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    Chemistry

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    Also known as: Methyl 2-hydroxybenzoate, 119-36-8, Wintergreen oil, Gaultheria oil, Betula oil, Sweet birch oil
    Molecular Formula
    C8H8O3
    Molecular Weight
    152.15  g/mol
    InChI Key
    OSWPMRLSEDHDFF-UHFFFAOYSA-N
    FDA UNII
    LAV5U5022Y
    Methyl Salicylate
    Methyl 2-hydroxy benzoate is a metabolite found in or produced by Saccharomyces cerevisiae.
    1 2D Structure

    Methyl Salicylate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl 2-hydroxybenzoate
    2.1.2 InChI
    InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
    2.1.3 InChI Key
    OSWPMRLSEDHDFF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC(=O)C1=CC=CC=C1O
    2.2 Other Identifiers
    2.2.1 UNII
    LAV5U5022Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hewedolor

    2. Linsal

    3. Methyl Salicylate Sodium Salt

    4. Methylsalicylate

    5. Metsal Liniment

    6. Rheumabal

    2.3.2 Depositor-Supplied Synonyms

    1. Methyl 2-hydroxybenzoate

    2. 119-36-8

    3. Wintergreen Oil

    4. Gaultheria Oil

    5. Betula Oil

    6. Sweet Birch Oil

    7. Teaberry Oil

    8. Oil Of Wintergreen

    9. Analgit

    10. 2-hydroxybenzoic Acid Methyl Ester

    11. Spicewood Oil

    12. 2-carbomethoxyphenol

    13. Gaultheriaoel

    14. Wintergruenoel

    15. Flucarmit

    16. Betula

    17. Exagien

    18. Natural Wintergreen Oil

    19. Methyl O-hydroxybenzoate

    20. 2-(methoxycarbonyl)phenol

    21. Methylsalicylate

    22. Betula Lenta

    23. Salicylic Acid, Methyl Ester

    24. Benzoic Acid, 2-hydroxy-, Methyl Ester

    25. Synthetic Wintergreen Oil

    26. Gaultheria Oil, Artificial

    27. Wintergreen Oil, Synthetic

    28. Methyl2-hydroxybenzoate

    29. O-hydroxybenzoic Acid, Methyl Ester

    30. Fema No. 2745

    31. Birch Oil, Sweet

    32. Salicylic Acid Methyl Ester

    33. Mfcd00002214

    34. 68917-75-9

    35. Flavor,wintergreen

    36. Nsc 8204

    37. 2-hydroxybenzoic Acid, Methyl Ester

    38. Metylester Kyseliny Salicylove

    39. Fema No. 2154

    40. Fema No. 3113

    41. Nsc-8204

    42. 2-hydroxy-benzoic Acid Methyl Ester

    43. Benzoic Acid, Hydroxy-, Methyl Ester

    44. Methyl Salicylate,synthetic

    45. Lav5u5022y

    46. Chebi:31832

    47. 135952-76-0

    48. Ncgc00091106-02

    49. Dsstox_cid_5659

    50. Dsstox_rid_77872

    51. Dsstox_gsid_25659

    52. Caswell No. 577

    53. Panalgesic

    54. Theragesic

    55. 2,4-cyclohexadien-1-one,6-(hydroxymethoxymethylene)-(9ci)

    56. Predalure

    57. Fema Number 2745

    58. Black Birch Oil

    59. Methyl Salicylate [jan]

    60. Anthrapole Nd

    61. Betula Lenta Oil

    62. Ben Gay

    63. Methyl Salicylate (natural)

    64. 68917-50-0

    65. Cas-119-36-8

    66. Ccris 6259

    67. Hsdb 1935

    68. Winter Green Oil

    69. Einecs 204-317-7

    70. Epa Pesticide Chemical Code 076601

    71. Metylester Kyseliny Salicylove [czech]

    72. Methylester Kyseliny Salicylove [czech]

    73. Brn 0971516

    74. Unii-lav5u5022y

    75. Wintergreen

    76. Methyl Salicylate [jan:nf]

    77. Methylester Kyseliny Salicylove

    78. Ai3-00090

    79. Methyl-salicylate

    80. Salicylic Acid Methyl

    81. 1-o-methylsalicylate

    82. Salonpas (salt/mix)

    83. Salicylate Methyl Ester

    84. Birch Oil Sweet

    85. Methyl Salicylate,(s)

    86. Theragesic (salt/mix)

    87. Methyl Salicylate (tn)

    88. Methyl Salicylate, 8ci

    89. Methyl-2-hydroxybenzoate

    90. Enamine_001611

    91. Teaberry Leaf Oil

    92. Methyl Salicylate, 98%

    93. Birch, Sweet, Oil

    94. Methyl Salicylate, Bioxtra

    95. Salicylic-acid Methyl Ester

    96. Wln: Qr Bvo1

    97. Ec 204-317-7

    98. Wintergreen [vandf]

    99. Wintergreen Leaf Oil

    100. Schembl5312

    101. Betula Oil, Wintergreen Oil

    102. Checkerberry Leaf Oil

    103. Sweet Birch Bark Oil

    104. Betula Lenta Bark Oil

    105. Cherry Birch Bark Oil

    106. Mountain-tea Leaf Oil

    107. Zinc490

    108. 4-10-00-00143 (beilstein Handbook Reference)

    109. 90045-28-6

    110. Bidd:er0323

    111. Wintergreen Oil [fcc]

    112. Wintergreen Oil, China Origin

    113. Methyl Salicylate [ii]

    114. Methyl Salicylate [mi]

    115. Wintergreen Oil [fhfi]

    116. Chembl108545

    117. Gtpl2431

    118. Methyl Salicylate (jp17/nf)

    119. Birch Sweet Oil [fhfi]

    120. Methyl Salicylate [fcc]

    121. Dtxsid5025659

    122. Methyl Salicylate [fhfi]

    123. Methyl Salicylate [hsdb]

    124. Methyl Salicylate [inci]

    125. Sweet Birch Oil [vandf]

    126. Eastern Teaberry Leaf Oil

    127. Fema 2745

    128. Methyl Salicylate [vandf]

    129. Nsc8204

    130. Methyl Salicylate [mart.]

    131. Hms1398j05

    132. Hms2089h12

    133. Hms3885c04

    134. O-hydroxybenzoic Acid Methyl Ester

    135. Methyl Salicylate [usp-rs]

    136. Methyl Salicylate [who-dd]

    137. Bcp29151

    138. Cs-b1799

    139. Hy-y0189

    140. Methyl Ester 2-hydroxy-benzoic Acid

    141. Tox21_111081

    142. Tox21_201543

    143. Tox21_300137

    144. Bbl010504

    145. S3756

    146. Stk397388

    147. Betula Lenta Bark Oil [inci]

    148. Gaultheria Procumbens Leaf Oil

    149. Methyl Salicylate, Analytical Standard

    150. Akos000118977

    151. Ccg-266225

    152. Db09543

    153. Methyl Ester Of 2-hydroxy-benzoic Acid

    154. Methyl Salicylate [ep Impurity]

    155. Methyl Salicylate [orange Book]

    156. Methyl Salicylate [ep Monograph]

    157. Methyl Salicylate, >=98%, Fcc, Fg

    158. Ncgc00091106-01

    159. Ncgc00091106-03

    160. Ncgc00091106-04

    161. Ncgc00091106-05

    162. Ncgc00254104-01

    163. Ncgc00259093-01

    164. 8024-54-2

    165. Ac-11584

    166. Sy008800

    167. Ts-02010

    168. Methyl Salicylate,synthetic [vandf]

    169. Salonpas Component Methyl Salicylate

    170. Db-012808

    171. Ft-0612582

    172. Ft-0622968

    173. Ft-0695782

    174. Ft-0698844

    175. Methyl Salicylate, Natural, 98%, Fcc, Fg

    176. Methyl Salicylate Component Of Salonpas

    177. Methyl Salicylate, Puriss., 99.0-100.5%

    178. D01087

    179. D70335

    180. Methyl Salicylate, Saj First Grade, >=98.0%

    181. Methyl Salicylate, Tested According To Ph.eur.

    182. Ab01275470-01

    183. Methyl Salicylate 100 Microg/ml In Acetonitrile

    184. A804265

    185. Methyl Salicylate, Reagentplus(r), >=99% (gc)

    186. Methyl Salicylate, Vetec(tm) Reagent Grade, 99%

    187. Q407669

    188. Sr-05000001473

    189. Gaultheria Procumbens (wintergreen) Leaf Oil

    190. Q-100939

    191. Sr-05000001473-1

    192. Z19703590

    193. 2-[hydroxy(methoxy)methylene]-3,5-cyclohexadiene-1-one

    194. F0001-0306

    195. 6-[(e)-methoxyhydroxymethylene]-2,4-cyclohexadiene-1-one

    196. Gaultheria Procumbens (wintergreen) Leaf Oil [inci]

    197. Methyl Salicylate, United States Pharmacopeia (usp) Reference Standard

    198. Methyl Salicylate, Pharmaceutical Secondary Standard; Certified Reference Material

    199. 9041-28-5

    200. Gaultheria Oil Pound>>wintergreen Oil Pound>>2-hydroxy-benzoicacimethylester Pound>>methyl 2-hydroxybenzoate

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 152.15 g/mol
    Molecular Formula C8H8O3
    XLogP32.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass152.047344113 g/mol
    Monoisotopic Mass152.047344113 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity144
    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 Therapeutic Uses

    OINTMENTS OR LINIMENTS CONTAINING METHYL SALICYLATE ARE APPLIED TOPICALLY AS COUNTERIRRITANTS FOR RELIEF OF PAIN ASSOCIATED WITH LUMBAGO, SCIATICA, AND RHEUMATIC CONDITIONS. FORMERLY USED INTERNALLY IN SMALL DOSES AS A CARMINATIVE.

    American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 84:2404

    MEDICATION (VET): ORALLY, PRIMARILY AS FLAVORING AGENT OR AS CARMINATIVE; TOPICALLY, AS IRRITANT OR COUNTERIRRITANT AIDED BY MASSAGE OR RUBBING AS IN UDDER OINTMENTS (1-3% CONCN), POULTICES & COUNTERIRRITANT MIXT (@ LEAST 5-10%) OVER SORE JOINT, MUSCLE, & BONE AREAS.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 360

    LOCAL ANALGESIC FOR HUMAN AND VETERINARY MEDICINE

    SRI

    4.2 Drug Warning

    OINTMENTS OR LINIMENTS ... . SHOULD NOT BE APPLIED TO BURNED AREAS OR TO OTHERWISE DAMAGED SKIN...USUALLY IN CONCN FROM 10-25% ... .

    American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 84:2404

    ABSORPTION OF METHYL SALICYLATE CAN OCCUR THROUGH THE SKIN, & DEATH HAS RESULTED FROM SYSTEMIC POISONING FROM THE LOCAL MISAPPLICATION OF THE DRUG. IT IS A COMMON PEDIATRIC POISON, & ITS USE SHOULD BE STRONGLY DISCOURAGED.

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 653

    Children with fever and dehydration are particularly prone to intoxication from relatively small doses of salicylate. ... The use of aspirin is contraindicated in children and adolescents with febrile viral illnesses because of the risk of Reye's syndrome. /Salicylates/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 651

    4.3 Minimum/Potential Fatal Human Dose

    4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON &1 OZ FOR 70 KG PERSON (150 LB).

    Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-205

    4.4 Drug Indication

    Ointments or liniments containing methyl salicylate are applied topically as counter irritant for relief of acute pain associated with lumbago,sciatica and rheumatic conditions. Local analgesics for human and veterinary medicine.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Methyl salicylate relieve musculoskeletal pain in the muscles, joints, and tendons by causing irritation and reddening of the skin due to dilated capillaries and increased blood flow. It is pharmacologically similar to aspirin and other NSAIDs but as a topical agent it primarily acts as a rubefacient and skin irritant. Counter-irritation is believed to cause a soothing sensation of warmth.

    5.2 MeSH Pharmacological Classification

    Antirheumatic Agents

    Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

    Fixatives

    Agents employed in the preparation of histologic or pathologic specimens for the purpose of maintaining the existing form and structure of all of the constituent elements. Great numbers of different agents are used; some are also decalcifying and hardening agents. They must quickly kill and coagulate living tissue. (See all compounds classified as Fixatives.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    Approximately 12-20% of topically applied methyl salicylate may be systemically absorbed through intact skin within 10 hours of application, and absorption varies with different conditions such as surface area and pH. Dermal bioavailability is in the range of 11.8 30.7%. For the assessment of potential oral exposure to salicylates, bioavailability is assumed to be 100%.

    Route of Elimination

    Excreted by kidneys as free salicylic acid (10%), salicyluric acid (75%), salicylic phenolic (10%) and acyl glucuronide (5%), and gentisic acid (less than 1%).

    Volume of Distribution

    After absorption, methyl salicylate is distributed throughout most body tissues and most transcellular fluids, primarily by pH dependent passive processes. Salicylate is actively transported by a low-capacity, saturable system out of the CSF across the choroid plexus. The drug readily crosses the placental barrier.

    MAY BE ABSORBED RAPIDLY THROUGH INTACT SKIN. BOWEL ABSORPTION IS SOMEWHAT ERRATIC ... ABSORBED AT LEAST IN PART AS THE INTACT ESTER AND SMALL AMT ARE EVEN EXCRETED AS SUCH BY THE KIDNEYS ... .

    Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-205

    HUMAN SUBJECTS WERE GIVEN 7 MG/KG OF METHYL SALICYLATE BY MOUTH. AFTER 0.25 HOURS THE BLOOD CONCN WAS 1.28 MG%. AFTER 1.5 HOURS THE BLOOD CONCN WAS 1.33 MG%. /FROM TABLE/

    Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 362

    At therapeutic doses, conjugation accounts for most salicylic elimination, whereas renal elimination becomes more important with large or multiple doses. A substantial first-pass effect occurs at therapeutic doses. /Salicylates/

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 563

    Orally ingested salicylates are absorbed rapidly, partly from the stomach but mostly from the upper small intestine. Appreciable conc are found in plasma in less than 30 min; after a single dose, a peak value is reached in about 2 hr and then gradually declines. /Salicylates/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 649

    For more Absorption, Distribution and Excretion (Complete) data for METHYL SALICYLATE (6 total), please visit the HSDB record page.

    5.4 Metabolism/Metabolites

    Minor metabolism may occur in various tissues but hepatic metabolism constitutes the majority of metabolic processes of absorbed methyl salicylate. It is mainly hydrolyzed to salicylic acid via hepatic esterase enzymes. Conjugation with glycine forms salicyluric acid and conjugation with glucuronic forms ester or acyl and ether or phenolic glucuronide, which are the three main metabolites.

    ...EVIDENCE THAT CONSIDERABLE HYDROLYSIS OF ESTER OCCURS IN INTESTINAL TRACT... IN SOME SPECIES, SUCH AS RABBIT, MAY BE PARTLY EXCRETED AS SULFATE OR GLUCURONIC ACID CONJUGATE ON THE FREE HYDROXYL GROUP. CONJUGATION APPEARS TO TAKE PLACE BEFORE HYDROLYSIS OF THE METHYL ESTER.

    Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1899

    For small doses 80% of the hepatic metabolism results from conjugation with glycine to form salicyluric acid and with glucuronic acid to form salicyl acyl and phenolic glucuronide. The two parallel pathways (glycine, glucuronide conjugation) have limited capacity and saturate easily above therapeutic doses. /Salicylates/

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 563

    The biotransformation of salicylates takes place in many tissues, but particularly in the hepatic endoplasmic reticulum and mitochondria. The three chief metabolic products are salicyluric acid (the glycine conjugate), the ether or phenolic glucuronide, and the ester or acyl glucuronide. In addition, a small fraction is oxidized to gentisic acid (2,5-dihydroxybenzoic acid) and to 2,3-dihydroxybenzoic and 2,3,5-trihydroxybenzoic acids; gentisuric acid, the glycine conjugate of gentisic acid, is also formed. /Salicylates/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 649

    5.5 Biological Half-Life

    The plasma half-life for salicylate is 2 to 3 hr in low doses and about 12 hr at usual anti-inflammatory doses. The half-life of salicylate may be as long as 15 to 30 hr at high therapeutic doses or when there is intoxication.

    The plasma half-life for ... salicylate is 2 to 3 hr in low doses and about 12 hr at usual antiinflammatory doses. The half-life of salicylate may be as long as 15 to 30 hr at high therapeutic doses or when there is intoxication. /Salicylates/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 650

    5.6 Mechanism of Action

    Counter-irritation is thought to be effective at alleviating musculoskeletal pain as the irritation of the sensory nerve endings is thought to alter or offset pain in the underlying muscle or joints that are served by the same nerves. This is thought to mask the underlying musculoskeletal pain and discomfort. When applied topically, methyl salicylate is thought to penetrate the skin and underlying tissues where it reversibly inhibits cyclooxygenase enzyme and locally and peripherally prevents the production of inflammatory mediators such as prostaglandin and thromboxane A2.

    API Reference Price

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    02-Jan-2021
    31-Aug-2024
    KGS
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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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