Dihydrokainic acid

Base Information

• Chemical Name: Dihydrokainic acid
• CAS No.: 52497-36-6
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Hs Code.: 2933990090
• European Community (EC) Number: 637-065-5
• UNII: MQ4LMC2HN5
• DSSTox Substance ID: DTXSID20200489
• Nikkaji Number: J493.199H
• Wikipedia: Dihydrokainic_acid
• Wikidata: Q76009955
• Metabolomics Workbench ID: 56516
• ChEMBL ID: CHEMBL279561
• Mol file: 52497-36-6.mol

Synonyms:dihydrokainate;dihydrokainic acid

Chemical Property of Dihydrokainic acid

Chemical Property:

• Vapor Pressure: 4.14E-08mmHg at 25°C
• Melting Point: 285 °C (decomp)
• Boiling Point: 416.6°Cat760mmHg
• PKA: 2.11±0.60(Predicted)
• Flash Point: 205.8°C
• PSA: 86.63000
• Density: 1.187g/cm³
• LogP: 0.73470
• Storage Temp.: 2-8°C
• Solubility.: H2O: >10 mg/mL
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dihydrokainic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36

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: Dihydrokainic acid (DHK) is an inhibitor of excitatory amino acid transporter 2 (EAAT2; Ki = 23 μM for glutamate uptake by COS cells expressing EAAT2). It is selective for EEAT2 over EAAT1 and EAAT3 (Ki = >3 mM for both). DHK microinfusion (5 nmol) into the rat infralimbic cortex reduces the time spent immobile in the forced swim test, indicating antidepressant-like behavior, an effect that is blocked by the AMPA receptor antagonist NBQX and the serotonin (5-HT) receptor subtype 5-HT1A antagonist WAY-100635 . It also increases glutamate and serotonin levels and the expression of c-Fos in the dorsal raphe nucleus. In contrast, DHK microinjection (6.25 nmol) into the rat prefrontal cortex (PFC) increases the latency to drink sucrose in a sucrose intake test, indicating anhedonia-like behavior. It also impairs memory acquisition, consolidation, and retrieval in mice in the novel object recognition test.
• Uses: Dihydrokainic acid has been used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes and glial cells. It may be used as a GLT-1 inhibitor in Lateral habenula (LHb).

Technology Process of Dihydrokainic acid

There total 24 articles about Dihydrokainic 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:

(2S,3S,4S)-3-Carboxymethyl-4-isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 11h;

DOI:10.1055/s-2005-868477

Reference yield:

N-Boc-3-(carboxymethyl)-4-(i-propylidene)-2-pyrrolidinecarboxylic acid dimethyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / H₂ / PtO₂ / methanol / 14 h / 20 °C / 760 Torr

2: KOH / tetrahydrofuran; H₂O / 15 h / 20 °C

3: 55 mg / TFA / CH₂Cl₂ / 11 h / 20 °C

With potassium hydroxide; hydrogen; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo0513865

Reference yield:

(2S,3S)-3-Carboxymethyl-4-isopropylidene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 174 mg / toluene; methanol; hexane / 16 h / 20 °C

2: 98 percent / H₂ / PtO₂ / methanol / 14 h / 20 °C / 760 Torr

3: KOH / tetrahydrofuran; H₂O / 15 h / 20 °C

4: 55 mg / TFA / CH₂Cl₂ / 11 h / 20 °C

With potassium hydroxide; hydrogen; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;

DOI:10.1021/jo0513865

upstream raw materials:

(-)-kainic acid

(+/-)-(3,3-dichloro-5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

(+/-)-(5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

(+/-)-(3ξ-ethoxycarbonyl-5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

Refernces

• 1、 Hodgson, David M.,Hachisu, Shuji,Andrews, Mark D.. "Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement". . p. 8866 - 8876. Retrieved 2007/10/03.