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Chemistry

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Also known as: 118-55-8, Phenyl 2-hydroxybenzoate, Salol, Phenol salicylate, Salphenyl, Musol
Molecular Formula
C13H10O3
Molecular Weight
214.22  g/mol
InChI Key
ZQBAKBUEJOMQEX-UHFFFAOYSA-N
FDA UNII
28A37T47QO

Phenyl Salicylate
Phenyl salicylate is a 2-hydroxybenzoic acid phenyl ester. It is utilized in some manufacturing processes of polymers, lacquers, adhesives, waxes, as well as polishes. It is an active ingredient in some pharmaceutical products as a mild analgesic for pain relief by releasing salicylate (found in [DB00945] ). Phenyl salicylate may also be found in some antiseptic agents. It is synthesized by heating salicylic acid with phenol, [MSDS]. Phenyl salicylate is used as a food additive in the USA. This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
1 2D Structure

Phenyl Salicylate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
phenyl 2-hydroxybenzoate
2.1.2 InChI
InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
2.1.3 InChI Key
ZQBAKBUEJOMQEX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2O
2.2 Other Identifiers
2.2.1 UNII
28A37T47QO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Salol

2.3.2 Depositor-Supplied Synonyms

1. 118-55-8

2. Phenyl 2-hydroxybenzoate

3. Salol

4. Phenol Salicylate

5. Salphenyl

6. Musol

7. Benzoic Acid, 2-hydroxy-, Phenyl Ester

8. 2-phenoxycarbonylphenol

9. Salicylic Acid, Phenyl Ester

10. 2-hydroxybenzoic Acid Phenyl Ester

11. Phenyl-2-hydroxybenzoate

12. 2-hydroxy-benzoic Acid Phenyl Ester

13. Fenylester Kyseliny Salicylove

14. Nsc 33406

15. Salicylic Acid Phenyl Ester

16. Nsc-33406

17. Seesorb 201

18. Seesorb K 201

19. 2-hydroxybenzoic Acid, Phenyl Ester

20. Fema No. 3960

21. Chebi:34918

22. 28a37t47qo

23. Nsc33406

24. Phenyl Salicylate Melting Point Standard

25. Ncgc00090887-02

26. Dsstox_cid_1957

27. Dsstox_rid_76426

28. Dsstox_gsid_21957

29. Cas-118-55-8

30. Ccris 4859

31. Phenyl Salicylate [nf]

32. Einecs 204-259-2

33. Mfcd00002213

34. Fenylester Kyseliny Salicylove [czech]

35. Brn 0393969

36. Phenylsalicylate

37. Unii-28a37t47qo

38. Ai3-00195

39. Phenyl-salicylate

40. Salicylic Acid Phenyl

41. Salicylic Phenyl Ester

42. Salol [vandf]

43. Salol [hpus]

44. Wln: Qr Bvor

45. Salol [mart.]

46. Oprea1_020651

47. Oprea1_771794

48. Schembl24326

49. Bidd:er0018

50. Phenyl Salicylate [mi]

51. Chembl1339216

52. Dtxsid6021957

53. Phenyl Salicylate [fhfi]

54. Phenyl Salicylate [inci]

55. Zinc38545

56. Phenyl Salicylate [vandf]

57. Phenyl Salicylate, >=99%, Fg

58. Phenyl Salicylate [usp-rs]

59. Phenyl Salicylate [who-dd]

60. Str06361

61. Tox21_113459

62. Tox21_201811

63. Tox21_302949

64. Phenyl Salicylate, Crystal, Purified

65. Stk052177

66. Akos000121203

67. Nsc33406nsc 33406

68. Tox21_113459_1

69. Db11071

70. Ps-7960

71. Ncgc00090887-01

72. Ncgc00090887-03

73. Ncgc00090887-04

74. Ncgc00090887-05

75. Ncgc00091499-03

76. Ncgc00256612-01

77. Ncgc00259360-01

78. Ac-11469

79. Phenyl Salicylate, Reagentplus(r), 99%

80. Db-024372

81. Ft-0689174

82. S0017

83. Ab00443435-03

84. A804056

85. Phenyl Salicylate, Vetec(tm) Reagent Grade, 98%

86. Q421259

87. Sr-01000883691

88. J-200110

89. Sr-01000883691-1

90. Z57206005

91. Mettler-toledo Calibration Substance Me 30034252, Phenyl Salicylate

92. Mettler-toledo Calibration Substance Me 30034252, Phenyl Salicylate, Traceable To Primary Standards

93. Phenyl Salicylate Melting Point Standard, Approximately 41 Degrees, United States Pharmacopeia (usp) Reference Standard

94. Phenyl Salicylate Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 214.22 g/mol
Molecular Formula C13H10O3
XLogP33.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass214.062994177 g/mol
Monoisotopic Mass214.062994177 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count16
Formal Charge0
Complexity233
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 Drug Indication

Pain and fever.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Phenyl salicylate has several medical uses. It can be used as an analgesic to relieve pain, as an antiseptic with antibacterial effect as well as a kind of antipyretic for the treatment of fever. It is also used for the treatment of inflammation in the lower urinary tract. It is no longer commonly applied to human medical practice but is still used in veterinary medicine [MSDS]. When it is combined with methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate, it is used to relieve the discomfort, pain, frequent urge to urinate, and cramps/spasms of the urinary tract caused by a urinary tract infection or a diagnostic procedure.


5.2 ATC Code

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BX - Other urologicals

G04BX12 - Phenyl salicylate


5.3 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed. Refer to [DB00945] for detailed salicylate absorption information.


Route of Elimination

Please refer to [DB00945] for the route of elimination.


Volume of Distribution

Steady-state plasma salicylate concentrations increase more than proportionally with increasing dosages; the time required to reach steady state increases with increasing daily dose. Dosage intervals of 8-12 h are sufficient to maintain plasma salicylate concentrations in the normal therapeutic anti-inflammatory concentration range.


Clearance

Please refer to [DB00945] for more information.


5.4 Metabolism/Metabolites

Hydrolyzed to salicylic acid. Salicylic acid elimination kinetics are dependent on drug concentration because of the limited capacity of two major biotransformation pathways: formation of salicyluric acid and of salicyl phenolic glucuronide. Metabolism of this drug occurs mainly in the liver, like other salicylates. Metabolism of salicylic acid occurs through glucuronide formation (to produce salicyluric acid), and salicyl phenolic glucuronide), conjugation with glycine (to produce salicyluric acid), and oxidation to form gentisic acid. The rate of formation of salicyl phenolic glucuronide and salicyluric acid are easily saturated at low salicylic acid concentrations and their formation can be described by Michaelis-Menten kinetics.


5.5 Biological Half-Life

Mean half-life of 1.1 h.


5.6 Mechanism of Action

Inhibits the activity of the enzyme known as cyclooxygenase (COX) which causes the formation of prostaglandins, substances which cause inflammation, swelling, pain, and fever. For more information, refer to the drug entry [DB00945].


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08-Feb-2024
08-Feb-2024
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