4-Aminobutanoate

Base Information

• Chemical Name: 4-Aminobutanoate
• CAS No.: 56-12-2
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.121
• Hs Code.: 29224995
• Pharos Ligand ID: 1S8NDJGNKAGX
• Mol file: 56-12-2.mol

Synonyms:4-azaniumylbutanoate;4-aminobutanoate;4-aminobutyrate;gamma-aminobutyrate;4euo;4-ammoniobutanoate;gamma-amino-N-butyrate;g-amino-n-butyric acid;3ip9;D04QAC;CHEBI:59888;gamma-aminobutyric acid zwitterion;4-Aminobutyric acid;A830919

Chemical Property of 4-Aminobutanoate

Chemical Property:

• Appearance/Colour: White microcrystalline powder
• Vapor Pressure: 0.00798mmHg at 25°C
• Melting Point: 195 °C (dec.)(lit.)
• Refractive Index: 1.465
• Boiling Point: 247.985 °C at 760 mmHg
• PKA: 4.031(at 25℃)
• Flash Point: 103.778 °C
• PSA: 63.32000
• Density: 1.11 g/cm³
• LogP: 0.51020
• Storage Temp.: Store at RT.
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: SOLUBLE
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 103.063328530
• Heavy Atom Count: 7
• Complexity: 57.2

Purity/Quality:

≥ 99% ^*data from raw suppliers

GABA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(=O)[O-])C[NH3+]
• 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.
• 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.
• Biological Functions: Neuro transmitter In vertebrates, GABA acts at inhibitory synapses in the brain by binding to specific transmembrane receptors in the plasma membrane of both pre- and postsynaptic neuronal processes. This binding causes the opening of ion channels to allow the flow of either negatively charged chloride ions into the cell or positively charged potassium ions out of the cell. This action results in a negative change in the transmembrane potential, usually causing hyperpolarization. Two general classes of GABA receptor are known: GABAA in which the receptor is part of a ligand-gated ion channel complex, and GABAB metabotropic receptors, which are G protein-coupled receptors that open or close ion channels via intermediaries (G proteins).Neurons that produce GABA as their output are called GABAergic neurons, and have chiefly inhibitory action at receptors in the adult vertebrate. Medium Spiny Cells are a typical example of inhibitory CNS GABAergic cells. In contrast, GABA exhibits both excitatory and inhibitory actions in insects, mediating muscle activation at synapses between nerves and muscle cells, and also the stimulation of certain glands. In mammals, some GABAergic neurons, such as chandelier cells, are also able to excite their glutamatergic counterparts.Brain developmentWhile GABA is an inhibitory transmitter in the mature brain, its actions are primarily excitatory in the developing brain. The gradient of chloride is reversed in immature neurons, and its reversal potential is higher than the resting membrane potential of the cell; activation of a GABA-A receptor thus leads to efflux of Cl- ions from the cell, i.e. a depolarizing current. The differential gradient of chloride in immature neurons is primarily due to the higher concentration of NKCC1 co-transporters relative to KCC2 cotransporters in immature cells. GABA itself is partially responsible for orchestrating the maturation of ion pumps . GABA-ergic interneurons mature faster in the hippocampus and the GABA signalling machinery appears earlier than glutamatergic transmission. Thus, GABA is the major excitatory neurotransmitter in many regions of the brain before the maturation of glutamateergic synapses.Beyond the nervous systemGABAergic mechanisms have been demonstrated in various peripheral tissues and organs including, but not restricted to the intestine, stomach, pancreas, Fallopian tube, uterus, ovary, testis, kidney, urinary bladder, lung, and liver.

Technology Process of 4-Aminobutanoate

There total 105 articles about 4-Aminobutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-<<(allyloxy)carbonyl>amino>butyric acid (80127-29-3) → 4-amino-n-butyric acid (56-12-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; triphenylphosphine; In diethyl ether; dichloromethane; at 25 ℃; for 18h;

DOI:10.1021/jo00342a048

Reference yield: 91.0%

C12H11NO2 (100340-10-1) → 4-amino-n-butyric acid (56-12-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h; under 750.075 Torr;

DOI:10.1021/jo0104227

Reference yield: 91.0%

4-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)butanamide (1180819-69-5) → 4-amino-n-butyric acid (56-12-2)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 16h;

DOI:10.1021/jacs.6b02718

upstream raw materials:

pyrrolidine

2-pyrrolidinon

2-oxopyrrolidine-3-carboxylic acid ethyl ester

trans-4-aminocrotonic acid

Downstream raw materials:

4-phthalimidobutyric acid

N-Acetyl-4-aminobutyric acid

4-(2,4-dinitro-anilino)-butyric acid

4-guanidinobutyric acid

Refernces

Regioselective synthesis of γ-amino esters, nitriles, sulfones, and pyrrolidinones by nickel-catalyzed reductive coupling of aldimines and activated alkenes

10.1002/anie.200800825

The study presents a nickel-catalyzed reductive coupling reaction for the regioselective synthesis of γ-amino esters, γ-aminonitriles, γ-aminosulfones, and pyrrolidinones, which are derivatives of γ-aminobutyric acid (GABA) and exhibit various biological properties with industrial applications. The reaction involves the coupling of aldimines and activated alkenes using a nickel-1,10-phenanthroline complex as the catalyst. Key chemicals used include 4-fluorobenzaldimine, ethyl acrylate, [NiBr2(phen)], [NiBr2(bipy)], [NiCl2(bipy)], and [NiBr2(phen)] as catalysts, with phenanthroline (phen) and bipyridine (bipy) as ligands. Zn and H2O were used as the reducing agent and proton source, respectively. The study highlights the importance of the choice of ligand and metal in the success of the reaction, with bipyridine-type ligands, particularly phen, being essential. The synthesized products serve as valuable building blocks in the pharmaceutical and chemical industries due to their potential biological activities.