サリチル酸メチル

外観

無色～わずかにうすい黄色, 澄明の液体

定義

本品は、サリチル酸(*)のメチルエステルであり、次の化学式で表される。
参照表示名称：サリチル酸

溶解性

エタノール及びアセトンに極めて溶けやすく、水に溶けにくい。

解説

methyl 2-hydroxybenzoate．C8H8O3(152.15)．C6H4(OH)COOCH3．冬緑油，白カバ皮油に90％ 以上含まれるほか，多くの精油に存在する．サリチル酸をエステル化して合成される．強い香気をもつ液体．融点－8.6 ℃，沸点244 ℃．d₁₅¹⁵"1.188．n_D²⁰"1.535～1.538．有機溶媒に可溶，水に微溶．香料として，また消炎剤，神経痛，リウマチ治療薬に用いられる．[CAS 119-36-8]
森北出版「化学辞典（第2版）

解説

サリチル酸の代表的なエステル。o(オルト)-ヒドロキシ安息香酸メチルともよばれる。天然には冬緑(とうりょく)油や白樺(しらかば)油の主成分として存在するほか、広く植物精油中に分布している。実験室的には工業的にもサリチル酸とメタノール（メチルアルコール）とを酸の存在下で反応させて合成する。特有の芳香をもつ無色の液体で、種々の有機溶媒と任意の割合で混じり合う。菓子、チューインガム、歯みがきなどの香料となるほか、消炎剤、神経痛の治療などに軟膏(なんこう)や塗布剤として用いられる。毒性があるので、大量の使用にあたっては注意が必要である。

用途

香料、医薬品原料

用途

サリチル酸にメチル基が付加 された化合物です。プロスタグランジン生合 成阻害作用を示します。

用途

サリチル酸にメチル基が付加 された化合物です。プロスタグランジン生合 成阻害作用を示します。

化粧品の成分用途

変性剤、口腔衛生剤、外用鎮痛剤、香料、香味剤

効能

鎮痛薬, 抗炎症薬

商品名

サリチル酸メチル (東豊薬品)

説明

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).

化学的特性

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 sweet, phenolic odor.

天然物の起源

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.

使用

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.

調製方法

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.

定義

ChEBI: A benzoate ester that is the methyl ester of salicylic acid.

製造方法

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).

一般的な説明

Colorless yellowish or reddish liquid with odor of wintergreen.

空気と水の反応

Insoluble in water.

反応プロフィール

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.

危険性

Toxic by ingestion; use in foods restrictedby FDA, lethal dose 30 cc in adults, 10 cc in chil-dren.

健康ハザード

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.

火災危険

Methyl salicylate is combustible.

接触アレルゲン

This anti-inflammatory agent is found in a wide number of ointments and can induce allergic contact dermatitis.

安全性プロファイル

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.

安全性

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.

発がん性

Available data suggest that methyl salicylate is not carcinogenic.

純化方法

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.