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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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