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Chelidamic acid, commonly known as Chelidonic acid or Jervaic acid, is an acidic compound derived from the plant Chelidonium majus L. It possesses analgesic, antimicrobial, anti-inflammatory, and central nervous system depressant properties. It shows anti-inflammatory effects by potentially inhibiting NF-κB and caspase-1 in HMC-1 cells, leading to a reduction in the production of IL-6. This indicates its potential in treating allergic diseases and other inflammatory conditions. It is a potent inhibitor of glutamate decarboxylase (GAD), an enzyme that catalyzes the decarboxylation of L-glutamic acid to form γ-aminobutyric acid (GABA). Its Ki value for GAD inhibition is 1.2 μM, suggesting a strong affinity for the enzyme. While not explicitly stated in the references, its antimicrobial activity is likely due to its ability to disrupt cellular processes or membrane integrity in microorganisms. This potential makes it a candidate for antibacterial or antifungal agents. It acts as a central nervous system depressant, though the specific mechanism of action is not detailed. This property may contribute to its sedative effects and potential use in treating anxiety or insomnia.
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Chemical Formula |
C7H5NO5 |
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Exact Mass |
183.02 |
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Molecular Weight |
183.12 |
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m/z |
183.02 (100.0%), 184.02 (7.6%), 185.02 (1.0%) |
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Elemental Analysis |
C, 45.91; H, 2.75; N, 7.65; O, 43.68 |
Applications in medicine
Anti-Inflammatory Agent
It has been found to exhibit anti-inflammatory properties. By inhibiting NF-κB and caspase-1, it reduces the production of inflammatory cytokines such as IL-6, making it a potential candidate for treating inflammatory diseases like allergies, rheumatoid arthritis, and asthma.
Neuroprotective Agent
As a glutamate decarboxylase (GAD) inhibitor, it reduces the levels of the neurotransmitter GABA (γ-aminobutyric acid). This modulation of neurotransmitter levels may be useful in treating certain neurological disorders such as epilepsy and anxiety. However, further research is needed to fully understand its effects on the nervous system.
Antimicrobial Agent
It possesses antimicrobial properties, though its exact mechanism of action is not fully understood. It may disrupt cellular processes or membrane integrity in bacteria and fungi, making it a potential candidate for antibacterial or antifungal agents.
Analgesic Agent
The mild analgesic properties suggest its potential use in treating mild to moderate pain conditions. However, further clinical studies are required to validate its efficacy and safety.
Cancer Research
Although still in the preliminary stages, it has shown some promising results in cancer research. It may have the potential to inhibit the growth and spread of cancer cells, but more in-depth studies are necessary to confirm these findings.
Topical Applications
It may also be useful in topical applications for treating skin conditions such as acne, psoriasis, and eczema due to its anti-inflammatory and antimicrobial properties. However, clinical trials are needed to evaluate its safety and efficacy for these uses.
It is important to note that while Chelidamic acid shows promise in these medicinal applications, it is still in the early stages of research and development. Further clinical studies are required to fully understand its efficacy, safety, and mechanism of action in treating various diseases.
Applications in Cosmetic
Antioxidant Properties: While not explicitly stated for it, antioxidants are commonly used in cosmetics to protect skin cells from damage caused by free radicals. Its potential bioactivity could indicate similar protective effects.
Anti-Inflammatory Effects: Given its presence in plants known for their medicinal properties, it may have anti-inflammatory effects that could be beneficial in soothing irritated or inflamed skin.
Moisturizing Agent: Although not directly mentioned, compounds with similar chemical properties and molecular weights are often used as moisturizing agents in cosmetics. Its hydrophilic nature suggests it could potentially function in this role.
Preparation Methods
- Naturally found in the plant Chelidonium majus L., commonly known as greater celandine.
- The plant material can be extracted using suitable solvents, such as ethanol or methanol, to obtain an extract containing it and other compounds.
- The crude extract obtained from the plant material can be further processed to isolate and purify Chelidamic acid.
- Techniques such as chromatography (e.g., liquid-liquid chromatography, column chromatography) can be employed to separate it from other components in the extract.
- Crystallization or recrystallization methods may also be used to purify it and obtain it in a more concentrated form.
- While it is typically obtained from its natural source, chemical synthesis may be possible under certain conditions.
- The synthesis route would likely involve organic chemistry reactions to construct the desired molecular structure.
- However, specific synthesis methods are not widely reported and would require detailed research and experimentation.
- The exact production method may vary depending on the source material, equipment available, and the desired purity level.
- Extraction from the natural source is the most common approach due to the presence in certain plants.
- If chemical synthesis is required, it would likely involve complex organic chemistry reactions and may not be economically feasible for large-scale production.
Precautions
Personal Protective Equipment (PPE):
Wear laboratory attire and disposable gloves while handling the compound.
Avoid inhalation, ingestion, or direct contact with skin and eyes.
Storage and Handling:
Store in a cool, dry place, protected from light. Avoid repeated freeze-thaw cycles.
Ensure the product is at the bottom of the container before dissolving by briefly centrifuging it.
Use in Experiments:
Use the compound only for research purposes and not on humans.
Dissolve the powder and, if possible, use it on the same day. If storing for later use, keep the solution in sealed vials at -20°C for up to two weeks.
Allow the product to equilibrate to room temperature for at least 1 hour before use.
Disposal:
Follow local regulations for the safe disposal of any unused or expired compound. Do not dispose of it in sewers or the natural environment.
General Safety Measures:
Keep the compound away from heat, open flames, and other ignition sources.
Avoid mixing it with incompatible substances, such as oxidizers or alkalis, which may cause hazardous reactions.
Ensure the work area is well-ventilated to prevent the accumulation of fumes or vapors.
In Case of Spillage or Exposure:
In case of accidental spillage or contact with skin or eyes, immediately rinse with plenty of water and seek medical assistance.
Remember to follow all safety guidelines and regulations specific to your laboratory or research institution.
In-depth dissection of molecular structure
Chelidamic Acid (chemical formula C₇H₅NO₅, also known as 4-hydroxypyridine-2,6-dicarboxylic acid) has a molecular structure consisting of a pyridine-oxime ring and two carboxylic acid groups. Its unique electron distribution and spatial configuration endow it with excellent coordination ability and reactivity, making it a key molecule connecting chemistry, materials, and biomedical fields. The following provides a deep dissection from four dimensions: molecular framework, functional groups, electronic effects, and spatial configuration.
Core Structure: Conjugated System of Pyridinone Ring
The molecular core of Chelidamic Acid is a 1,4-dihydro-4-oxo-pyridine ring (C₅H₄NO), which consists of five carbon atoms, one nitrogen atom and one oxygen atom. Among them, the nitrogen atom (N) is at the 1st position, and the oxygen atom (O) is connected to the 4th carbon atom in the form of a carbonyl group (C=O), forming a conjugated π-electron system. This structure has the following characteristics:
Aromaticity retained
Although the pyridinone ring deviates from complete aromaticity due to the presence of a saturated carbon (at position 1), its conjugated system can still disperse the electron cloud, giving the molecule stability similar to that of aromatic compounds. For example, its measured molar refractive index is 37.95, indicating a high degree of electron delocalization.
Reactivity sites
The hydrogen atom at position 1 (C-H) is significantly enhanced in acidity due to the electron-withdrawing effect of the adjacent carbonyl group (pKa ≈ 4.5). It readily loses a proton in an alkaline environment to form a negative ion, thereby participating in nucleophilic reactions or coordination interactions.
Functional groups: The dual role of carboxylic acid groups
The chelidamic acid group is connected to a carboxylic acid group (-COOH) at positions 2 and 6 of the pyridinone ring. These two groups are not only key to the functionalization of the molecule but also affect the overall properties through electronic effects and steric hindrance.
Electron effect
The electron-withdrawing effect of the carboxyl group (-I effect) reduces the electron density of the pyridinone ring, further enhancing the acidity of the 1-position C-H bond. At the same time, the oxygen atom (O) of the carboxyl group carries lone pairs of electrons, which can act as a hydrogen bond donor or coordination atom, participating in intermolecular interactions or metal coordination.
Spatial steric hindrance
The two carboxyl groups are located in the para position of the pyridinone ring (1,4 relationship), forming a certain spatial separation, reducing the electrostatic repulsion between them, allowing the molecule to form a stable layered structure in the crystal through hydrogen bonds (such as O-H⋯O). For example, single-crystal X-ray diffraction analysis shows that there are N-H⋯O and O-H⋯O hydrogen bond networks in its crystal, enhancing the stability of molecular stacking.
Electron effect: Synergy of hydrogen bond and coordination ability
The electron distribution of Chelidamic Acid makes it an excellent hydrogen bond donor and metal ligand.
Hydrogen bond network: The three hydrogen donor groups (1-position C-H and two carboxylic acid O-H) in the molecule and the six hydrogen receptor groups (carbonyl O, carboxylic acid O) can form a complex hydrogen bond system. In the solid state, this system presents a three-dimensional network structure, while in the solution it affects the solubility and reaction selectivity of the molecule. For example, in an aqueous solution, Chelidamic Acid can combine with water molecules through hydrogen bonds, forming a stable solvation layer, thereby regulating its reactivity.
Metal coordination: The oxygen atom of the carboxylic acid group and the nitrogen atom of the pyridinone ring can both act as coordination atoms and form stable complexes with metal ions (such as Cu²⁺, Ni²⁺, Fe³⁺). This coordination mode has the following characteristics:
Multidentate coordination: A single Chelidamic Acid molecule can simultaneously provide 3-4 coordination atoms (such as two carboxylic acid O, one pyridinone N and one carboxylic acid O), forming a pentagonal or hexagonal coordination ring, enhancing the stability of the complex.
Geometric configuration diversity: Depending on the coordination number of the metal ion and spatial requirements, Chelidamic Acid can form mononuclear, dinuclear or polynuclear complexes. For example, when coordinating with Cu²⁺, it often forms a planar quadrilateral configuration, while when coordinating with Ni²⁺, it may present an octahedral configuration.
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Spatial configuration: Molecular flexibility and functional adaptation
Although the molecular framework of Chelidamic Acid has a certain rigidity, the spatial arrangement of its functional groups still allows for certain conformational adjustments to adapt to different functional requirements.
Rotational freedom of carboxyl groups: The two carboxyl groups are connected to the pyridinone ring through a single bond and can rotate within a certain range (with a rotational barrier of approximately 10-15 kcal/mol), thereby adjusting the charge distribution on the molecular surface and the hydrogen bond pattern. This flexibility enables it to bind to different shapes of metal ions or biological molecules.
Isomerization phenomenon: Under specific conditions (such as acidic or basic environments), Chelidamic Acid can undergo isomerization, forming an equilibrium system of 4-hydroxypyridine-2,6-dicarboxylic acid and 4-oxopyridine-2,6-dicarboxylic acid. This isomerization not only affects the electronic structure of the molecule, but also changes its coordination ability and reactivity. For example, in alkaline conditions, the 4-hydroxy form is more stable, and the deprotonation degree of the carboxyl group is higher, thereby enhancing its metal coordination ability.
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