γ-Aminobutyric acid（GABA） - BioReagent, ≥99% , CAS No.56-12-2

CAS: 56-12-2 Cat. No.: A755686 Peso molecular: 103.12 Beilstein Registry Number: 4(3)1316 Número EC: 200-258-6

GRADE & PURITY BioReagent, ≥99%

Synonyms

NSC45460 | DF 468 | 3-Carboxypropylamine | Gammalone | gamma Aminobutyric acid | GABA | 4-amino-n-butyric acid | butanoic acid, 4-amino- | gamma-Aminobutryic acid | EPA Pesticide Chemical Code 030802 | UNII-2ACZ6IPC6I | Aminobutyric acid,-4-

Storage

Room temperature

Shipped In

Normal

Descripción general

γ-Aminobutyric acid (GABA) is a non-protein amino acid associated with the brain. Being synthesized in the nervous system, it is packed into synaptic vesicles. It is present naturally in green tea, soybean, germinated rice, and in some fermented foods.

Application:

γ-Aminobutyric acid (GABA) has been used to treat dorsal root ganglion neurons for electrophysiological recordings studies to test its effect on neuropathic pain in rats. It has also been used to test its protective effects in an ex vivo machine perfusion system of small-for-size grafts (SFSG) injury model.

Specifications

Sinónimos

NSC45460 | DF 468 | 3-Carboxypropylamine | Gammalone | gamma Aminobutyric acid | GABA | 4-amino-n-butyric acid | butanoic acid, 4-amino- | gamma-Aminobutryic acid | EPA Pesticide Chemical Code 030802 | UNII-2ACZ6IPC6I | Aminobutyric acid, -4-

Especificaciones y pureza

BioReagent, ≥99%

Mecanismos bioquímicos y fisiológicos

γ-Aminobutyric acid (GABA) is a mammalian inhibitory neurotransmitter with multiple functions. It is crucial for the normal central nervous system (CNS) functioning. A few documented functions of GABA include its protective role in toxin-induced damage. I

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Grado

BioReagent

Pureza

≥99%

Nombres e identificadores

• Sonrisas canónicas: C(CC(=O)O)CN
• IUPAC Name: 4-aminobutanoic acid
• InChIKey: BTCSSZJGUNDROE-UHFFFAOYSA-N
• INCHI: 1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
• Isómeros SMILES: C(CC(=O)O)CN
• WGK Alemania: 2
• RTECS: ES6300000
• CAS alternativo: 56-12-2,70582-09-1 (calcium salt (2:1))
• Número NSC: 27418
• Términos de entrada MeSH: 4 Aminobutanoic Acid;4 Aminobutyric Acid;4-Aminobutanoic Acid;4-Aminobutyric Acid;Acid, Hydrochloride gamma-Aminobutyric;Aminalon;Aminalone;GABA;GABA, Lithium;gamma Aminobutyric Acid;gamma Aminobutyric Acid, Hydrochloride;gamma Aminobutyric Acid, Monolith
• Peso molecular: 103.12
• Beilstein: 4(3)1316
• Reaxy-Rn: 906818
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=906818&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Gamma amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Gamma amino acids and derivatives
• Alternative Parents: Amino fatty acids Straight chain fatty acids Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Gamma amino acid or derivatives - Amino fatty acid - Straight chain fatty acid - Fatty acid - Fatty acyl - Amino acid - Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxide - Organopnictogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Amine - Hydrocarbon derivative - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
• External Descriptors: Amino fatty acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: H 2 O: 0.5 M at 20 °C, clear, colorless
• Punto de fusión (°C): 195°C
• Peso molecular: 103.120 g/mol
• XLogP3: -3.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 103.063 Da
• Monoisotopic Mass: 103.063 Da
• Topological Polar Surface Area: 63.300 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 62.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

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56. Lili Zhang, Wen Duan, Yan Huang, Yuyu Zhang, Baoguo Sun, Dandan Pu, Yizhuang Tang, Chao Liu.  (2020)  Sensory taste properties of chicken (Hy-Line brown) soup as prepared with five different parts of the chicken.  INTERNATIONAL JOURNAL OF FOOD PROPERTIES,      [PMID:] [10.1080/10942912.2020.1828455]

57. Yong-hong Liu, Ting-ting Du, Jing-yuan Wan, Hua Zhao, Dan Huang, Jian-sha Li, Xin-hui Jiang.  (2019)  Simultaneous determination of thirteen substances related to NAFLD in mouse brain tissue using 3-aminobutyric acid as internal standard by HPLC–FLD.  BIOMEDICAL CHROMATOGRAPHY,  34  (3): (e4767).  [PMID:31785600] [10.1002/bmc.4767]

58. Si Chen, Huihui Liu, Xiaoman Zhao, Xinlei Li, Wenna Shan, Xiaxia Wang, Shanshan Wang, Wenquan Yu, Zhenbiao Yang, Xiaomin Yu.  (2019)  Non-targeted metabolomics analysis reveals dynamic changes of volatile and non-volatile metabolites during oolong tea manufacture.  FOOD RESEARCH INTERNATIONAL,      [PMID:31955752] [10.1016/j.foodres.2019.108778]

59. Wei Xia, Zhu Qingfen, Liu Na, Xu Lihua, Wei Sheng, Fan Zhiyun, Sun Changhua, Zhao Yan, Qiao Mingqi, Wu Jibiao, Hu Defu, Wang Yang, Sun Peng.  (2019)  Neuroprotective Effects and Mechanisms of Zhenlong Xingnao Capsule in In Vivo and In Vitro Models of Hypoxia.  Frontiers in Pharmacology,      [PMID:31611791] [10.3389/fphar.2019.01096]

60. Yan YAN, Qiang LI, Hui-Zhi DU, Chen-Xi SHEN, Ai-Ping LI, Xiang-Ping PEI, Chen-Hui DU, Xue-Mei QIN.  (2019)  Determination of five neurotransmitters in the rat brain for the study of the hypnotic effects of Ziziphi Spinosae Semen aqueous extract on insomnia rat model by UPLC-MS/MS.  Chinese Journal of Natural Medicines,      [PMID:31514987] [10.1016/S1875-5364(19)30077-9]

61. Xue-Mei Han, Yan-Jie Qin, Ying Zhu, Xin-Lin Zhang, Nan-Xi Wang, Ying Rang, Xue-Jia Zhai, Yong-Ning Lu.  (2019)  Development of an underivatized LC-MS/MS method for quantitation of 14 neurotransmitters in rat hippocampus, plasma and urine: Application to CUMS induced depression rats.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:31288191] [10.1016/j.jpba.2019.06.043]

62. Yongshun Gao, Shuo Zhang, Wenlong Hou, Huiyun Guo, Qizhe Li, Danyang Dong, Siyu Wu, Shiyuan Zhao, Haiquan Zhang.  (2019)  Perylene diimide derivative regulate the antimony sulfide morphology and electrochemical sensing for hydrazine.  APPLIED SURFACE SCIENCE,      [PMID:] [10.1016/j.apsusc.2019.06.149]

63. Mengying Wei, Yuanyuan Liu, Zifeng Pi, Shizhe Li, Mingxin Hu, Yang He, Kexin Yue, Tianshu Liu, Zhiqiang Liu, Fengrui Song, Zhongying Liu.  (2019)  Systematically Characterize the Anti-Alzheimer’s Disease Mechanism of Lignans from S. chinensis Based on In-Vivo Ingredient Analysis and Target-Network Pharmacology Strategy by UHPLC–Q-TOF-MS.  MOLECULES,  24  (7): (1203).  [PMID:30934777] [10.3390/molecules24071203]

64. Ni Pengjuan, Xie Junfeng, Chen Chuanxia, Jiang Yuanyuan, Lu Yizhong, Hu Xun.  (2019)  Fluorometric determination of the activity of alkaline phosphatase and its inhibitors based on ascorbic acid-induced aggregation of carbon dots.  MICROCHIMICA ACTA,  186  (3): (1-8).  [PMID:30796533] [10.1007/s00604-019-3303-2]

65. Jing Chen, Ying Yuan, Xiaoku Ran, Na Guo, Deqiang Dou.  (2018)  Metabolomics analysis based on a UPLC-Q-TOF-MS metabolomics approach to compare Lin-Xia-Shan-Shen and garden ginseng.  RSC Advances,  8  (53): (30616-30623).  [PMID:35546833] [10.1039/C8RA04823A]

66. Wang Xiao-mei, Ren Hao-hao, Yan Yong-gang, Ji Mi-zhi.  (2018)  A Novel Bio-based Polyaspartic Acid Copolymer: Synthesis, Structure and Performance of Degradation.  JOURNAL OF POLYMERS AND THE ENVIRONMENT,  26  (11): (4201-4210).  [PMID:] [10.1007/s10924-018-1293-5]

67. Dan Huang, Qing-Song Jiang, Jun-Qing Yang, Ting Cui, Nian-Ru Wang, Ting-Ting Du, Xin-Hui Jiang.  (2018)  Simultaneous determination of nine analytes related to the pathogenesis of diabetic encephalopathy in diabetic rat cortex and hippocampus by HPLC-FLD.  BIOMEDICAL CHROMATOGRAPHY,  32  (11): (e4338).  [PMID:30003560] [10.1002/bmc.4338]

68. Ming Wang, Qi-jian Zhang, Zhuang Li, Hua Li, Jian-Mei Lu.  (2018)  Solvents Effects on Film Morphologies and Memory Behavior of a Perylenediimide-Containing Pendent Polymer.  Chemistry-An Asian Journal,  13  (14): (1784-1790).  [PMID:29741817] [10.1002/asia.201800331]

69. Ding Shen, Jie Zheng, Xiping Cui, Yingshan Chen, Qiyi He, Rui Lv, Zhaoxia Li, Suqing Zhao.  (2017)  Analysis of cholyglycine acid as a biomarker for the early diagnosis of liver disease by fluorescence polarization immunoassay.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2017.10.013]

70. Zhang Qian, Wang Junsong, Liao Shanting, Li Pei, Xu Dingqiao, Lv Yan, Yang Minghua, Kong Lingyi.  (2017)  Optimization of Huang-Lian-Jie-Du-Decoction for Ischemic Stroke Treatment and Mechanistic Study by Metabolomic Profiling and Network Analysis.  Frontiers in Pharmacology,      [PMID:28400733] [10.3389/fphar.2017.00165]

71. Ren Wenkai, Yin Jie, Xiao Hao, Chen Shuai, Liu Gang, Tan Bie, Li Nengzhang, Peng Yuanyi, Li Tiejun, Zeng Benhua, Li Wenxia, Wei Hong, Yin Zhinan, Wu Guoyao, Hardwidge Philip R., Yin Yulong.  (2017)  Intestinal Microbiota-Derived GABA Mediates Interleukin-17 Expression during Enterotoxigenic Escherichia coli Infection.  Frontiers in Immunology,      [PMID:28138329] [10.3389/fimmu.2016.00685]

72. Lin Luo, Hong-Tao Lei, Jin-Yi Yang, Gong-Liang Liu, Yuan-Ming Sun, Wei-Dong Bai, Hong Wang, Yu-Dong Shen, Sui Chen, Zhen-Lin Xu.  (2016)  Development of an indirect ELISA for the determination of ethyl carbamate in Chinese rice wine.  ANALYTICA CHIMICA ACTA,      [PMID:27916121] [10.1016/j.aca.2016.11.008]

73. Kaifei Zhao, Peng Yang, Shichao Du, Kangli Li, Xiaona Li, Zhenfang Li, Yumin Liu, Lanlan Lin, Baohong Hou, Junbo Gong.  (2016)  Determination and correlation of solubility and thermodynamics of mixing of 4-aminobutyric acid in mono-solvents and binary solvent mixtures.  JOURNAL OF CHEMICAL THERMODYNAMICS,      [PMID:] [10.1016/j.jct.2016.07.014]

74. Lili Wang, Wencheng Gong, Fang Wang, Zhenya Yu, Zilin Chen.  (2016)  Efficient bienzyme nanocomposite film for chiral recognition of L-tryptophan, L-phenylalanine and L-tyrosine.  Analytical Methods,  8  (17): (3481-3487).  [PMID:] [10.1039/C5AY03290C]

75. Wang Fang, Gong Wencheng, Wang Lili, Chen Zilin.  (2015)  Enhanced amperometric response of a glucose oxidase and horseradish peroxidase based bienzyme glucose biosensor modified with a film of polymerized toluidine blue containing reduced graphene oxide.  MICROCHIMICA ACTA,  182  (11): (1949-1956).  [PMID:] [10.1007/s00604-015-1535-3]

76. Lihuan Xu, Fang Yang, Chang Su, Lvlv Ji, Cheng Zhang.  (2014)  Synthesis and properties of novel TEMPO-contained polypyrrole derivatives as the cathode material of organic radical battery.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2014.03.017]

77. Xiaolu Chen, Dawei Yan, Hao Deng, Hulin Yang, Suping Peng, Wei Zhang, Shijie Cai, Qiyi Zhang, Haohao Ren, Yonggang Yan.  (2024)  CuSO4/H2O2 induced polydopamine/polysulfobetaine methacrylate co-deposition on poly(amino acid) membranes for improved anti-protein adsorption and antibacterial activity.  Biomedical Materials,      [PMID:38917812] [10.1088/1748-605X/ad5ba6]

78. Zhihui Yu, Yating Gao, Huiling Duan, Dan Zheng, Ziqi Shang, Lixin Zhang, Yisheng Chen.  (2024)  Ultrasound-assisted germination of red kidney beans: Enhancements in physicochemical and nutritional profiles.  FOOD CHEMISTRY,      [PMID:38810443] [10.1016/j.foodchem.2024.139829]

79. Yongchen Yu, Xiaona Qian, Xiwang Li, Zhichao Chai, Dejiang Ni, Xiaoling Sun.  (2025)  Ectropis obliqua-Induced Secondary Metabolites Are Regulated by Methyl Jasmonate in a Threshold-Dependent Manner.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  26  (9): (4248).  [PMID:40362484] [10.3390/ijms26094248]

80. Meng-xiao Wang, Ke-ke Luo, Meng-yao Tian, Wen-ya Gao, Shan Jiang, Yan Zhang, Jian Yang, Nan Si, Shi-lan Ding, Xiao-lu Wei, Yu-yang Liu, Bao-lin Bian, Yan-yan Zhou, Hong-jie Wang.  (2025)  Study on the mechanism of acteoside in treating purinomycin aminonucleoside-induced chronic glomerulonephritis in childhood rats based on Cxcr4-PI3K-Akt-eNOS axis.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40389008] [10.1016/j.ijbiomac.2025.144180]

81. Mengsheng Deng, Tuankui Ou, Wanying Gan, Huina Li, Wenao Sun, Linghong Xie, Yu Lei.  (2025)  Integrated Transcriptomics and Physiological Analysis Reveal the Mechanism of γ-Aminobutyric Acid Inhibiting Enzymatic Browning in Fresh-Cut Potatoes.  JOURNAL OF FOOD BIOCHEMISTRY,  2025  (1): (1499526).  [PMID:] [10.1155/jfbc/1499526]

82. Bo Niu, Chen Zhu, Haiyang Yuan, Wence Xu, Yanqin Liang, Zhaoyang Li, Hui Jiang, Zhenduo Cui, Zhonghui Gao, Shengli Zhu.  (2025)  Organic Molecular Amino Acids Additives Containing Amide Groups for Uniform Zinc Deposition in Aqueous Zinc Ion Batteries.  Small,      [PMID:39924861] [10.1002/smll.202409556]

83. Yao Zimin, Zheng Guoliang, Zheng Yonggui, Wen Xiaokun, Hong Xia, Yan Jiayi, Liu Wen, Wang Jiwei, Wang Kexin, Cao Shuo.  (2025)  Ratiometric fluorescence sensing of sialic acid based on dual-emission carbon dots.  MICROCHIMICA ACTA,  192  (7): (1-9).  [PMID:40473999] [10.1007/s00604-025-07237-3]

84. Tiancun Liu, Gangyong Huang, Zhonghua Wei, Lu Zheng, Zhubing Sun, Xusheng Wang, Chaofei Guo.  (2025)  Relieving interface corrosion and inducing planar Zn plating achieved by γ-aminobutyric acid towards stable and high-performance Zn ion batteries.  NEW JOURNAL OF CHEMISTRY,  49  (25): (10928-10935).  [PMID:] [10.1039/D5NJ01320H]

85. Chongqi Liu, Wei Zheng, Lingyan Xu, Yingming Wang, Lixiang Lian, Lu Liang, Zhentao Qin, Yanyan Lei, Qinzeng Hu, Wanqi Jie.  (2025)  High-Performance X-ray Detection and Imaging Using ⟨110⟩-Oriented 2D (AABA)PbBr3·H2O Perovskite Single Crystals.  CRYSTAL GROWTH & DESIGN,      [PMID:] [10.1021/acs.cgd.5c00367]

86. Zhang Shuo, Gao Peichao, Wang Qunxin, Liu Shuhui, Okoth Sheila, Zhang Meihua, Ji Helong, Yan Liping, Fan Wentao, Song Suquan.  (2025)  Lactobacillus plantarum 1–2-3 Ameliorates the Corticosterone-Induced Fatty Liver Hemorrhagic Syndrome in Laying Hens by Biosynthesizing Gamma-Aminobutyric Acid.  Probiotics and Antimicrobial Proteins,      [PMID:40956568] [10.1007/s12602-025-10759-0]

87. Jiansen Wen, Ping Li, Linqin Jiang, Baisheng Sa, Hao Xiong, Lingyan Lin, Xiaokun Huang, Aijun Yang, Yu Qiu.  (2025)  Alkyl-chain engineering of bifunctional amino acids in optoelectronically superior lead-free copper-based perovskite Cs3Cu2I5.  Journal of Materials Chemistry C,      [PMID:] [10.1039/D5TC02973B]

88. Xi Huang, Zhangshan Gao, Peichao Gao, Helong Ji, Laizhi Xu, Dengfei Feng, Wentao Fan, Suquan Song.  (2025)  Postbiotic GABA and Lactobacillus plantarum 1-2-3 alleviate stress-induced ovarian dysfunction and improve reproductive performance in laying hens through multi-mechanistic pathways.  ANIMAL REPRODUCTION SCIENCE,      [PMID:41166798] [10.1016/j.anireprosci.2025.108026]

89. Tianping Chen, Yanru Tao, Xi Cao, Shiyi He, Hua Zhao, Jiangling Hu, Hongmei Wang, Xinhui Jiang.  (2025)  Development of an HPLC method for the determination of amines in a leukemia mouse model.  Analytical Methods,      [PMID:41160401] [10.1039/D5AY01549A]

90. Huang Huiping, Zhou Haiyan, Tao Qinqin, Li Zhuyao, Dai Ying.  (2025)  The uranium adsorption capacity of amino acid-modified silica: is there a critical carbon chain length threshold?.  JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY,      [PMID:] [10.1007/s10967-025-10428-0]

91. Huang Xi, Gao Zhangshan, Gao Peichao, Ji Helong, Xu Laizhi, Fan Wentao, Song Suquan.  (2025)  Postbiotic GABA and Lactobacillus plantarum 1-2-3 Alleviate Corticosterone-induced Abdominal Fat Deposition in Laying Hens by Suppressing Adipogenesis and Enhancing Lipolysis.  Probiotics and Antimicrobial Proteins,      [PMID:41339616] [10.1007/s12602-025-10869-9]

92. Yingming Wang, Lingyan Xu, Chongqi Liu, Lu Liang, Binghui Zhang, Zhentao Qin, Lixiang Lian, Wei Zheng, Yanyan Lei, Qinzeng Hu, Shuai Song, Chaopeng Mi, Tao Wang, Yadong Xu, Gangqiang Zha, Wanqi Jie.  (2025)  Structure-Function Integration in 2D Hybrid Perovskite for Fast Neutron and Gamma Ray Discrimination.  Advanced Science,      [PMID:41391044] [10.1002/advs.202518905]

93. Yuexiao Jia, Zhencheng Sun, Ke Zhang, Ruijia Huang, Guoshuai Zhu, Jidong Wang, Wenwen Chen.  (2026)  Repurposing a Nonessential Amino Acid γ-Aminobutyric Acid To Treat Multidrug-Resistant Bacteria.  ACS Applied Materials & Interfaces,      [PMID:41645771] [10.1021/acsami.5c22655]

94. Xinyu Dong, Peng Zhou, Qiaomei Lou, Chang Li, Yu Du, Yu He.  (2026)  Optimal Compatibility of Main Effective Parts of Astragali Radix-Safflower for the Treatment of Cerebral Ischemia/Reperfusion by Pharmacokinetics-Pharmacodynamics Analysis Based on Microdialysis and Liquid Chromatography–Tandem Mass Spectrometry.  PHYTOCHEMICAL ANALYSIS,      [PMID:41708321] [10.1002/pca.70055]

95. Dang Yanqing, Xiang Yanju, Abudula Adila, Hou Xujie, Pu Yunfeng.  (2026)  Impact of γ-aminobutyric acid and 1-methylcyclopropene on qualitative attributes of apples (Malus domestica Borkh. cv. Fuji) during cold storage.  Scientific Reports,      [PMID:] [10.1038/s41598-026-44765-1]

96. Rong Zhu, Guifang Zhang, Nuo Li, Jiling Li, Dongjie Zhang.  (2026)  A study on γ-Aminobutyric acid (GABA) enrichment and its metabolic mechanism in germinating mung beans under the stress of ultrasound combined with slightly acidic electrolyzed water.  ULTRASONICS SONOCHEMISTRY,      [PMID:] [10.1016/j.ultsonch.2026.107812]