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Methyl salicylate

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Methyl salicylate Chemical Properties
mp -8 °C
bp 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)
refractive index n20/D 1.536(lit.)
FEMA 2745
Fp 226 °F
Water Solubility 0.07 g/100 mL (20 ºC)
Merck 14,6120
BRN 971516
Stability:Stable. Incompatible with strong oxidizing agents, strong bases.
CAS DataBase Reference119-36-8(CAS DataBase Reference)
NIST Chemistry Reference2-Hydroxybenzoic acid methyl ester(119-36-8)
EPA Substance Registry SystemBenzoic acid, 2-hydroxy-, methyl ester(119-36-8)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/38-36/37/38
Safety Statements 26-36-24/25
RIDADR 3082
WGK Germany 1
RTECS VO4725000
8
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data119-36-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Birch-Me English
SigmaAldrich English
ACROS English
ALFA English
Methyl salicylate Usage And Synthesis
Flavors and fragrancesNatural 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
Dermatology drugsMethyl 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.
Content AnalysisMeasure using Method 1 of ester assay (OT-18) . The amount of sample is 2 g. With 0.5mol / L potassium hydroxide ethanol solution 50.0 ml reflux 2h, phenol red test solution (TS-166) as an titration indicator . Calculation of equivalency factors (e) takes 76.08.
Or it is measured using the non-polar column method of gas chromatography(GT-10-4) .
The above information is edited by the Chemicalbook of Tian Ye.
ToxicityAdl 0 ~ 0.5 mg / kg (FAO / WHO.1994).
LD50887 mg / kg (rat, oral).
Application limitationFEMA (mg / kg): soft drinks 59; cold 27; confectionery 840 ; bakery 54; gum 8400; syrup 200.
The maximum amount permitted of food additives maximum allowable residue limitsThe maximum amount permitted  of food additives  maximum allowable residue limits
Chemical propertiesColorless, oily liquid with holly leaf flavor. Soluble in alcohol, ether, acetic acid, slightly soluble in water.
UsesAppropriately 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. It 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.
It 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 MethodMethyl 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.
CategoryFlammable liquid
Acute toxicityOral - rat LD50: 887 mg / kg; Oral - Mouse LD50: 1110 mg / kg
Chemical Propertiescolourless liquid with an odour of wintergreen
Usageantipyretic analgesics
UsageMethyl 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.
UsagePotent inhibitor of ornithine decarboxylase
Data irritationSkin - rabbit 500 mg / 24 hours of moderate; Eye - rabbit 500 mg / 24 hr mild
Flammability hazard characteristicsCombustible in case of fire, high temperature, strong oxidants ; combustion exhausts irritation smoke
Storage Characteristicspackaging integrity, light loading and unloading; warehouse ventilation, away from open flame, heat, and separate from oxidants
Extinguishing agentMedia Foam, dry powder, carbon dioxide, sand
General DescriptionColorless yellowish or reddish liquid with odor of wintergreen.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileBirch-Me 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.
Health HazardHarmful 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.
Fire HazardBirch-Me is combustible.
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