 |
| Synonyms:DPA Dipicolinic acid 2,6-Pyridinedicarboxylic acid 2,6-Dicarboxypyridine Molecular Formula:C7H5NO4 Molecular Weight: 167.12 HS Code: 2914399090 Grade:99% Hazard Class:General Cargo | |||||||||
499-83-2
bosschemical
499-83-2
Pyridine-2,6-dicarboxylic acid (also known as 2,6-pyridinedicarboxylic acid, 2,6-dipyridinecarboxylic acid, dipicolinic acid, 2,6-pyridinedicarboxylic acid, 2,6-dicarboxypyridine, DPAC, pydcH2), with the chemical formula C7H5NO4, a molecular weight of 167.12, CAS number 499-83-2, EINECS 207-894-3, UNII UE81S5CQ0G, InChIKey WJJMNDUMQPNECX-UHFFF AOYSA-N, is a dicarboxylic acid containing two carboxyl groups at positions 2 and 6 of the pyridine ring. It belongs to the pyridine carboxylic acid class of organic compounds and is also a natural marker molecule (dipicolinic acid, DPA) in the bacterial spore cortex. It is an important raw material for fine chemicals, analytical chemistry, and biological detection: a white crystalline powder with a melting point of approximately 248-250℃ (decomposes), slightly soluble in cold water, soluble in hot water, ethanol, and dilute alkaline solutions, and capable of sublimation. Due to its tripentate chelate coordination structure composed of pyridine nitrogen and two carboxyl groups, its strong complexing ability with metal ions, its sensitizing and luminescent ability for rare earth elements, and its labeling properties for bacterial spores, pyridine-2,6-dicarboxylic acid is widely used in biological indicators and sterilization validation, spore detection, ion chromatography, chemical sensing, metal complexation, metal-organic framework materials, catalysis, antibacterial and preservative applications, and rare earth separation.
Basic identification information : Chemical formula C7H5NO4; Molecular weight 167.12; CAS number 499-83-2; EINECS 207-894-3; UNII UE81S5CQ0G; InChIKey WJJMNDUMQPNECX-UHFFFAOYSA-N; IUPAC name pyridine-2,6-dicarboxylic acid; ChEBI 46837; ChEMBL 284104; Synonyms: pyridine-2,6-dicarboxylic acid, 2,6-pyridinedicarboxylic acid, 2,6-dipyridinecarboxylic acid, dipicolinic acid, 2,6-dicarboxypyridine, DPAC, pydcH2, NSC-176, etc.
Structurally , pyridine-2,6-dicarboxylic acid consists of two carboxyl groups (-COOH) at the 2 and 6 positions of the pyridine ring and a nitrogen atom on the ring. The three coordinating atoms (one pyridine nitrogen and two carboxyl oxygens) naturally form a stable tripentate chelate ligand, which forms a five-membered chelate ring with metal ions. The two carboxyl groups are electron-withdrawing groups and can be deprotonated in sequence, giving the molecule both coordination sites and pH responsiveness.
Physically , pyridine-2,6-dicarboxylic acid is a white crystalline powder with a melting point of approximately 248-250℃ (decomposes simultaneously); it is slightly soluble in cold water, soluble in hot water, ethanol, dilute alkaline solutions, and organic solvents, but insoluble in ether and chloroform; it sublimes upon heating; it has an extremely low vapor pressure; it is weakly acidic, and the pH of its aqueous solution varies with the degree of deprotonation; as a high-purity product for ion chromatography, its purity can reach over 99.5%.
Chemically , pyridine-2,6-dicarboxylic acid is a multidentate chelating ligand: the pyridine nitrogen and two carboxyl oxygen groups can coordinate with metal ions such as calcium, iron, zinc, copper, aluminum, and rare earth elements to form stable five-membered chelate ring complexes (such as the Ca-DPA complex in spores); the two carboxyl groups can be deprotonated and participate in derivatization reactions such as esterification and acylation; after coordination with lanthanide ions (europium, terbium), it sensitizes rare earth luminescence through the antenna effect; multiple coordination sites enable it to bridge metal ions to form one-dimensional to three-dimensional coordination polymers and metal-organic frameworks (MOFs); it is also a natural marker component of bacterial spore cortex, giving spores heat resistance; at the same time, it has antibacterial activity and can inhibit spore germination and microbial growth.
Why does pyridine-2,6-dicarboxylic acid play these roles in various fields? Its mechanism of action mainly includes the following:
Tridentate chelation coordination mechanism : The nitrogen atom of the pyridine ring and the two carboxyl oxygen atoms form a tridentate coordination site, which forms a stable five-membered chelate ring with metal ions. It has a strong complexing ability for metals such as calcium, iron, zinc, and lanthanides. After coordination, the overall molecular structure becomes rigid and stable, which is the basis for its use as a metal complexing agent, ligand and building block of materials.
Spore marker mechanism : Bacterial spores contain a large amount of Ca-DPA complex (accounting for about 5-15% of the dry weight of the spore), which endows the spores with extremely strong heat resistance, radiation resistance and chemical disinfection resistance; DPA is released when the spores germinate or die, and the detection of DPA can determine the presence and survival status of the spores, making it the core marker molecule for sterilization effect verification and spore detection.
Rare earth sensitized luminescence mechanism : After pyridine-2,6-dicarboxylic acid coordinates with lanthanide ions such as europium and terbium, the ligand absorbs ultraviolet light and transfers energy to rare earth ions (antenna effect), producing characteristic fluorescence emission with a large Stokes shift, making it possible to detect ultra-low concentration metal ions with fluorescence.
Coordination polymerization and framework construction mechanism : Two carboxyl groups can be deprotonated and bridge multiple metal ions, extending along space to form a one-dimensional chain, two-dimensional layer or three-dimensional porous framework (coordination polymer/metal-organic framework), with adjustable pore size and channels, used for gas adsorption, separation, catalysis and sensing materials.
pH response and ion exchange mechanism : The two carboxyl groups have different pKa and can be deprotonated in a stepwise manner, so that they can compete with metal ions for coordination as eluent ligands in ion chromatography and elute and separate cations in sequence according to the difference in affinity; the same property is also used in pH-responsive materials and controlled release systems.
Antibacterial and germination inhibition mechanism : Pyridine-2,6-dicarboxylic acid can inhibit bacterial growth and spore germination by chelating essential metal ions for microbial growth and interfering with spore germination signaling pathways, thus exhibiting broad-spectrum antibacterial activity.
Corresponding products: high-pressure steam sterilization biological indicator, ethylene oxide sterilization indicator, irradiation sterilization validation indicator, dry heat sterilization indicator, disinfection efficacy validation tablet, sterilization validation kit, laboratory sterilization monitoring tablet, etc.
Why it can be used for this purpose: The biological indicator uses heat-resistant spores as a carrier. During the sterilization process, the spores are inactivated and release pyridine-2,6-dicarboxylic acid (DPA) markers. By detecting whether DPA can still be detected, it can be determined whether all spores have been killed, thereby verifying whether the sterilization process meets the standards. It is a key quality control method for sterilization and release in the food industry.
Corresponding products: spore detection kits, bacterial spore staining reagents, foodborne spore detection kits, milk spore detection kits, drinking water spore monitoring kits, environmental spore monitoring tablets, biological pollution early warning kits, etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid is a specific marker of spore cortex. Detecting the DPA content in a sample can quickly determine the presence and quantity of spores. It is used for monitoring spore contamination in food, dairy products, drinking water, and clean environments, and is faster and more specific than traditional culture methods.
Corresponding products: ion chromatography eluent, cation analysis eluent, transition metal separation eluent, ion chromatography standard reagent, high-purity pyridine-2,6-dicarboxylic acid (purity above 99.5%), etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid acts as an eluent ligand in ion chromatography, forming complexes with alkali metal, alkaline earth metal and transition metal ions with different stabilities, and eluting and separating them sequentially according to the difference in affinity. It is a classic eluent component for ion chromatography analysis of cations and metal ions.
Corresponding products: rare earth sensitized fluorescent probes, europium/terbium complex fluorescent labeling reagents, metal ion fluorescent sensors, water quality heavy metal detection reagents, environmental pollutant fluorescent probes, biofluorescent probes, chemiluminescence analysis reagents, etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid coordinates with rare earth elements such as europium and terbium, and then sensitizes and emits light through the antenna effect. The fluorescence intensity is related to the concentration of the analyte, and a highly sensitive fluorescence sensor can be constructed to detect metal ions, biomolecules and harmful substances for environmental, water quality and biological analysis.
Matching products: complexing agents of metals, chelating agents, scale inhibitors for water treatment, metal ion collectors, complexing agents for electroplating, complexing agents for surface treatment, mineral flotation collectors, cleaning agents, scale remover, rust-proofing complexing agents etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid is a tridentate chelate that can form stable complexes with metal ions such as calcium, iron, copper, zinc and aluminum. It is used for metal ion chelation, scale and precipitation control, control of metal ion concentration, and can also be used as a complexing aid in electroplating, surface treatment and cleaning.
Corresponding products are: metal-organic framework materials, porous coordination polymers, gas adsorption and storage materials, hydrogen energy storage materials, CO2 capture materials, MOF separation membranes, MOF sensors, catalyst support materials, fluorescent MOF materials, wastewater adsorption materials, etc.
Why it can be used for this purpose Pyridine-2,6-dicarboxylic acid can form one-dimensional to three-dimensional porous networks by connecting metal ions with dicarboxyl groups, resulting in metal-organic frameworks with large specific surface areas and tunable pore sizes, which are applicable for the development of functional materials such as gas adsorption and separation, hydrogen and carbon dioxide storage, sensing, catalysis and adsorption of wastewater pollutants.
Corresponding products: metal complex catalysts, catalysts for oxidation reactions, catalysts for polymerization, catalytic systems for synthesis of organic compounds, photocatalytic complexes, supported catalysts, green catalytic materials and etc.
Why use it for this purpose: Pyridine-2,6-dicarboxylic acid forms stable chelate complexes with transition metals, which control the electronic environment and spatial arrangement of the metal center. It can be employed in catalytic reactions such as oxidation, polymerization and coupling and improve the activity and selectivity as a ligand for homogeneous or supported catalysts.
Related products: Bactericides, preservatives, antibacterial additives in daily chemicals, preservatives in cosmetics, antifungal agents in feed, antibacterial agents in aquaculture, bactericides in industry, spore germination inhibitors, antibacterial finishing agents for fabrics, preservatives for paper products, etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid has broad spectrum antibacterial activity by inhibiting bacterial growth and spore germination through chelating essential metal ions for microorganisms and interfering spore germination signals. It can be used in daily chemicals, food, feed, aquatic products and industries for antibacterial and preservative formulations.
Corresponding products: lanthanide separating agents, rare earth extractants, light rare earth/heavy rare earth separation reagents, nuclear fuel reprocessing chemicals, lanthanide purification ligands, rare earth metallurgical additives, high-purity rare earth separation materials, etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid forms complexes with different lanthanide ions that have slightly different stability. This difference can be used to achieve the stepwise separation and purification of lanthanide elements, which can be used for lanthanide separation in rare earth metallurgy and nuclear industry.
Corresponding products: HPLC analytical standards, ion chromatography standards, analytical grade reagents, spectroscopic analysis standard substances, coordination chemistry research reagents, materials synthesis reagents, teaching reagents, etc.
Why it can be used for this purpose: Pyridine-2,6-dicarboxylic acid has a purity of over 99.5% and is stable. It can be used as an analytical standard for high performance liquid chromatography and ion chromatography for content determination and method calibration. It is also a commonly used scientific research reagent in coordination chemistry, sensing, materials and biological detection research.
Pyridine-2,6-dicarboxylic acid (CAS 499-83-2) is a pyridine carboxylic acid with two carboxyl groups at the 2 and 6 positions of the pyridine ring. Its core structure is a tridentate chelate structure of "one pyridine nitrogen + two carboxyl oxygens," exhibiting strong coordination, rare-earth-sensitized luminescence, spore labeling, coordination polymerization, and antibacterial properties. It is mainly used as a biological indicator and sterilization validation, spore detection, ion chromatography eluent, chemical sensor, metal complexation, MOF materials, catalyst ligands, antibacterial and preservative applications, and rare-earth separation, covering a wide range of fields including disinfection quality control, food safety, analytical chemistry, materials science, catalysis, daily chemical food, and metallurgy. Understanding its tridentate coordination structure and the deprotonation capability of the two carboxyl groups explains why it can stably complex metal ions, sensitize rare-earth luminescence, construct porous materials, and detect spores—this is precisely why it spans so many niche applications.
