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Methyl salicylate

Names

[ CAS No. ]:
119-36-8

[ Name ]:
Methyl salicylate

[Synonym ]:
2-HYDROXY-BENZOIC ACID METHYL ESTER
2-Hydroxybenzoic acid methyl ester
Benzoic acid, 2-hydroxy-, methyl ester
salicylic-acid methyl ester
Wintergreen oil (generic)
2-Hydroxybenzoic acid methyl ester,Methyl 2-hydroxybenzoate,Oil of wintergreen
METHYL SALICYLATE NF FCC
2-Hydroxybenzoic acid methyl ester,Methyl 2-hydroxybenzoate,Methylis salicylas
2-METHYL-5-(PROPAN-2-YL)PHENOL
methyl 2-hydroxybenzoate
Oil of wintergreen
methyl-2-hydroxybenzoate
methyl o-hydroxybenzoate
2-hydroxymethylbenzoate
QR BVO1
2-CARBOMETHOXYPHENOL
METHYL SALICYLATE NF
salicylic acid methyl ester
METHYL SALICYLATE: NF
Methyl salicylate
Wintergreen oil
METHYL SAL ICY LATE/METHYL 2-HYDROXYBENZOATE/SALICYLIC ACID METHYL ESTER
EINECS 204-317-7
MFCD00002214
methylsalicylate
METHYL SALICYLATE 1 L
SALICYLIC ACID METHYLESTER
GAULTHERIN
BIRCH OIL

Biological Activity

[Description]:

Methyl Salicylate (Wintergreen oil) is a topical analgesic and anti-inflammatory agent. Also used as a pesticide, a denaturant, a fragrance ingredient, and a flavoring agent in food and tobacco products[1]. A systemic acquired resistance (SAR) signal in tobacco[2]. A topical nonsteroidal anti-inflammatory drug (NSAID). Methyl salicylate lactoside is a COX inhibitor[4].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> COX
Natural Products >> Acids and Aldehydes
Research Areas >> Inflammation/Immunology

[In Vitro]

Methyl Salicylate is a systemic acquired resistance signal in tobacco. It (0-1 mg/L) esterases activity of salicylic acid–binding protein 2 (SABP2), which converts MeSA into salicylic acid (SA), is required for SAR signal perception in systemic tissue[2].

[References]

[1]. Greene T, et al. A critical review of the literature to conduct a toxicity assessment for oral exposure to methyl salicylate. Crit Rev Toxicol. 2017 Feb;47(2):98-120.

[2]. Park SW, et al. Methyl salicylate is a critical mobile signal for plant systemic acquired resistance. Science. 2007 Oct 5;318(5847):113-6.

[3]. Lapczynski A, et al. Fragrance material review on methyl salicylate. Food Chem Toxicol. 2007;45 Suppl 1:S428-52.

[4]. Xin W, et al. Methyl salicylate lactoside inhibits inflammatory response of fibroblast-like synoviocytes and joint destruction in collagen-induced arthritis in mice. Br J Pharmacol. 2014 Jul;171(14):3526-38.


[Related Small Molecules]

4-Acetamidophenol | Aspirin | Paradol | Ginsenoside Rg3 | Ginsenoside Compound K | Xanthohumol | Ibuprofen | Diclofenac | NS-398 | Meloxicam | Flufenamic Acid | Epicatechin | Salicylic acid | ketoprofen | Naproxen

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
222.0±0.0 °C at 760 mmHg

[ Melting Point ]:
-8 °C

[ Molecular Formula ]:
C8H8O3

[ Molecular Weight ]:
152.147

[ Flash Point ]:
86.8±12.6 °C

[ Exact Mass ]:
152.047348

[ PSA ]:
46.53000

[ LogP ]:
2.23

[ Vapour density ]:
5.26 (vs air)

[ Vapour Pressure ]:
0.1±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.547

[ Stability ]:
Stable. Incompatible with strong oxidizing agents, strong bases.

[ Water Solubility ]:
0.07 g/100 mL (20 ºC)

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VO4725000
CHEMICAL NAME :
Salicylic acid, methyl ester
CAS REGISTRY NUMBER :
119-36-8
BEILSTEIN REFERENCE NO. :
0971516
LAST UPDATED :
199710
DATA ITEMS CITED :
45
MOLECULAR FORMULA :
C8-H8-O3
MOLECULAR WEIGHT :
152.16
WISWESSER LINE NOTATION :
QR BVO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - guinea pig
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
101 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1329 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma Blood - hemorrhage
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
228 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - general anesthetic Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
355 mg/kg
TOXIC EFFECTS :
Behavioral - coma Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
1480 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
506 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
522 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
887 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1110 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2100 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
4250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
71400 mg/kg/17W-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
546 gm/kg/2Y-C
TOXIC EFFECTS :
Cardiac - changes in heart weight Kidney, Ureter, Bladder - changes in kidney weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
40 mg/m3/4H/17W-I
TOXIC EFFECTS :
Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
85200 mg/kg/10W-C
TOXIC EFFECTS :
Musculoskeletal - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
40800 mg/kg/59D-I
TOXIC EFFECTS :
Liver - fatty liver degeneration Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
330 gm/kg/90D-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of endocrine pancreas Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
36450 mg/kg
SEX/DURATION :
multigenerations
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
400 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 mg/kg
SEX/DURATION :
female 11-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1750 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
5250 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria - Salmonella typhimurium
DOSE/DURATION :
100 ug/disc
REFERENCE :
JNUDAT Journal of Nihon University School of Dentistry. (Nihon University School of Dentistry, 1-8-13 Surugadai, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1958- Volume(issue)/page/year: 34,183,1992 *** REVIEWS *** TOXICOLOGY REVIEW DICPBB Drug Intelligence and Clinical Pharmacy. (POB 42435, Cincinnati, OH 45242) V.3- 1969- Volume(issue)/page/year: 9,350,1975 TOXICOLOGY REVIEW CLCHAU Clinical Chemistry (Winston-Salem, NC). (American Assoc. for Clinical Chemistry, 1725 K St., NW, Washington, DC 20006) V.1- 1955- Volume(issue)/page/year: 19,361,1973 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 38,409,1965 TOXICOLOGY REVIEW EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 15,121,1976 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 48320 No. of Facilities: 15668 (estimated) No. of Industries: 138 No. of Occupations: 80 No. of Employees: 105490 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 48320 No. of Facilities: 30724 (estimated) No. of Industries: 193 No. of Occupations: 134 No. of Employees: 454822 (estimated) No. of Female Employees: 134722 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R36/38

[ Safety Phrases ]:
S26-S36-S24/25

[ RIDADR ]:
3082

[ WGK Germany ]:
1

[ RTECS ]:
VO4725000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2918219000

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2918230000

[ Summary ]:
2918230000 other esters of salicylic acid and their salts VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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