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| | Kainic acid Basic information |
| Product Name: | Kainic acid | | Synonyms: | -Dihydroxyandrost-5-en-17-one;12-dihydroxyguaian-6,10-diene;)]-Hexahydro-2-oxo-1,3-bis(phenylmethyl)-1H-Thieno[3,4-d]imidazole-4-pentanoic Acid Phenylmethyl Ester;[3aS-(3aα(3aα)-3a,4,7,7a-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione;7-p-Toluenesulfonylhydrazide 3β-Dihydroxy-chol-5-ene-24-carboxylic Acid Ethyl Ester | | CAS: | 487-79-6 | | MF: | C10H15NO4 | | MW: | 213.23 | | EINECS: | | | Product Categories: | Glutamate receptor | | Mol File: | 487-79-6.mol |  |
| | Kainic acid Chemical Properties |
| Melting point | 253-254 C | | alpha | D24 -14.8° (c = 1.01) | | Boiling point | 353.22°C (rough estimate) | | density | 1.2177 (rough estimate) | | refractive index | 1.4368 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,2-8°C | | solubility | H2O: soluble | | form | White to off-white solid. | | pka | 2.03±0.60(Predicted) | | color | White | | Optical Rotation | -14.824 (H2O) | | Water Solubility | Soluble to 25 mM in water | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months. | | InChI | InChI=1S/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 | | InChIKey | VLSMHEGGTFMBBZ-OOZYFLPDSA-N | | SMILES | N1C[C@H](C(C)=C)[C@H](CC(O)=O)[C@H]1C(O)=O | | EPA Substance Registry System | 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- (487-79-6) |
| Hazard Codes | Xn | | Risk Statements | 20/21/22 | | Safety Statements | 22-24/25-36 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | Kainic acid Usage And Synthesis |
| 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 | excitory amino acid, neurotoxin, neurobiology tool | | Uses | Neurobiological tool. | | Uses | glutamate receptor agonist, anthelmintic | | Uses | (-)-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. | | Definition | ChEBI: Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a L-proline derivative and a non-proteinogenic L-alpha-amino acid. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-). | | Biological Activity | Selective agonist at kainate receptors. Potent excitant and neurotoxin. Also available as part of the Kainate Receptor Tocriset™ . | | storage | Room temperature | | 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] J C WATKINS R H E. Excitatory amino acid transmitters.[J]. Annual review of pharmacology and toxicology, 1981, 21: 165-204. DOI:10.1146/annurev.pa.21.040181.001121 |
| | Kainic acid Preparation Products And Raw materials |
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