What is Pipecolic Acid?
Pipecolic acid (CAS No. 3105-95-1), also known as L-Pipecolic acid powder, piperidine-2-carboxylic acid, homoproline, or 2-piperidinecarboxylic acid, is a cyclic amino acid with the molecular formula C₆H₁₁NO₂ and a molecular weight of 129.16 g/mol. It naturally occurs in the human body as a metabolite of lysine. It can be found in various food sources, including legumes, particularly soybeans, and certain vegetables and fruits. Commercially available pipecolic acid typically appears as a white to off-white crystalline powder with a characteristic odor.
The compound is highly soluble in water, moderately soluble in alcohols like methanol and ethanol, and poorly soluble in non-polar solvents like chloroform and ether. Cima Science is the leading bulk L-pipecolic acid powder manufacturer in China, providing 98% to 99% purity product that meets pharmaceutical and research-grade specifications.
Pipecolic Acid Forms: L-Pipecolic Acid VS D-Pipecolic Acid VS DL-Pipecolic acid
Pipecolic acid is a non-genetically encoded amino acid in L, D, and DL forms, each with unique properties and uses. Below, we compare L-Pipecolic acid (CAS 3105-95-1), D-Pipecolic acid (CAS 1723-00-8), and DL-Pipecolic acid (CAS 535-75-1) based on various parameters.
L-Pipecolic acid is naturally occurring, playing a key role in plant defense and acting as a compatible solute in microorganisms like Corynebacterium glutamicum, helping them thrive under hyperosmolar conditions. It’s also linked to certain metabolic disorders.
L-Pipecolic acid (the naturally occurring L-form, S-enantiomer) is generally the most widely used and preferred form of pipecolic acid. It is the predominant form in biological systems and is heavily studied as a human metabolite and disease marker.
D-Pipecolic acid is produced by intestinal bacteria from dietary lysine, suggesting a role in human metabolism, particularly in conditions like hepatic encephalopathy. In contrast, D-pipecolic acid (R-enantiomer) and the racemic DL mixture serve more specialized or niche roles. D-pipecolic acid is available for research (e.g., in synthetic peptide chemistry or metabolic studies) but is less commonly used than the L-form.
DL-Pipecolic acid, a racemic mixture, is primarily used in research and synthesis where chirality isn’t critical, offering a cost-effective option for industrial applications. The DL form is often chosen only for cost-effective or industrial applications when chirality is not vital or as a starting material to obtain pure enantiomers.
L-Pipecolic acid is a precursor to various derivatives with significant biological and chemical applications. Notable derivatives include:
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Baikiain (CAS 31456-71-0): Also known as (S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid, baikiain is structurally related to L-pipecolic acid and has been identified in natural sources such as dates.
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L-Pipecolic Acid, 2TBDMS Derivative (CAS 107715-91-3): This derivative involves the silylation of L-pipecolic acid to form the N-(tert-butyldimethylsilyl) ester, enhancing its volatility and stability for analytical purposes.
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L-Pipecolic Acid Hydrochloride (CAS 2133-33-7): This hydrochloride salt form of L-pipecolic acid is utilized in various chemical syntheses and research applications.
L‐Pipecolic Acid Uses
The main use of L-pipecolic acid is as a multifunctional scaffold, and the biological activity of these drugs depends on the stereochemical structure of the piperidine portion. New-generation local anesthetic ropivacaine, anesthetic levobupivacaine, anticoagulant agatroban, immunosuppressant sirolimus, and immunosuppressant tacrolimus are all produced using L-pipecolic acid or its derivatives as the primary raw material.
Cima Science’s Breakthrough L-Pipecolic Acid Biosynthesis Manufacturing Process
The Cima Science research team has developed an innovative biosynthetic method that transforms L-lysine into L-pipecolic acid in a single step, achieving an impressive 98% final content purity. This represents a significant advancement over traditional chemical synthesis methods.
Traditional chemical synthesis produces both L and R isomers simultaneously, creating significant challenges:
- Difficult separation of isomers
- Nearly impossible to completely remove the R isomer
- Limited ability to achieve high-purity L-pipecolic acid
Cima Science’s biosynthetic approach eliminates these issues by producing only the L isomer, producing a pure L-type product with 100% optical purity.
Key Technical Advantages of Our Biosynthetic Method
1. Enhanced Strain Engineering
- Utilizes a knockout strain from the lysine degradation pathway
- Features an optimized promoter system
- Achieves >90% stability
- Demonstrates superior lysine utilization efficiency
2. Improved Process Parameters
- Reduced Reaction Time: Significantly shorter production cycles
- Lower Temperature Requirements: Minimizes microbial contamination risk
- Superior Product Purity: Achieves 100% optical purity
- Economic Efficiency: Lower production costs with higher economic benefits
This innovative approach to L-pipecolic acid production represents a sustainable, efficient, and economically viable alternative to traditional chemical synthesis methods.
Where to buy L-pipecolic acid bulk powder?
Looking for high-purity L-pipecolic acid bulk powder? Cima Science is your trusted supplier for pharmaceutical and research-grade L-pipecolic acid. Our biosynthetic production method ensures consistent 98% purity with 100% optical purity—specifications that are critical for your applications.
Why Choose Cima Science for L-Pipecolic Acid Bulk Powder:
- Free Sample Program: Evaluate our L-pipecolic acid bulk powder quality with no obligation
- Comprehensive Documentation: Complete technical package including COA, MSDS, and MOA
- Third-Party Verified: Independent laboratory testing reports available upon request
- Bulk Ordering Options: Competitive pricing with volume discounts
- Global Shipping: Fast, secure delivery to research facilities worldwide
Quality Assurance for L-Pipecolic Acid
Each L-pipecolic acid bulk powder batch undergoes rigorous testing to ensure it meets the highest quality standards for research and pharmaceutical applications.
Contact Cima Science Today
Contact our sales team to request your free L-pipecolic acid sample or technical documentation.
We welcome customers to visit our state-of-the-art production facility in Wuxi City, Jiangsu province, China, to observe our advanced biosynthetic process firsthand.
