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4-Ammoniobutanoate

HCID 6992099
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
56-12-2
Standard SMILES
[NH3+]CCCC(=O)[O-]
InChIKey
BTCSSZJGUNDROE-UHFFFAOYSA-N
Molecular formula
C4H9NO2
Average molar mass
103.12 g/mol
Monoisotopic mass
103.06332853

Overview

Gamma-aminobutyric acid zwitterion is zwitterionic form of gamma-aminobutyric acid having an anionic carboxy group and a protonated amino group. It is a tautomer of a gamma-aminobutyric acid.

Names & identifiers

Preferred name
4-Ammoniobutanoate
IUPAC
4-azaniumylbutanoate
English name
4-Aminobutyric acid
Molecular formula
C4H9NO2
Molecular weight
103.12

Names & synonyms

4euo4-ammoniobutanoategamma-amino-N-butyrateg-amino-n-butyric acid3ip9CHEBI:59888gamma-aminobutyric acid zwitterionGABA4-AMINOBUTANOIC ACIDGAMMA-AMINOBUTYRIC ACIDgammaγ-Aminobutyric acid
Show more names
Y-Aminobutyric acid56-12-6H-GABA-OHGammaloneaminobutyric

Database identifiers

CAS
56-12-2
PubChem CID
6992099
ChEBI
CHEBI:59888
Nikkaji
J437.062G

Properties

Computed structural properties

XLogP
-2.5
Topological polar surface area
67.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
7
Formal charge
0
Complexity
57.2

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
LogP-3.17
Solubility1300.0 mg/mL
Melting Point203 °C
Physical DescriptionSolid

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

Tissue LocationsAdrenal Cortex
Cellular LocationsExtracellular
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)
Applications · 4 items

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).

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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
Preparation methods · 1 item

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

Cation exchange resin,strong acidic styrenePotassium phthalimideN-Methyl-2-pyrrolidoneSoybean oilHexanoyl chloride2-Pyrrolidinone4-ChlorobutyronitrileN,N,N-Tri(polyoxypropylene polyoxyethylene)aminecorn syrupAmmonium bicarbonate

Downstream products

2-Hydroxy-4-amino butanoic acidAlendronic acidAniracetam4-Maleimidobutyric acid4-Dimethylaminobutyric acid hydrochlorideMethyl 4-aminobutyrate hydrochloride4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid4-(4-Oxo-2-thioxo-thiazolidin-3-yl)-butyric acid

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创之源生物科技有限公司13012111162 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
Ascent Scientific4401179829988 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
上海耐士化工科技有限公司400-188-0725 +86 21 34310725 13611771617
天津希恩思生化科技有限公司400 638 7771 · [email protected]
南京维奥化工有限公司Please Send Email 18652950785 · [email protected]
Connect Chemicals GmbH+49 2102 2077 19 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
北京泰亚杰科技有限公司021-33690831-8001 13552411790;18616022633 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
上海特伯化学科技有限公司+86-21-60341587 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
Additional notes · 1 item

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.