U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of Methyl salicylate

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.48 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
Palliative
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
Palliative
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
Palliative
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
Primary
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
Primary
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
Primary
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
238 min
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

Doses

DosePopulationAdverse 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:
unhealthy, 23.05 ± 5.7 years
n = 43
Health Status: unhealthy
Condition: Acne vulgaris
Age Group: 23.05 ± 5.7 years
Sex: M+F
Population Size: 43
Sources:
Other AEs: Redness, Scales...
Other AEs:
Redness
Scales
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 23.05 ± 5.7 years
n = 43
Health Status: unhealthy
Condition: Acne vulgaris
Age Group: 23.05 ± 5.7 years
Sex: M+F
Population Size: 43
Sources:
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:
unhealthy, 23.05 ± 5.7 years
n = 43
Health Status: unhealthy
Condition: Acne vulgaris
Age Group: 23.05 ± 5.7 years
Sex: M+F
Population Size: 43
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
major
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Cyanide-resistant alternative respiration is strictly correlated to intracellular peroxide levels in Acremonium chrysogenum.
2001 Apr
Abnormal callose response phenotype and hypersusceptibility to Peronospoara parasitica in defence-compromised arabidopsis nim1-1 and salicylate hydroxylase-expressing plants.
2001 Apr
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
Nuclear factor-kappaB activation is not involved in a MPTP model of Parkinson's disease.
2001 Apr 17
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
Hereditary palmoplantar keratoderma (four cases in three generations).
2001 Feb
A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics.
2001 Feb
Molecular responses to aphid feeding in Arabidopsis in relation to plant defense pathways.
2001 Feb
The spinning disc reactor--studies on a novel TiO2 photocatalytic reactor.
2001 Feb
A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus.
2001 Feb 28
Non-uniform mapping of stress-induced, motility-related charge movement in the outer hair cell plasma membrane.
2001 Jan
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.
2001 Jan
Microfabrication of individual 200 microm diameter transdermal microconduits using high voltage pulsing in salicylic acid and benzoic acid.
2001 Jan
Reversed-phase high-performance liquid chromatography versus spectrophotometric assay for thimerosal in Cuban recombinant hepatitis B vaccine.
2001 Jan 12
Release of salicylic acid, diclofenac acid and diclofenac acid salts from isotropic and anisotropic nonionic surfactant systems across rat skin.
2001 Jan 5
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.
2001 Jul 13
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.
2001 Jul 6
Selective suppression of CCAAT/enhancer-binding protein beta binding and cyclooxygenase-2 promoter activity by sodium salicylate in quiescent human fibroblasts.
2001 Jun 1
A recessive mutation in the Arabidopsis SSI2 gene confers SA- and NPR1-independent expression of PR genes and resistance against bacterial and oomycete pathogens.
2001 Mar
Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways.
2001 Mar
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.
2001 Mar
Identification of free radicals produced during phacoemulsification.
2001 Mar
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.
2001 Mar 1
Differential vulnerability of basal and apical hair cells is based on intrinsic susceptibility to free radicals.
2001 May
Asbestos causes apoptosis in alveolar epithelial cells: role of iron-induced free radicals.
2001 May
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.
2001 May 1
Laryngeal oedema caused by accidental ingestion of Oil of Wintergreen.
2001 May 11
Patents

Sample Use Guides

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 Fri Dec 15 15:08:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:20 GMT 2023
Record UNII
LAV5U5022Y
Record Status Validated (UNII)
Record Version
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Name Type Language
Methyl salicylate
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   ORANGE BOOK   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
METHYL SALICYLATE [MI]
Common Name English
METHYL SALICYLATE [EP IMPURITY]
Common Name English
METHYL SALICYLATE [MART.]
Common Name English
WINTERGREEN
VANDF  
Common Name English
BETULA LENTA BARK OIL [INCI]
Common Name English
BETULA LENTA OIL
Common Name English
WINTERGREEN OIL
FCC   FHFI  
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
METHYL SALICYLATE COMPONENT OF SALONPAS
Brand Name English
SWEET BIRCH BARK OIL
Common Name English
SALONPAS COMPONENT METHYL SALICYLATE
Brand Name English
BETULA LENTA BARK OIL
INCI  
INCI  
Official Name English
METHYL SALICYLATE [INCI]
Common Name English
MOUNTAIN-TEA LEAF OIL
Common Name English
SWEET BIRCH OIL
VANDF  
Common Name English
METHYL SALICYLATE [JAN]
Common Name English
BIRCH, SWEET, OIL
Common Name English
METHYL SALICYLATE,SYNTHETIC
VANDF  
Common Name English
CHECKERBERRY LEAF OIL
Common Name English
GAULTHERIA PROCUMBENS (WINTERGREEN) LEAF OIL
INCI  
INCI  
Official Name English
METHYL SALICYLATE [HSDB]
Common Name English
FLAVOR,WINTERGREEN
VANDF  
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
GAULTHERIA PROCUMBENS (WINTERGREEN) LEAF OIL [INCI]
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
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
CFR 21 CFR 310.531
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
DSLD 1268 (Number of products:9)
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
JECFA EVALUATION METHYL SALICYLATE
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
Code System Code Type Description
DAILYMED
LAV5U5022Y
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
PUBCHEM
4133
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
MERCK INDEX
m7463
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY Merck Index
NSC
8204
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
DRUG BANK
DB09543
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
CAS
68917-50-0
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
ALTERNATIVE
CAS
68917-75-9
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
ALTERNATIVE
EVMPD
SUB60752
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
CHEBI
31832
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
DRUG CENTRAL
4245
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
CAS
119-36-8
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
MESH
C033069
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
SMS_ID
100000084885
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
EVMPD
SUB15729MIG
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
FDA UNII
LAV5U5022Y
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
NCI_THESAURUS
C80564
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
RS_ITEM_NUM
1437450
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
HSDB
1935
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
EVMPD
SUB14545MIG
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID5025659
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
RXCUI
29787
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL108545
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-317-7
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
JECFA MONOGRAPH
800
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
WIKIPEDIA
METHYL SALICYLATE
Created by admin on Fri Dec 15 15:08:20 GMT 2023 , Edited by admin on Fri Dec 15 15:08:20 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
PARENT -> IMPURITY
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY