56-12-2

Basic information

• Product Name: 4-Aminobutyric acid
• Synonyms: 4-AMINOBUTANOIC ACID;4-AMINOBUTYRIC ACID;4-AMINO-N-BUTYRIC ACID;ALPHA-AMINOBUTANOIC ACID;AMINOBUTYRIC ACID, 4-;AMINOBUTYRIC-4 ACID;AURORA KA-1053;H-4-AMINOBUTYRIC ACID
• CAS NO: 56-12-2
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• EINECS: 200-258-6
• Product Categories: Pharmaceutical Raw Materials;Starting Raw Materials & Intermediates;Amino Acids;Biochemistry;non-Proteinorganic Amino Acids;omega-Aminocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Amino Acids;Food Additives;Peptide;GABA/Glycine receptor;GABA;Aliphatics;Amino Acids & Derivatives;API;Pharmaceutical intermediates
• Mol File: 56-12-2.mol
• Article Data: 148

Chemical Properties

• Melting Point: 195 °C (dec.)(lit.)
• Boiling Point: 247.985 °C at 760 mmHg
• Flash Point: 103.778 °C
• Appearance: White to almost white/Powder
• Density: 1.2300 (estimate)
• Vapor Pressure: 0.00798mmHg at 25°C
• Refractive Index: 1.4650 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 4.031(at 25℃)
• Water Solubility: SOLUBLE
• Merck: 14,430
• BRN: 906818
• CAS DataBase Reference: 4-Aminobutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aminobutyric acid(56-12-2)
• EPA Substance Registry System: 4-Aminobutyric acid(56-12-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: ES6300000
• TSCA: Yes
• Hazardous Substances Data: 56-12-2(Hazardous Substances Data)

Usage

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.

Chemical Properties

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.

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

ChEBI: 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 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.

Aroma threshold values

Medium strength odor; savory meaty type; recommend smelling in a 1.00% solution or less.

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.

General Description

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).

Mechanism of action

4-Aminobutyric acid (GABA) probably represents the most important inhibitory transmitter of the mammalian CNS. Both types of GABAergic inhibition (pre- and postsynaptic) use the same GABAA receptor subtype, which acts by regulation of the chloride channel of the neuronal membrane. A second GABA receptor type, GABAB, that is a G protein–coupled receptor is not considered to be important in understanding the mechanism of hypnotics. Activation of a GABAA receptor by an agonist increases the inhibitory synaptic response of central neurons to GABA through hyperpolarization. Because many, if not all, central neurons receive some GABAergic input, this leads to a mechanism by which CNS activity can be depressed. For example, if the GABAergic interneurons are activated by an agonist that inhibits the monoaminergic structures of the brainstem, hypnotic activity will be observed. The specific neuronal structures in different brain regions affected by GABAA agonist continues to be better defined.

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.

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.

Purification Methods

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.

GABA as a supplement

A number of commercial sources sell formulations of GABA for use as a dietary supplement, sometimes for sublingual administration. These sources typically claim that the supplement has a calming effect. These claims are not yet scientifically proven. For example, there is evidence stating that the calming effects of GABA can be seen observably in the human brain after administration of GABA as an oral supplement. However, there is also evidence that GABA does not cross the blood – brain barrier at significant levels. There are some over-the-counter supplements such as phenylated GABA itself directly, or Phenibut; and Picamilon (both Soviet cosmonaut products) – Picamilon combines niacin and phenylated GABA and crosses the blood–brain barrier as a prodrug that later hydrolyzes into GABA and niacin.

Structure and conformation

4-Aminobutyric acid (GABA) is found mostly as a zwitterion, that is, with the carboxy group deprotonated and the amino group protonated. Its conformation depends on its environment. In the gas phase, a highly folded conformation is strongly favored because of the electrostatic attraction between the two functional groups. The stabilization is about 50 kcal/mol, according to quantum chemistry calculations. In the solid state, a more extended conformation is found, with a trans conformation at the amino end and a gauche conformation at the carboxyl end. This is due to the packing interactions with the neighboring molecules. In solution, five different conformations, some folded and some extended, are found as a result of solvation effects. The conformational flexibility of GABA is important for its biological function, as it has been found to bind to different receptors with different conformations. Many GABA analogues with pharmaceutical applications have more rigid structures in order to control the binding better.

InChI:InChI=1/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)

Synthetic route

calcium 4-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]butanoate (1990-07-4, 16498-47-8, 17097-76-6) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
In water at 100℃; for 1.5h; pH: 0.9;	95.3%
With buffer solutions (acid, neutral and alkaline media) Rate constant; Kinetics; Mechanism; pH range: 2.0 - 10.2, temperature range 60 - 90 deg C, influence of the ionic strength and dielectric constant of the medium;

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

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 2-Ethylhexanoic acid; triphenylphosphine In diethyl ether; dichloromethane at 25℃; for 18h;	92%

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

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 750.075 Torr; for 24h;	91%

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

Conditions	Yield
With hydrogenchloride In water at 110℃; for 16h;	91%

methyl 1-(4-aminobutanoyl)-7-nitroindoline-5-acetate → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
In water pH=7.0; Reactivity; Ammonium phosphate; Photolysis;	88%

L-glutamic acid (56-86-0) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogenchloride; immobilized L-glutamate decarboxylate at 37℃; pH = 4.6;	85%
durch Einwirkung von Decarboxylase-Praeparaten aus Rhizobium leguminosarum;
durch Einwirkung von Decarboxylase-Praeparaten aus Escherichia coli;

3-cyanopropanoic acid (16051-87-9) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With platinum(IV) oxide; hydrogen Acidic conditions;	80%
With ethanol; sodium
With sodium tetrahydroborate; nickel dichloride In N,N-dimethyl-formamide at 20℃;

ethyl 3-cyanopropionate (10137-67-4) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
Stage #1: ethyl 3-cyanopropionate With water; sodium hydroxide for 1.5h; Reflux; Stage #2: With sodium tetrahydroborate; cobalt(II) chloride hexahydrate at 20℃;	50%
With sulfuric acid; acetic acid; platinum Hydrogenation.und Erhitzen des Reaktionsprodukts mit wss.Ba(OH)2;

4-Aminobutanol (13325-10-5) → 4-aminobutyraldehyde (4390-05-0) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With 1H-imidazole; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 1h;	A 39% B 2%

formic acid (64-18-6) + 1-amino-2-propene (107-11-9) → propylamine (107-10-8) + DL-3-aminoisobutyric acid (10569-72-9) + glycine (56-40-6) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogen; oxygen In water for 3h; Product distribution; various unsaturated amines; investigation of the direct carboxylation of C=C bond, the effect of formic acid concentration as well as the flame composition on product(s); radical mechanism is proposed;	A n/a B 38% C n/a D n/a E 5%

formic acid (64-18-6) + 1-amino-2-propene (107-11-9) → DL-3-aminoisobutyric acid (10569-72-9) + glycine (56-40-6) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogen; oxygen In water for 3h; Further byproducts given;	A 38% B n/a C n/a D 5%

propylamine (107-10-8) + formic acid (64-18-6) → DL-3-aminoisobutyric acid (10569-72-9) + glycine (56-40-6) + 2-aminobutanoic acid (2835-81-6) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
In water at 10 - 20℃; for 1h; Product distribution; contact glow discharge electrolysis; variation of pH, effect of time;	A 9.8% B 0.2% C 0.9% D 3.4% E 8.1%

propylamine (107-10-8) + formic acid (64-18-6) → DL-3-aminoisobutyric acid (10569-72-9) + rac-Ala-OH (302-72-7) + 2-aminobutanoic acid (2835-81-6) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA); Further byproducts given;	A 9.8% B 3.4% C 0.9% D 8.1%

propylamine (107-10-8) + formic acid (64-18-6) → DL-3-aminoisobutyric acid (10569-72-9) + 2-aminobutanoic acid (2835-81-6) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA); Further byproducts given;	A 9.8% B 0.9% C 3.4% D 8.1%

(2S,3'S,5'R,6'R)-6'-(3-Carboxy-propyl)-[2,3']bipiperidinyl-5'-carboxylic acid (117614-90-1) → pipecolinic acid (3105-95-1) + 3-amino propanoic acid (107-95-9) + 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With chromium(VI) oxide In sulfuric acid at 100℃; for 6h;	A 9% B n/a C n/a

pyrrolidine (123-75-1) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid

2-pyrrolidinon (616-45-5) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With sulfuric acid at 25℃; Rate constant; Thermodynamic data; variation of the concenntration of sulfuric acid;ΔH (excit.), ΔS (excit.); 4.72 percent H2SO4;
With sulfuric acid; water at 94℃; Rate constant; Mechanism; effective rate constants for hydrolysis at different temperatures; further temperatures;
With sulfuric acid

2-oxopyrrolidine-3-carboxylic acid ethyl ester (36821-26-8) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogenchloride

trans-4-aminocrotonic acid (38090-53-8) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With palladium on activated charcoal; water Hydrogenation;

Glutamic acid (617-65-2) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
bei Faeulnis;

4-Aminobutanol (13325-10-5) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With sulfuric acid bei der elektrochemischen Oxidation an einer Blei-Anode;

bromobutyric acid (2623-87-2) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With ammonia; water

ethyl 4-aminobutyrate (5959-36-4) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With sulfuric acid

succinic acid (110-15-6) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With ammonium sulfate; sulfuric acid bei der elektrolytischen Reduktion;

ethyl 4-oxobutanoate (10138-10-0) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With ethanol; ammonia; nickel Hydrogenation;

methyl 4-nitrobutyrate (13013-02-0) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With nickel Hydrogenation;

4-guanidinobutyric acid (463-00-3) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
mit Leberpresssaft;

4-phthalimidobutyric acid (3130-75-4) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogenchloride
With hydrogen bromide

(1-phthalimido-ethyl)-malonic acid diethyl ester (101585-64-2) → 4-amino-n-butyric acid (56-12-2)

Conditions	Yield
With hydrogenchloride at 170 - 180℃;

phthalic anhydride (85-44-9) + 4-amino-n-butyric acid (56-12-2) → 4-phthalimidobutyric acid (3130-75-4)

Conditions	Yield
at 170℃; for 6h;	100%
at 180℃;	94%
In neat (no solvent) at 170℃; for 3h; Inert atmosphere; Schlenk technique;	94%

4-amino-n-butyric acid (56-12-2) → sodium salt of γ-amino-n-butyric acid (6610-05-5)

Conditions	Yield
With sodium hydroxide In water	100%
With sodium hydrogencarbonate In water at 20℃; for 3h;	72%
With ammonia; sodium

Allyl chloroformate (2937-50-0) + 4-amino-n-butyric acid (56-12-2) → 4-<<(allyloxy)carbonyl>amino>butyric acid (80127-29-3)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0.5℃; for 0.5h;	100%
Stage #1: 4-amino-n-butyric acid With sodium carbonate In water Stage #2: Allyl chloroformate In water at 0 - 20℃; for 32h; pH=> 9; Stage #3: With hydrogenchloride In water at 0℃; pH=1 - 2;
With sodium hydroxide In tetrahydrofuran; water at -20 - 0℃; for 1h;

methanol (67-56-1) + 4-amino-n-butyric acid (56-12-2) → methyl γ-aminobutyrate hydrochloride (13031-60-2)

Conditions	Yield
With thionyl chloride Ambient temperature;	100%
With acetyl chloride at 0 - 20℃;	100%
With thionyl chloride at 0 - 20℃;	100%

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-n-butyric acid (56-12-2) → N-(tert-butoxycarbonyl)-4-aminobutanoic acid (57294-38-9)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 3h;	100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;	100%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 16h;	100%

4-hydroxy-benzaldehyde (123-08-0) + 4-amino-n-butyric acid (56-12-2) → 4-{[1-(4-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-butyric acid

Conditions	Yield
at 20℃; for 12h;	100%
With sodium hydroxide In methanol; benzene at -4℃; for 0.0833333h;

m-chlorophenyl isocyanate (2909-38-8) + 4-amino-n-butyric acid (56-12-2) → 4-[3-(3-chloro-phenyl)-ureido]-butyric acid

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	100%
In N,N-dimethyl-formamide at 20℃; for 24h;	75%

1-adamantyl isocyanate (4411-25-0) + 4-amino-n-butyric acid (56-12-2) → 4-(3-(adamantan-1-yl)ureido)-butyric acid (39540-57-3)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	100%
Stage #1: 1-adamantyl isocyanate; 4-amino-n-butyric acid In N,N-dimethyl-formamide at 20℃; Stage #2: With hydrogenchloride In water at 0℃; for 0.5h;	100%
In N,N-dimethyl-formamide at 20℃; for 24h;

5-phenylisoxazole-3-carbaldehyde (59985-82-9) + 4-amino-n-butyric acid (56-12-2) → C14H13N2O3(1-)*Li(1+)

Conditions	Yield
With lithium hydride In methanol Reflux;	100%

5-phenylisoxazole-3-carbaldehyde (59985-82-9) + 4-amino-n-butyric acid (56-12-2) → C14H13N2O3(1-)*Na(1+)

Conditions	Yield
With sodium methylate In methanol Reflux;	100%

5-phenylisoxazole-3-carbaldehyde (59985-82-9) + 4-amino-n-butyric acid (56-12-2) → C14H13N2O3(1-)*Cs(1+)

Conditions	Yield
With caesium carbonate In methanol Reflux;	100%

5-phenylisoxazole-3-carbaldehyde (59985-82-9) + 4-amino-n-butyric acid (56-12-2) → 2C14H13N2O3(1-)*Ca(2+)

Conditions	Yield
With calcium hydride In methanol Reflux;	100%

4-amino-n-butyric acid (56-12-2) + 5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde (640292-02-0) → C15H15N2O3(1-)*Li(1+)

Conditions	Yield
With lithium hydride In methanol Reflux;	100%

4-amino-n-butyric acid (56-12-2) + 5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde (640292-02-0) → C15H15N2O3(1-)*Na(1+)

Conditions	Yield
With sodium methylate In methanol Reflux;	100%

4-amino-n-butyric acid (56-12-2) + 5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde (640292-02-0) → C15H15N2O3(1-)*Cs(1+)

Conditions	Yield
With caesium carbonate In methanol Reflux;	100%

4-amino-n-butyric acid (56-12-2) + 5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde (640292-02-0) → 2C15H15N2O3(1-)*Ca(2+)

Conditions	Yield
With calcium hydride In methanol Reflux;	100%

doxepin (1668-19-5, 3607-18-9, 3607-34-9) + linoleic acid (60-33-3) + 4-amino-n-butyric acid (56-12-2) → C18H32O2*C19H21NO*C4H9NO2

Conditions	Yield
Stage #1: doxepin; linoleic acid In tetrahydrofuran at 40 - 50℃; for 5h; Stage #2: 4-amino-n-butyric acid In tetrahydrofuran; methanol at 50℃; for 1h;	100%

linoleic acid (60-33-3) + benzydamine (642-72-8) + 4-amino-n-butyric acid (56-12-2) → C19H23N3O*C18H32O2*C4H9NO2

Conditions	Yield
Stage #1: linoleic acid; benzydamine In tetrahydrofuran at 40 - 50℃; for 5h; Stage #2: 4-amino-n-butyric acid In tetrahydrofuran; methanol at 50℃; for 1h;	100%

(R)-Pantolacton (599-04-2) + 4-amino-n-butyric acid (56-12-2) → hopantenic acid (18679-90-8)

Conditions	Yield
Stage #1: 4-amino-n-butyric acid With sodium hydroxide In water Stage #2: (R)-Pantolacton at 130℃; for 17h; Inert atmosphere;	99%
With triethylamine In methanol at 65℃; for 24h; Inert atmosphere;	89%
With diethylamine In methanol at 60℃;	53%
With sodium methylate
With diethylamine In methanol

4-amino-n-butyric acid (56-12-2) → 2-pyrrolidinon (616-45-5)

Conditions	Yield
With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h;	99%
With aluminum oxide In toluene for 5h; Heating;	97%
With di(n-butyl)tin oxide In xylene for 12h; Heating;	95%

benzenesulfonic acid (98-11-3) + benzyl alcohol (100-51-6) + 4-amino-n-butyric acid (56-12-2) → benzyl γ-aminobutyrate benzenesulfonate salt (86272-16-4)

Conditions	Yield
In benzene Heating;	99%

toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) + 4-amino-n-butyric acid (56-12-2) → 4-(benzyloxy)-4-oxobutan-1-aminium 4-methylbenzenesulfonate (26727-22-0)

Conditions	Yield
In toluene for 5h; Reflux;	99%
In toluene for 5h; Reflux;	97.1%
In benzene for 24h; Reflux;	96%

benzyl formate (104-57-4) + 4-amino-n-butyric acid (56-12-2) → 4-(benzyloxycarbonylamino)butyric acid (5105-78-2)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 4h;	99%

tetrachlorophthalic anhydride (117-08-8) + 4-amino-n-butyric acid (56-12-2) → 4-(4,5,6,7-Tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid (10312-24-0)

Conditions	Yield
With acetic acid at 100℃; for 3h;	98.7%

4-amino-n-butyric acid (56-12-2) → 4-aminobutyric acid hydrochloride (5959-35-3)

Conditions	Yield
With hydrogenchloride In water	98.1%
With hydrogenchloride at 50℃; under 11400.9 Torr; Equilibrium constant; Thermodynamic data; Kinetics; various temperatures, protonation;
With hydrogenchloride at 20℃; for 1h;

benzyl alcohol (100-51-6) + 4-amino-n-butyric acid (56-12-2) → benzyl 4-aminobutanoate (46347-99-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 5h; Reflux;	98%
With PPA
In water; benzene Heating;
With toluene-4-sulfonic acid In benzene Reflux; Dean-Stark;

benzyl chloroformate (501-53-1) + 4-amino-n-butyric acid (56-12-2) → 4-(benzyloxycarbonylamino)butyric acid (5105-78-2)

Conditions	Yield
With sodium hydroxide at 0 - 20℃; for 14h;	98%
With sodium hydroxide In water	97%
With sodium hydrogencarbonate In 1,4-dioxane; water for 17h;	95%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4-amino-n-butyric acid (56-12-2) → 4-(pyrrol-1-yl)-butyric acid (70686-51-0)

Conditions	Yield
With sodium acetate; acetic acid In water; 1,2-dichloro-ethane at 90℃; for 15h;	98%
Stage #1: 4-amino-n-butyric acid With sodium acetate; acetic acid In 1,2-dichloro-ethane at 90℃; Stage #2: cis,trans-2,5-dimethoxytetrahydrofuran In 1,2-dichloro-ethane at 90℃; for 16h;	90%
With sodium acetate; acetic acid In water at 75℃; for 2h; Clauson-Kaas reaction;	76%

phenyl isothiocyanate (103-72-0) + 4-amino-n-butyric acid (56-12-2) → N-(phenylthiocarbamoyl)-γ-aminobutyric acid (25759-76-6)

Conditions	Yield
With sodium carbonate In acetone for 4h; Ambient temperature;	98%

toluene-4-sulfonic acid (104-15-4) + 4-amino-n-butyric acid (56-12-2) → toluene-4-sulfonic acid ; 4-amino-butyric acid-salt (71890-28-3)

Conditions	Yield
In tetrahydrofuran at 25℃; for 2.5h;	98%

Upstream product

• 1066-33-7 Ammonium bicarbonate 
• 872-50-4 1-Methyl-2-pyrrolidinone 
• 616-45-5 2-Pyrrolidinone 
• 628-20-6 4-Chlorobutyronitrile 
• 8001-22-7 SOYBEAN OIL 
• 142-61-0 Hexanoyl chloride 

Downstream Products

• 13477-53-7 2-Hydroxy-4-amino butanoic acid 
• 13031-60-2 Methyl 4-aminobutyrate hydrochloride 
• 66376-36-1 Alendronic Acid 
• 72432-10-1 Aniracetam 
• 57078-98-5 4-MALEIMIDOBUTYRIC ACID 
• 69954-66-1 4-DIMETHYLAMINOBUTYRIC ACID HYDROCHLORIDE 

Recommend Products

• 110-15-6  succinic acid 
• 7663-77-6  1-(3-aminopropyl)-2-pyrrolidone 
• 107-13-1  acrylonitrile 
• 2937-01-1  4-[(phenylacetyl)amino]butanoic acid 
• 103-80-0  phenylacetyl chloride 
• 3251-07-8  methyl 4-aminobutyrate 
• 67-56-1  methanol 
• 6937-16-2  ethyl γ-aminobutyrate hydrochloride 
• 64-17-5  ethanol 
• 407-64-7  4-aminobutyric acid betaine 
• 67-66-3  chloroform 
• 463-00-3  4-guanidinobutyric acid 
• 420-04-2  CYANAMID 
• 3025-96-5  N-Acetyl-4-aminobutyric acid