Methyl salicylate

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O3
Molecular Weight	152.1473
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=C(O)C=CC=C1

InChI

InChIKey=OSWPMRLSEDHDFF-UHFFFAOYSA-N

InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3

HIDE SMILES / InChI

Molecular Formula	C8H8O3
Molecular Weight	152.1473
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00936https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html

Methyl salicylate (or methyl 2-hydroxybenzoate), also known as wintergreen oil, is a natural product and is present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. Methyl salicylate is topically used in combination with methanol and under brand name SALONPAS to temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises. The precise mechanism of action of methyl salicylate is not known, but there is suggested, that it cause dilation of the capillaries thereby increasing blood flow to the area.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8504
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 8504	1.48 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Strains and sprains 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 2008
Simple backache 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 2008
Arthritis 87 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 2008
Bruises 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 2008
Psoriasis 87 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 2012
Keratosis palmaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 2012
Ichthyosis vulgaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 2012

T_1/2

Value	Dose	Co-administered	Analyte	Population
238 min EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022354915364558	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SALICYLIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	Other AEs: Redness, Scales... Other AEs: Redness Scales Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/

AEs

AE	Significance	Dose	Population
Redness		30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/
Scales		30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 810 CYP2C19 1119 CYP2E1 729 CYP2A6 626 CYP2B6 776 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237	CYP2E1 131

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 1146	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16914	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16914
ChemicalBook	CB1680010	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1680010
eMolecules	478035	https://www.emolecules.com/cgi-bin/more?vid=478035
MolPort	MolPort-001-769-476	https://www.molport.com/shop/molecule-link/MolPort-001-769-476
ZINC	ZINC000000001554	http://zinc15.docking.org/substances/ZINC000000001554

PubMed

Title	Date	PubMed
Effects of salicylates on evoked otoacoustic emissions and remote masking in humans.	1999 May-Jun	10437688
Microdialysis vs. suction blister technique for in vivo sampling of pharmacokinetics in the human dermis.	1999 Sep	10494706
Hydroxyl radical adduct of 5-aminosalicylic acid: a potential marker of ozone-induced oxidative stress.	2001	11235916
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Arabidopsis genome sequence as a tool for functional genomics in tomato.	2001	11178283
Unraveling regulatory networks in plant defense using microarrays.	2001	11178281
[Principal constituents from flowering aerial parts of wild pansy].	2001 Apr	11320336
Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane.	2001 Apr	11305600
Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo).	2001 Apr 13	11334847
Nuclear factor-kappaB activation is not involved in a MPTP model of Parkinson's disease.	2001 Apr 17	11303744
Effect of fluvastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase, on nitric oxide-induced hydroxyl radical generation in the rat heart.	2001 Apr 30	11335104
[Tolerability of a selective cyclooxygenase-2-inhibitor (rofecoxib) in patients with intolerance reactions to nonsteroidal anti-inflammatory agents].	2001 Apr 6	11332239
Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine.	2001 Feb	11281196
Increased leukotriene production by food additives in patients with atopic dermatitis and proven food intolerance.	2001 Feb	11251628
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction.	2001 Feb	11236213
A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics.	2001 Feb	11205435
The spinning disc reactor--studies on a novel TiO2 photocatalytic reactor.	2001 Feb	11100791
Effect of jasmonic, salicylic, and abscisic acids on [(14)C]leucine incorporation into proteins of pea leaves.	2001 Jan	11240395
Non-uniform mapping of stress-induced, motility-related charge movement in the outer hair cell plasma membrane.	2001 Jan	11212214
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.	2001 Jan	11192496
Manipulation of salicylate content in Arabidopsis thaliana by the expression of an engineered bacterial salicylate synthase.	2001 Jan	11169183
Guidelines for the management of cutaneous warts.	2001 Jan	11167676
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.	2001 Jan	11161607
Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors.	2001 Jan	11154339
Cause of high variability in drug dissolution testing and its impact on setting tolerances.	2001 Jan	11113646
Induction of cell death in arabidopsis by superoxide in combination with salicylic acid or with protein synthesis inhibitors.	2001 Jan 1	11134900
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.	2001 Jan 15	11163537
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.	2001 Jan 15	11145657
Characterization of a rice (Oryza sativa L.) Bowman-Birk proteinase inhibitor: tightly light regulated induction in response to cut, jasmonic acid, ethylene and protein phosphatase 2A inhibitors.	2001 Jan 24	11223257
Synthesis and metal binding properties of salicylate-, catecholate-, and hydroxypyridinonate-functionalized dendrimers.	2001 Jan 5	11205020
Release of salicylic acid, diclofenac acid and diclofenac acid salts from isotropic and anisotropic nonionic surfactant systems across rat skin.	2001 Jan 5	11165822
Broad-spectrum mildew resistance in Arabidopsis thaliana mediated by RPW8.	2001 Jan 5	11141561
Combined cryotherapy/70% salicylic acid treatment for plantar verrucae.	2001 Jan-Feb	11202766
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.	2001 Jul 13	11335717
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
Selective suppression of CCAAT/enhancer-binding protein beta binding and cyclooxygenase-2 promoter activity by sodium salicylate in quiescent human fibroblasts.	2001 Jun 1	11278846
Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways.	2001 Mar	11306516
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.	2001 Mar	11256485
Identification of free radicals produced during phacoemulsification.	2001 Mar	11255062
Quantitative analysis of analgoantipyretics in dosage form using planar chromatography.	2001 Mar	11248516
Potentiometric determination of acetylsalicylic acid by sequential injection analysis (SIA) using a tubular salicylate-selective electrode.	2001 Mar	11248498
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.	2001 Mar 1	11182525
Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption.	2001 Mar 14	11250091
Action of 2,3-butanedione monoxime on capacitance and electromotility of guinea-pig cochlear outer hair cells.	2001 Mar 15	11251049
Selective inhibition of interleukin-4 gene expression in human T cells by aspirin.	2001 Mar 15	11238116
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.	2001 Mar 5	11254191
Differential vulnerability of basal and apical hair cells is based on intrinsic susceptibility to free radicals.	2001 May	11335071
Acanthoamoeba attachment to contact lenses.	2001 May	11320007
Laryngeal oedema caused by accidental ingestion of Oil of Wintergreen.	2001 May 11	11335011
6-hydroxydopamine increases hydroxyl free radical production and DNA damage in rat striatum.	2001 May 8	11338183

Patents

Sample Use Guides

In Vivo Use Guide

The preferable method of use is to apply Salicylic Acid 6% thoroughly to the affected area and to cover the treated area at night after washing and before retiring. Preferably, the skin should be hydrated for a least five minutes prior to application.

Route of Administration: Topical

In Vitro Use Guide

Salicylic acid inhibited hippuric acid formation in the homogenates obtained from the specimens of human liver with IC50 value 0.19 mM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:45 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:45 GMT 2025`
Record UNII	LAV5U5022Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BETULA LENTA BARK OIL

Preferred Name

English

GAULTHERIA PROCUMBENS (WINTERGREEN) LEAF OIL

Preferred Name

English

Methyl salicylate

Official Name

English

METHYL SALICYLATE [MI]

Common Name

English

METHYL SALICYLATE [EP IMPURITY]

Common Name

English

METHYL SALICYLATE [MART.]

Common Name

English

WINTERGREEN

Common Name

English

BETULA LENTA OIL

Common Name

English

WINTERGREEN OIL

Common Name

English

FEMA NO. 2745

Code

English

2-HYDROXYBENZOIC ACID METHYL ESTER

Systematic Name

English

METHYL SALICYLATE [USP-RS]

Common Name

English

TEABERRY LEAF OIL

Common Name

English

GAULTHERIA OIL

Common Name

English

METHYL SALICYLATE [VANDF]

Common Name

English

METHYL SALICYLATE [EP MONOGRAPH]

Common Name

English

CHERRY BIRCH BARK OIL

Common Name

English

Methyl salicylate [WHO-DD]

Common Name

English

WINTERGREEN LEAF OIL

Common Name

English

WINTERGREEN OIL [FHFI]

Common Name

English

WINTERGREEN [VANDF]

Common Name

English

WINTERGREEN OIL [FCC]

Common Name

English

SWEET BIRCH OIL [VANDF]

Common Name

English

METHYL SALICYLATE [FHFI]

Common Name

English

SWEET BIRCH BARK OIL

Common Name

English

SALONPAS COMPONENT METHYL SALICYLATE

Brand Name

English

MOUNTAIN-TEA LEAF OIL

Common Name

English

SWEET BIRCH OIL

Common Name

English

METHYL SALICYLATE [JAN]

Common Name

English

BIRCH, SWEET, OIL

Common Name

English

METHYL SALICYLATE,SYNTHETIC

Common Name

English

CHECKERBERRY LEAF OIL

Common Name

English

METHYL SALICYLATE [HSDB]

Common Name

English

FLAVOR,WINTERGREEN

Common Name

English

BIRCH OIL SWEET

Common Name

English

BENZOIC ACID, 2-HYDROXY-, METHYL ESTER

Common Name

English

METHYL SALICYLATE [FCC]

Common Name

English

NSC-8204

Code

English

O-HYDROXYBENZOIC ACID METHYL ESTER

Common Name

English

BLACK BIRCH OIL

Common Name

English

FEMA NO. 3113

Common Name

English

FEMA NO. 2154

Common Name

English

GAULTHERIA PROCUMBENS LEAF OIL

Common Name

English

BIRCH SWEET OIL [FHFI]

Common Name

English

EASTERN TEABERRY LEAF OIL

Common Name

English

METHYL SALICYLATE [II]

Common Name

English

METHYL SALICYLATE [ORANGE BOOK]

Common Name

English

METHYL SALICYLATE,SYNTHETIC [VANDF]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.544