1. 2-hydroxybiphenyl
2. 2-hydroxydiphenyl
3. 2-phenylphenol Sodium
4. Dowicide
5. Lyorthol
6. O-phenylphenate
7. O-phenylphenol
8. Ortho-phenylphenate
9. Orthophenylphenol
10. Sodium O-phenylphenoate
11. Sodium Ortho-phenylphenate
12. Sodium Ortho-phenylphenol
1. 2-hydroxybiphenyl
2. 90-43-7
3. O-phenylphenol
4. Biphenyl-2-ol
5. 2-biphenylol
6. O-hydroxybiphenyl
7. 2-hydroxydiphenyl
8. O-hydroxydiphenyl
9. O-phenyl Phenol
10. Phenylphenol
11. Biphenylol
12. [1,1'-biphenyl]-2-ol
13. Orthophenylphenol
14. Orthoxenol
15. O-diphenylol
16. Dowicide 1
17. Torsite
18. O-xenol
19. O-biphenylol
20. Preventol O Extra
21. Orthohydroxydiphenyl
22. Nectryl
23. (1,1'-biphenyl)-2-ol
24. Tumescal Ope
25. Ortho-phenylphenol
26. Remol Trf
27. Phenol, O-phenyl-
28. Tetrosin Oe
29. 1-hydroxy-2-phenylbenzene
30. 2-fenylfenol
31. 2-hydroxybifenyl
32. O-xonal
33. 2-phenyl Phenol
34. Biphenyl, 2-hydroxy-
35. Invalon Op
36. Anthrapole 73
37. 2-hydroxy Biphenyl
38. Usaf Ek-2219
39. 1,1'-biphenyl-2-ol
40. Dowicide
41. Kiwi Lustr 277
42. Hydroxdiphenyl
43. (1,1-biphenyl)-2-ol
44. O-phenylphenol, Cosmetic Grade
45. Dowicide 1 Antimicrobial
46. Orthophenyl Phenol
47. Orthohydroxydipbenyl
48. Nci-c50351
49. Hydroxy-2-phenylbenzene
50. 2-phenyl-phenol
51. Nipacide Opp
52. Nsc 1548
53. 2-hydroxy-1,1'-biphenyl
54. [1,1'-biphenyl]ol
55. Chembl108829
56. Chebi:17043
57. D343z75ht8
58. Nsc-1548
59. Dowicide A
60. E231
61. O-phenylphenate
62. Dsstox_cid_1151
63. Phenyl-2 Phenol
64. Ortho-phenylphenate
65. Dsstox_rid_75978
66. Dsstox_gsid_21151
67. Biphenyl-2-o1
68. Hydroxybiphenyl
69. 2-fenylfenol [czech]
70. Caswell No. 623aa
71. 2-hydroxybifenyl [czech]
72. Cas-90-43-7
73. Opp [pesticide]
74. 2-phenylphenol [bsi:iso]
75. Ccris 1388
76. Phenyl-2 Phenol [iso-french]
77. Hsdb 1753
78. Einecs 201-993-5
79. Epa Pesticide Chemical Code 064103
80. Brn 0606907
81. Stellisept
82. Manusept
83. Rotoline
84. Unii-d343z75ht8
85. O-phenyl-phenol
86. Ai3-00062
87. Tetrosin Oe-n
88. Amocid (tn)
89. Mfcd00002208
90. Preventol 3041
91. Ortofenilfenol
92. Phenylphenol (ortho-)
93. 2-phenylphenol, 99%
94. Opp?
95. Phenylphenol, O-
96. Wln: Qr Br
97. Ortho Phenyl Phenol
98. Ec 201-993-5
99. O-phenylphenol [mi]
100. 2-phenylphenol, Bsi, Iso
101. Schembl29811
102. 4-06-00-04579 (beilstein Handbook Reference)
103. Mls002415765
104. 2-phenylphenol [iso]
105. Bidd:er0664
106. O-phenylphenol [inci]
107. [1,1''-biphenyl]-2-ol
108. 2-phenylphenol [fhfi]
109. 2-phenylphenol [hsdb]
110. Dtxsid2021151
111. Fema 3959
112. 2-phenylphenol, >=99%, Fg
113. Nsc1548
114. Ortho-phenylphenol [iarc]
115. Orthophenylphenol [mart.]
116. Orthophenylphenol [who-dd]
117. Zinc968134
118. Amy40390
119. Str07240
120. Tox21_202415
121. Tox21_300674
122. Bdbm50308551
123. Orthophenyl Phenol (e 231)
124. Stk177354
125. Akos000118750
126. Ps-8698
127. Ncgc00091595-01
128. Ncgc00091595-02
129. Ncgc00091595-03
130. Ncgc00091595-04
131. Ncgc00091595-05
132. Ncgc00091595-06
133. Ncgc00254582-01
134. Ncgc00259964-01
135. 2-phenylphenol 100 Microg/ml In Acetone
136. Ac-10362
137. Smr000778031
138. 2-phenylphenol 100 Microg/ml In Methanol
139. 2-phenylphenol 10 Microg/ml In Cyclohexane
140. 2-phenylphenol 1000 Microg/ml In Acetone
141. 2-phenylphenol 10 Microg/ml In Acetonitrile
142. Bb 0223993
143. Ft-0654846
144. P0200
145. 1,1'-biphenyl-2-ol; 2-phenylphenol
146. C02499
147. D08367
148. E79453
149. 2-phenylphenol, Pestanal(r), Analytical Standard
150. Q209467
151. Sr-01000944520
152. Sr-01000944520-1
153. W-100332
154. F0001-2206
155. Z1262254253
156. Ch9
| Molecular Weight | 170.21 g/mol |
|---|---|
| Molecular Formula | C12H10O |
| XLogP3 | 3.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Exact Mass | 170.073164938 g/mol |
| Monoisotopic Mass | 170.073164938 g/mol |
| Topological Polar Surface Area | 20.2 Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 149 |
| 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 |
Based on animal studies, 5 oz would be lethal to a 150 lb healthy adult.
Sittig, M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 2002. 4th ed.Vol 1 A-H Norwich, NY: Noyes Publications, 2002., p. 1843
Disinfectants
Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)
Carcinogens
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
Anti-Infective Agents
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)
Fungicides, Industrial
Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)
D08AE06
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
D - Dermatologicals
D08 - Antiseptics and disinfectants
D08A - Antiseptics and disinfectants
D08AE - Phenol and derivatives
D08AE06 - Biphenylol
The pharmacokinetics and metabolism of uniformly labeled 14C/13C-ortho-phenylphenol (OPP) were followed in six human male volunteers given a single 8 hr dermal dose of 6 ug OPP/kg body weight formulated as a 0.4% (w/v) solution in isopropyl alcohol. The application site was covered with a non-occlusive dome allowing free movement of air, but preventing the loss of radioactivity due to physical contact. At 8 hr post-exposure the non-occlusive dome was removed, the dose site was wiped with isopropyl alcohol containing swabs and the skin surface repeatedly stripped with tape. Blood specimens, urine, and feces were collected from each volunteer over a 5 day post-exposure period and were analyzed for radioactivity and metabolites (urine only). Following dermal application, peak plasma levels of radioactivity were obtained within 4 hr post-exposure and rapidly declined with virtually all of the absorbed dose rapidly excreted into the urine within 24 hr post-exposure. A one-compartment pharmacokinetic model was used to describe the time-course of OPP absorption and clearance in male human volunteers. Approximately 43% of the dermally applied dose was absorbed through the skin with an average absorption half-life of 10 hr. Once absorbed the renal clearance of OPP was rapid with an average half-life of 0.8 hr. The rate limiting step for renal clearance was the relatively slower rate of dermal absorption; therefore the pharmacokinetics of OPP in humans was described by a 'flip-flop' single compartment model. Overall, the pharmacokinetics were similar between individuals, and the model parameters were in excellent agreement with the experimental data. Approximately 73% of the total urinary radioactivity was accounted for as free OPP, OPP-sulfate and OPP-glucuronide conjugates. The sulfate conjugate was the major metabolite (approximately 69%). Therefore, total urinary OPP equivalents (acid-labile conjugates+free OPP) can be used to estimate the systemically absorbed dose of OPP. The rapid excretion of OPP and metabolites into the urine following dermal exposure indicates that OPP is unlikely to accumulate in humans upon repeated exposure ...
PMID:9756132 Timchalk C et al; Hum Exp Toxicol 17 (8): 411-7 (1998).
Male F344 rats were treated with 0, 15, 50, 125, 250, 500, 1000 mg/kg of ortho-phenylphenol (OPP) and its radiocarbon analogue via oral gavage. The dosed rats were euthanized after 24 hr, and the proteins were extracted from the liver, kidney, and bladder. The amount of radioactivity associated with the extracted protein was quantified ... Protein binding in liver and kidney exhibited a linear or modest curvilinear relationship over the dose range studied. In the urinary bladder, however, a pronounced nonlinear relationship between protein adduct levels and administered dose was observed. The measured protein adduct levels were in agreement with the predicted concentrations of phenylbenzoquinone based on a proposed mechanism involving free phenylhydroquinone autoxidation in the urine. Unlike protein binding, DNA adducts measured from the same bladder samples did not show a significant difference from the control group ...
PMID:10448121 Kwok ES et al; Toxicol Appl Pharmacol 159 (1): 18-24 (1999).
The validity of in vitro and in vivo methods for the prediction of percutaneous penetration in humans was assessed using the fungicide ortho-phenylphenol (OPP) (log Po/w 3.28, MW 170.8, solubility in water 0.7 g/L). In vivo studies were performed in rats and human volunteers, applying the test compound to the dorsal skin and the volar aspect of the forearm, respectively. In vitro studies were performed using static diffusion cells with viable full-thickness skin membranes (rat and human), nonviable epidermal membranes (rat and human), and a perfused pig ear model. For the purpose of conducting in vitro/in vivo comparisons, standardized experimental conditions were used with respect to dose (120 ug OPP/sq cm), vehicle (60% aqueous ethanol), and exposure duration (4 hr). In human volunteers, the potentially absorbed dose (amount applied minus dislodged) was 105 ug/sq cm, while approximately 27% of the applied dose was excreted with urine within 48 hr. In rats these values were 67 ug/sq cm and 40%, respectively. In vitro methods accurately predicted human in vivo percutaneous absorption of OPP on the basis of the potential absorbed dose. With respect to the other parameters studied (amount systemically available, maximal flux), considerable differences were observed between the various in vitro models ...
PMID:12052004 Cnubben NH et al; Regul Toxicol Pharmacol 35 (2 Pt 1): 198-208 (2002).
Excreted in mammals principally as the parent compound & as the glucuronide & sulfate conjugates.
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 795
For more Absorption, Distribution and Excretion (Complete) data for o-Phenylphenol (7 total), please visit the HSDB record page.
Ortho-phenylphenol (OPP) was well absorbed in the male B6C3F1 mouse, with 84 and 98% of the administered radioactivity recovered in the 0-48-hr urine of animals administered a single oral dose of 15 or 800 mg/kg respectively. High absorption and rapid elimination were also seen in the female and male F344 rat with 86 and 89% respectively of a single oral dose (27-28 mg/kg) found in the urine in 24 hr. OPP was also rapidly eliminated from human volunteers following dermal exposure for 8 hr (0.006 mg/kg), with 99% of the absorbed dose in the urine in 48 hr.. Sulfation of OPP was found to be the major metabolic pathway at low doses in all three species, accounting for 57, 82 and 69% of the urinary radioactivity in the male mouse (15 mg/kg, po), male rat (28 mg/kg, po) and male human volunteers (0.006 mg/kg, dermal). OPP-glucuronide was also present in all species, representing 29, 7 and 4% of the total urinary metabolites in the low dose groups of mouse, rat and human volunteers respectively. Conjugates of 2-phenylhydroquinone (PHQ) in these single-dose studies accounted for 12, 5 and 15% of the dose in mouse, rat and human, respectively. Little or no free OPP was found in any species. No free PHQ or PBQ was found in the mouse, rat or human (LOD = 0.1-0.6%). A novel metabolite, the sulfate conjugate of 2,4'-dihydroxybiphenyl, was identified in rat and man, comprising 3 and 13% of the low dose respectively. Dose-dependent shifts in metabolism were seen in the mouse for conjugation of parent OPP, indicating saturation of the sulfation pathway. Dose-dependent increases in total PHQ were also observed in mouse. This study was initiated to elucidate a mechanistic basis for the difference in carcinogenic potential for OPP between rat and mouse. However, the minor differences seen in the metabolism of OPP in these two species do not appear to account for the differences in urinary bladder toxicity and tumor response between mouse and rat.
PMID:9667081 Bartels MJ et al; Xenobiotica 28 (6): 579-94 (1998).
Dogs & cats also excrete urinary sulfonic acid & glucuronic acid metabolites of o-phenylphenol, although the parent compound predominates.
DHHS/NTP; Toxicology and Carcinogenesis Studies of ortho-Phenylphenol alone and with 7,12-Dimethylbenz(a)anthracene in Swiss CD-1 Mice (Dermal Studies) p.14 (1986) Technical Rpt Series No. 301 NIH PUb No. 86-2557
(14)C-ortho-Phenylphenol was applied onto the skin of the forearm of 6 volunteers for 8 hr at a dose of 0.4 mg/person (0.006 mg/kg bw). ... Sulfation was the major metabolic pathway, accounting for 69% of the metabolites, while conjugates of 2-phenylhydroquinone accounted for 15%. Little or no free ortho-phenylphenol was present in the urine, & no free 2-phenylhydroquinone or 2-phenyl-1,4-benzoquinone was detected.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 460 (1999)
ortho-Phenylphenol was converted to phenylhydroquinone by microsomal cytochrome P450 in vitro. Phenylhydroquinone was oxidized to phenylquinone by cumene hydroperoxide-supported microsomal cytochrome P450, & phenylquinone was reduced back to phenylhydroquinone by cytochrome P450 reductase, providing direct evidence of redox cycling of ortho-phenylphenol.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 461 (1999)
For more Metabolism/Metabolites (Complete) data for o-Phenylphenol (12 total), please visit the HSDB record page.
2-phenylphenol has known human metabolites that include 2,5-dihydroxybiphenyl.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
... A genome-wide transcriptome analysis of the cellular responses of Pseudomonas aeruginosa (P. aeruginosa) exposed to 0.82 mM OPP for 20 and 60 minutes /was performed/ ... Ortho-phenylphenol (OPP) upregulated the transcription of genes encoding ribosomal, virulence and membrane transport proteins after both treatment times. After 20 minutes of exposure to 0.82 mM OPP, genes involved in the exhibition of swarming motility and anaerobic respiration were upregulated. After 60 minutes of OPP treatment, the transcription of genes involved in amino acid and lipopolysaccharide biosynthesis were upregulated. Further, the transcription of the ribosome modulation factor (rmf) and an alternative sigma factor (rpoS) of RNA polymerase were downregulated after both treatment times. Results from this study indicate that after 20 minutes of exposure to OPP, genes that have been linked to the exhibition of anaerobic respiration and swarming motility were upregulated. This study also suggests that the downregulation of the rmf and rpoS genes may be indicative of the mechanism by which OPP causes decreases in cell viability in P. aeruginosa. Consequently, a protective response involving the upregulation of translation leading to the increased synthesis of membrane related proteins and virulence proteins is possibly induced after both treatment times. In addition, cell wall modification may occur due to the increased synthesis of lipopolysaccharide after 60 minutes exposure to OPP. This gene expression profile can now be utilized for a better understanding of the target cellular pathways of OPP in P. aeruginosa and how this organism develops resistance to OPP.
PMID:18847467 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2577666 Nde CW et al; BMC Genomics 9: 473 (2008).
A genome-wide transcriptome analysis of the cellular responses of Staphylococcus aureus (S. aureus) when exposed to 0.82 mM of ortho-phenylphenol (OPP) for 20 and 60 min /was performed/ ... OPP downregulated the biosynthesis of many amino acids, which are required for protein synthesis. In particular, the genes encoding the enzymes of the diaminopimelate (DAP) pathway which results in lysine biosynthesis were significantly downregualted. Intriguingly, ... the transcription of genes encoding ribosomal proteins was upregulated by OPP and at the same time, the genes encoding iron acquisition and transport were downregulated. The genes encoding virulence factors were upregulated and genes encoding phospholipids were downregulated upon 20 min exposure to OPP ... Using microarray analysis ... revealed novel information regarding the mode of action of OPP on Staphylococcus: OPP inhibits anabolism of many amino acids and highly downregulates the genes that encode the enzymes involved in the DAP pathway. Lysine and DAP are essential for building up the peptidoglycan cell wall. It was concluded that the mode of action of OPP is similar to the mechanism of action of some antibiotics. The discovery of this phenomenon provides useful information that will benefit further antimicrobial research on S. aureus.
PMID:18793396 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2562396 Jang HJ et al; BMC Genomics 9: 411 (2008).
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