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KAINIC ACID

CAS No.
487-79-6
Chemical Name:
KAINIC ACID
Synonyms
KAINATE;(-)-α-Kainic Acid;C12819;Kainic;digenin;helminal;(3aαKainicaci;,4-beta))-;KAINIC ACID
CBNumber:
CB2351306
Molecular Formula:
C10H15NO4
Molecular Weight:
213.23
MDL Number:
MFCD00077806
MOL File:
487-79-6.mol
MSDS File:
SDS
Last updated:2024-08-28 13:53:22

KAINIC ACID 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 activity -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
FDA UNII SIV03811UC
EPA Substance Registry System 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- (487-79-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H312-H332
Precautionary statements  P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
Hazard Codes  Xn
Risk Statements  20/21/22
Safety Statements  22-24/25-36
WGK Germany  3

KAINIC ACID price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Tocris 0222 Kainicacid ≥98%(HPLC) 487-79-6 1 $82 2021-12-16 Buy
Tocris 7065 Kainicacid(synthetic) ≥98%(HPLC) 487-79-6 10 $159 2021-12-16 Buy
Tocris 0222 Kainicacid ≥98%(HPLC) 487-79-6 10 $173 2021-12-16 Buy
Tocris 7065 Kainicacid(synthetic) ≥98%(HPLC) 487-79-6 50 $669 2021-12-16 Buy
Tocris 0222 Kainicacid ≥98%(HPLC) 487-79-6 50 $718 2021-12-16 Buy
Product number Packaging Price Buy
0222 1 $82 Buy
7065 10 $159 Buy
0222 10 $173 Buy
7065 50 $669 Buy
0222 50 $718 Buy

KAINIC ACID Chemical Properties,Uses,Production

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

(-)-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.

Uses

Neurobiological tool.

Uses

excitory amino acid, neurotoxin, neurobiology tool

Uses

glutamate receptor agonist, anthelmintic

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) Watkins et al. (1981), Excitatory amino acid transmitters; Ann. Rev. Pharmacol. Toxicol., 21 165

301832-55-3
487-79-6
Synthesis of KAINIC ACID from 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-1-[(4-methylphenyl)sulfonyl]-, (2S,3S,4S)-

KAINIC ACID Preparation Products And Raw materials

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Aladdin Scientific
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(-)-A-KAINIC ACID KAINIC ACID KAINIC ACID SYNTHETIC KAINIC ACID (OPIKA-1(TM)) Kainic C12819 (2S,3S,4S)-Carboxy-4-(1-methylethenyl)-3-pyrrolidineaceticacid 3-(carboxyMethyl)-4-prop-1-en-2-ylproline (2S,3S,4S)-2-Carboxy-4-isopropenylpyrrolidine-3-acetic acid L-alpha-Kainic acid 3-Pyrrolidineaceticacid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- ,4-beta))- 2-carboxy-4-isopropenyl-3-pyrrolidineaceticaci 3-pyrrolidineaceticacid,2-carboxy-4-(1-methylethenyl)-,(2s-(2-alpha,3-beta alpha-kainicacid digenicacid digenin helminal (2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE) 2-CARBOXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID 2-CARBOXYL-3-CARBOXYMETHYL-4-ISOPROPENYL PYRROLIDINE [2S-(2A,3B,4B)]-2-CARBOXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID (2S,3S,4R)-CARBOXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID -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-(3a&alpha (3a&alpha )-3a,4,7,7a-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 7-p-Toluenesulfonylhydrazide 3&beta -Dihydroxy-chol-5-ene-24-carboxylic Acid Ethyl Ester -glucopyranosyl-(1&rarr Periplogenin 3-[O-&beta -sarmentopyranoside] -Hydroxy Cholesterol-d4 (Major) [2S-[1(S*),2&alpha ]]-4-Methyl-1-(1-phenylethyl)-2-piperidinecarboxylic Acid Ethyl Ester )-7-Dehydro-4,25-dihydroxycholesterol -Hydroxy Cholesterol 4-Acetate )-3,4-Dihydroxy-chol-5,7-diene-24-carboxylic Acid Methyl Ester -Allopyranosyl-(1&rarr -oleandropyranosyl-11-O-isobutyryl-12-O-acetyl- Tenacigenin B, 3-O-&beta )]-4-[2-(2,5-Dihydroxyphenyl)ethyl]octahydro-1-hydroxy-7a-methyl-5H-inden-5-one (2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid -Hydroxy Cholesterol-d7 4-Acetate -Diacetyloxy-chol-5-ene-24-carboxylic Acid Ethyl Ester )-4,5-Epoxy-13-ethyl-17-hydroxy-18,19-dinorpregn-20-yn-3-one Kainicaci KAINATE (-)-α-Kainic Acid α-Kainic acid 487-79-6 Glutamate receptor