4-アミノ酪酸
4-アミノ酪酸 · γ-アミノブタン酸 · γ-アミノ酪酸 · γ-アミノ-酪酸 · ミエロゲン · ギャバ · ガバ · アミナロン
識別子と物理属性
| CAS No. | 56-12-2 |
|---|---|
| 分子式 | C4H9NO2 |
| 平均分子量 | 103.12 g/mol |
| 単同位体質量 | 103.06332853 g/mol |
| SMILES | NCCCC(=O)O |
| InChIKey | BTCSSZJGUNDROE-UHFFFAOYSA-N |
| PubChem CID | 119 |
| ChEMBL | CHEMBL96 |
| ChEBI | CHEBI:16865 |
| DTXSID | DTXSID6035106 |
| 現地名 | 4-アミノ酪酸 |
化学・物理的性質
| XLogP | -3.2 |
|---|---|
| 極性表面積 | 63.3 |
| 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 | 3 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 62.7 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110] |
| 化粧品 | Hair conditioning |
| LogP（分配係数） | -3.17 |
| 香味料 | EU Flavoring substances |
| 溶解度 | 1300.0 mg/mL1.2 [ug/mL] (The mean of the results at pH 7.4)H2O: 1M at20℃、透明、無色溶ける |
| 融点 | 203 °C195 °C (dec.) (lit.) |
| Physical Description | Solid |
| Ionization Efficiency | Negative-1.5210.5Agilent XCTElectrospray ionizationammonia (10nM) |
| Dissociation Constants | 10.6 |
| 沸点 | 248.0±23.0 °C(Predicted) |
| 密度 | 1.2300 (estimate) |
| 屈折率 | 1.4650 (estimate) |
| FEMA | 4288 | 4-AMINOBUTYRIC ACID |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 4.031(at 25℃) |
| 外観・状態 | 粉 |
| 色 | 白～ほぼ白 |
| 臭い | プロピレングリコール中1.00%。おいしい肉のような |
| においのタイプ | 肉の風味 |
| Merck | 14,430 |
| JECFA Number | 1771 |
| BRN | 906818 |
| 化粧品成分の機能 | ヘアコンディショニング |
| InChI | 1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7) |
| InChIKey | BTCSSZJGUNDROE-UHFFFAOYSA-N |
| SMILES | NCCCC(O)=O |
| LogP（分配係数） | -3.17 |
| CAS データベース | 56-12-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 4-Aminobutanoic acid(56-12-2) |
| EPAの化学物質情報 | 4-Aminobutanoic acid (56-12-2) |
化学的特性
4-Aminobutyric acid is a white flake or needle-like crystal; slightly odorous, deliquescence; easily soluble in water, slightly soluble in hot ethanol, insoluble in cold ethanol, ether and benzene; decomposition point is 202°C; LD50 (rat, abdominal cavity) 5400mg/kg.
安全性と法規制
| 規制情報 | Chemical: Butanoic acid, 4-amino-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)gamma-Aminobutyric acid: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 健康影響 | Chronically high levels of GABA are associated with at least 5 inborn errors of metabolism including: D-2-Hydroxyglutaric Aciduria, 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency, GABA-Transaminase Deficiency, Homocarnosinosis and Succinic semialdehyde dehydrogenase deficiency. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | ES6300000 |
| 税関コード | 29224995 |
| 危険文句（R） | 36/37/38-20/21/22 |
| 化審法 | (9)-114 |
| 危険表示 | Xi,Xn |
| hazard_note | Irritant |
| 安全措置（S） | 26-36 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
4-アミノ酪酸,ジャガイモの根茎，リンゴの果肉，マメ科植物の根粒，タバコやチャの葉，哺乳動物の脳髄など，動植物界にかなり広く遊離状態で存在する。4-アミノ酪酸,無色針状晶。4-アミノ酪酸略称 GABA 。融点 203℃ (分解) 。水に易溶，有機溶媒に不溶。生体内でグルタミン酸から脱炭酸酵素の作用で生じる。神経伝達物質の一つ。ブリタニカ国際大百科事典 小項目事典 ブリタニカ
用途
薬理及び生理作用研究用、医薬原料、有機合成原料。
説明
4-Aminobutyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays a role in regulating neuronal excitability throughout the nervous system. In humans, GABA is also directly responsible for the regulation of muscle tone. Although chemically it is an amino acid, GABA is rarely referred to as such in the scientific or medical communities, because the term "amino acid," used without a qualifier, conventionally refers to the alpha amino acids, which GABA is not, nor is it ever incorporated into a protein. In spastic diplegia in humans, GABA absorption becomes impaired by nerves damaged from the condition's upper motor neuron lesion, which leads to hypertonia of the muscles signaled by those nerves that can no longer absorb GABA.
来歴
4-Aminobutyric acid was first synthesized in 1883, and was first known only as a plant and microbe metabolic product. In 1950, however, GABA was discovered to be an integral part of the mammalian central nervous system.
使用
4-Aminobutyric acid is an important inhibitory neurotransmitter in the central nervous system, which has good water solubility and thermal stability. It has been confirmed that GABA, as a small molecular weight non protein amino acid, has edible safety and can be used in the production of beverages and other foods. Studies have shown that a certain amount of GABA can improve the body's sleep quality and reduce blood pressure.The foods contain γ-aminobutyric acid (GABA) at an amount that shows immediate effect of suppressing autonomic nerve activity related to blood pressure increase. Reacts with isothiocyanates to produce thioureas which have antifungal activity.
一般的な説明
4-Aminobutyric acid is a chief inhibitory neurotransmitter, which is found in the cerebellum, hypothalamus, thalamus and hippocampus. It is formed via the decarboxylation of L-glutamate catalyzed by the enzyme, glutamic acid decarboxylase(GAD).
製法・合成法
製造方法
The synthesis of 4-aminobutyric acid mainly includes the following: the first is the use of potassium Phthaloyl imine and γ- Chloroprene cyanogen or butyrolactone is used as the raw material of GABA. The final product obtained after violent reaction and hydrolysis is GABA; The second is to use pyrrolidone as the initial raw material, hydrolyze it through calcium hydroxide and ammonium bicarbonate, and finally open its ring to obtain GABA; The third is to use butyric acid and ammonia as raw materials of GABA γ GABA was obtained by light reaction under X-ray conditions; The fourth method is to synthesize GABA with propylamine and formic acid by glow discharge; The fifth is to use methyl bromoacetate and ethylene as raw materials to prepare GABA. Methyl 4-bromobutyrate is obtained through polymerization. Finally, the product after ammonolysis and hydrolysis is GABA. The chemical synthesis methods of GABA have the disadvantages of difficult reaction control and high cost.
純化方法
Crystallise GABA from aqueous EtOH or MeOH/Et2O. Also crystallise it by dissolving it in the least volume of H2O and adding 5-7 volumes of absolute EtOH.