487-79-6 Usage
Description
Kainic acid (487-79-6) is a conformationally restricted glutamate analog which acts as a selective agonist at kainate receptors. CNS stimulant and neurotoxin. Kainic acid is a classic neuroexcitatory agent for induction of seizures in laboratory animals (typical dose 10-30 mg/kg).
Chemical Properties
soluble in 0.1 M NaOH
Uses
Different sources of media describe the Uses of 487-79-6 differently. You can refer to the following data:
1. excitory amino acid, neurotoxin, neurobiology tool
2. glutamate receptor agonist, anthelmintic
3. (-)-α-Kainic Acid is a naturally occurring neuroexcitatory chemical that is an selective agonist for a subtype of ionotropic glutamate receptor. Administration of (-)-α-Kainic Acid has been shown to increase production of reactive oxygen species, mitochondrial dysfunction, and apoptosis in neurons in many regions of the brain, particularly in the hippocampal subregions and in the hilus of dentate gyrus.
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.
