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4-Aminobutyric acid

4-Aminobutyric acid Structure
CAS No.
56-12-2
Chemical Name:
4-Aminobutyric acid
Synonyms
GABA;4-AMINOBUTANOIC ACID;GAMMA-AMINOBUTYRIC ACID;gamma;56-12-6;H-GABA-OH;Y-Aminobutyric acid;4-Aminobutyric acid(GABA);Gammalone;aminobutyric
CBNumber:
CB3184042
Molecular Formula:
C4H9NO2
Molecular Weight:
103.12
MOL File:
56-12-2.mol
MSDS File:
SDS
Modify Date:
2024/6/27 13:31:27

4-Aminobutyric acid Properties

Melting point 195 °C (dec.) (lit.)
Boiling point 248.0±23.0 °C(Predicted)
Density 1.2300 (estimate)
refractive index 1.4650 (estimate)
FEMA 4288 | 4-AMINOBUTYRIC ACID
storage temp. 2-8°C
solubility H2O: 1 M at 20 °C, clear, colorless
pka 4.031(at 25℃)
form Powder
color White to almost white
Odor at 1.00 % in propylene glycol. savory meaty
Odor Type meaty
Water Solubility SOLUBLE
Merck 14,430
JECFA Number 1771
BRN 906818
InChIKey BTCSSZJGUNDROE-UHFFFAOYSA-N
LogP -3.17
CAS DataBase Reference 56-12-2(CAS DataBase Reference)
NIST Chemistry Reference 4-Aminobutanoic acid(56-12-2)
EPA Substance Registry System 4-Aminobutanoic acid (56-12-2)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H312-H315-H319-H332
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-20/21/22
Safety Statements  26-36
WGK Germany  2
RTECS  ES6300000
Hazard Note  Irritant
TSCA  Yes
HS Code  29224995
NFPA 704
1
0 0

4-Aminobutyric acid price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) A5835 γ-Aminobutyric acid BioXtra, ≥99% 56-12-2 10MG ₹1753.65 2022-06-14 Buy
Sigma-Aldrich(India) A5835 γ-Aminobutyric acid BioXtra, ≥99% 56-12-2 10G ₹3680.5 2022-06-14 Buy
Sigma-Aldrich(India) A5835 γ-Aminobutyric acid BioXtra, ≥99% 56-12-2 25G ₹5488.28 2022-06-14 Buy
Sigma-Aldrich(India) A5835 γ-Aminobutyric acid BioXtra, ≥99% 56-12-2 100G ₹11431.2 2022-06-14 Buy
Sigma-Aldrich(India) A2129 γ-Aminobutyric acid ≥99% 56-12-2 10G ₹2013.45 2022-06-14 Buy
Product number Packaging Price Buy
A5835 10MG ₹1753.65 Buy
A5835 10G ₹3680.5 Buy
A5835 25G ₹5488.28 Buy
A5835 100G ₹11431.2 Buy
A2129 10G ₹2013.45 Buy

4-Aminobutyric acid Chemical Properties,Uses,Production

Description

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.

Uses

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.

Preparation

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.

Definition

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.

Pharmacology

Drugs that act as allosteric modulators of GABA receptors (known as GABA analogues or GABAergic drugs) or increase the available amount of GABA typically have relaxing, anti-anxiety, and anti-convulsive effects. Many of the substances below are known to cause anterograde amnesia and retrograde amnesia.
In general, GABA does not cross the blood–brain barrier, although certain areas of the brain that have no effective blood–brain barrier, such as the periventricular nucleus, can be reached by drugs such as systematically injected GABA. At least one study suggests that orally administered GABA increases the amount of Human Growth Hormone. GABA directly injected to the brain has been reported to have both stimulatory and inhibitory effects on the production of growth hormone, depending on the physiology of the individual.

Side effects

When taken as recommended, side effects of GABA supplements are few and rare. However, researchers have reported some temporary effects, especially when taking higher doses. These side effects may include: Slight burning in the throat; Intermittent and brief shortness of breath; Moderate drop in blood pressure; Tingling in the skin; Drowsiness.

Source

4-Aminobutyric acid can be found in various foods, including:
Tea
Tomatoes
Soybeans
Germinated rice
Some fermented foods, such as tempe and kimchi
Some vegetables, such as broccoli, spinach, and kale
GABA is also widely available as a supplement in either powder or pill form.

Metabolism

GABA transaminase enzyme catalyzes the conversion of 4- aminobutanoic acid and 2-oxoglutarate into succinic semialdehyde and glutamate. Succinic semialdehyde is then oxidized into succinic acid by succinic semialdehyde dehydrogenase and as such enters the citric acid cycle as a usable source of energy.

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