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1. 2-nitrophenol, Ammonium Salt
2. 2-nitrophenol, Sodium Salt
3. Ortho-nitrophenol
1. O-nitrophenol
2. 88-75-5
3. 2-hydroxynitrobenzene
4. Phenol, 2-nitro-
5. O-hydroxynitrobenzene
6. Nitrophenol
7. Phenol, O-nitro-
8. O-nitrofenol
9. 2-nitro-phenol
10. Mfcd00011688
11. 25154-55-6
12. Bd148e95kd
13. Chebi:16260
14. Hydroxy(2-hydroxyphenyl)oxoammonium
15. Nsc-1552
16. Ortho-nitrophenol
17. 2-hydroxynitrobenzene[qr]
18. Dsstox_cid_1790
19. Dsstox_rid_76328
20. Dsstox_gsid_21790
21. O-nitrofenol [czech]
22. Cas-88-75-5
23. Ccris 2314
24. Hsdb 1133
25. O-nitrophenol (molten)
26. Nsc 1552
27. Einecs 201-857-5
28. Unii-bd148e95kd
29. Ai3-14893
30. O-nitro-phenol
31. 0-nitrophenol
32. 2-nitro Phenol
33. Hydroxynitrobenzene
34. Cg3
35. Nitrophenolate
36. 2-nitrophenyl Alcohol
37. O-nitrophenol [un1663] [poison]
38. 2-nitrophenol, 98%
39. Phenol, O-nitro
40. 2-nitrophenol-ul-14c
41. Wln: Wnr Bq
42. Ec 201-857-5
43. 2-nitrophenol, 99.0%
44. O-nitrophenol [mi]
45. Schembl26026
46. 2-nitrophenol [hsdb]
47. Bidd:er0656
48. Chembl14205
49. 1-oh
50. Sr-1c4
51. Dtxsid1021790
52. Schembl11524557
53. Schembl16254545
54. Nsc1552
55. Bcp25852
56. Str00905
57. Tox21_201442
58. Tox21_302758
59. Stk011520
60. Zinc34719541
61. Akos000118749
62. Am10677
63. Ccg-321789
64. Un 1663
65. Ncgc00090898-01
66. Ncgc00090898-02
67. Ncgc00256357-01
68. Ncgc00258993-01
69. 2-nitrophenol 100 Microg/ml In Methanol
70. 2-nitrophenol, Purum, >=98.0% (hplc)
71. Ft-0613201
72. Ft-0693760
73. N0153
74. N0219
75. C01988
76. N-3590
77. 2-nitrophenol, Pestanal(r), Analytical Standard
78. Ab-131/40228446
79. Q18907378
80. Z57201355
81. F3146-3482
82. 78813-12-4
83. Opo
| Molecular Weight | 139.11 g/mol |
|---|---|
| Molecular Formula | C6H5NO3 |
| XLogP3 | 1.8 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 139.026943022 g/mol |
| Monoisotopic Mass | 139.026943022 g/mol |
| Topological Polar Surface Area | 66 Ų |
| Heavy Atom Count | 10 |
| Formal Charge | 0 |
| Complexity | 131 |
| 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 |
Partition and permeance coefficients were determined for phenol, 2-nitrophenol and 4-nitrophenol with isolated cuticles from mature tomato (Lycopersicon esculentum) and green pepper (Capsicum annuum) fruits and from the adaxial surface of rubber (Ficus elastica) leaves. Plant cuticular membranes are composed of a lipophilic, insol polymer matrix membrane, and sol cuticular lipids. Partition coefficients of the phenols (pH 3.0) for the system insol polymer matrix/buffer ranged from 43.6 to 164.9 and could be predicted from n-octanol/buffer partition coefficients using the equation log partition insol polymer matrix/buffer= 0.363 + 0.952 log partition n-octanol/buffer where r= 0.986. In cuticular membranes the partition values were lower, especially for 4-nitrophenol, ranging from 32.4 to 110.8. The role of hydrogen bonding in partitioning of phenols into cuticles is discussed. Permeance coefficient for the cuticular membranes ranged from 10-10 (Ficus) to 10-8 m/s (Lycopersicon, Capsicum), with 2-nitrophenol permeating more rapidly than the other 2 phenols. Extention of the SCL increased the permeance coeff by factors of approximately 5 (Lycopersicon), 50 (Capsicum), and 1000 (Ficus), respectively. The transport-limiting layer in plant cuticles acts as a diffusion and solubility barrier.
PMID:4085383 Shafer WE, Schoenherr J; Ecotoxicol Environ Saf 10 (2): 239-52 (1985)
The permeation of nitrophenols through epidermal cells from newborn rat skin cultured on type IV collagen-coated Millipore filters was studied under various conditions. The order of permeation through the cultured skin cells was found to be p-> m- > o-nitrophenol at both 10 and approx 37 C. This order was the same as that of their affinities to isolated skin cells. The permeation of nitrophenols was not inhibited by the inhibitors of energy transduction 2-deoxyglucose and NaN3. These results suggest that the permeation of nitrophenols across a cultured cell layer occurs by simple diffusion. The order of permeation of nitrophenols across newborn abdominal epidermis was exactly the opposite of that of their permeation across a cultured cell layer.
PMID:2076563 Ohkura K et al; Chem Pharm Bull (TOKYO) 38 (10):2788-91 (1990)
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
Yields o-aminophenol, 3-nitrocatechol, o-nitrophenyl-beta-d-glucuronide, o-nitrophenyl sulfate, & nitroquinol in rabbits.
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-17
o-Nitrophenol causes methemoglobinemia, but is metabolically reduced less readily than the meta or para isomers to the corresponding amino derivatives.
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 974
The metabolic capacity of rat brain slices for m-dinitrobenzene was assessed /in/ male Fischer-344-rats ... Slices from both brain stem or forebrain (400 um thick) or liver tissue (control) were incubated with a 0.2 mM m-dinitrobenzene containing medium for 2 hours. The m-dinitrobenzene was metabolized in the two brain tissues and the liver tissue. No metabolism occurred in heat inactivated tissues. Metabolic disposal of m-dinitrobenzene was 1.05+/-0.11 umol/g wet weight per hour in the liver, 0.49+/-0.05 umol/g wet weight per hour in brain stem, and 0.44+/0.05 umol/g wet weight per hour in the forebrain. The main metabolite produced by both brain and liver slices was m-nitroaniline, which represented 57 to 66% of the disposal of m-dinitrobenzene. In the liver, 2-aminophenol, 4-aminophenol, 4-nitrophenol, or 2-nitrophenol was produced, but they were not detected in the brain slices. Nitrosonitrobenzene was detected in slices from both parts of the brain, but not in the liver slices. In the presence of m-dinitrobenzene the glucose consumption of brain slices was significantly increased; 26% in the brain stem and 17.9% in the cerebral cortex, which may have been a precytotoxic effect. ... The brain has considerable nitroreductive capacity towards m-dinitrobenzene and in-situ reduction of m-dinitrobenzene may be responsible for its neurotoxicity.
PMID:9291486 Hu H-L et al; Neurotoxicology 18 (2): 363-70 (1997)
... An experimental study of the metabolism of o-nitrophenol, m-nitrophenol, and p-nitrophenol in the rabbit /is described/. All three phenols are excreted in conjugated forms, there being only small amounts (less than 1 percent) of the unchanged free phenols excreted. The main metabolites are the nitrophenylglucuronides which account for about 70 percent of the dose. The corresponding ethereal sulfates are also excreted. The nitro group of the nitrophenols undergoes reduction in-vivo only to a minor extent, and some 80 percent of it is excreted unchanged. The extent of reduction is about 6 percent for o-nitrophenol, 10 percent for m-nitrophenol and 14 percent for p-nitrophenol. The nitrophenols also undergo oxidation to a very small extent (less than 1 percent); o-nitrophenol yields traces of nitroquinol, m-nitrophenol, nitroquinol and 4-nitrocatechol and p-nitrophenol, 4-nitrocatechol. The dihydric phenols produced are similar to those formed during the Elbs persulfate oxidation of the mononitrophenols. The significance of the similarity in relation to free radicals is discussed. The paper chromatography of the monohydric and dihydric nitrophenols has been studied. The beta-glucuronides of the nitrophenols have been isolated and characterized as amides and triacetyl methyl esters. The abnormal positive rotations of triacetyl-beta-o-nitrophenyl-D-glucuronide and its methyl ester have been investigated, and it has been shown that in the case of the ester this rotation becomes negative on raising the temperature, a behavior reminiscent of tetra-acetyl-beta-o-nitrophenylglucoside. The metabolic results have been discussed in relation to the toxicity of p-nitrophenol and the nontoxicity of o-nitrophenol
Robinson D et al; Biochemical Journal 50: 221-7 (1951)
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)
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