyperiz

46. Hydroperoxide, Alpha,alpha-dimethylbenzyl-

47. Cumyl-hydroperoxide

48. Ph 80

49. Trigonox K 80

50. Trigonox K-95

51. Trigonox R 239a

52. Hydroperoxide, Alpha,alpha-dimethylbenzyl

53. Alpha-cumyl Hydroperoxide

54. Alpha-cumene Hydroperoxide

55. Dsstox_cid_4869

56. Luperox Cu 80

57. Trigonox K 90

58. Ec 201-254-7

59. .alpha.-cumyl Hydroperoxide

60. Chp-5

61. Dsstox_rid_77559

62. .alpha.-cumene Hydroperoxide

63. Dsstox_gsid_24869

64. Schembl15251

65. 4-06-00-03221 (beilstein Handbook Reference)

66. Chembl1518369

67. Schembl11210695

68. Chp-158

69. 2-phenylpropan-2-yl Hydroperoxide

70. Cumene Hydroperoxide [hsdb]

71. Zinc8585911

72. Tox21_300283

73. Mfcd00002129

74. Stl453641

75. Akos015841738

76. Ccg-207896

77. Un 2116

78. Cas-80-15-9

79. Ncgc00091748-01

80. Ncgc00091748-02

81. Ncgc00091748-03

82. Ncgc00254045-01

83. Cumene Hydroperoxide, Technical Grade, 80%

84. Cumene Hydroperoxide, Technical, ~80% In Cumene

85. Q414439

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₂O₂
Molecular Weight	152.19 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	152.083729621 g/mol
Monoisotopic Mass	152.083729621 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	115
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 MeSH Pharmacological Classification

Oxidants

Electron-accepting molecules in chemical reactions in which electrons are transferred from one molecule to another (OXIDATION-REDUCTION). (See all compounds classified as Oxidants.)

4.2 Absorption, Distribution and Excretion

Liquid peroxides can be absorbed through the skin. /Organic peroxides/

Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 166

4.3 Metabolism/Metabolites

Cumene hydroperoxide penetrates human red blood cells ... reduced by glutathione in the reaction catalyzed by glutathione peroxidase. Cumenol, water, and oxidized gluthathione were products.

PMID:4447610 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1166284 Srivastava SK et al; Biochem J 139: 289-95 (1974)

Enzymatic reduction of cumene hydroperoxide leads to the formation of cumenol (2-phenylpropan-2-ol) in vitro.

PMID:4319399 Little CR et al; J Biol Chem 245 (14): 3632-6 (1970)

Cumene hydroperoxide has known human metabolites that include (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(2-phenylpropan-2-ylperoxysulfanyl)propan-2-yl]amino]-5-oxopentanoic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

4.4 Mechanism of Action

The cumene hydroperoxide-hematin system reacts with 5,5-dimethyl-1-pyrroline-1-oxide to form the nitroxide 5,5-dimethyl-pyrrolidone-(2)-oxyl-(1) (DMPOX). DMPOX is formed via spin trapping of a cumene hydroperoxyl radical followed by an intramolecular carbanion displacement. Activation of carcinogen n-hydroxy-2-acetyl aminofluorene by cumene hydroperoxide-hematin system is most likely mediated by cumene hydroperoxyl radical.

PMID:6248759 Rosen GM, Rauckman EJ; Mol Pharmacol 17 (2): 233-8 (1980)

Cumene hydroperoxide oxidized cholesterol to the carcinogen 5,6-epoxide (5,6-alpha-epoxy-5-alpha-cholestan-3-beta-ol).

Smith LL, Kulig MJ; Cancer Biochem Biophys 1: 79-84 (1975)

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