L-プロリン
L-プロリン · プロリン · L(-)-プロリン · L-2-ピロリジンカルボン酸 · L(-)‐プロリン · L‐プロリン · L‐プロリン CRM6016‐A · L-プロリン-D7
識別子と物理属性
| CAS No. | 147-85-3 |
|---|---|
| 分子式 | C5H9NO2 |
| 平均分子量 | 115.13 g/mol |
| 単同位体質量 | 115.06332853 g/mol |
| SMILES | O=C(O)C1CCCN1 |
| InChIKey | ONIBWKKTOPOVIA-UHFFFAOYSA-N |
| PubChem CID | 614 |
| ChEBI | CHEBI:26271 |
| EC No. | 210-189-3 |
| DTXSID | DTXSID9041104 |
| 現地名 | L-プロリン |
化学・物理的性質
| XLogP | -2.5 |
|---|---|
| 極性表面積 | 49.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 103 |
| 物質分類 | Biological Agents -> Amino Acids and Derivatives |
| 医薬品 | Pharmaceuticals |
| Physical Description | Beige solid[Sigma-Aldrich MSDS] |
| 融点 | 228 °C (dec.) (lit.) |
| 比旋光度 | -85.5 º (c=4, H2O) |
| 沸点 | 215.41°C (rough estimate) |
| 密度 | 1.35 |
| 蒸気圧 | 0Pa at 25℃ |
| FEMA | 3319 | L-PROLINE |
| 屈折率 | -85 ° (C=4, H2O) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | H2O: 50 mg/mL溶ける |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 1.95, 10.64(at 25℃) |
| 色 | 白い |
| pH | 6.0-7.0 (25℃, 1M in H2O) |
| 臭い | 100.00%で。無臭 |
| においのタイプ | 無臭 |
| 由来生物 | synthetic |
| JECFA Number | 1425 |
| Merck | 14,7780 |
| BRN | 80810 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 化粧品成分の機能 | スキンコンディショニングヘアコンディショニング |
| InChI | 1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 |
| InChIKey | ONIBWKKTOPOVIA-UHFFFAOYSA-N |
| SMILES | OC(=O)[C@@H]1CCCN1 |
| LogP（分配係数） | -2.54 at 20℃ |
| CAS データベース | 147-85-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Proline(147-85-3) |
| EPAの化学物質情報 | L-Proline (147-85-3) |
化学的特性
L-Proline, an amino acid, is colorless to white crystal or crystalline powder that has a slight, characteristic odor with a slightly sweet taste. It is soluble in water, insoluble in ethanol, diethyl ether and n-butanol, yellow in case of hydrated ninhydrin test solution, glacial acetic acid Red after acidification; pH=6.3, decomposition point is 220-222°C; specific optical rotation [α]20D-85° (0.5-2.0mg/ml, H2O), [α]20D-60.4° (0.5-2.0mg /ml, 5mol/LHCl). It is synthesized from L-glutamine and L-glutamate via L-ornithine in intestine, and from L-ornithine in liver. It is widely used as an ingredient in infusion and infant formula.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 95.5% (21 of 22) of all reports.Not ClassifiedAggregated GHS information provided per 22 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: DL-Proline |
| その他の安全情報 | IMAP assessments - DL-Proline: Environment tier I assessment |
| 有害性の概要 | May cause irritation[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Not Classified |
| F | 3-10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TW3584000 |
| 毒性 | LD50 orally in Rabbit: > 5110 mg/kg |
| 税関コード | 29339990 |
| 危険文句（R） | 36/37/38-22 |
| 化審法 | (9)-1626 届出不要化学物質 |
| 危険表示 | Xi,Xn |
| 安全措置（S） | 24/25-36/37/39-26 |
| 貯蔵分類 | 13 - Non Combustible Solids |
| 有害物質データ | 147-85-3(Hazardous Substances Data) |
用途
解説
L-プロリン，プロリン，(S)-pyrrolidine-2-carboxylic acid．C5H9NO2(115.13)．略号ProまたはP．非必須アミノ酸．タンパク質構成アミノ酸として，また遊離の状態で広く分布している．タンパク質中では，ペプチド鎖の折れ曲がる位置に存在し，特殊な立体構造の保持に役立っている．ゼラチン，ツェイン，グリアジンなどの加水分解物からロダニル酸塩，ライネッケ塩を用いる沈殿法や，亜硝酸を作用させ，α-アミノ酸を分解する方法，あるいは発酵法で製造する．生体内ではグルタミン酸から合成される．L-プロリンは針状晶．分解点220～222 ℃．[α]20D－52.6°(0.5 mol L－1 塩酸)．pK1 1.99，pK2 10.60，pI6.30．水，エタノールに易溶，エーテル，クロロホルムに不溶．γ-ヒドロキシ-，γ-メチル-，γ-メチル-γ-ヒドロキシプロリン類やプロリンベタインもコラーゲンや植物中に見いだされている．弱い甘味がある．
天然物の起源
Reported found as a component in many proteins; also widely occurring as the free acid in natural products. A major constituent of collagen, the main fibrous protein found in bone, cartilage and other connective tissue.
使用
L-Proline is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.
一般的な説明
L-Proline is a non-essential amino acid, which is a building block of proteins. Peptides bond to proline, making it a useful building block for proteins. It can be used as a cell culture media component for the commercial biomanufacturing of therapeutic recombinant proteins and monoclonal antibodies. L-Proline plays important roles in various biological processes. It is involved in the synthesis of collagen, which is one of the most abundant proteins in the human body and provides structural support to tissues such as skin, bone, cartilage, and tendons.
製法・合成法
製造方法
Synthesis of L-proline: Using glutamic acid as a raw material, it is esterified with absolute ethanol under the catalysis of sulfuric acid, and triethanolamine is added to free the aminosulfate to obtain glutamic acid-δ-ethyl ester. The glutamic acid-δ-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.
純化方法
A likely impurity is hydroxyproline. Purify L-proline via its picrate which is crystallised twice from water, then decomposed with 40% H2SO4. The picric acid is extracted with diethyl ether, the H2SO4 in solution is precipitated with Ba(OH)2, and the filtrate is evaporated. The residue is crystallised from hot absolute EtOH [Mellan & Hoover J Am Chem Soc 73 3879 1951] or EtOH/Et2O. Its solubility in H2O is >100%. It sublimes at 182-187o/0.3mm with 99.4% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. It is hygroscopic and is stored in a desiccator. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2178-2199 1961, Beilstein 22 III/IV 8, 22/1 V 31.]