Kainic acid

Base Information

• Chemical Name: Kainic acid
• CAS No.: 487-79-6
• Deprecated CAS: 4071-38-9,46398-96-3
• Molecular Formula: C10H15NO4
• Molecular Weight: 213.233
• NSC Number: 136038
• UNII: SIV03811UC
• DSSTox Substance ID: DTXSID7040526
• Nikkaji Number: J9.244D
• Wikipedia: Kainic_acid
• Wikidata: Q390239
• NCI Thesaurus Code: C79132
• Pharos Ligand ID: JLPFBN5364Y2
• Metabolomics Workbench ID: 54445
• ChEMBL ID: CHEMBL275040
• Mol file: 487-79-6.mol

Synonyms:Acid, Digenic;Acid, Kainic;Digenic Acid;Kainate;Kainic Acid

Chemical Property of Kainic acid

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Melting Point: 253-254 °C
• Refractive Index: 1.508
• Boiling Point: 439.9 °C at 760 mmHg
• PKA: 2.03±0.60(Predicted)
• Flash Point: 219.8 °C
• PSA: 86.63000
• Density: 1.22 g/cm³
• LogP: 0.65480
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 213.10010796
• Heavy Atom Count: 15
• Complexity: 300

Purity/Quality:

99%, ^*data from raw suppliers

Kainic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=C)C1CNC(C1CC(=O)O)C(=O)O
• Isomeric SMILES: CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
• 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).
• Uses: excitory amino acid, neurotoxin, neurobiology tool glutamate receptor agonist, anthelmintic (-)-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.

Technology Process of Kainic acid

There total 526 articles about Kainic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl (2S,3S,4S)-3-((tert-butoxycarbonyl)methyl)-4-((E)-1-(tributylstannyl)prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate (1293306-04-3) → (-)-kainic acid (487-79-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1039/c1cc00048a

Reference yield: 97.0%

((2R,3S,4S)-2-Cyano-4-isopropenyl-pyrrolidin-3-yl)-acetic acid ethyl ester (329055-36-9) → (-)-kainic acid (487-79-6)

Guidance literature:

((2R,3S,4S)-2-Cyano-4-isopropenyl-pyrrolidin-3-yl)-acetic acid ethyl ester; With hydrogenchloride; In methanol; at 20 ℃; for 24h;

With potassium hydroxide; In water; at 20 ℃; for 20h; Further stages.;

DOI:10.1021/ol007009q

Reference yield: 78.0%

C19H31NO6 (1603824-11-8) → (-)-kainic acid (487-79-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/ol5009526

upstream raw materials:

(3S,4S)-3-hydroxymethyl-4-isopropenylpyrrolidine-1-carboxylic acid methyl ester

(1R,3aR,6aS)-1-acetoxy-3-oxo-tetrahydrofuro[3,4-c]pyrrole-5-carboxylic acid methyl ester

(3S,4S)-3-hydroxymethyl-4-isopropenylpyrrolidine-1-carboxylic acid tert-butyl ester

(3S,4S)-3-isopropenyl-4-methoxymethoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

Kainic acid dimethyl ester

[(3S)-2t-carboxy-4c-isopropenyl-1-(4-nitro-benzoyl)-pyrrolidin-3r-yl]-acetic acid

dihydrokainic acid

α-kainic acid norketone

Refernces

• 1、 Chekan, Jonathan R.,McKinnie, Shaun M. K.,Moore, Bradley S.,Noel, Joseph P.. "Algal neurotoxin biosynthesis repurposes the terpene cyclase structural fold into an N-prenyltransferase". . p. 12799 - 12805. Retrieved 2020.
• 2、 Cooper, Jeremy,Knight, David W.,Gallagher, Peter T.. "Total Synthesis of (-)-α-Kainic Acid". . p. 553 - 560. Retrieved 1992.
• 3、 Chekan, Jonathan R.,McKinnie, Shaun M. K.,Moore, Malia L.,Poplawski, Shane G.,Michael, Todd P.,Moore, Bradley S.. "Scalable Biosynthesis of the Seaweed Neurochemical, Kainic Acid". . p. 8454 - 8457. Retrieved 2019/05/21.