Work

A Study on the Synergistic Cocrystallization of Chemically Related Curcuminoids with Hydroxybenzenes

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Cocrystallization of the curcuminoids (CURDs) curcumin (CUR), demethoxycurcumin (DMC), and bis(demethoxy)curcumin (BDMC) with the coformers resorcinol (RES) and hydroxyquinol (HYQ) from solution was investigated toward its potential of being used as a synergistic separation technique of the CURDs from their ternary mixtures. Therefore, solubilities of single CURDs with the respective coformer in toluene-ethyl acetate 90/10 v/v at 25 °C were measured, and ternary phase diagrams were constructed. CUR·RES and BDMC·HYQ cocrystals were identified, revealing an incongruent solubility behavior. All other CURD-coformer systems showed eutectic behavior. Separation experiments were performed using a CUR-rich and almost equimolar CURD mixture. Solubility measurements of CURD mixtures revealed large influences on each other’s solubility and high potential of DMC being integrated into CUR crystals and cocrystals. Cocrystallization of CUR·RES from the CUR-rich mixture outperformed direct CUR crystallization. In the case of BDMC·HYQ, the presence of the other CURDs suppressed cocrystal formation. Using the universal cocrystal solubility product K s, CUR·RES cocrystal solubilities were predicted in ethanol, a solvent exhibiting large solubility differences between CUR and other CURDs. Subsequent separation experiments showed no benefit of cocrystallization over direct CUR crystallization.

Source: Crystal Growth & Design

DOI: 10.1021/acs.cgd.5c00558

Authors: Steffi Wünsche, Andreas Seidel-Morgenstern, Heike Lorenz

Institution: Max Planck Institute for Dynamics of Complex Technical Systems

Language: English

Topic: Crystallization and Solubility Studies

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Max-Planck-Gesellschaft