Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate
The approach presented in this study is the first for the hemisynthesis of methylated anthocyanins. It was possible to obtain cyanidin-3-<i>O</i>-glucoside derivatives with different degrees of methylation. Cautious identification of 4′-, 5-, and 7-OH monomethylated derivatives was also...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/5/1342 |
| _version_ | 1827603972953735168 |
|---|---|
| author | Sarah Straßmann Tillman Brehmer Maike Passon Andreas Schieber |
| author_facet | Sarah Straßmann Tillman Brehmer Maike Passon Andreas Schieber |
| author_sort | Sarah Straßmann |
| collection | DOAJ |
| description | The approach presented in this study is the first for the hemisynthesis of methylated anthocyanins. It was possible to obtain cyanidin-3-<i>O</i>-glucoside derivatives with different degrees of methylation. Cautious identification of 4′-, 5-, and 7-OH monomethylated derivatives was also accomplished. The methylation agent used was the “green chemical” dimethyl carbonate (DMC), which is characterized by low human and ecological toxicity. The influence of the temperature, reaction time, and amount of the required diazabicyclo[5.4.0]undec-7-en (DBU) catalyst on the formation of the products was examined. Compared to conventional synthesis methods for methylated flavonoids using DMC and DBU, the conditions identified in this study result in a reduction of reaction time, and an important side reaction, so-called carboxymethylation, was minimized by using higher amounts of catalyst. |
| first_indexed | 2024-03-09T05:50:27Z |
| format | Article |
| id | doaj.art-95b04bb5e3454f87965f995f387d88be |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:50:27Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-95b04bb5e3454f87965f995f387d88be2023-12-03T12:17:57ZengMDPI AGMolecules1420-30492021-03-01265134210.3390/molecules26051342Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl CarbonateSarah Straßmann0Tillman Brehmer1Maike Passon2Andreas Schieber3Department of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyDepartment of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyDepartment of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyDepartment of Nutritional and Food Sciences, Molecular Food Technology, University of Bonn, Friedrich-Hirzebruch-Allee 7, D-53115 Bonn, GermanyThe approach presented in this study is the first for the hemisynthesis of methylated anthocyanins. It was possible to obtain cyanidin-3-<i>O</i>-glucoside derivatives with different degrees of methylation. Cautious identification of 4′-, 5-, and 7-OH monomethylated derivatives was also accomplished. The methylation agent used was the “green chemical” dimethyl carbonate (DMC), which is characterized by low human and ecological toxicity. The influence of the temperature, reaction time, and amount of the required diazabicyclo[5.4.0]undec-7-en (DBU) catalyst on the formation of the products was examined. Compared to conventional synthesis methods for methylated flavonoids using DMC and DBU, the conditions identified in this study result in a reduction of reaction time, and an important side reaction, so-called carboxymethylation, was minimized by using higher amounts of catalyst.https://www.mdpi.com/1420-3049/26/5/1342cyanidin-3-<i>O</i>-glucosidecyanidinanthocyaninsLC-IMSHRMSmethylation |
| spellingShingle | Sarah Straßmann Tillman Brehmer Maike Passon Andreas Schieber Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate Molecules cyanidin-3-<i>O</i>-glucoside cyanidin anthocyanins LC-IMS HRMS methylation |
| title | Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate |
| title_full | Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate |
| title_fullStr | Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate |
| title_full_unstemmed | Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate |
| title_short | Methylation of Cyanidin-3-<i>O</i>-Glucoside with Dimethyl Carbonate |
| title_sort | methylation of cyanidin 3 i o i glucoside with dimethyl carbonate |
| topic | cyanidin-3-<i>O</i>-glucoside cyanidin anthocyanins LC-IMS HRMS methylation |
| url | https://www.mdpi.com/1420-3049/26/5/1342 |
| work_keys_str_mv | AT sarahstraßmann methylationofcyanidin3ioiglucosidewithdimethylcarbonate AT tillmanbrehmer methylationofcyanidin3ioiglucosidewithdimethylcarbonate AT maikepasson methylationofcyanidin3ioiglucosidewithdimethylcarbonate AT andreasschieber methylationofcyanidin3ioiglucosidewithdimethylcarbonate |