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2D Structure
Also known as: P-nitrophenol, 100-02-7, Phenol, 4-nitro-, Niphen, Paranitrophenol, 4-hydroxynitrobenzene
Molecular Formula
C6H5NO3
Molecular Weight
139.11  g/mol
InChI Key
BTJIUGUIPKRLHP-UHFFFAOYSA-N
FDA UNII
Y92ZL45L4R

4-Nitrophenol is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-nitrophenol
2.1.2 InChI
InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
2.1.3 InChI Key
BTJIUGUIPKRLHP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1[N+](=O)[O-])O
2.2 Other Identifiers
2.2.1 UNII
Y92ZL45L4R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-nitrophenol, (18)o-labeled Cpd

2. 4-nitrophenol, 1-(13)c-labeled Cpd

3. 4-nitrophenol, 14c-labeled Cpd

4. 4-nitrophenol, 2,6-(13)c2-labeled Cpd

5. 4-nitrophenol, 2,6-(14)c2-labeled Cpd

6. 4-nitrophenol, 2-(14)c-labeled Cpd

7. 4-nitrophenol, Aluminum Salt

8. 4-nitrophenol, Ammonium Salt

9. 4-nitrophenol, Cesium Salt

10. 4-nitrophenol, Copper(1+) Salt

11. 4-nitrophenol, Ion(1-)

12. 4-nitrophenol, Ion(1-) Hydride

13. 4-nitrophenol, Iron(3+) Salt

14. 4-nitrophenol, Lithium Salt

15. 4-nitrophenol, Manganese (2+) Salt

16. 4-nitrophenol, Manganese Salt

17. 4-nitrophenol, Potassium Salt

18. 4-nitrophenol, Silver(2+) Salt

19. 4-nitrophenol, Sodium Salt

20. 4-nitrophenol, Sodium Salt, (2:1), Dihydrate

21. 4-nitrophenol, Tin (2+) Salt

22. 4-nitrophenol, Tin (4+) Salt

23. 4-nitrophenol, Zinc Salt

24. P-nitrophenol

2.3.2 Depositor-Supplied Synonyms

1. P-nitrophenol

2. 100-02-7

3. Phenol, 4-nitro-

4. Niphen

5. Paranitrophenol

6. 4-hydroxynitrobenzene

7. P-hydroxynitrobenzene

8. Phenol, P-nitro-

9. Para-nitrophenol

10. Mononitrophenol

11. Paranitrofenol

12. Paranitrofenolo

13. P-nitrofenol

14. 4-nitrofenol

15. Rcra Waste Number U170

16. Caswell No. 603

17. Nci-c55992

18. P-nitrofenol [czech]

19. Paranitrofenol [dutch]

20. 4-nitrofenol [dutch]

21. Paranitrofenolo [italian]

22. 1-hydroxy-4-nitrobenzene

23. Pnp

24. Paranitrophenol [french,german]

25. 4-nitro-phenol

26. Rcra Waste No. U170

27. Nsc 1317

28. Un1663

29. Epa Pesticide Chemical Code 056301

30. Chebi:16836

31. Ai3-04856

32. Mfcd00007331

33. Y92zl45l4r

34. Nsc-1317

35. P-nitrophenol [un1663] [poison]

36. 4-nitrophenol-15n

37. Dsstox_cid_1834

38. Dsstox_rid_76356

39. Dsstox_gsid_21834

40. Cas-100-02-7

41. Npo

42. Ccris 2316

43. Hsdb 1157

44. Einecs 202-811-7

45. Unii-y92zl45l4r

46. P-nitro Phenol

47. 4-nitryl Phenol

48. 4- Nitrophenol

49. 4-nitro Phenol

50. 4-nitrophenol-

51. 4-nitrophenol,

52. 3qvu

53. Rpn

54. Nitrophenol, P-

55. Phenol,4-nitro

56. Para Nitro Phenol

57. Wln: Wnr Dq

58. 4-hydroxy-1-nitrobenzene

59. Bmse000223

60. Epitope Id:161303

61. O2nc6h4oh

62. Ec 202-811-7

63. P-nitrophenol [mi]

64. Schembl1839

65. 4-nitrophenol [hsdb]

66. Chembl14130

67. P-nitrophenol [mart.]

68. Sgcut00249

69. Sr-1c2

70. 4-nitrophenol Solution, 10 Mm

71. 4-nitrophenol, Puriss., 99%

72. Dtxsid0021834

73. H-m-fluoro-d-phe-omehcl

74. Schembl13906248

75. Schembl14501907

76. Bdbm31678

77. Nsc1317

78. 4-nitrophenol, Reference Material

79. To_000002

80. Tox21_202444

81. Tox21_300117

82. 4-nitrophenol, Reagent Grade, 98%

83. S6196

84. Stl281865

85. Zinc34828682

86. Akos000118985

87. 4-nitrophenol, Spectrophotometric Grade

88. Acetaminophen Related Compound F

89. Db04417

90. Ncgc00247904-01

91. Ncgc00247904-02

92. Ncgc00254220-01

93. Ncgc00259993-01

94. 4-nitrophenol 100 Microg/ml In Methanol

95. 4-nitrophenol, Reagentplus(r), >=99%

96. As-13146

97. Bp-20405

98. 4-nitrophenol 10 Microg/ml In Acetonitrile

99. Ds-005476

100. Ft-0600022

101. Ft-0672814

102. N0161

103. N0162

104. N0220

105. Paracetamol Impurity F [ep Impurity]

106. 4-nitrophenol, Jis Special Grade, >=99.0%

107. C00870

108. N-3600

109. N-3610

110. 4-nitrophenol, Pestanal(r), Analytical Standard

111. A800004

112. Acetaminophen Related Compound F [usp-rs]

113. Ae-562/40217722

114. Q656269

115. Z57127483

116. F9995-1636

117. 4-nitrophenol, Certified Reference Material, Tracecert(r)

118. 4-nitrophenol Solution, Stock Solution, For Mass Spectrometry

119. 4-nitrophenol Solution, Working Solution, For Mass Spectrometry

120. 4-nitrophenol Solution, Certified Reference Material, 5000 Mug/ml In Methanol

121. Acetaminophen Related Compound F, United States Pharmacopeia (usp) Reference Standard

122. 4-nitrophenol (acetaminophen Related Compound F)(paracetamol Impurity F), Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 139.11 g/mol
Molecular Formula C6H5NO3
XLogP31.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass139.026943022 g/mol
Monoisotopic Mass139.026943022 g/mol
Topological Polar Surface Area66 Ų
Heavy Atom Count10
Formal Charge0
Complexity123
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

... Shown to permeate the skin and produce damage at threshold concentration of 0.9 percent (wt/vol).

USEPA; Ambient Water Quality Criteria Doc: Nitrophenol p.C-13 (1980) EPA 440/5-80-063


Excretion by mice, rats, rabbits, and guinea pigs is ... rapid. Most doses were completely eliminated from blood within 2 hr after admin. Rates at which 4-nitrophenol disappeared from blood decreased in following descending order: mouse, rabbit, guinea pig, rat, and monkey.

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 232


Elimination of 4-nitrophenol by monkey following oral and ip doses of 20 mg/kg ... complete within 5 hr.

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 232


The distribution of phenol, p-cyanophenol, p-nitrophenol, p-hydroxybenzoic-acid, and p-heptyloxyphenol after intraperitoneal (ip) and dermal exposure was examined. Young female Fischer-344-rats were exposed to radiolabeled phenol and p-substituted phenol congeners via ip administration at a dose of 2.5 ug or dermal administration at a dose of 5 ug. ... Following ip administration, urinary excretion rates ranged from 8% of the dose per hour for heptyloxyphenol to 20 to 25% of the dose per hour for phenol, cyanophenol, hydroxybenzoic-acid, and nitrophenol. After 120 hr, 87% to 97% and 1% to 4% of the phenol, cyanophenol, hydroxybenzoic-acid, and nitrophenol doses were excreted in the urine and feces, respectively. ... Carcasses contained 0.5% of the phenol, cyanophenol, and nitrophenol doses and 7% to 10% of the heptyloxyphenol and hydroxybenzoic-acid doses. After dermal administration, urinary excretion rates ranged from 0.4% of the dose per hour for hydroxybenzoic-acid to 10% of the dose per hour for phenol. After 120 hr, urinary and fecal excretion of the phenol, cyanophenol, and nitrophenol doses ranged from 65% to 77% and 1% to 3% of the dose, respectively. ... After 120 hr, dermal absorption ranged from less than 2.3% of the hydroxybenzoic-acid dose to 80% of the phenol dose. ... The ionization potential of the p-substituted functional group may affect the dermal absorption of phenol congeners.

PMID:9301654 Hughes MF, Hall LL; Food and Chemical Toxicology 35 (7): 697-704 (1997)


For more Absorption, Distribution and Excretion (Complete) data for 4-NITROPHENOL (7 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Rana temporaria and Xenopus laevis excrete 90-95% dose, and metabolize 50-65% dose of phenol, 4-nitrophenol, and 2-methylphenol within 24 hr, to about the same extent. Kinetic data for the excretion of phenols from both species fit a 2 compartment model. The elimination constants of Rana and Xenopus are not significantly different. Metabolism is mostly conjugation by glucuronidation and sulfation of the original phenols. Additionally, oxidations leading to dihydroxyphenols and benzoic acid from 2-methylphenol, and reduction of 4-nitrophenol, occur, followed by conjugation. There is an important difference between the metabolite patterns of Rana and Xenopus in that the latter is unable to glucuronidate phenols. As the amt of metabolites produced is similar in both species, Xenopus compensates for its inability to glucuronidate by increasing other metabolites.

PMID:3501639 Goerge G et al; Xenobiotica 17 (11): 1293-8 (1987)


In vivo studies with nitrophenols ... meta-& para-nitrophenol are reduced more readily than the ortho isomer ...

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 125


p-Nitrophenol yields p-aminophenol in rat, bass, carp, catfish, lamprey, perch, pike, salmon, sturgeon. Yields p-aminophenol & p-nitrophenyl sulfate, 4-nitrocatechol in rabbit. From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-18


Sulfate conjugation of 4-nitrophenol ... is decreased during pregnancy in rabbits ... and increases with age in rat, guinea pig, and humans ... relative rates of glucuronide versus sulfate conjugation of 4-nitrophenol may depend on levels of phenol present.

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 233


For more Metabolism/Metabolites (Complete) data for 4-NITROPHENOL (14 total), please visit the HSDB record page.


4-Nitrophenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid and 4-nitrocatechol (4NC).

4-Nitrophenol is a known human metabolite of 4-nitroanisole.

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


4.3 Biological Half-Life

The pharmacokinetics and placental transfer of a single oral dose of 100 mg/kg (10 uCi/kg, 16% of acute oral LD50) of uniformly phenyl-labeled (14)C-p-nitrophenol were investigated in pregnant Sprague-Dawley rats at 14-18 days of gestation. ... The half-lives of elimination of (14)C were 34.65 hr and 69.30 hr for maternal and fetal plasma, respectively. ...

PMID:11043494 Abu-Qare AW et al; Arch Toxicol 74 (7): 388-96 (2000)


4.4 Mechanism of Action

The effects of phenobarbital treatment on the biotransformation of parathion by intact mouse liver were investigated, and the subsequent effect of phenobarbital on the acute toxicity of parathion were examined. Daily intraperitoneal treatment of male Hla(SW)BR Swiss Webster mice with 80 mg/kg phenobarbital for 4 days induced hepatic cytochrome p450 content, as well as hepatic oxidative activation and oxidative detoxification of parathion, while antagonizing the acute toxicity of parathion without directly affecting tissue cholinesterase activities. Perfusion of mouse livers from control and phenobarbital treated mice resulted in the generation of paraoxon, p-nitrophenol, and p-nitrophenyl sulfate, and p-nitrophenyl glucuronide; phenobarbital increased production of p-nitrophenol, p-nitrophenyl glucuronide, and p-nitrophenyl sulfate from livers perfused with parathion but had no effect on the production of paraoxon.

PMID:3764930 Sultatos LG; Toxicol Appl Pharmacol 86 (1): 105-11 (1986)


Nitrophenols interfere with normal metabolism by uncoupling oxidative phosphorylation. For the mononitrophenols, the order of severity of effects is 4->3-> 2-nitrophenol.

USEPA; Nitrophenols: Hazard Profile (Draft) p.18 (1980)