Solvate Formation of Bis(demethoxy)curcumin: Screening and Characterization

Yuan, Lina; Lorenz, Heike

doi:10.3390/cryst8110407

Cited by 15 publications

(11 citation statements)

References 30 publications

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“…Different methods to produce co-crystals have been investigated to screen for co-crystals of BDMC and hydroxybenzenes. Ethanol was used for every technique requiring a solvent since it forms no solvate with BDMC and has low toxicity [ 30 ]. Results of the screening including DSC thermograms and PXRD patterns are shown in Figure 4 to 6 for resorcinol (RES), pyrogallol (PYR), and hydroxyquinol (HYQ), respectively.…”

Section: Resultsmentioning

confidence: 99%

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A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

et al. 2021

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Bis(demethoxy)curcumin (BDMC) is one of the main active components found in turmeric. Major drawbacks for its usage are its low aqueous solubility, and the challenging separation from other curcuminoids present in turmeric. Co-crystallization can be applied to alter the physicochemical properties of BDMC in a desired manner. A co-crystal screening of BDMC with four hydroxybenzenes was carried out using four different methods of co-crystal production: crystallization from solution by slow solvent evaporation (SSE), and rapid solvent removal (RSR), liquid-assisted grinding (LAG), and crystallization from the melt phase. Two co-crystal phases of BDMC were obtained with pyrogallol (PYR), and hydroxyquinol (HYQ). PYR-BDMC co-crystals can be obtained only from the melt, while HYQ-BDMC co-crystals could also be produced by LAG. Both co-crystals possess an equimolar composition and reveal an incongruent melting behavior. Infrared spectroscopy demonstrated the presence of BDMC in the diketo form in the PYR co-crystals, while it is in a more stable keto-enol form in the HYQ co-crystals. Solubility measurements in ethanol and an ethanol-water mixture revealed an increase of solubility in the latter, but a slightly negative effect on ethanol solubility. These results are useful for a prospective development of crystallization-based separation processes of chemical similar substances through co-crystallization.

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Section: Resultsmentioning

confidence: 99%

“…In a patent 6 co-crystals with piperazine, caffeine, L-proline, nicotinamide, isonicotinamide and piperidine are reported but not fully proved [ 26 ]. The formation of BDMC solvates was investigated extensively by Yuan et al [ 30 , 31 ].…”

Section: Introductionmentioning

confidence: 99%

A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

et al. 2021

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“…One hypothesis explaining this behavior might be incorporation of small amounts of respective alcohol molecules in the crystal structure without changing the structure type. Further, according to the known complex solid phase behavior of CUR [42][43][44][45][46][47][48] and BDMC [49,50], also the formation of a new metastable form of CUR in the three alcohols or a solvate phase from ethanol are possible explanations. Since elucidation of the CUR phase behavior was not the main focus of the present study, this issue has to be verified in future investigations.…”

Section: Selection Of Solvents For Crystallizationmentioning

confidence: 99%

Purification of Curcumin from Ternary Extract-Similar Mixtures of Curcuminoids in a Single Crystallization Step

et al. 2020

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Crystallization-based separation of curcumin from ternary mixtures of curcuminoids having compositions comparable to commercial extracts was studied experimentally. Based on solubility and supersolubility data of both, pure curcumin and curcumin in presence of the two major impurities demethoxycurcumin (DMC) and bis(demethoxy)curcumin (BDMC), seeded cooling crystallization procedures were derived using acetone, acetonitrile and 50/50 (wt/wt) mixtures of acetone/2-propanol and acetone/acetonitrile as solvents. Starting from initial curcumin contents of 67–75% in the curcuminoid mixtures single step crystallization processes provided crystalline curcumin free of BDMC at residual DMC contents of 0.6–9.9%. Curcumin at highest purity of 99.4% was obtained from a 50/50 (wt/wt) acetone/2-propanol solution in a single crystallization step. It is demonstrated that the total product yield can be significantly enhanced via addition of water, 2-propanol and acetonitrile as anti-solvents at the end of a cooling crystallization process.

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“…Yuan and Lorenz (Yuan and Lorenz 2018 ) used hot stage microscopy to screen bis (demethoxy) curcumin with nineteen different solvents for solvate formation. They obtained three solvates with tetrahydrofuran, 1,4-dioxane and dimethyl sulfoxide.…”

Section: Introductionmentioning

confidence: 99%

Hot stage microscopy and its applications in pharmaceutical characterization

2020

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Hot stage microscopy (HSM) is a thermal analysis technique that combines the best properties of thermal analysis and microscopy. HSM is rapidly gaining interest in pharmaceuticals as well as in other fields as a regular characterization technique. In pharmaceuticals HSM is used to support differential scanning calorimetry (DSC) and thermo-gravimetric analysis (TGA) observations and to detect small changes in the sample that may be missed by DSC and TGA during a thermal experiment. Study of various physical and chemical properties such sample morphology, crystalline nature, polymorphism, desolvation, miscibility, melting, solid state transitions and incompatibility between various pharmaceutical compounds can be carried out using HSM. HSM is also widely used to screen cocrystals, excipients and polymers for solid dispersions. With the advancements in research methodologies, it is now possible to use HSM in conjunction with other characterization techniques such as Fourier transform infrared spectroscopy (FTIR), DSC, Raman spectroscopy, scanning electron microscopy (SEM) which may have additional benefits over traditional characterization techniques for rapid and comprehensive solid state characterization.

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Solvate Formation of Bis(demethoxy)curcumin: Screening and Characterization

Cited by 15 publications

References 30 publications

A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization

Purification of Curcumin from Ternary Extract-Similar Mixtures of Curcuminoids in a Single Crystallization Step

Hot stage microscopy and its applications in pharmaceutical characterization

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