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DL-Pipecolinic acid, also known as DL piperidinecarboxylic acid or DL-2-piperidinecarboxylic acid, has a molecular formula of C6H11NO2, a molecular weight of 133.16, and a CAS of 535-75-1. It is typically a white or off white crystalline solid at room temperature and pressure. It has a certain solubility in water, but the specific value may vary due to factors such as temperature and pH. Its water solubility allows it to react or dissolve with aqueous solutions in living organisms or laboratory environments, facilitating subsequent processing and analysis. The volatility is relatively low, which means it is not easily volatilized into the air at room temperature. It has broad application value in multiple fields. For example, in drug synthesis, its solubility and stability can be utilized to optimize synthesis conditions and improve yield; In biochemical research, its optical and electromagnetic properties can be utilized to study its molecular structure and interaction mechanisms; In materials science, its unique physical properties can be utilized to develop new functional materials, etc.
|
Chemical Formula |
C6H11NO2 |
|
Exact Mass |
129.08 |
|
Molecular Weight |
129.16 |
|
m/z |
129.08 (100.0%), 130.08 (6.5%) |
|
Elemental Analysis |
C, 55.80; H, 8.58; N, 10.84; O, 24.77 |
DL-Pipecolinic acid, as an important amino acid derivative, has shown broad application prospects in the fields of agriculture and plant physiology. Its unique chemical structure and biological activity make it a powerful tool for enhancing plant stress resistance, promoting growth and development, and regulating soil microbial communities.
Application under drought stress
Under drought stress, plants accumulate a large amount of proline to cope with osmotic stress. DL proline, as a form of proline, also has this function. Research has shown that exogenous application of DL proline can significantly improve the drought resistance of crops. For example, under drought stress, rice seedlings treated with DL high proline had higher leaf moisture content and milder wilting compared to the control group.
In addition, DL high proline can also regulate the root morphology and physiological characteristics of plants, such as increasing root growth and the ability to absorb nutrients, thereby improving crop tolerance to drought.
Application example: In a study conducted by the Chinese Academy of Sciences, researchers applied DL homoproline to rice seedlings under drought stress. The results showed that the application of DL high proline significantly increased the leaf water content of rice seedlings, and the degree of wilting was significantly reduced.
Application under salt stress
Salt stress is one of the important factors limiting plant growth and yield. DL high proline also exhibits significant stress resistance under salt stress. By exogenous application of DL proline, the ion balance inside plants can be regulated, reducing the toxicity of salt alkali to cells and improving crop tolerance to salt alkali stress. In addition, DL high proline can promote the accumulation of osmotic substances such as proline and betaine in plants, thereby further enhancing their stress resistance.
Application example: An experiment conducted by the Chinese Academy of Agricultural Sciences found that wheat seedlings treated with DL high proline under salt stress showed better growth and more robust root growth. At the same time, the content of proline and betaine in its leaves significantly increased, indicating that DL proline plays an important role in promoting the accumulation of osmotic substances in plants.
High temperature stress also has adverse effects on plant growth. DL proline also exhibits significant stress resistance under high temperature stress. By exogenous application of DL proline, the high temperature resistance of crops can be significantly improved, and the inhibitory effect of high temperature on plant growth can be alleviated.
Application example: A foreign experiment showed that the growth status of rice plants treated with DL-Pipecolinic acid high proline under high temperature stress was significantly better than that of the control group. Meanwhile, the antioxidant enzyme activity in its leaves significantly increased, indicating that DL proline plays an important role in enhancing plant antioxidant capacity.
DL high proline can promote the growth and development of plant roots. By exogenous application of DL proline, the growth of roots and their ability to absorb nutrients can be significantly increased. This is of great significance for improving soil quality, enhancing soil fertility, and increasing crop yields.
Application example: In agricultural production, foliar spraying of DL proline can significantly increase the root growth and nutrient absorption capacity of crops. For example, in corn production, foliar spraying of DL high proline can significantly increase the growth and root hair quantity of corn roots, thereby enhancing their ability to absorb soil nutrients.
Chlorophyll is an important biological pigment in plants, which participates in the capture and transfer of energy during photosynthesis. DL high proline can increase plant chlorophyll content, improve photosynthetic efficiency, and promote plant growth and development. By exogenous application of DL proline, the chlorophyll content and photosynthetic efficiency of crops can be significantly increased, thereby increasing crop yield and quality.
Application example: In wheat production, foliar spraying of DL proline can significantly increase the chlorophyll content and photosynthetic efficiency in wheat leaves. At the same time, yield indicators such as plant height, spike length, and thousand grain weight of wheat have also been significantly improved.
DL high proline can also promote fruit development and quality improvement. By exogenous application of DL proline, the quality and yield of fruits can be significantly improved. For example, in peach tree production, foliar spraying of DL proline can significantly increase the hardness and soluble solids content of peach fruits, thereby extending their storage and shelf life.
Application example: In peach tree production, researchers found that the hardness and soluble solids content of peach fruits were significantly improved by foliar spraying of DL high proline. Meanwhile, the storage and shelf life of the fruit have also been extended. This indicates that DL proline plays an important role in promoting fruit development and quality improvement.
DL proline can be used as a plant growth regulator to improve soil nutrient status by regulating soil microbial community structure and function. Research has shown that exogenous addition of appropriate amounts of DL proline can significantly increase soil bacterial diversity, reduce fungal diversity, and increase the relative abundance of beneficial microorganisms, thereby improving soil nutrient status and increasing crop yield.
Application example: In cotton production, researchers found a significant increase in bacterial diversity, a decrease in fungal diversity, and an increase in the relative abundance of beneficial microorganisms in the rhizosphere soil of cotton by exogenous addition of an appropriate amount of DL high proline. At the same time, the growth status and yield of cotton have also been significantly improved. This indicates that DL proline plays an important role in regulating soil microbial communities and improving soil nutrients.
DL-Pipecolinic acid high proline can also activate the expression of crop defense genes, enhance the function of the immune system, and improve crop resistance to pathogens and pests. By exogenous application of DL proline, the disease and insect resistance of crops can be significantly improved, reducing the occurrence and harm of pests and diseases.
Application example: In corn production, researchers found that the resistance of corn plants to corn borers was significantly improved by foliar spraying of DL high proline. At the same time, the number and area of disease spots on corn leaves were significantly reduced. This indicates that DL proline plays an important role in enhancing crop resistance to pathogens.
The microbial transformation process of soil nitrogen is the core of determining nitrogen fertilizer utilization efficiency. DL piperidine acid can selectively regulate the community structure of nitrogen cycling functional microorganisms: it can significantly increase the abundance of nitrogen fixing bacteria and ammonifying bacteria in soil, promote the mineralization and decomposition of inert organic nitrogen in soil, and enhance the effective nitrogen supply capacity of soil;
Soil Health and Yield Increase Application of Grain Crops
In the production of staple crops such as wheat and rice, DL piperidinoic acid is mainly used as a functional component for regulating microbial communities, and is combined with slow-release nitrogen fertilizers and bio organic fertilizers. In the experiment in the main wheat production area of Henan Province, 200 g DL piperidine acid and bio organic fertilizer compound products were applied per mu, the abundance of beneficial bacteria in the wheat rhizosphere was significantly increased, the incidence rate of root rot disease was reduced by 72%, and the root activity of wheat was increased by 50%.
Under the premise of reducing 25% nitrogen fertilizer, the yield per mu of wheat was increased by more than 12%, and the protein content of grains was increased by 1.2 percentage points, realizing the coordinated improvement of yield and quality. In the application of rice in the northeast cold region, DL piperidic acid can promote the proliferation of low-temperature growth promoting bacteria in the rice rhizosphere, improve the ability of rice to resist low-temperature cold damage, and effectively solve the pain point of slow turning green after transplanting rice in the northeast. The turning green period of rice is 3-5 days earlier, the incidence rate of sheath blight is reduced by 68%, and the yield per mu is more than 100 jin.
Quality improvement application of high value-added economic crops
In the production of high value-added economic crops such as tea, fruit trees, and traditional Chinese medicine, DL piperidine acid can regulate soil microbial communities, not only to prevent and control soil borne diseases, but also to promote the accumulation of secondary metabolites in crops by regulating the metabolism of rhizosphere microorganisms, significantly improving the quality of agricultural products. In the experiment of Fujian Tieguanyin Tea Garden, after the application of DL piperidine acid, the abundance of beneficial bacteria in the rhizosphere of tea plants increased significantly,
the incidence rate of root rot disease of tea plants decreased by 90%, the content of tea polyphenols and amino acids in tea increased significantly, the aroma level of tea increased significantly, and the comprehensive economic benefits of tea gardens per mu increased by more than 40%. In the cultivation of traditional Chinese medicinal materials such as ginseng and Panax notoginseng that are not suitable for continuous cropping,
DL piperidine acid can effectively restore the soil microbial community of old ginseng fields, allowing old ginseng fields that originally required 30 years to be replanted to be replanted after 1 year of DL piperidine acid regulation and restoration, greatly alleviating the land resource bottleneck of traditional Chinese medicinal material cultivation.
Adverse reactions
DL Pipecolic Acid (also known as DL-2-piperidinecarboxylic acid) is a nitrogen-containing heterocyclic compound with the molecular formula C ₆ H ₁ NO ₂ and a molecular weight of 129.16. This compound is stable at room temperature and pressure, and should be stored in a sealed, dark, ventilated, and dry place. The following is a detailed explanation of its adverse reactions:
Skin and mucosal irritation response
Skin irritation (GHS classification: Category 2)
The dust or vapor of DL Pipecolic Acid may directly irritate the skin and cause contact dermatitis. The mechanism may be related to the alkaline properties of the pyridine ring, as alkaline substances can disrupt the lipid barrier of the skin's stratum corneum, leading to dehydration of epidermal cells and release of inflammatory factors such as histamine and leukotrienes. Typical symptoms include erythema, itching, blisters, and in severe cases, skin cracks or ulcers may occur.
Preventive measures: Wear protective gloves (such as nitrile rubber gloves) and long sleeved clothing during operation to avoid direct contact; If contact occurs, immediately rinse with plenty of soapy water and apply moisturizer (such as Vaseline) to repair the barrier.
Eye irritation (GHS classification: Category 2A)
After entering the conjunctiva, the alkaline environment can damage corneal epithelial cells, leading to corneal opacity, photophobia, and tearing. Animal experiments have shown that piperidine compounds with similar structures (such as piperidine-4-carboxylic acid) can cause significant eye congestion in rabbits at a concentration of 0.1%.
Emergency treatment: Immediately rinse with physiological saline or flowing water for at least 15 minutes, flip the eyelids to ensure thorough rinsing; If the symptoms persist, seek medical attention to assess the degree of corneal damage.
Potential risks of excessive intak
Gastrointestinal mucosal injury
If DL Pipecolic Acid is ingested by mistake, its alkalinity may directly corrode the gastric mucosa, causing abdominal pain, nausea, vomiting, and in severe cases, gastric ulcers or bleeding may occur. In a similar case, the patient experienced vomiting blood after mistakenly taking 5% piperidine solution, and gastroscopy showed extensive erosion in the gastric antrum.
Treatment principle: Take milk or egg white orally immediately to neutralize alkalinity and avoid using emetics; Severe cases require intravenous infusion of proton pump inhibitors (such as omeprazole) and hemostatic drugs.
Electrolyte imbalance and metabolic acidosis
Excessive intake may lead to lactate accumulation, inhibit renal tubular reabsorption of bicarbonate, and subsequently cause a decrease in blood pH (metabolic acidosis). The patient may experience deep and rapid breathing, fatigue, and blurred consciousness. Blood gas analysis shows pH<7.35 and HCO ∝⁻<22 mmol/L.
Corrective measures: Intravenous infusion of 5% sodium bicarbonate solution, while monitoring blood potassium levels (acidosis can cause potassium ions to transfer to the extracellular space, leading to hyperkalemia).
FAQ
1. What is DL-Pipecolinic Acid?
It is an organic compound with the chemical formula C6H11NO2. It belongs to heterocyclic amino acids. It mainly exists in the form of white to light brown crystals or powders and is commonly used as a chiral ligand or catalyst in organic synthesis. It is also a reference substance in scientific research for analyzing specific metabolic pathways.
2. What are its main application fields?
It has extensive uses in the field of research, especially in biochemistry analysis. This compound can serve as a diagnostic marker for pyridoxine-dependent epilepsy. Additionally, in organic chemistry, it participates in copper-catalyzed coupling reactions as a ligand, or is used as an organic catalyst for the synthesis of new compounds.
3. What should be noted during use and storage?
To ensure the stability of the product, it is recommended to store it in a room temperature, dry and well-ventilated environment. After use, it should be sealed and protected from light to prevent moisture absorption or oxidation, which may lead to a decrease in content. When operating, it is recommended to wear laboratory coats and disposable gloves. This product is only for professional scientific research and must not be used for clinical diagnosis or treatment.
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