ChemicalBook > CAS DataBase List > (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID

(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID

Product Name
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
CAS No.
52497-36-6
Chemical Name
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
Synonyms
DHK;DIHYDROKAINIC ACID;Dihydrokainic acid, EAAT2 (GLT-1) inhibitor;2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid;(2S,3S,4R)-3-(carboxymethyl)-4-isopropyl-proline;(2S,3R,4R)-2-Carboxy-4-iospropyl-3-pyrrolidineacetic acid;(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID;3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)-;(2S,3S,4R)-3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid;(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-2-pyrrolidinecarboxylic acid
CBNumber
CB7153569
Molecular Formula
C10H17NO4
Formula Weight
215.25
MOL File
52497-36-6.mol
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(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Property

Melting point:
285 °C (decomp)
Boiling point:
416.6±30.0 °C(Predicted)
Density 
1.187±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
H2O: >10 mg/mL
form 
solid
pka
2.11±0.60(Predicted)
color 
White
Water Solubility 
Soluble to 25 mM in water
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
26-36
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D1064
Product name
Dihydrokainic acid
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$279
Updated
2025/07/31
Sigma-Aldrich
Product number
D1064
Product name
Dihydrokainic acid
Purity
≥98% (HPLC), powder
Packaging
50mg
Price
$938
Updated
2025/07/31
Cayman Chemical
Product number
28478
Product name
Dihydrokainic Acid
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
28478
Product name
Dihydrokainic Acid
Packaging
25mg
Price
$442
Updated
2024/03/01
Cayman Chemical
Product number
28478
Product name
Dihydrokainic Acid
Packaging
5mg
Price
$127
Updated
2024/03/01
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(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Chemical Properties,Usage,Production

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).

Definition

ChEBI: Dihydrokainic acid is a dicarboxylic acid. It is functionally related to a kainic acid.

Biological Activity

EAAT2(GLT1)-selective non-transportable inhibitor of L-glutamate and L-aspartate uptake (K i = 23 μ M). 130-fold selective over EAAT1 and EAAT3 (K i > 3 mM). Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset™ .

Biochem/physiol Actions

Dihydrokainic favors neuronal cell death. It modulates anxiety and depression behaviors.

storage

Room temperature

References

[1] J. ARRIZA. Functional comparisons of three glutamate transporter subtypes cloned from human motor cortex[J]. Journal of Neuroscience, 1994, 42 1: 5559-5569. DOI: 10.1523/jneurosci.14-09-05559.1994
[2] J GASULL-CAMóS. Glial GLT-1 blockade in infralimbic cortex as a new strategy to evoke rapid antidepressant-like effects in rats[J]. Translational Psychiatry, 2017, 7 2: e1038-e1038. DOI: 10.1038/tp.2017.7
[3] JúLIA GASULL-CAMóS . Serotonergic mechanisms involved in antidepressant-like responses evoked by GLT-1 blockade in rat infralimbic cortex[J]. Neuropharmacology, 2018, 139: Pages 41-51. DOI: 10.1016/j.neuropharm.2018.06.029
[4] CATHERINE S JOHN. Blockade of Astrocytic Glutamate Uptake in the Prefrontal Cortex Induces Anhedonia[J]. Neuropsychopharmacology, 2012, 37 11: 2467-2475. DOI: 10.1038/npp.2012.105
[5] SHAO-WEN TIAN . Glutamate transporter GLT1 inhibitor dihydrokainic acid impairs novel object recognition memory performance in mice[J]. Physiology & Behavior, 2019, 199: Pages 28-32. DOI: 10.1016/j.physbeh.2018.10.019

(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Suppliers

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52497-36-6, (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACIDRelated Search:

Ethyl chloroacetate (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID 2-(ISOAMYLAMINO)ETHANOL 2-AMINO-3-METHYL-HEXANOIC ACID 3-isopropylglutaric acid 3-(Aminomethyl)-5-methylhexanoic acid (2S,3S)-3-METHYLPYRROLIDINE-2-CARBOXYLIC ACID 4-METHYL-2-PYRROLIDINE CARBOXYLIC ACID 2-AMINO-3-ETHYL-PENTANOIC ACID B-N-PROPYLGLUTARIC ACID (R/S)-2-AMINO-5-METHYLHEXANOIC ACID 3-Pyrrolidineethanol 3-Pyrrolidineacetic acid (+/-)-THREO-3-METHYLGLUTAMIC ACID

  • DHK
  • DIHYDROKAINIC ACID
  • (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
  • 2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid
  • (2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-pyrrolidine-2-carboxylic acid
  • (2S,3S,4R)-3-(carboxymethyl)-4-isopropyl-proline
  • (2S,3R,4R)-2-Carboxy-4-iospropyl-3-pyrrolidineacetic acid
  • (2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-2-pyrrolidinecarboxylic acid
  • 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)-
  • (2S,3S,4R)-3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid
  • Dihydrokainic acid, EAAT2 (GLT-1) inhibitor
  • 52497-36-6
  • Cell Signaling and Neuroscience
  • Cell Biology
  • BioChemical
  • Ligand-Gated Ion Channels
  • Ionotropic Glutamate Receptor Modulators
  • Ion Channels
  • Glutamate receptor
  • Glutamate