487-79-6 Usage
Description
Kainic acid (487-79-6) is a conformationally restricted glutamate analog that acts as a selective agonist at kainate receptors. It is a potent neuroexcitatory agent and neurotoxin, commonly used as a tool in neurobiology research. Kainic acid is also known for its ability to induce seizures in laboratory animals, making it a classic agent for studying seizure activity.
Uses
Used in Pharmaceutical Industry:
Kainic acid is used as an excitatory amino acid and neurotoxin for the development and testing of drugs targeting the central nervous system. Its ability to induce seizures in laboratory animals makes it a valuable tool for understanding the mechanisms behind epilepsy and other seizure disorders.
Used in Neurobiology Research:
Kainic acid is used as a neurobiology tool to study the effects of glutamate receptor activation on neuronal function and the underlying mechanisms of neurodegenerative diseases. It helps researchers investigate the role of kainate receptors in various brain regions and their contribution to cognitive and motor functions.
Used in Veterinary Medicine:
Kainic acid is used as an anthelmintic, specifically for the treatment of parasitic worm infections in animals. Its neuroexcitatory properties can help in the elimination of parasites by causing their paralysis and subsequent expulsion from the host.
Used in Neuroscience:
Kainic acid is used as a glutamate receptor agonist in neuroscience research to study the role of ionotropic glutamate receptors in various brain functions and disorders. Administration of (-)-α-Kainic Acid has been shown to increase the production of reactive oxygen species, mitochondrial dysfunction, and apoptosis in neurons, particularly in the hippocampal subregions and the hilus of the dentate gyrus. This helps researchers understand the impact of glutamate receptor activation on neuronal health and the development of neurodegenerative diseases.
Chemical Properties:
Kainic acid is soluble in 0.1 M NaOH, which is an important property for its use in various applications, including pharmaceutical and neurobiology research.
Biological Activity
Selective agonist at kainate receptors. Potent excitant and neurotoxin. Also available as part of the Kainate Receptor Tocriset? .
Purification Methods
Purify the acid by adsorbing on to a strongly acidic ion-exchange resin (Merck), elute the diacid with aqueous M NaOH, the eluate is evaporated, H2O is added, and filtered through a weakly acidic ion-exchange resin (Merck). The filtrate is then evaporated and recrystallised from EtOH. Its solubility is 0.1g in 1mL of 0.5N HCl. (±)--Kainic acid is recrystallised from H2O with m 230-260o. UV (MeOH): 219 (log 3.9); max 1HNMR (CCl4, 100MHz, Me4Si standard) : 1.64 (s 1H), 1.70 (s 3H), 3.24 (d J 7.5, 2H), 3.3-4.2 (1H), 3.70 (s 3H), 3.83 (s 3H), 4.35 (dd J 7.5, J 14.5, 1H), 5.21 (t J 7.5, 1H), 7.26 (t J 7.5, 1H). [Oppolzer & Andres Helv Chim Acta 62 2282 1979, Beilstein 22 III/IV 1523.]
References
1) Watkins et al. (1981), Excitatory amino acid transmitters; Ann. Rev. Pharmacol. Toxicol., 21 165
Check Digit Verification of cas no
The CAS Registry Mumber 487-79-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 7 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 487-79:
(5*4)+(4*8)+(3*7)+(2*7)+(1*9)=96
96 % 10 = 6
So 487-79-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
487-79-6Relevant articles and documents
Enantioselective total synthesis of (-)-α-kainic acid
Farwick, Andreas,Helmchen, Guenter
, p. 1108 - 1111 (2010)
(Figure Presented) An enantioselective total synthesis of (-)-α-kainic acid is described. Key steps are an lr-catalyzed allylic amination with a propargyllc amine to provide an enyne and a diastereoselective intramolecular Pauson-Khand reaction. Subsequent steps involve a Baeyer-Villiger reaction, reduction of the resulting lactone, and direct Jones oxidation of a silyl ether.
High-pressure Diels-Alder approach to natural kainic acid
Pandey, Sushil K.,Orellana, Arturo,Greene, Andrew E.,Poisson, Jean-Francois
, p. 5665 - 5668 (2006)
The first Diels-Alder based synthesis of (-)-kainic acid is described. Danishefsky's diene and a vinylogous malonate derived from 4-hydroxyproline combine under high pressure to afford a key bicyclic intermediate with virtually no loss of enantiopurity. This adduct can be converted into the natural product with complete stereocontrol.
Enantioselective total synthesis of (-)-kainic acid and (+)-acromelic acid C: Via Rh(i)-catalyzed asymmetric enyne cycloisomerization
Lei, Honghui,Xin, Shan,Qiu, Yifan,Zhang, Xumu
, p. 727 - 730 (2018)
A diversity-oriented synthetic strategy was developed for the total synthesis of kainoid amino acids, which led to the enantioselective synthesis of (-)-kainic acid and the first total synthesis of (+)-acromelic acid C. Rh(i)-catalyzed asymmetric enyne cycloisomerization served as the key reaction in this strategy for the rapid construction of highly functionalized lactam, and the resulting vinyl acetate moiety was further utilized as a versatile building block for the installation of both isopropylidene and 2-pyridone units existing in natural kainoids.
Synthesis of (±)-β-Allokainic Acid
Piotrowski, Mathew L.,Kerr, Michael A.
, p. 3122 - 3126 (2019/06/08)
The total synthesis of kainoid alkaloid, (+/–)-β-allokainic acid is reported. The key step is a vinylogous Cloke–Wilson rearrangement followed by Lewis acid and transition metal induced transformations to prepare a highly functionalized pyrrolidine suitable for conversion to the target molecule.
