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Home > Encyclopedia > Methyl salicylate

Methyl salicylate

pharmaceutical raw materials
Methyl salicylate structure

Methyl salicylate 

structure
  • CAS No:

    119-36-8

  • Formula:

    C8H8O3

  • Chemical Name:

    Methyl salicylate

  • Synonyms:

    Benzoic acid,2-hydroxy-,methyl ester;Salicylic acid,methyl ester;Methyl o-hydroxybenzoate;Methyl salicylate;Methyl 2-hydroxybenzoate;o-Hydroxybenzoic acid methyl ester;2-Hydroxybenzoic acid methyl ester;Analgit;Exagien;Flucarmit;2-(Methoxycarbonyl)phenol;Anthrapole ND;Wintergreen oil;2-Carbomethoxyphenol;NSC 8204;Ben Gay;Methyl ester of 2-hydroxy benzoic acid;Methyl ester 2-hydroxy benzoic acid;PredaLure;Holly oil;8022-86-4;8024-54-2;648434-07-5

  • Categories:

    Cosmetic Ingredient  >  Perfuming

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].


Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. (USCG, 1999)|DryPowder; Liquid|Liquid|COLOURLESS OR YELLOW-TO-RED OILY LIQUID WITH CHARACTERISTIC ODOUR.|colourless to yellowish liquid with a characteristic wintergreen odour


Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. (USCG, 1999)|Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. It has a role as a flavouring agent, a metabolite and an insect attractant. It is a benzoate ester and a member of salicylates. It derives from a salicylic acid.|Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic ester naturally produced by many species of plants, particularly wintergreens. The compound was first extracted and isolated from plant species Gaultheria procumbens in 1843. It can be manufactured synthetically and it used as a fragrance, in foods, beverages, and liniments. It forms a colorless to yellow or reddish liquid and exhibits a characteristic odor and taste of wintergreen. For acute joint and muscular pain, methyl salicylate is used as a rubefacient and analgesic in deep heating liniments. It is used as a flavoring agent in chewing gums and mints in small concentrations and added as antiseptic in mouthwash solutions.

Methyl salicylate Basic Attributes

152.14700

152.15

614-802-9

LAV5U5022Y

1505

8204

DTXSID5025659|DTXSID60101668|DTXSID60101688|DTXSID9043724

COLORLESS, YELLOWISH OR REDDISH, OILY LIQ

2918219000

Characteristics

46.53000

2.3

Methyl salicylate appears as colorless yellowish or reddish liquid with odor of wintergreen. (USCG, 1999)

1.184 g/cm3 @ Temp: 25 °C

-8.6 °C

220-224 °C

110ºC

1.523

H2O: 0.07 g/100 mL (20 ºC)

Keep from contact with oxidizing materials. Store in a cool, dry, well-ventilated area away from incompatible substances.

1 mm Hg ( 54 °C)

5.26 (vs air)

LIQUID HAVING THE CHARACTERISTIC ODOR OF WINTERGREEN

LIQUID HAVING THE CHARACTERISTIC TASTE OF WINTERGREEN

pKa = 9.8

WINTERGREEN ESSENTIAL OIL: ESTER VALUE: 354-356; OPTICAL ROTATION: -0 DEG 25' TO -1 DEG 30'|1 MM HG @ 54.0 °C|Heat capacity = 59.46 cal/deg K-mol @ 15-30 °C

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

METHYL SALICYLATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This chemical is incompatible with oxidizers. It is also incompatible with strong bases. It may react with iron salts. (NTP, 1992)

847 °F (USCG, 1999)|850 °F|451 °C

-902.2 kcal/mole @ 25 °C

11.155 kcal/mol @ the boiling point

Safety Information

III

6.1(b)

3082

1

R22; R36/38

S24/25

VO4725000

Xn

Separated from strong oxidants and strong bases.

Stable. Incompatible with strong oxidizing agents, strong bases.

P301 + P312 + P330

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

INCOMPATIBILITIES: DECOMP BY ALKALIES TO FORM METHYL ALC & SALICYLATE.

This chemical is combustible. (NTP, 1992)|Combustible.

|Warning|H302 (72.63%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 95 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (99.93%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 1480 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (97.49%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 2515 companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (61.54%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 65 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

Self contained breathing apparatus, rubber boots, and heavy rubber gloves. (USCG, 1999)

SLIGHT, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.

WATER, FOAM, CARBON DIOXIDE, DRY CHEMICAL.

Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from strong oxidants and strong bases.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes and skin. The substance may cause effects on the central nervous system. This may result in shock and death. The effects may be delayed. Medical observation is indicated.

NO open flames.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, methyl salicylate was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): organics and plastics (2; 419), aluminum (3; 127), electronics (1; 29) and organic chemicals (2; 6.2)(1). The highest effluent concn was 1881 ppb in the organics and plastics industry(1).

Toxicity

Oral LD50 values (mg/kg) for mouse, rat and rabbit are 1110, 887 and 1300, respectively. Oral LD50 values for child and adult human (mg/kg) are 228 and 506, respectively. Although systemic toxicity from topical administration is rare, methyl salicylate can be absorbed in intract skin to cause stimulation of the central nervous system respiratory center, disturbance of lipid and carbohydrate metabolism, and disturbance of intracellular respiration. Severe toxicity can result in acute lung injury, lethargy, coma, seizures, cerebral edema, and death. In case of salicylate poisoning, the treatment consists of general supportive care, gastrointestinal decontamination with activated charcoal in cases of salicylate ingestion, and monitoring of serum salicylate concentrations. Bicarbonate infusions or hemodialysis can be used to achieve enhanced salicylate elimination.

... The prolonged and excessive ingestion of analgesic mixtures containing salicylates in combination with acetaminophen or salicylamide can produce papillary necrosis and interstitial nephritis. /Salicylates/

LDLO Child oral 0.17 g/kg; LD50 Adult oral 0.5 g/kg

LD50 Rat oral 0.887 g/kg|LD50 Rabbit oral 2.8 g/kg|LD50 Guinea pig oral 1.060 g/kg|LD50 Dog oral 2.1 g/kg|LD50 Guinea pig dermal 0.70 ml/kg

Methyl salicylate (MS) ... was tested to update & expand the reproductive toxicity database, & used, in part, as a known positive: this is the second of two simultaneous studies conducted at different labs, using the RACB protocol & Swiss mice. Food & water consumptions, clinical signs, & body weights were used in the Task 1 dose-range-finding study to set doses for the continuous cohabitation phase (Task 2) at 25, 50, & 100 mg/kg/day by gavage in corn oil. Deaths occurred at a rate of 2, 1, 5, & 3 mice in the control to high dose groups, respectively. Some of these deaths were apparently due to gavage trauma; the cause of death was not determined in the remaining cases. MS exposure had no effect on parental body weights or clinical signs. There was no adverse effect of MS exposure on the reproductive endpoints measured in Task 2. Since there were no treatment-related changes, no Task 3 was conducted. The last litter in Task 2 from the control & high dose groups was reared by the dams until weaning (/postnatal day/ 21), & then dosed with MS until the Task 4 mating at nearly =/postnatal day/ 74. There were no reductions in pup viability or weight during nursing, & no differences between treated & control mice before & during the wk of mating in Task 4. In the single mating that comprises Task 4, there were no MS-related changes in the number of pups/litter, their viability or sex ratio, or their body weight adjusted for litter size. After the F2 litters were evaluated, all animals were killed, & the F1 adults necropsied. For males & females, there were no effects on body weights or organ weights. The % motile, density, & % morphologically abnormal endpoints were all unchanged for epididymal sperm. No estrous cyclicity evaluation was performed. At the doses used for this study (which were 20% the dose used in the previous positive study), MS caused no adverse effects on body weight or reproductive indices in either the first or second generation.|Methyl salicylate (MS) ... was tested to update & expand the reproductive toxicity database, & used, in part, as a known positive: it was simultaneously tested by two different labs at different doses, using the RACB protocol & Swiss mice. Food & water consumptions, clinical signs, & body weights were used in the Task 1 dose-range-finding study to set doses for the continuous cohabitation phase (Task 2) at 100, 250, & 500 mg/kg/day by gavage in corn oil. Deaths occurred at a rate of 3, 2, 2, & 4 mice/group in the control to high dose groups, respectively. The causes of death varied, & were ultimately not considered due to MS exposure. There were no effects of MS exposure on body weights during Task 2. There was a 9% reduction in the mean number of litters/pair at the high dose, & a 31% reduction in the number of live pups/litter (from a control value of 11.3, to 7.8 pups/litter). While the viability & sex ratio of these pups was not altered, the pup weight adjusted for litter size in the middle & high dose groups was decreased by 3% & 6%, respectively. MS exposure increased the time to deliver each litter in the high dose group, starting with the second litter, by 2-3 days. These effects led to Task 3 in an attempt to define the affected sex using the control & high dose groups. MS exposure caused no discernible effects on the proportion of pairs mating or delivering pups, nor on the number, viability, or adjusted weight of those pups. Because only 5 of 17 control X control pairs delivered any young, Task 3 was repeated. Though 7 of 17 pairs delivered young, the same lack of MS effects were observed as in the first trial. It was decided that the animals should be killed & discarded. No necropsy was performed, & the second generation was not evaluated. In summary, MS exposure, at dose levels that did not alter body weight or produce adverse clinical signs, adversely affected reproduction (reduced numbers of litters/pair, & number of pups/litter) in Swiss mice.

Degree of albumin binding depends on the plasma concentration of the compound

Methyl salicylate occurs in the leaves of Gaulteria procumbens L. Ericacae, in the bark of Betula lenta L. Betulaceae(1) and in the leaves of Burnum dilitatum(2). It was tentatively identified in emissions from agricultural and natural plant species in the San Joaquin and Sacramento Valley in California(3).

Methyl salicylate may be released to the environment in effluent and emission as a result of its production, transport, disposal and use as a flavoring in foods, beverages, pharmaceuticals(1) and dentrifices(2), fragrance agent in cosmetics and perfumes(2), UV-absorber in sunburn lotions(1) counterirritant in some ointments and linaments(3), carrier for fabric dyes and UV stabilizer in acrylic resins(2).

TERRESTRIAL FATE: If released on soil, methyl salicylate would readily leach. It would also be expected to partially volatilize from dry soil and photolyze on the soil surface. Based on the results of sceening tests, it would be expected to readily biodregrade. Chemical hydrolysis may be important in alkaline soil. (SRC)|AQUATIC FATE: Methyl salicylate is readily biodegradable in screening tests and may be expected to biodegrade in surface waters. Methyl salicylate is expected to hydrolyze in water, the hydrolysis rate increasing with pH. At pH 7.5, its hydrolysis half-life is estimated to be 14.1 days(1,2,SRC). Methyl salicylate will react with singlet oxygen in natural surface waters resulting in a half-life of about 52 hr(3). Methyl salicylate absorbs UV radiation >290 nm and therefore may undergo direct photolysis under environmental conditions. Based on an estimated Henry's Law constant of 9.3X10-7 atm-cu-m/mol(4,5,SRC), a volatilization half-life of 49 days would be expected in a model river(SRC).|ATMOSPHERIC FATE: Methyl salicylate reacts with photochemically-produced hydroxyl radicals in the atmosphere resulting in an estimated half-life of 1.4 days(1,SRC). It is fairly soluble in water, 7400 mg/L(2) and may be washed out by rain.

Methyl salicylate hydrolyzes in water by acid and base-catalyzed reaction(3). The base-catalyzed rate constant can be estimated to be 4.0X10-2 L/mole-sec if the ortho consituents to the phenyl ring are ignored(4). The half-life of methyl salicylate calculated from this rate constant is 201 days at pH 8(SRC). A rate constant of 1.59X10(-5) sec(-1) was determined for the hydrolysis of methyl salicylate at pH 9.2 and a temperature of 25 °C(1). A half-life of 12.1 hours was calculated from this rate constant(SRC). At pH 11.26 the hydrolysis rate constant was 3.62X10(-3) min(-1) at 24 C(2). A half-life value of 3.2 hours was calculated from this rate constant. Another investigator measured a hydrolysis half-life of 57 min at a pH of 9.48 and temperature of 44 °C(5). Data from these studies indicate a general increase in rate constant with increasing pH as would be expected from abase-catalyzed reaction. Although the two first order rate constants do not lead to identical second order rate constants, an approximate half-life at pH 7.5 of 22 days can be estimated(SRC).|The UV absorption maximum of a methanol solution of methyl salicylate is 305 nm(1) which indicates that methyl salicylate can undergo direct photolysis. One photolysis study was performed which yielded a half-life of methyl salicylate in solution of about 48 min(2). The exact medium was not identified, but the authors stated that compounds with low water solubilities were dissolved in a 10% ethanol-water mixture. Based on the concentration of methyl salicylate which was used (3.5 g/L), and the water solubility of the ester of 7.4 g/L(3), it is likely that the result above was obtained using an ethanol-water mixture or absolute ethanol. The UV dose used in the study was 0.0077 erg/sq cm/min, and the UV wavelengths ranged from 300 nm to 400 nm with a maximum at 350 nm. Direct photolysis may, therefore, be an important degradative process in the environment; no available data, however, were collected under environmental conditions.|Methyl salicylate, which has a pKa of 9.8, reacts with singlet oxygen in water which is produced by sunlight absorbed by humic substances in natural surface waters(1). The rate of the ionized phenol is much greater than that of the neutral molecule and therefore the rate increases with pH. Assuming a steady state concentration of singlet oxygen of 4X10-14 moles/L (47 deg N latitude with noon summer sunlight), the half life of methyl salicylate is 52 hr(1). In the atmosphere, methyl salicylate reacts with photochemically-produced hydroxyl radicals with an estimated rate constant of 11.6X10-12 cu cm/molecule-s(2). Assuming a hydroxyl radical concn of 5X10+5 radicals/cu cm, the half-life of methyl salicylate in the atmosphere would be 1.4 days(SRC).

The log octanol/water partition coefficient for methyl salicylate is 2.55(1). The BCF estimated from this log Kow using a regression equation is 4 which indicates that the ester will not bioconcentrate in fish(SRC).

The Koc for methyl salicylate estimated from molecular structure is 128(1) and is 33(3,SRC) estimated from its water solubility, 7400 mg/L(2), using a regression equation. According to a suggested classification scheme(4), these low Koc values suggest that methyl salicylate would be highly or very highly mobile in soil(SRC).

The Henry's Law constant for methyl salicylate is 9.3X10-7 atm-cu-m/mol(SRC) calculated from its vapor pressure, 0.0343 mm Hg(1), and water solubility, 7400 mg/L(2). Using this value for the Henry's Law constant, one can estimate a volatilization half-life of 49 days in a model river 1 m deep flowing at 1 m/s with a wind speed of 3 m/s(3). Similarly, the volatilization half-life of methyl salicylate from a model lake 1 m deep, with a 0.05 m/s current and a 0.5 m/s wind is estimated to be 359 days. Methyl salicylate sprayed onto air-dried soil volatilizes rapidly(4). The amount of chemical that is adsorbed to the soil, evaporates more slowly by a diffusion-controlled mechanism(4).

SURFACE WATER: Methyl salicylate was identified in 2 surface water within the blast zone of Mount St Helens, WA, 3 months after the volcano erupted(1). In another surface water it was identified 2 months after the volcano erupted but not after 3 months(1).

Methyl salicylate concentrations of 54 ppm in bakery goods, 840 ppm in candy, 59 ppm in non-alcoholic beverages, 8400 ppm in chewing gum, 27 ppm in ice cream and 200 ppm in syrups. Methyl salicylate has been identified as a volatile component of meat(2).|FLAVOR INGREDIENT, METHYL SALICYLATE...NON-ALCOHOLIC BEVERAGES 59 PPM; ICE CREAM, ICES, ETC 27 PPM; CANDY 840 PPM; BAKED GOODS 54 PPM; CHEWING GUM 8400 PPM; SYRUPS 200 PPM.

The primary route of human exposure is the consumption of consumer products which contain methyl salicylate as a flavoring agent. Methyl salicylate is used in chewing gum, baked goods, syrups, candy, non-alcoholic beverages and ice cream. Other potential routes of exposure include dermal contact resulting from its use in perfumes. (SRC)|NIOSH (NOES Survey 1981-1983) has statistically estimated that 284,093 workers are exposed to methyl salicylate in the USA(1). Ninety five percent of exposures are with trade name products containing methyl salicylate(1).

Drug Information

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.

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.|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.|LOCAL ANALGESIC FOR HUMAN AND VETERINARY MEDICINE

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

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

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.

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

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%.|Excreted by kidneys as free salicylic acid (10%), salicyluric acid (75%), salicylic phenolic (10%) and acyl glucuronide (5%), and gentisic acid (less than 1%).|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 ... .|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/|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/|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/|For more Absorption, Distribution and Excretion (Complete) data for METHYL SALICYLATE (6 total), please visit the HSDB record page.

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.|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/|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/

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/

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.

Harmful if swallowed, inhaled, absorbed through skin. Vapor mist is irritating to the eyes, mucous membranes, upper respiratory tract and skin. Ingestion of relatively small amount causes severe poisoning and death. Causes nausea, vomiting, acidosis, pulmonary edema, pneumonia, convulsions and death. (USCG, 1999)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

THE LETHAL DOSE OF METHYL SALICYLATE IS CONSIDERABLY LESS THAN THAT OF SODIUM SALICYLATE. AS LITTLE AS 4 ML (4.7 G) OF METHYL SALICYLATE MAY BE FATAL IN CHILDREN. /METHYL SALICYLATE/|Symptoms of poisoning by methyl salicylate differ little from those described for aspirin. Central excitation, intense hyperpnea, and hyperpyrexia are prominent features. The odor of the drug can easily be detected on the breath and in the urine and vomitus. /Methyl salicylate/|In reviews of methyl salicylate poisoning, dimness of vision is mentioned as occurring in about 15% of all cases, but the nature of the impairment has been poorly characterized, and the impression is given that it is a manifestation of disturbance of the CNS. /Methyl salicylate/|MILD CHRONIC SALICYLATE INTOXICATION IS TERMED SALICYLISM /&/...SYNDROME INCLUDES HEADACHE, DIZZINESS, RINGING IN EARS, DIFFICULTY IN HEARING, DIMNESS OF VISION, MENTAL CONFUSION, LASSITUDE, DROWSINESS, SWEATING, THIRST, HYPERVENTILATION, NAUSEA, VOMITING, & OCCASIONALLY DIARRHEA. /SALICYLATES/|For more Human Toxicity Excerpts (Complete) data for METHYL SALICYLATE (15 total), please visit the HSDB record page.

Hewedolor

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cough. Sore throat. Further see Ingestion.


MAY BE ABSORBED! Redness.


Redness. Pain.

Methyl salicylate Use and Manufacturing

Methods of Manufacturing

...OIL IS WATER-STEAM DISTILLED FROM LEAVES CHARGED INTO THE STILL AND ALLOWED TO MACERATE FOR SEVERAL HR TO HYDROLYZE GAULTHERIN GLUCOSIDE (METHYL SALICYLATE + GLUCOSE). DISTILLATION FROM 5-6 HR YIELDS APPROXIMATELY 0.7% ESSENTIAL OIL. OFTEN ADULTERATED BY CO-DISTILLING SWEET BIRCH BARK.|MOSTLY PREPD BY ESTERIFICATION OF SALICYLIC ACID WITH METHANOL. PRODUCT OF COMMERCE IS ABOUT 99% PURE.

Uses

Used in the preparation of spices, also used as solvents, preservatives and disinfectants. This product has anti-inflammatory and analgesic effects and is widely used in joint and muscle analgesic creams, tinctures and oils. It is also used as a solvent and various intermediates in the manufacture of insecticides, fungicides, polishes, anti-copper agents, spices, food, cosmetics, toothpaste, coatings, inks and fiber dye additives. Use solvent, stimulant. Topically used for joint or muscle pain. UV absorber in fragrance and sunscreen lotion.


Odor agents


Air care products

Production

1,000,000 - 10,000,000 lb|25,000 - 100,000 lb|(1976) 1.27X10+8 G (MIN CONSUMPTION IN FOODS)|(1978) 4.09X10+7 G (CONSUMPTION AS FRAGRANCE)

USP: LINIMENT, COMPOUND: MENTHOL 4.5 G, CAMPHOR OIL RECTIFIED 25 ML, OLIVE OR PEANUT OIL 30 ML, METHYL SALICYLATE TO MAKE 100 ML. OINTMENT, COMPOUND: METHYL SALICYLATE 10 ML, MENTHOL 10 G, WHITE WAX 5 G, HYDROUS WOOL FAT TO MAKE 100 G.|USP: SPIRIT, PHENOLATED (PODIATRY): LIQUEFIED PHENOL 1 ML, METHYL SALICYLATE 3 ML, COMPOUND MYRCIA SPIRIT 25 ML, ALCOHOL RUBBING COMPOUND TO MAKE 100 ML.|GRADES: TECHNICAL; USP; FCC.

All other chemical product and preparation manufacturing|Benzoic acid, 2-hydroxy-, methyl ester: ACTIVE|Oils, wintergreen: ACTIVE|Oils, sweet birch: ACTIVE|WINTERGREEN: DESCRIPTION OF BOTANICAL SOURCE: EVERGREEN SHRUB WITH SLENDER, CREEPING STEMS, ASSURGENT, FLOWERING BRANCHES WITH LEAVES CLUSTERED AT TOP, WHITE, BELL-SHAPED FLOWERS BLOSSOMING IN JULY-AUGUST, FOLLOWED BY RED BERRIES (CHECKERBERRY). ...IN WOODS OF CANADA AND US.|VET: NATURAL & SYNTHETIC GRADES ARE USED INTERCHANGEABLY.|METHYL SALICYLATE MUST BE LABELED TO INDICATE WHETHER IT WAS MADE SYNTHETICALLY OR DISTILLED FROM...PLANTS...|IN USP, GAULTHERIA OIL, BETULA OIL, & METHYL SALICYLATE ARE COMBINED UNDER SAME TITLE...IT IS DIFFICULT TO DISTINGUISH BETWEEN THEM CHEMICALLY &...SAME TEST APPLY TO ALL. ...SLIGHT DIFFERENCES IN SPECIFIC GRAVITY & OPTICAL ACTIVITY BUT THESE FACTORS ARE NOT SUFFICIENTLY CHARACTERISTIC TO ENABLE DETECTION OF EITHER IN MIXT.

QUANTITATIVE FOR METHYL SALICYLATE OFFICIAL FINAL ACTION, GAS CHROMATOGRAPHY.|NMR PROCEDURE IS DESCRIBED FOR QUANTITATIVE DETERMINATION OF METHYL SALICYLATE AS DRUG ENTITY & IN WINTERGREEN OIL.|CONCN OF SALICYLATES OR OTHER COMPLEXING AGENTS IN 26 SAMPLES OF 20 DIFFERENT FLAVORS WAS DETERMINED. COLORIMETRIC METHOD PROVIDING SENSITIVITY TO APPROX 1 PPM WAS USED.

Food additives -> Flavoring Agents|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Pharmaceuticals|Cosmetics -> Denaturant; Skin conditioning; Soothing; Tonic

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:152.15
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:152.047344113
Monoisotopic Mass:152.047344113
Topological Polar Surface Area:46.5
Heavy Atom Count:11
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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  • Data: 2026-08-16
  • Price: 19400.00Yuan/ton
  • Change: 0

Drug Function and Efficacy

The various aconitines contained in Chuanwu and Caowu have obvious analgesic, sedative, anti-inflammatory and local anesthetic effects. Caowu also has obvious effects of promoting swelling reduction and antipyretic. Chuanxiong, Angelica, Carthamus tinctorius, and Paeonia lactiflora all have the effects of improving blood circulation, anti-inflammatory, sedative and analgesic. Paeonia lactiflora also has antispasmodic, antipyretic, anticonvulsant and anti-ulcer effects. Cinnamon twig, Nepeta tenuifolia, Saposhnikovia divaricata, and Notopterygium incisum all contain volatile oils, which have the effects of vasodilating, sweating, antipyretic, antibacterial and analgesic. Duhuo contains volatile oils, angelica alcohol, angelicain, etc., which have anti-arthritis, analgesic, sedative and hypnotic effects, and can directly dilate blood vessels, lower blood pressure, and excite the central nervous system. Gentiana macrophylla alkaloid A has antipyretic, sedative, analgesic and anti-inflammatory effects. Its efficacy on animal formaldehyde or egg white arthritis is similar to that of salicylic acid, and it has anti-histamine and capillary permeability reducing effects. Asarum contains volatile oils, which have sedative, analgesic, antitussive, antipyretic and local anesthetic effects. Pepper contains capsaicin and dihydrocapsaicin, which can cause redness on the skin when applied externally, causing the local blood vessels of the skin to dilate reflexively and promote the vigorous local blood circulation. Camphor also has a foaming and reddening effect. In addition to its antibacterial, sweating, antipyretic and central nervous system stimulating effects, mint can also paralyze nerve endings when applied externally, and has anti-inflammatory, analgesic, antipruritic and cooling effects. The whole recipe has the effects of dilating skin blood vessels, improving microcirculation, anti-inflammatory and analgesic, reducing capillary permeability, relieving spasms, antipyretic and local anesthesia.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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Registered Holders

  • JQC HUAYIN PHARMACEUTICAL CO LTD

    United States United States
    Active
  • UBE CORPORATION

    United States United States
    Active
  • UBE株式会社

    Japan Japan
    Active

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