A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization
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...
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| Format: | Article |
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/3/720 |
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| author | Steffi Wünsche Lina Yuan Andreas Seidel-Morgenstern Heike Lorenz |
| author_facet | Steffi Wünsche Lina Yuan Andreas Seidel-Morgenstern Heike Lorenz |
| author_sort | Steffi Wünsche |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T03:15:49Z |
| format | Article |
| id | doaj.art-4708ea653b6042d58d8729663cda6ac7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T03:15:49Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4708ea653b6042d58d8729663cda6ac72023-12-03T15:21:35ZengMDPI AGMolecules1420-30492021-01-0126372010.3390/molecules26030720A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and CharacterizationSteffi Wünsche0Lina Yuan1Andreas Seidel-Morgenstern2Heike Lorenz3Max Planck Insitute for Dynamics of Complex Technical Systems, 39106 Magdeburg, GermanyGlobal Drug Development, Novartis, Shanghai 201203, ChinaDepartment of Chemical Engineering, Otto von Guericke University, 39106 Magdeburg, GermanyMax Planck Insitute for Dynamics of Complex Technical Systems, 39106 Magdeburg, GermanyBis(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.https://www.mdpi.com/1420-3049/26/3/720natural compoundcurcuminoidsbis(demethoxy)curcuminco-crystalshydroxybenzenesthermal analysis |
| spellingShingle | Steffi Wünsche Lina Yuan Andreas Seidel-Morgenstern Heike Lorenz A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization Molecules natural compound curcuminoids bis(demethoxy)curcumin co-crystals hydroxybenzenes thermal analysis |
| title | A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization |
| title_full | A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization |
| title_fullStr | A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization |
| title_full_unstemmed | A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization |
| title_short | A Contribution to the Solid State Forms of Bis(demethoxy)curcumin: Co-Crystal Screening and Characterization |
| title_sort | contribution to the solid state forms of bis demethoxy curcumin co crystal screening and characterization |
| topic | natural compound curcuminoids bis(demethoxy)curcumin co-crystals hydroxybenzenes thermal analysis |
| url | https://www.mdpi.com/1420-3049/26/3/720 |
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