Basic information
- Standard SMILES
NCCCC(=O)O- InChIKey
BTCSSZJGUNDROE-UHFFFAOYSA-N- Molecular formula
- C4H9NO2
- Average molar mass
- 103.12 g/mol
- Monoisotopic mass
- 103.06332853
Overview
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.
Names & identifiers
- Preferred name
- Gamma-Aminobutyric Acid
- IUPAC
- 4-aminobutanoic acid
- English name
- 4-Aminobutyric acid
- Molecular formula
- C4H9NO2
- Molecular weight
- 103.12
Names & synonyms
Show more names
Database identifiers
- CAS
56-12-2- PubChem CID
- 119
- DTXSID
DTXSID6035106- ChEMBL
CHEMBL96- ChEBI
CHEBI:16865- UNII
- 2ACZ6IPC6I
- Nikkaji
- J1.375G
Properties
Computed structural properties
- XLogP
- -3.2
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 62.7
Experimental & physicochemical properties
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)
Physicochemical properties
- Melting point
- 195 °C · 195 °C (dec.) (lit.)
- Boiling point
- 248 · 248.0±23.0 °C(Predicted)
- Density
- 1.23 · 1.2300 (estimate)
- refractive index
- 1.465 · 1.4650 (estimate)
- FEMA
- 4288 · 4288 | 4-AMINOBUTYRIC ACID
- FLAVIS Number
- 17.035 · 17.035 | 4-Amino-butyric acid
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 1 M at 20 °C, clear, colorless
- pka
- 4.031 · 4.031(at 25℃)
- form
- Powder
- color
- White to almost white
- Odor
- 1 % · at 1.00 % in propylene glycol. savory meaty
- Odor Type
- meaty
- Water Solubility
- SOLUBLE
- Merck
- 14 · 14,430
- JECFA Number
- 1771 · 1771
- BRN
- 906818 · 906818
- Cosmetics Ingredients Functions
- 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 DataBase Reference
- 56 · 56-12-2(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 4 · 4-AMINOBUTYRIC ACID
- FDA UNII
- 2 ACZ6IPC6I · 2ACZ6IPC6I
- NIST Chemistry Reference
- 4 · 4-Aminobutanoic acid(56-12-2)
- EPA Substance Registry System
- 4 · 4-Aminobutanoic acid (56-12-2)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H315-H319-H332
- Precautionary statements
- 280 · P280-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-20/21/22
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 6300000 · ES6300000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29224995 · 29224995
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
Hazard information
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
Toxicology
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.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- ES6300000
- hs_code
- 29224995
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H312-H315-H319-H332
- REACH Registrations
- Active
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Uses & manufacturing
Applications
Description4-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.
Uses4-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.
General Description4-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).
Preparation methods
PreparationThe 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
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.
Related reactions
Linked notes
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