Cannabidiolic Acid Cocrystals for Purity and Crystalline Stability
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Solution Overview
Problem
The lack of availability and chemical instability of cannabidiolic acid (CBDA) hampers its pharmacological exploration and exploitation due to inevitable contamination with cannabidiol (CBD) during extraction and degradation during crystallization, limiting its potential medicinal benefits.
Innovation Solution
Development of stable crystalline forms of CBDA in the form of cocrystals with coformers such as L-phenylalanine, vanillin, betaine, ethyl maltol, L-proline, and D-proline, characterized by specific X-ray diffraction and infrared spectra patterns.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If CBDA is extracted from cannabis plants using heat, then CBD is obtained, but CBDA is contaminated with CBD due to decarboxylation
Solution Approach 1:
The patent introduces coformers (such as L-phenylalanine, vanillin, betaine, ethyl maltol, L-proline, or D-proline) as intermediary substances that form cocrystals with CBDA. These coformers act as mediators to stabilize CBDA in a crystalline form, preventing decarboxylation and contamination with CBD while enabling extraction from cannabis plants.
Solution Approach 2:
The patent creates composite crystalline structures by combining CBDA with coformers to form cocrystals. This composite approach stabilizes the unstable CBDA molecule, allowing it to be extracted and stored without degradation to CBD, thus resolving the purity issue while maintaining availability.
2Reliability
If CBDA is produced synthetically, then pure CBDA is obtained, but the CBDA is not crystalline and crystallization results in degradation
Solution Approach 1:
The patent uses coformers as intermediary substances that facilitate the formation of stable crystalline structures. These coformers mediate between the synthetic CBDA production process and the crystallization step, enabling CBDA to form stable cocrystals without degrading to CBD during the crystallization process.
Solution Approach 2:
The patent creates composite crystalline materials by combining synthetically produced CBDA with coformers. This composite approach transforms the amorphous synthetic CBDA into stable crystalline cocrystals, preventing degradation while maintaining purity, thus resolving the contradiction between purity and stability.
3Reliability
If CBDA is stored under typical conditions, then CBDA degrades, but the medicinal properties are lost
Solution Approach 1:
The patent forms composite crystalline structures with coformers that stabilize CBDA against degradation. This composite approach extends the shelf life and maintains the medicinal properties of CBDA under typical storage conditions, as the cocrystal structure prevents the decarboxylation reaction that would otherwise occur over time.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The cocrystals provide a stable form of CBDA that maintains its medicinal properties, enabling effective treatment of diseases and disorders like anxiety, depression, and cancer, with improved bioavailability and solubility.
Implementation Method 1
characterized by a powder X-ray diffraction pattern having at least three peaks selected from 3.1, 6.4, 18.4, 19.8, and 23.7°2θ+0.2° 2θ
Implementation Method 2
an infrared spectrum having at least three peaks selected from 1606, 1409, 1296, 1240 and 1184 cm−1±1 cm−1
Data Source
AI summary
The present invention relates to compositions comprising a cannabidolic acid cocrystal. In particular, the cannabidiolic acid cocrystals include a cannabidiolic acid L-phenylalanine cocrystal, a cannabidiolic acid vanillin cocrystal, a cannabidiolic acid betaine cocrystal, a cannabidiolic acid ethyl maltol cocrystal, a cannabidiolic acid L-proline cocrystal and a cannabidiolic acid D-proline cocrystal. The present invention also relates to compositions, particularly pharmaceutical compositions comprising a cannabidiolic acid cocrystal and a pharmaceutically acceptable carrier. The present invention further relates to methods to treat a disease, disorder or condition in a patient by administering to the patient a therapeutically effective amount of cannabidiolic acid cocrystal or a pharmaceutical composition comprising a therapeutically effective amount of cannabidiolic acid cocrystal.