Grundinformationen
- Standard-SMILES
NCCCC(=O)O- InChIKey
BTCSSZJGUNDROE-UHFFFAOYSA-N- Summenformel
- C4H9NO2
- Durchschnittliche Molmasse
- 103,12 g/mol
- Monoisotopische Masse
- 103,06332853
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Gamma-Aminobutyric Acid
- IUPAC
- 4-aminobutanoic acid
- Lokaler Name
- 4-Aminobuttersure
- Englischer Name
- 4-Aminobutyric acid
- Summenformel
- C4H9NO2
- Molmasse
- 103.12
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
56-12-2- PubChem CID
- 119
- DTXSID
DTXSID6035106- ChEMBL
CHEMBL96- ChEBI
CHEBI:16865- UNII
- 2ACZ6IPC6I
- Nikkaji
- J1.375G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -3,2
- Polarare Oberfläche (TPSA)
- 63,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 62,7
Experimentelle und physikochemische Eigenschaften
Solubility
1300.0 mg/mL
1.2 [ug/mL] (The mean of the results at pH 7.4)
Ionization Efficiency
Negative
-1.52
10.5
Agilent XCT
Electrospray ionization
ammonia (10nM)
Physikochemische Eigenschaften
- Schmelzpunkt
- 195 °C · 195 °C (dec.) (lit.)
- Siedepunkt
- 248 · 248.0±23.0 °C(Predicted)
- Dichte
- 1.23 · 1.2300 (estimate)
- Brechungsindex
- 1.465 · 1.4650 (estimate)
- FEMA
- 4288 · 4288 | 4-AMINOBUTYRIC ACID
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 O: · H2O: 1 M at 20 °C, clear, colorless
- pka
- 4.031 · 4.031(at 25℃)
- Aggregatzustand
- Powder
- Farbe
- White to almost white
- Geruch (Odor)
- 1 % · at 1.00 % in propylene glycol. savory meaty
- Geruchsart
- meaty
- Wasserlöslichkeit
- SOLUBLE
- Merck
- 14 · 14,430
- JECFA Number
- 1771 · 1771
- BRN
- 906818 · 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
- -3.17 · -3.17
- CAS Datenbank
- 56 · 56-12-2(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · 4-Aminobutanoic acid(56-12-2)
- EPA chemische Informationen
- 4 · 4-Aminobutanoic acid (56-12-2)
Sicherheit und Regulatorisches
Gefahrenhinweise
Regulatory Information
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
Toxikologische Informationen
Health Effects
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.
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29224995
- RTECS-Nr.
- ES6300000
- risk_code
- 36/37/38-20/21/22
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
Verwendung und Herstellung
Anwendungen
Beschreibung4-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.
History4-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.
Verwenden4-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.
Darstellung
synthetischeThe 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
Definition4-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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…