Methyl salicylate
- CAS No.
- 119-36-8
- Chemical Name:
- Methyl salicylate
- Synonyms
- METHYL 2-HYDROXYBENZOATE;METHYL HYDROXYBENZOATE;OIL OF WINTERGREEN;GAULTHERIN;WINTERGREEN;hydroxybenzoate;2-HYDROXYBENZOIC ACID METHYL ESTER;Benzoicacid,2-hydroxy-,methylester;Benzoic acid, 2-hydroxy-, methyl ester;Betula
- CBNumber:
- CB8491046
- Molecular Formula:
- C8H8O3
- Molecular Weight:
- 152.15
- MDL Number:
- MFCD00002214
- MOL File:
- 119-36-8.mol
- MSDS File:
- SDS
| Melting point | -8--7 °C (lit.) |
|---|---|
| Boiling point | 222 °C (lit.) |
| Density | 1.174 g/mL at 25 °C (lit.) |
| vapor density | 5.26 (vs air) |
| vapor pressure | 1 mm Hg ( 54 °C) |
| FEMA | 2745 | METHYL SALICYLATE |
| refractive index |
n |
| Flash point | 226 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Very slightly soluble in water, miscible with ethanol (96 per cent) and with fatty and essential oils. |
| form | Liquid |
| pka | pKa 9.90 (Uncertain) |
| color | Clear colorless to pale yellow |
| Odor | at 10.00 % in dipropylene glycol. wintergreen mint |
| Odor Type | minty |
| Water Solubility | 0.07 g/100 mL (20 ºC) |
| JECFA Number | 899 |
| Merck | 14,6120 |
| BRN | 971516 |
| Dielectric constant | 9.0（20℃） |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| InChIKey | OSWPMRLSEDHDFF-UHFFFAOYSA-N |
| LogP | 2.55 |
| Substances Added to Food (formerly EAFUS) | METHYL SALICYLATE |
| FDA 21 CFR | 175.105; 177.1010; 310.545 |
| CAS DataBase Reference | 119-36-8(CAS DataBase Reference) |
| EWG's Food Scores | 1-3 |
| FDA UNII | LAV5U5022Y |
| NIST Chemistry Reference | 2-Hydroxybenzoic acid methyl ester(119-36-8) |
| EPA Substance Registry System | Methyl salicylate (119-36-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS05,GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H318 | |||||||||
| Precautionary statements | P264-P270-P280-P301+P312-P305+P351+P338-P501 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22-36/38-36/37/38 | |||||||||
| Safety Statements | 26-36-24/25 | |||||||||
| RIDADR | 3082 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | VO4725000 | |||||||||
| F | 8 | |||||||||
| Autoignition Temperature | 847 °F | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29182300 | |||||||||
| Hazardous Substances Data | 119-36-8(Hazardous Substances Data) | |||||||||
| Toxicity | LD50 orally in rats: 887 mg/kg (Jenner) | |||||||||
| NFPA 704 |
|
Methyl salicylate price More Price(53)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | W274518 | Methyl salicylate ≥98%, FCC, FG | 119-36-8 | 1kg | $73.3 | 2024-03-01 | Buy |
| Sigma-Aldrich | W274518 | Methyl salicylate ≥98%, FCC, FG | 119-36-8 | 5kg | $161 | 2024-03-01 | Buy |
| Sigma-Aldrich | W274518 | Methyl salicylate ≥98%, FCC, FG | 119-36-8 | 10Kg | $174 | 2024-03-01 | Buy |
| Sigma-Aldrich | M6752 | Methyl salicylate ReagentPlus?, ≥99% (GC) | 119-36-8 | 1gal | $266 | 2024-03-01 | Buy |
| Sigma-Aldrich | 76631 | Methyl salicylate analytical standard | 119-36-8 | 1mL | $38.7 | 2024-03-01 | Buy |
Methyl salicylate Chemical Properties,Uses,Production
description
Natural material is found in wintergreen oil, oil of wintergreen, birch oil, green tea seed oil, clove oil, Quercetin tree oil, tuberose oil, small when medicated oil, tea oil, ylang ylang oil and cherry, apple, strawberry fruit juice. It is colorless or pale yellow, red or light yellow transparent oily liquid. A strong aroma of wintergreen oil. Relative molecular mass of 152.16. The relative density of 1.1738. Melting point-8.6 ℃. Boiling point 223.3 ℃. A flash point of 96 ℃. The refractive index of 1.5360. It is insoluble in water, soluble in alcohol, ether, acetic acid and other common organic solvents. It is easy to change when exposed in air . Rat oral LD50887mg/kg.
Salicylic acid and methanol are heated to prepare it in the presence of sulfuric acid . Or it is made of stone STSP plant holly leaf through distillation.
Methyl salicylate can be used in the formulation of flavors, mainly for the deployment of ylang ylang, tuberose, chypre, acacia, fougere, orchids. But the most common use is perfuming toothpaste. IFRA has no restrictions.
Methyl salicylate is recognized as GRAS by FEMA, FEMA number 2745, the European Council includes methyl salicylate in health artificial flavorants table which can be used in food without harm to human , the maximum amount is 8400mg/kg, ADI value is 0.5mg/kg.
Methyl salicylate can be used for food flavor formula, is a food flavor within China's GB2760-1996 provisions of the temporary use , ADI value of 0 to 0.5, is commonly used in the deployment of strawberry, vanilla, grapes and other fruit-flavor flavor for food and beer, but also flavor fructose, soft drinks.Methyl salicylate is also used as preservatives, pesticides, polishes, inks, paints, polyester dye carriers in industrial fields
application
Methyl salicylate ointment is a common dermatology drug with analgesic, anti-inflammatory, bactericidal effect. Because it can induce local irritation, it is rarely orally used.When spread in the skin,it is easily absorbed. Its liniments, ointments can be used for acute rheumatoid arthritis, low back pain and muscle pain, also itching and flavoring agents, flavoring agents, preservatives.
Uses
Appropriately use it as modifiers for some floral types , such as ylang ylang, magnolia, acacia, shy flower, tuberose, gardenia, bloom, sweet clover grass.It is mainly used for medicine and hygiene products such as toothpaste, tooth powder, mouthwash, talcum powder, carminative oil. Methyl salicylate can also be used for industrial products such as glue, glue paper, card paste, paste. It can also be used for food flavor,such as strawberries, grapes, walnuts, spearmint, spicy flavor as a special green gas.
Methyl salicylate is used as high-temperature heat carrier in dyeing industry .
The product has similar-Pyrola odor ,when used as a spice, it is often used as flavoring agent for pharmaceutical drugs and the pigmentum.It also has applications in blending spices, such as Quercetin trees in general flavors. Methyl salicylate is also used as solvents and intermediates for the manufacture of pesticides, fungicides, perfumes, paints, cosmetics, ink and dye fibers such help. Methyl salicylate reacts with ammonia to make salicylamide which is used for production of antipyretic analgesics salicylaldehyde ethyl amine ,and salicylamide itself is an anti-inflammatory drug. Methyl salicylate can be obtained by acetylation using acetylsalicylic acid methyl ester (C10H10O4, [580-02-9]). Add methyl salicylate and acetic anhydride into pot ,put sulfuric acid under stirring, the reaction temperature does not exceed 60 ℃ for about 1h, the reaction is completed, the reaction is poured into ice water and precipitated crystals are filtered, washed, dried, and acetylsalicylic acid methyl ester is obtained. Acetylsalicylic acid can be prepared by cyclization to get 4-hydroxy coumarin. Methyl salicylate is used as a pharmaceutical for external application agent.
Perfumes and suntan lotion ultraviolet absorber.
Production Method
Methyl salicylate is widespread in nature, and it is a main ingredient of wintergreen, small medicated oil . Alsoit is present in essential oils of the tuberose, Quercetin tree, ylang ylang, cloves, tea. Salicylic acid and methanol are used to make it in the presence of sulfuric acid through esterification. Salicylic acid is dissolved in methanol, add sulfuric acid, heat with stirring, the reaction time is 3h,90-100℃, cool to below 30 ℃,take oil ,wash with sodium carbonate solution to pH8 above, and then wash 1 time with water. Vacuum distillation, collect 95-110 ℃ (1.33-2.0kPa) distillate, obtain methyl salicylate. The yield is over 80%. General industrial methyl salicylate content is 99.5%. Material consumption fixed: Acid 950kg/t, methanol 400kg/t.
Description
Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic ester that is naturally produced by many species of plants. Some of the plants which produce it are called wintergreens, hence the common name. This compound is used as a fragrance. It is also found in liniments (rubbing ointments).
Chemical Properties
Wintergreen is an evergreen shrub with slender, creeping stems, assurgent, flowering branches with toothed leaves clustered at the top, white, bell-shaped flowers blossoming July to August, followed by red berries (checkerberries). The plant grows extensively in the woods of Canada and the United States (Pennsylvania). The leaves are harvested between June and September. Wintergreen has an aromatic odor and flavor similar to methyl salicylate.
Chemical Properties
Methyl Salicylate is the main component of wintergreen oil and occurs in small quantities in other essential oils and fruits. It is a colorless liquid with a characteristic wintergreen-like odor. May be prepared by extraction from natural sources; or by esterification of salicylic acid with methanol.
Occurrence
Numerous plants produce methyl salicylate in very small amounts. Some plants, such as the following, produce more:
Some species of the genus Gaultheria in the family Ericaceae, including Gaultheria procumbens, the wintergreen or eastern teaberry;
Some species of the genus Betula in the family Betulaceae, particularly those in the subgenus Betulenta such as B. lenta, the black birch;
All species of the genus Spiraea in the family Rosaceae, also called the meadowsweets.
This compound is produced most likely as an anti-herbivore defense. If the plant is infected with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of beneficial insects to kill the herbivorous insects.Aside from its toxicity, methyl salicylate may also be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus.
Uses
Potent inhibitor of ornithine decarboxylase
Uses
Methyl salicylate is used in high concentrations as a rubefacient in deep heating liniments (such as Bengay) to treat joint and muscular pain. Randomised double blind trial reviews report evidence of its effectiveness that is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counter-irritation. However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.
It is used in low concentrations as a flavoring agent (no more than 0.04 %; it is toxic). It is also used to provide fragrance to various products and as an odor-masking agent for some organophosphate pesticides . If used excessively, it can cause stomach and kidney problems.
Methyl salicylate is among the compounds that attract male orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.
Uses
Methyl salicylate occurs in the leaves ofGaultheria procumbens L. and in the barkof Betulaceae. It is produced by esterificationof salicylic acid with methanol. It is used inperfumery and as a flavoring agent.
Uses
In high concentrations as a rubefacient in deep heating liniments (such as Bengay) to treat joint and muscular pain. Randomised double blind trial reviews report evidence of its effectiveness that is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counter-irritation. However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.
In low concentrations as a flavoring agent (no more than 0.04%; it is toxic).
providing fragrance to various products and as an odor-masking agent for some organophosphate pesticides. If used excessively, it can cause stomach and kidney problems.
Attracting male orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.
Clear plant or animal tissue samples of color, and as such is useful for microscopy and immunohistochemistry when excess pigments obscure structures or block light in the tissue being examined. This clearing generally only takes a few minutes, but the tissue must first be dehydrated in alcohol.
A mint flavoring in some kinds of chewing gum and candy, as an alternative to the more common peppermint and spearmint oils. It can also be found as a flavoring of root beer. It is also a potentially entertaining source of tri boluminescence ; when mixed with sugar and dried, it gains the tendency to build up electrical charge when crushed or rubbed. This effect can be observed by crushing wintergreen Life Savers candy in a dark room.
Uses
Methyl salicylate is an organic ester that is commonly produced naturally by wintergreens. Methyl salicylate is utilize as a anti-herbivore defense system in various plants that produces it. Methyl sa licylate is also used in high concentrations as a rubefacient to treat joint, muscular pain and acute pain. Methyl slicylate is also used as a flavoring agent and often used to provide fragrance to pr oducts.
Definition
ChEBI: 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, a member of salicylates and a methyl ester. It is functionally related to a salicylic acid.
Production Methods
Methyl acetate, a novel acyl acceptor for biodiesel production has been developed, and a comparative study on Novozym 435-catalyzed transesterification of soybean oil for biodiesel production with different acyl acceptors has been studied (Noureddini et al., 2005).
Figure 1 shows the effect of the molar ratio of methanol to sunflower oil on the methyl ester yield for catalytic (3% CaO) transesterification in supercritical methanol at 523 K.
Preparation
Methyl salicylate can be produced by esterifying salicylic acid with methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens (eastern teaberry or winter green).
Composition
The leaves of wintergreen are reported to contain arbutin, caffeic acid, ericolin, ferulic acid, gaultherase, gaultheric acid, gaultherin, gentisinc acid, methyl salicylate (5445 to 7920 ppm) o-pyrocatachuic acid, p-coumaric acid, p-hydroxybenzoic acid, primverose, protocatachuic acid, syringic acid, tannic acid, tannin, tricontane and vallininc acid.
Aroma threshold values
Detection: 40 ppb
Taste threshold values
Taste characteristics at 10 ppm: sweet, salicylate and root beer with aromatic and balsamic nuances
Synthesis Reference(s)
Canadian Journal of Chemistry, 61, p. 688, 1983 DOI: 10.1139/v83-127
The Journal of Organic Chemistry, 40, p. 3649, 1975 DOI: 10.1021/jo00913a007
Tetrahedron Letters, 37, p. 153, 1996 DOI: 10.1016/0040-4039(95)02120-5
General Description
Colorless yellowish or reddish liquid with odor of wintergreen.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
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. Birch-Me is incompatible with oxidizers. Birch-Me is also incompatible with strong bases. Birch-Me may react with iron salts.
Hazard
Toxic by ingestion; use in foods restrictedby FDA, lethal dose 30 cc in adults, 10 cc in chil-dren.
Health Hazard
Methyl salicylate is a highly toxic compound.The toxic symptoms in humans include nausea, vomiting, gastritis, diarrhea, respiratorystimulation, labored breathing, pulmonaryedema, convulsions, and coma. Ingestion of15 to 25 mL of this compound may befatal to humans. Application of the liquidon the skin and eyes produced severe irrita tion in rabbits. Oral, subcutaneous, or der mal administration of methyl salicylate intest animals produced specific developmen tal abnormalities affecting the eyes, ears, andcentral nervous system
Toxicity of this compound is relativelymore severe in humans than in many com mon laboratory animals. The oral LD50 values in test animals were within the range800–1300 mg/kg.
Fire Hazard
Methyl salicylate is combustible.
Flammability and Explosibility
Non flammable
Contact allergens
This anti-inflammatory agent is found in a wide number of ointments and can induce allergic contact dermatitis.
Biochem/physiol Actions
Methyl salicylate plays an important role in fruit ripening. It is known to attract natural enemies of herbivores. MeSA inhibits the activity of aminocyclopropane-1-carboxylic acid synthase (ACC synthase) and aminocyclopropane-1-carboxylic acid oxidase (ACC oxidase) in plums and tomatoes, it can inhibit fungal infections and reduce chilling injury symptoms in fruits like pomegranates. This oil of wintergreen is of great interest in the tobacco industry as a flavorant. It has counter irritant and anti-inflammatory effects.
Safety
In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate, which is equivalent to more than twenty- three 300 mg aspirin tablets. The lowest published lethal dose is 101 mg / kg body weight in adult humans , (or 7.07 grams for a 70 - kg adult). It has proven fatal to small children in doses as small as 4 ml.[6] A seventeen-year- old cross - country runner at Notre Dame Academy on Staten Island, died in April 2007, after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products.
Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children. Some people have intentionally ingested large amounts of oil of wintergreen. Salicylate, the major metabolite of methyl salicylate, may be quantitated in blood, plasma or serum to confirm a diagnosis of poisoning in hospitalized patients or to assist in an autopsy.
Safety Profile
Human poison by ingestion. Moderately toxic to humans by an unspecified route. Moderately toxic experimentally by intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: flaccid paralysis without anesthesia, general anesthesia, dyspnea, nausea, vomiting, and respiratory stimulation. Experimental reproductive effects. A severe skin and eye irritant. Ingestion of relatively small amounts has caused severe poisoning and death. Combustible liquid when exposed to heat or flame; can react with oxibzing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Synthesis
By esterification from natural sources; by esterification of salicylic acid with methanol
Carcinogenicity
Available data suggest that methyl salicylate is not carcinogenic.
Purification Methods
Dilute the ester with Et2O, wash with saturated NaHCO3 (it may effervesce due to the presence of free acid), brine, dry MgSO4, filter, evaporate and distil it. Its solubility is 1g/1.5L of H2O. The benzoyl derivative has m 92o (b 270-280o/120mm), and the 3,5-dinitrobenzoate has m 107.5o, and the 3,5-dinitrocarbamoyl derivative has m 180-181o. [Hallas J Chem Soc 5770 1965, Beilstein 10 IV 143.]
Toxicity evaluation
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. Topical methyl salicylate generally rarely causes systemic toxicity, but it can be absorbed by the skin leading to stimulation of the central nervous system respiratory center, disturbance of lipid and carbohydrate metabolism, and disturbance of intracellular respiration. Severe poisoning can lead to acute lung injury, lethargy, coma, seizures, cerebral edema, and death. In the case of salicylate intoxication, treatment includes general supportive care, purification of the gastrointestinal tract with activated charcoal in the case of ingestion of salicylic acid, and monitoring of serum salicylic acid concentration. Bicarbonate infusion or hemodialysis can be used to enhance the elimination of salicylic acid.
Methyl salicylate Preparation Products And Raw materials
Raw materials
1of2
Preparation Products
1of3
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | Mandy@hangyubiotech.com | China | 10986 | 58 |
| Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418679 +8618949832763 | info@tnjchem.com | China | 2986 | 55 |
| Baoji Guokang Healthchem co.,ltd | +8615604608665 15604608665 | dominicguo@gk-bio.com | CHINA | 9414 | 58 |
| ChemFine International Co.,Ltd. | +86-510-82753588 +86-13806194144 | info@chemfineinternational.com | China | 300 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8615531157085 | abby@weibangbio.com | China | 8810 | 58 |
| Shaanxi Dideu Medichem Co. Ltd | +86-29-81148696 +86-15536356810 | 1022@dideu.com | China | 3882 | 58 |
| Wuhan Fortuna Chemical Co., Ltd | +86-027-59207850 | info@fortunachem.com | China | 5975 | 58 |
| Hebei Chuanghai Biotechnology Co,.LTD | +86-13131129325 | sales1@chuanghaibio.com | China | 5889 | 58 |
| Hebei Dangtong Import and export Co LTD | +86-13910575315 +86-13910575315 | admin@hbdangtong.com | China | 1000 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8617732866630 | bess@weibangbio.com | China | 18151 | 58 |
Related articles
- Methyl Salicylate: Synthesis, Composition, Applications, and Storage Insights
- Methyl salicylate is more than just an ingredient; it is a multifaceted compound with broad applications that underscore its s....
- May 22，2024
- Preparation and application of methyl salicylate
- Methyl salicylate is often used as a food additive, and changes in its concentration can also reflect crop diseases.
- Sep 11，2023
- Methyl salicylate: Applications, toxicity, storage, Preparation
- Methyl salicylate, also known as wintergreen oil, is a colorless to pale yellow liquid. It has a characteristic odor of winter....
- Apr 21，2023
View Lastest Price from Methyl salicylate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-12-22 | Methyl salicylate
119-36-8
|
US $1000.00-800.00 / kg | 1kg | 99% | 5000 | HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD | |
 |
2024-12-20 | Methyl salicylate
119-36-8
|
US $0.00 / kg | 1kg | 99.0% | 1tons | Henan Suikang Pharmaceutical Co.,Ltd. | |
 |
2024-12-20 | Methyl salicylate
119-36-8
|
US $6.00 / kg | 1kg | 99% | 2000KG/Month | HebeiShuoshengImportandExportco.,Ltd |
-
- Methyl salicylate
119-36-8
- US $1000.00-800.00 / kg
- 99%
- HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
-
- Methyl salicylate
119-36-8
- US $0.00 / kg
- 99.0%
- Henan Suikang Pharmaceutical Co.,Ltd.
-
- Methyl salicylate
119-36-8
- US $6.00 / kg
- 99%
- HebeiShuoshengImportandExportco.,Ltd