基本的な属性 MSDS 用途と合成の方法 サプライヤー

L-メチオニン

基本的な属性 MSDS 用途と合成の方法 サプライヤー
L-メチオニン
  • 化学名:L-メチオニン
  • 英語化学名:L-Methionine
  • CAS番号:63-68-3
  • 分子式:C5H11NO2S
  • 分子量:149.21
  • EINECS:200-562-9
  • Mol File:63-68-3.mol
  • L-メチオニン
L-メチオニン 性質
  • 融点 284 °C (dec.)(lit.)
  • 比旋光度 23.25 º (c=2, 6N HCl)
  • 沸点 393.91°C (estimate)
  • 比重(密度) 1,34g/cm
  • 屈折率 1.5216 (estimate)
  • 貯蔵温度 Store at RT.
  • 溶解性1 M HCl: 0.5 M at 20 °C, clear, colorless
  • 外見 Solid
  • 酸解離定数(Pka)2.13(at 25℃)
  • White
  • PH5-7 (10g/l, H2O, 20℃)
  • 光学活性 (optical activity)[α]20/D +23.7±0.5°, c = 5% in 5 M HCl
  • 水溶解度 Soluble
  • 極大吸収波長 (λmax)λ: 260 nm Amax: 0.40
    λ: 280 nm Amax: 0.05
  • Merck 14,5975
  • BRN 1722294
  • 安定性:Stable. Incompatible with strong oxidizing agents.
  • CAS データベース63-68-3(CAS DataBase Reference)
  • NISTの化学物質情報L-Methionine(63-68-3)
  • EPAの化学物質情報L-Methionine (63-68-3)
セキュリティ情報
MSDS Information
L-メチオニン 用途と合成の方法
  • 外観白色, 結晶~結晶性粉末
  • 定義本品は、次の化学式で表されるアミノ酸である。
  • 溶解性水100gに3g (0℃), 5.6g (30℃)溶解。有機溶媒に不溶。酸, アルカリ溶液に可溶。水にやや溶けやすく、エタノールに極めて溶けにくく、ジエチルエーテルにほとんど溶けない。塩酸又は水酸化ナトリウム溶液に溶ける。
  • 化粧品の成分用途ヘアコンディショニング剤、皮膚コンディショニング剤
  • 効能解毒薬
  • 説明Colorless or white lustrous plates, or a white crystalline powder. It has a slight, characteristic odor. It is soluble in water, in alkali solutions, and in dilute mineral acids. It is slightly soluble in alcohol and practically insoluble in ether.
  • 化学的特性White crystalline powder
  • 化学的特性Methionine occurs as a white or almost white, crystalline powder or colorless crystals.
  • OriginatorMeonine ,Ives,US,1944
  • 使用methionine is slows down and normalizes oil gland sebum production. Methionine is also used as a texturizer in cosmetic creams. It is an essential amino acid found in a number of proteins and obtained by means of fermentation.
  • 使用Essential aminoacid for human development. Hepatoprotectant; antidote (acetominophen poisoning); urinary acidifier.
  • 定義ChEBI: The L-enantiomer of methionine.
  • 調製方法Numerous methods have been described for manufacture of methionine, including hydrolysis of methionine amide )and 5-(bmethylmercaptoethyl)- hydantoin.
  • Manufacturing ProcessA 3-necked flask fitted with a stirrer, thermometer, gas inlet, dropping funnel, and brine-cooled reflux condenser was charged with 53 g (1.1 mol) methyl mercaptan and 0.35 g mercuric methyl mercaptide. After admitting 56 g (1.0mol) of acrolein during the course of 15 minutes with an inside temperature of about 10°C, the temperature was allowed to rise spontaneously to 75°C, at which point an ice bath was applied. There was no indication of further reaction one hour after the addition of the acrolein. Distillation of the product gave 71 g (yield 68%) of β-methylmercaptopropionaldehyde, as described in US Patent 2,584,496.
    Then as described in US Patent 2,732,400, β-methylmercaptopropionaldehyde (0.60 M) (56.5 g) is added to a stirred solution of sodium cyanide (0.66 M) (32.4 g) and ammonium chloride (0.63 M) (33.7 g) in water (140 ml). The temperature of the mixture rises to 49°C and is maintained at this point by heat evolution for about 5 minutes when it slowly begins to fall. Methanol (50 ml) is added and the mixture is stirred for 4 hours as the temperature falls to 28°C (room temperature).
    After chilling to +12°C, additional methanol (35 ml) and a concentrated aqueous ammoniun hydroxide solution (1.4 M) (100 ml) are added and stirring is continued for 2 hours at a temperature maintained at from +5° to +15°C. The organic layer is separated and solvent is stripped from the aqueous layer at water aspirator pressure at a temperature below 40°C. The residue is extracted several times with chloroform and the chloroform extracts are combined with the separated oil. Chloroform is removed at water aspirator pressure at a temperature below 35°C to leave crude α-amino-γmethylmercaptobutyronitrile (methionine nitrile) in 88% yield (68 g) as a clear, somewhat viscous oil.
    The methionine nitrile (20 g) is dissolved in a solution prepared from 50 ml of aqueous 5 N sodium hydroxide solution and 65 ml of ethanol. The solution is then refluxed for 24 hours; ammonia is evolved. The solution is treated with activated carbon, filtered, acidified with glacial acetic acid (17 ml), chilled to - 10°C and filtered to give crude product. This crude product is then slurried with a solution made up of 20 ml of water and 20 ml of methanol, filtered at - 5° to +10°C and dried to give dl-methionine as white platelets.
  • Therapeutic FunctionLipotropic
  • Synthesis Reference(s)Canadian Journal of Chemistry, 47, p. 3271, 1969 DOI: 10.1139/v69-542
    Organic Syntheses, Coll. Vol. 2, p. 384, 1943
    Synthetic Communications, 26, p. 3619, 1996
  • 一般的な説明Minute hexagonal plates from dilute alcohol.
  • 空気と水の反応Reacts with water, steam, and/or acids to produce toxic and flammable vapors of hydrogen sulfide . Water soluble . pH of 1% aqueous solution is 5.6-6.0.
  • 反応プロフィールAn organosulfide and amine derivative, carboxylic acid. Look at Reactive Groups 20 (organosulfides), 7 (amines), and 3 (carboxylic acids) may give indications about reactive tendencies. L-Methionine is an amino acid essential in human nutrition.
  • 健康ハザードACUTE/CHRONIC HAZARDS: L-Methionine is dangerous when heated to decomposition; it emits dangerous and highly toxic fumes.
  • 火災危険Flash point data for L-Methionine is not available, but L-Methionine is probably combustible.
  • 応用例(製薬)Methionine is used in oral pharmaceutical formulations as a flavoring agent.It has been included in parenteral formulations as a pH controlling agent,and it has also been used experimentally as an antioxidant with antibodies.Methionine is also used therapeutically in oral tablets
  • 安全性プロファイルMildly toxic by ingestion and intraperitoneal routes. Human mutation data reported. An experimental teratogen. Experimental reproductive effects. An essential sulfur-containing amino acid. When heated to decomposition it emits very toxic fumes of NOx and SOx.
  • 安全性Methionine is used in oral pharmaceutical formulations. The pure form of methionine is mildly toxic by ingestion and by the IP route.
    LD50 (rat, IP): 4.328 g/k
    LD50 (rat, oral): 36 g/kg
  • 貯蔵Methionine is sensitive to light and should be stored in a cool, dark place.
  • 純化方法Crystallise L-methionine from aqueous EtOH. Also purify it by dissolving ~0.5g of amino acid in ~10mL of hot H2O, filtering, adjusting the pH to 5.8 with 5N HCl, collecting the solid after addition of ~20mL of EtOH. It is recrystallised by dissolving in H2O and adding EtOH. It sublimes at 197-208o/0.3mm with 99.8% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Milne & Peng J Am Chem Soc 79 647 1957, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2125-2152 1961, Beilstein 4 IV 3189.]
  • 不和合性Methionine is incompatible with strong oxidizing agents.
  • 規制状況(Regulatory Status)Included in the FDA Inactive Ingredients Database (oral tablets). Included in parenteral preparations (injection solutions; powders for reconstitution) licensed in the UK.
L-メチオニンサプライヤー
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