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4-アミノ酪酸

Gamma-Aminobutyric Acid

HCID 119
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
56-12-2
標準SMILES
NCCCC(=O)O
InChIKey
BTCSSZJGUNDROE-UHFFFAOYSA-N
分子式
C4H9NO2
平均分子量
103.12 g/mol
単同位体質量
103.06332853

概要

Gamma-aminobutyric acid is a gamma-amino acid that is butanoic acid with the amino substituent located at C-4. It has a role as a neurotransmitter, a signalling molecule, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a monocarboxylic acid and a gamma-amino acid. It is functionally related to a butyric acid. It is a conjugate acid of a gamma-aminobutyrate. It is a tautomer of a gamma-aminobutyric acid zwitterion.

名称と識別子

優先名称
Gamma-Aminobutyric Acid
IUPAC
4-aminobutanoic acid
現地名
4-アミノ酪酸
英語名
4-Aminobutyric acid
分子式
C4H9NO2
分子量
103.12

名称と別名

gamma-aminobutyric acidGABA56-12-2Piperidic acidPiperidinic acidAminalonGaballonMielomadeGamarexGammalonGammarGammasol
名称をさらに表示
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ガマルガマレックスガンマロンピペリジン酸ガンマソール4-アミノブタン酸ガバロンガンマ-アミノ酪酸ミエロマドγアミノ酪酸4-アミノ-n-酪酸4‐アミノ酪酸4-AMINOBUTANOIC ACIDgammaγ-Aminobutyric acidY-Aminobutyric acid56-12-6H-GABA-OHaminobutyric
butanoic acid, 4-amino-GammaloneButyric acid, 4-amino-gamma-Aminobutanoic acidImmu-Ggamma-amino-n-butyric acidGammageeGamulin

データベース識別子

CAS
56-12-2
PubChem CID
119
DTXSID
DTXSID6035106
ChEMBL
CHEMBL96
ChEBI
CHEBI:16865
UNII
2ACZ6IPC6I
Nikkaji
J1.375G

物性

構造計算による物性補完中

XLogP
-3.2
極性表面積
63.3 Ų
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

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
CosmeticsHair conditioning
LogP-3.17
Flavoring AgentsEU Flavoring substances
Solubility · 2 件

1300.0 mg/mL

1.2 [ug/mL] (The mean of the results at pH 7.4)

Melting Point203 °C
Physical DescriptionSolid
Ionization Efficiency · 6 件

Negative

-1.52

10.5

Agilent XCT

Electrospray ionization

ammonia (10nM)

Dissociation Constants10.6

物理化学的性質

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

危険有害性情報

Regulatory Information · 3 件

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Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

毒性情報

Health Effects · 1 件

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
2
tsca
TSCA listed
rtecs
ES6300000
hs_code
29224995
risk_code
36/37/38-20/21/22
化審法
(9)-114
hazard_code
Xi,Xn
hazard_note
Irritant
safety_code
26-36
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

MeSH Pharmacological ClassificationSubstances used for their pharmacological actions on GABAergic systems. GABAergic agents include agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function.
Tissue LocationsAdrenal Cortex
Cellular LocationsExtracellular
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)

用途と製造

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Use ClassificationCosmetics -> Hair conditioning
General Manufacturing InformationButanoic acid, 4-amino-: ACTIVE
応用分野 · 6 件

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.

関連反応

175 件
反応記録を作成
HRID 3261 の反応式
HRID 3261反応物としてuspto-grants-1998_03
HRID 27348 の反応式
HRID 27348反応物としてuspto-grants-1980_09
HRID 53673 の反応式
HRID 53673反応物としてuspto-grants-1997_04
HRID 88543 の反応式
HRID 88543反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 124149 の反応式
HRID 124149反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 178342 の反応式
HRID 178342反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 187270 の反応式
HRID 187270反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 189420 の反応式
HRID 189420反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
融点
195 °C · 195 °C (dec.) (lit.)
沸点
248 · 248.0±23.0 °C(Predicted)
比重(密度)
1.23 · 1.2300 (estimate)
屈折率
1.465 · 1.4650 (estimate)
FEMA
4288 · 4288 | 4-AMINOBUTYRIC ACID
貯蔵温度
2 · 2-8°C
溶解性
2 O: · H2O: 1M at20℃、透明、無色
酸解離定数(Pka)
4.031 · 4.031(at 25℃)
外見
粉
色
白~ほぼ白
臭い (Odor)
1 %。おいしい肉のような · 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
水溶解度
溶ける
Merck
14 · 14,430
JECFA Number
1771 · 1771
BRN
906818 · 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
-3.17 · -3.17
CAS データベース
56 · 56-12-2(CAS DataBase Reference)
NISTの化学物質情報
4 · 4-Aminobutanoic acid(56-12-2)
EPAの化学物質情報
4 · 4-Aminobutanoic acid (56-12-2)
化学的性質 · 1 件

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.

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).

調製方法 · 2 件

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.

上流・下流製品情報

上流原料

Cation exchange resin,strong acidic styrenePotassium phthalimide1-メチル-2-ピロリドン大豆油ヘキサンノイルクロリド2-ピロリドン4-クロロブチロニトリルN,N,N-Tri(polyoxypropylene polyoxyethylene)aminecorn syrup炭酸水素アンモニウム

下流製品

4-アミノ-2-ヒドロキシ酪酸アレンドロン酸アニラセタム4-マレイミド酪酸4-(ジメチルアミノ)ブタン酸塩酸塩4-アミノ酪酸メチル塩酸塩4-(1,3-ジオキソイソインドリン-2-イル)ブタン酸4-(4-Oxo-2-thioxo-thiazolidin-3-yl)-butyric acid
補足説明 · 2 件

定義本品は、次の化学式で表されるアミノ酸である。

定義4-Aminobutyric acid is a gamma-amino acid that is butanoic acid with the amino substituent located at C-4. It has a role as a signalling molecule, a human metabolite, a Saccharomyces cerevisiae metabolite and a neurotransmitter. It is a gamma-amino acid and a monocarboxylic acid. It derives from a butyric acid. It is a conjugate acid of a gamma-aminobutyrate. It is a tautomer of a gamma-aminobutyric acid zwitterion.