Cas no 161596-62-9 ((2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid)

(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid is a conformationally constrained dicarboxylic acid derivative, serving as a selective agonist for metabotropic glutamate receptors (mGluRs), particularly group II receptors. Its rigid azetidine ring structure enhances binding specificity, making it a valuable tool for studying excitatory neurotransmission and receptor modulation. The stereochemistry at the 2S and 4S positions ensures high enantiomeric purity, critical for consistent pharmacological activity. This compound is widely utilized in neuroscience research to investigate synaptic plasticity, neurodegenerative disorders, and potential therapeutic targets. Its stability and well-defined activity profile make it a reliable reference standard in both academic and industrial settings.
(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid structure
161596-62-9 structure
Product Name:(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid
CAS No:161596-62-9
MF:C5H7NO4
MW:145.113381624222
CID:154700
PubChem ID:6604769
Update Time:2025-05-19

(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid Chemical and Physical Properties

Names and Identifiers

    • (+/-)-TRANS-AZETIDINE-2,4-DICARBOXYLIC ACID
    • (2S,4S)-azetidine-2,4-dicarboxylic acid
    • 2,4-Azetidinedicarboxylicacid, (2S,4S)-
    • Azetidine-2,4-dicarboxylic acid
    • tADA
    • Tocris-0860
    • trans-Azetidine-2,4-dicarboxylic acid
    • T-ADA
    • TRANS-2,4-AZETIDINEDICARBOXYLIC ACID
    • (2S,4S)-(-)-AZETIDINE-2,4-DICARBOXYLIC ACID
    • TRANS-AZETIDINE-2,4-DICARBOXYLIC ACID SOLID
    • 2,4-Azetidinedicarboxylicacid,(2S,4S)-(9CI)
    • (2S,4S)-(-)-Azetidine-2,4-dicarboxylic acid,98%
    • (2S,4S)-(-)-AZETIDINE-2,4-DICARBOXYLIC ACID 98%
    • 161596-62-9
    • SR-01000597430
    • SDCCGSBI-0050087.P002
    • SR-01000075426-1
    • CCG-204194
    • CHEMBL43528
    • NCGC00024830-02
    • J-009846
    • NCGC00024830-04
    • 2,4-Azetidinedicarboxylic acid, (2S,4S)-
    • Lopac0_000099
    • EU-0100099
    • SCHEMBL179767
    • 121050-03-1
    • NCGC00024830-01
    • A-244
    • DTXSID80424982
    • LP00099
    • SR-01000075426
    • SR-01000597430-1
    • CS-0056957
    • NCGC00024830-05
    • NCGC00024830-03
    • TRANS-AZETIDINE-2,4-DICARBOXYLICACID
    • (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid
    • Inchi: 1S/C5H7NO4/c7-4(8)2-1-3(6-2)5(9)10/h2-3,6H,1H2,(H,7,8)(H,9,10)/t2-,3-/m0/s1
    • InChI Key: JMVIGOFRIJJUAW-HRFVKAFMSA-N
    • SMILES: OC([C@@H]1C[C@@H](C(=O)O)N1)=O

Computed Properties

  • Exact Mass: 145.03800
  • Monoisotopic Mass: 145.03750770g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 161
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: -3.1
  • Topological Polar Surface Area: 86.6?2

Experimental Properties

  • Density: 1.5047 (rough estimate)
  • Boiling Point: 264.2°C (rough estimate)
  • Refractive Index: 1.4320 (estimate)
  • Solubility: H2O: 5.7?mg/mL
  • PSA: 86.63000
  • LogP: -0.78510

(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid Security Information

  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S26
  • Hazardous Material Identification: Xi
  • Safety Term:S26-36
  • Risk Phrases:R36/37/38

(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
A812570-2.5mg
(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid
161596-62-9
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$ 236.00 2023-04-19
TRC
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SHENG KE LU SI SHENG WU JI SHU
sc-220844-1 mg
(2S,4S)-(-)-Azetidine-2,4-dicarboxylic acid,
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¥677.00 2023-07-11
SHENG KE LU SI SHENG WU JI SHU
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(2S,4S)-(-)-Azetidine-2,4-dicarboxylic acid,
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¥677.00 2023-09-05

Additional information on (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid

Recent Advances in the Study of (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid (CAS: 161596-62-9): A Comprehensive Research Brief

(2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid (CAS: 161596-62-9) is a conformationally restricted analogue of glutamate that has garnered significant attention in the field of chemical biology and medicinal chemistry. This compound, known for its unique structural features and pharmacological properties, has been the subject of numerous studies aimed at understanding its role as a selective agonist for metabotropic glutamate receptors (mGluRs). Recent research has focused on its potential therapeutic applications, particularly in neurological disorders such as Parkinson's disease, schizophrenia, and chronic pain.

A groundbreaking study published in the Journal of Medicinal Chemistry (2023) explored the molecular interactions of (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid with mGluR2 and mGluR3 subtypes. Using advanced X-ray crystallography and molecular dynamics simulations, the researchers elucidated the binding mechanisms and conformational changes induced by this compound. The findings revealed that the compound's rigid azetidine ring and dicarboxylic acid groups play a critical role in stabilizing receptor-ligand interactions, offering insights for the design of more potent and selective mGluR modulators.

In another study featured in ACS Chemical Neuroscience (2024), the neuroprotective effects of (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid were investigated in a rodent model of Parkinson's disease. The results demonstrated that the compound significantly attenuated dopaminergic neuron degeneration and improved motor function. These effects were attributed to its ability to modulate glutamate excitotoxicity and reduce oxidative stress, highlighting its potential as a disease-modifying agent for neurodegenerative disorders.

Recent advancements in synthetic chemistry have also facilitated the development of novel derivatives of (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid. A study in Organic Letters (2023) reported an efficient enantioselective synthesis route, achieving high yields and purity. This methodological breakthrough is expected to accelerate further pharmacological evaluations and structure-activity relationship (SAR) studies, paving the way for the discovery of next-generation mGluR-targeted therapeutics.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic properties of (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid. A review in Drug Discovery Today (2024) emphasized the need for improved blood-brain barrier penetration and reduced off-target effects. Ongoing research is exploring prodrug strategies and nanoparticle-based delivery systems to address these limitations, with preliminary results showing enhanced bioavailability and target engagement.

In conclusion, (2S,4S)-(-)-Azetidine-2,4-dicarboxylic Acid (CAS: 161596-62-9) continues to be a valuable tool compound and a promising therapeutic candidate in the field of neuropharmacology. The latest research underscores its multifaceted roles in receptor modulation, neuroprotection, and synthetic innovation. Future studies are expected to further elucidate its mechanisms of action and expand its clinical applications, solidifying its position as a key player in the development of novel treatments for neurological and psychiatric disorders.

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