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56-12-2

Basic Information
CAS No.: 56-12-2
Name: 4-Aminobutyric acid
Article Data: 148
Cas Database
Molecular Structure:
Molecular Structure of 56-12-2 (4-Aminobutyric acid)
Formula: C4H9NO2
Molecular Weight: 103.121
Synonyms: Butyricacid, 4-amino- (7CI,8CI);3-Carboxypropylamine;4-Aminobutanoic acid;4-Aminobutyric acid;Aminalon;GABA;Gaballon;Gamarex;Gammalon;Gammalone;Gammar;Gammasol;Mielogen;Mielomade;NSC 27418;NSC 32044;NSC 45460;NSC51295;Oryza GABA Extract HC 90;Pharma-GABA 20S;Pharmagaba;Pharmagaba 20;Pharmagaba 20D;Piperidic acid;Piperidinic acid;g-Aminobutanoic acid;g-Aminobutyric acid;w-Aminobutyric acid;γ-aminobutyric acid;GAMMA-AMINOBUTYRIC ACID;
EINECS: 200-258-6
Density: 1.11 g/cm3
Melting Point: 195 °C (dec.)(lit.)
Boiling Point: 247.985 °C at 760 mmHg
Flash Point: 103.778 °C
Solubility: soluble in water
Appearance: White microcrystalline powder
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 26-36
PSA: 63.32000
LogP: 0.51020
Synthetic route
1990-07-4, 16498-47-8, 17097-76-6

calcium 4-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]butanoate

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
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;
80127-29-3

4-<<(allyloxy)carbonyl>amino>butyric acid

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); 2-Ethylhexanoic acid; triphenylphosphine In diethyl ether; dichloromethane at 25℃; for 18h;92%
100340-10-1

C12H11NO2

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 750.075 Torr; for 24h;91%
1180819-69-5

4-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)butanamide

56-12-2

4-amino-n-butyric acid

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

methyl 1-(4-aminobutanoyl)-7-nitroindoline-5-acetate

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
In water pH=7.0; Reactivity; Ammonium phosphate; Photolysis;88%
56-86-0

L-glutamic acid

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
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;
16051-87-9

3-cyanopropanoic acid

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen Acidic conditions;80%
With ethanol; sodium
With sodium tetrahydroborate; nickel dichloride In N,N-dimethyl-formamide at 20℃;
10137-67-4

ethyl 3-cyanopropionate

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
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;
13325-10-5

4-Aminobutanol

A

4390-05-0

4-aminobutyraldehyde

B

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With 1H-imidazole; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 1h;A 39%
B 2%
64-18-6

formic acid

107-11-9

1-amino-2-propene

A

107-10-8

propylamine

B

10569-72-9

DL-3-aminoisobutyric acid

C

56-40-6

glycine

D

107-95-9

3-amino propanoic acid

E

56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
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%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is 4-aminobutanoic acid. With the CAS registry number 56-12-2, it is also named as Gammalone. The product's categorie are 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; GABA. It is white microcrystalline powder which is easily soluble in water, slightly soluble in hot ethanol, insoluble in cold ethanol, ether and benzene. Additionally, this chemical is sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 3; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 4; (8)Index of Refraction: 1.465; (9)Molar Refractivity: 25.68 cm3; (10)Molar Volume: 92.866 cm3; (11)Polarizability: 10.18×10-24 cm3; (12)Surface Tension: 46.208 dyne/cm; (13)Enthalpy of Vaporization: 53.425 kJ/mol; (14)Boiling Point: 247.985 °C at 760 mmHg; (15)Vapour Pressure: 0.008 mmHg at 25°C; (16)Rotatable Bond Count: 3; (17)Exact Mass: 103.063329; (18)MonoIsotopic Mass: 103.063329; (19)Topological Polar Surface Area: 63.3; (20)Heavy Atom Count: 7; (21)Complexity: 62.7.

Preparation of 4-Aminobutyric acid: It can be obtained by the ring opening of pyrrolidone. Digested quick lime to lime milk with distilled water, suction into the hydrolysis reactor, adding pyrrolidone, heating to 125-130 °C and the reaction pressure is maintained at 0.29MPa. Reacting above 10-14h at this temperature. After the reaction, cooling to 30 °C, filtered, and washed by distilled water. Adding ammonium bicarbonate to filtrate until no calcium ion detection. Adding activated carbon to decolorize 30min at 80 °C. Evaporated to precipitate crystals at 60 °C. Adding ethanol, cooling, filtration and drying, then we can get the product. The yield is 85%.

Uses of 4-Aminobutyric acid: It is not only used as pharmaceutical intermediate, but also used in biochemical research. And it has effect of lowering blood lipids that can be used in the treatment and prevention of various types of hepatic coma. In addition, it reacts with phthalic acid anhydride to get 4-phthalimido-butyric acid. This reaction needs reagent Et3N and solvent toluene by heating. The reaction time is 2 hours. The yield is 82%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:C(CC(=O)O)CN
2. InChI:InChI=1/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7) 
3. InChIKey:BTCSSZJGUNDROE-UHFFFAOYAC

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 5gm/kg (5000mg/kg)   Russian Pharmacology and Toxicology Vol. 47, Pg. 205, 1984.
mouse LD50 intraperitoneal 4950mg/kg (4950mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
 
mouse LD50 intravenous 2748mg/kg (2748mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 145, Pg. 233, 1963.
mouse LD50 oral 12680mg/kg (12680mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 85, Pg. 463, 1965.
mouse LD50 subcutaneous 9210mg/kg (9210mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 85, Pg. 463, 1965.
mouse LD50 unreported 7230mg/kg (7230mg/kg)   Bitamin. Vol. 25, Pg. 297, 1962.
rabbit LDLo intravenous 2400mg/kg (2400mg/kg)   Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
rat LD50 intraperitoneal 5400mg/kg (5400mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
 
rat LD50 intravenous > 5gm/kg (5000mg/kg)   United States Patent Document. Vol. #3380887,
rat LDLo intracrebral 18mg/kg (18mg/kg)   Biochemical Pharmacology. Vol. 14, Pg. 1901, 1965.

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