4-Aminobuttersure
GABA · 4-AMINOBUTANOIC ACID · GAMMA-AMINOBUTYRIC ACID · gamma · γ-Aminobutyric acid · Y-Aminobutyric acid · 56-12-6 · H-GABA-OH
Identifikatoren & physikalische Daten
| CAS No. | 56-12-2 |
|---|---|
| Summenformel | C4H9NO2 |
| Durchschnittliche Molmasse | 103,12 g/mol |
| Monoisotopische Masse | 103,06332853 g/mol |
| SMILES | NCCCC(=O)O |
| InChIKey | BTCSSZJGUNDROE-UHFFFAOYSA-N |
| PubChem CID | 119 |
| ChEMBL | CHEMBL96 |
| ChEBI | CHEBI:16865 |
| DTXSID | DTXSID6035106 |
| Lokaler Name | 4-Aminobuttersure |
Chemische & physikalische Eigenschaften
| XLogP | -3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 62,7 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110] |
| Kosmetika | Hair conditioning |
| LogP (Verteilungskoeffizient) | -3.17 |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | 1300.0 mg/mL1.2 [ug/mL] (The mean of the results at pH 7.4)H2O: 1 M at 20 °C, clear, colorlessSOLUBLE |
| Schmelzpunkt | 203 °C195 °C (dec.) (lit.) |
| Physical Description | Solid |
| Ionization Efficiency | Negative-1.5210.5Agilent XCTElectrospray ionizationammonia (10nM) |
| Dissociation Constants | 10.6 |
| Siedepunkt | 248.0±23.0 °C(Predicted) |
| Dichte | 1.2300 (estimate) |
| Brechungsindex | 1.4650 (estimate) |
| FEMA | 4288 | 4-AMINOBUTYRIC ACID |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 4.031(at 25℃) |
| Aggregatzustand | Powder |
| Farbe | White to almost white |
| Geruch | at 1.00 % in propylene glycol. savory meaty |
| Geruchsart | meaty |
| Merck | 14,430 |
| JECFA Number | 1771 |
| BRN | 906818 |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONING |
| 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 (Verteilungskoeffizient) | -3.17 |
| CAS Datenbank | 56-12-2(CAS DataBase Reference) |
| NIST chemische Informationen | 4-Aminobutanoic acid(56-12-2) |
| EPA chemische Informationen | 4-Aminobutanoic acid (56-12-2) |
Sicherheit & Vorschriften
| Regulatorische Informationen | Chemical: Butanoic acid, 4-amino-Commission Regulation (EC) No 1565/2000 (Repealed by Com.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 |
|---|---|
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gesundheitliche Auswirkungen | 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). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29224995 |
| RTECS-Nr. | ES6300000 |
| R-Sätze (R) | 36/37/38-20/21/22 |
| Gefahrensymbole | Xi,Xn |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
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.
History
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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.