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Preventol BP
Also known as: 120-32-1, Clorophene, Clorofene, Chlorophene, O-benzyl-p-chlorophenol, 4-chloro-2-benzylphenol
Molecular Formula
C13H11ClO
Molecular Weight
218.68  g/mol
InChI Key
NCKMMSIFQUPKCK-UHFFFAOYSA-N
FDA UNII
7560BB0BO3

chlorophene is a natural product found in Shewanella halifaxensis with data available.
1 2D Structure

Preventol BP

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-benzyl-4-chlorophenol
2.1.2 InChI
InChI=1S/C13H11ClO/c14-12-6-7-13(15)11(9-12)8-10-4-2-1-3-5-10/h1-7,9,15H,8H2
2.1.3 InChI Key
NCKMMSIFQUPKCK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CC2=C(C=CC(=C2)Cl)O
2.2 Other Identifiers
2.2.1 UNII
7560BB0BO3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chlorofene

2. Chlorophene

3. Clorofene

4. Clorophene

5. Clorophene Potassium Salt

6. Clorophene Sodium Salt

7. O-benzyl-p-chlorophenol

8. Ortho-benzyl-para-chlorophenol

9. Orthosan

2.3.2 Depositor-Supplied Synonyms

1. 120-32-1

2. Clorophene

3. Clorofene

4. Chlorophene

5. O-benzyl-p-chlorophenol

6. 4-chloro-2-benzylphenol

7. Santophen 1

8. 5-chloro-2-hydroxydiphenylmethane

9. Phenol, 4-chloro-2-(phenylmethyl)-

10. Neosabenyl

11. Septiphene

12. Bio-clave

13. Santophen I Germicide

14. P-chloro-o-benzylphenol

15. Santophen I

16. Santophen 1 Flake

17. Clorophene [usan]

18. Santophen 1 Solution

19. Ketolin H

20. Orthobenzylparachlorophenol

21. Orthobenzyl-p-chlorophenol

22. 2-benzyl-4-chloro-phenol

23. 4-chloro-2-(phenylmethyl)phenol

24. 4-chloro-.alpha.-phenyl-o-cresol

25. Nci-c61201

26. Clorofene [inn]

27. Nsc-59989

28. Phenol, 4-chloro-2-benzyl-

29. Nsc 59989;santophen

30. O-cresol, 4-chloro-.alpha.-phenyl-

31. 7560bb0bo3

32. Nsc59989

33. Clorophene (usan)

34. Ncgc00091532-02

35. Ncgc00091532-04

36. Dsstox_cid_154

37. Ketolin-h

38. Dsstox_rid_75406

39. Dsstox_gsid_20154

40. O-benzylchlorophenol

41. Ortho-benzyl-para-chlorophenol

42. Caswell No. 083

43. Clorofenum

44. Sentiphene

45. Clorofeno

46. Clorofenum [inn-latin]

47. Clorofeno [inn-spanish]

48. Cas-120-32-1

49. Ccris 6205

50. 4-chloro-alpha-phenyl-o-cresol

51. Hsdb 5179

52. O-cresol, 4-chloro-alpha-phenyl-

53. 4-chloro-alpha-phenyl-ortho-cresol

54. Einecs 204-385-8

55. Nsc 59989

56. 4-chloro-2-benzyl Phenol

57. Epa Pesticide Chemical Code 062201

58. Brn 1959194

59. Clorophen

60. Unii-7560bb0bo3

61. Ai3-08523

62. Preventol Bp

63. Nipacide Bcp

64. Benzyl Chloro Phenol

65. Mfcd00020140

66. Santophen 1 (tn)

67. Clorophene [mi]

68. Clorophene [hsdb]

69. Chlorophene [inci]

70. Wln: Qr Dg B1r

71. Clorofene [who-dd]

72. Clorophene [mart.]

73. Schembl78119

74. 4-06-00-04636 (beilstein Handbook Reference)

75. Mls002454423

76. Chembl1328919

77. Dtxsid5020154

78. 2-benzyl-4-chlorophenol, 95%

79. Nckmmsifqupkck-uhfffaoysa-

80. 2-hydroxy-5-chlorodiphenylmethane

81. Hms3041d07

82. Zinc136177

83. 4-chloranyl-2-(phenylmethyl)phenol

84. Tox21_111146

85. Tox21_202985

86. Tox21_400046

87. Akos001434264

88. Tox21_111146_1

89. Ncgc00091532-01

90. Ncgc00091532-03

91. Ncgc00091532-05

92. Ncgc00091532-06

93. Ncgc00260530-01

94. Ac-10752

95. Bs-20052

96. Smr000777843

97. Db-041547

98. B0812

99. Cs-0066335

100. Ft-0611303

101. D03564

102. D88696

103. A804486

104. W-108479

105. Q22829551

106. Z271137930

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 218.68 g/mol
Molecular Formula C13H11ClO
XLogP34
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass218.0498427 g/mol
Monoisotopic Mass218.0498427 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count15
Formal Charge0
Complexity189
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC:Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint for 70 kg person (150 lbs).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-193


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


5.2 Absorption, Distribution and Excretion

Chlorophene was applied to the intrascapular region of male Fischer-344 rats at a total dose of 10 mg/kg in dermal studies. Three days after exposure to Chlorophene, 59% of the dose was excreted in the urine and feces. Chlorophene was distributed, as a percent of the total dose, to large intestinal contents (1.58%), small intestinal contents (0.55%), the skin (0.23%), and the skin site (32.33%). Chlorophene was incompletely absorbed through the skin.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


Rats /were/ dosed with 10 mg/kg chlorophene /iv/ and three rats each were sacrificed at various time points from 15 min to 72 hr. After iv exposure, 88% of the dose was excreted by 72 hr. After 15 min of treatment, about 30% of the chlorophene dose administered was present in the intestinal contents. Radioactivity was greatest in the kidneys and liver at this same time point and remained the greatest after 72 hr. The relative percent of unmetabolized chlorophene increased with time in the blood and liver over 72 hr. However, in the kidneys, it decreased with time. The skin had significant chlorophene radioactivity, 7.92% of the total dose administered after 15 min, but little remained after 24 hr.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


/Investigators/ dosed rats orally with 10, 100, or 1000 mg/kg chlorophene. The relative concentration of chlorophene excreted in the urine and feces was dose dependent. At the low and high dose, feces were the major route of excretion, whereas at the intermediate dose, urinary excretion predominated. However, more than 92% of the radioactive chlorophene was excreted within 3 days by rats in all dose groups. Rats injected with 5, 10, or 25 mg/kg chlorophene in the femoral vein had a dose-related decrease in biliary excretion.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


Male Sprague-Dawley rats /were administered/ (3/dose level) a single dose of 69 or 206 mg/kg [14C]-chlorophene. The kidneys and liver had the highest radiochemical concentrations of chlorophene and its metabolites. The combined concentrations of these two organs accounted for 0.16% and 0.13% of the 69 and 206 mg/kg doses, respectively. Approximately 0.23% and 0.18% of the dose was associated with the body fat at the low and high dose, respectively.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


For more Absorption, Distribution and Excretion (Complete) data for O-BENZYL-P-CHLOROPHENOL (8 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

After iv treatment with 10 mg/kg chlorophene, the major metabolite formed was the glucuronic acid conjugate of the parent compound. The metabolite gradually decreased over a 6-hr period after treatment. The oxidative metabolite increased from 0.5% to 6% of the glucuronide acid conjugates in bile over 6 hr.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


In vitro metabolism studies found that about 95% of chlorophene was metabolized by liver supernatant in the presence of NADPH, uridine diphosphoglucuronic acid (UDPGA), and glutathione (GSH). Metabolism varied from 14% to 51% as the parent compound was exposed to various combinations of the cofactors, microsomes, and organ extracts.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


/Investigators/ isolated the metabolites of [14C]-chlorophene in urine and feces over a 5-day period. A significant percentage of the radioactive dose was present in the urine and feces from 12 to 24 hr. The majority of metabolites were present as either glucuronide or sulfate ester conjugates in the urine during this time period. Two additional metabolites were also identified, one in which the benzyl aromatic ring had a hydroxyl and a methoxyl substituent (22.9% and 17.6% of the low and high dose, respectively) and the second in which the benzyl aromatic ring had a hydroxyl substituent (12.7% and 29.4% of the low and high dose, respectively). These same metabolites were identified in feces but at a lower concentration. Chlorophene was also identified in the urine as 5.3% and 14.1% of the low and high dose, respectively. However, a larger percentage of [14C]-chlorophene was identified in feces, 21.4% and 22.4% of the low and high dose, respectively.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


Undiluted chlorophene (2 mL/kg) applied to the skin of rabbits lowered the percent of inorganic sulfates. However, the amount of glucuronate excreted was not affected. Application of 0.2 g/kg chlorophene in cottonseed oil and castor oil soap caused a slight increase in the output of glucuronates, but did not affect excretion of sulfates. The dilutions (1:100 and 1:300) produced no change in the excretion of glucuronates or sulfates.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


For more Metabolism/Metabolites (Complete) data for O-BENZYL-P-CHLOROPHENOL (7 total), please visit the HSDB record page.


5.4 Biological Half-Life

Male rats given an oral dose of 69 mg/kg or 206 mg/kg (14)C labeled o-benzyl-p-chlorophenol. ... Excretion of o-benzyl-p-chlorophenol was biphasic with an initial rapid alpha phase with a half life of 8 to 9 hr and slightly slower beta phase estimated to have a half life of 52 to 140 hr. ...

PMID:3712489 Ridley WP et al; J Toxicol Environ Health 18 (2): 267-83 (1986)


After iv injections of 10 mg/kg, ... feces, or feces and urine combined /were collected/, /investigators/ describe the elimination phase as a single-component model with a half-life of 14 hr.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)


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