Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates
Protein hydrolysates produced by hydrochloric acid hydrolysis were analysed for 3-chloropropane-1,2-diol and its enantiomers. It was found that (R)-3-chloropropane-1,2-diol and (S)-3-chloropropane-1,2-diol were present in the hydrolysates in equimolar concentrations. Model experiments with glycerol,...
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| Format: | Article |
| Language: | English |
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Czech Academy of Agricultural Sciences
2002-10-01
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| Series: | Czech Journal of Food Sciences |
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| Online Access: | https://cjfs.agriculturejournals.cz/artkey/cjf-200205-0001_optical-isomers-of-chloropropanediols-mechanisms-of-their-formation-and-decomposition-in-protein-hydrolysates.php |
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| author | J. Velíšek M. Doležal C. Crews T. Dvořák |
| author_facet | J. Velíšek M. Doležal C. Crews T. Dvořák |
| author_sort | J. Velíšek |
| collection | DOAJ |
| description | Protein hydrolysates produced by hydrochloric acid hydrolysis were analysed for 3-chloropropane-1,2-diol and its enantiomers. It was found that (R)-3-chloropropane-1,2-diol and (S)-3-chloropropane-1,2-diol were present in the hydrolysates in equimolar concentrations. Model experiments with glycerol, triolein and soy lecithin heated with hydrochloric acid in solution showed that these materials were precursors of 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol and, as expected, yielded racemic 3-chloropropane-1,2-diol. Yields of 3-chloropropane-1,2-diols decreased in the order triolein > lecithin > glycerol. The mechanisms of 3-chloropropane-1,2-diol enantiomers formation during the production of protein hydrolysates are presented and discussed as well as the reaction pathways of their decomposition in alkaline media via the corresponding intermediates, (R)- and (S)-glycidol, respectively. Both epoxides are hydrolysed to glycerol and form a variety of products with hydrolysate constituents. |
| first_indexed | 2024-04-10T08:36:39Z |
| format | Article |
| id | doaj.art-12b21a20694542b89dce16bb1b4c031b |
| institution | Directory Open Access Journal |
| issn | 1212-1800 1805-9317 |
| language | English |
| last_indexed | 2024-04-10T08:36:39Z |
| publishDate | 2002-10-01 |
| publisher | Czech Academy of Agricultural Sciences |
| record_format | Article |
| series | Czech Journal of Food Sciences |
| spelling | doaj.art-12b21a20694542b89dce16bb1b4c031b2023-02-23T03:26:37ZengCzech Academy of Agricultural SciencesCzech Journal of Food Sciences1212-18001805-93172002-10-0120516117010.17221/3527-CJFScjf-200205-0001Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysatesJ. Velíšek0M. Doležal1C. Crews2T. Dvořák32 Czech Republic; Central Science Laboratory, Sand Hutton, York, Great Britain2 Czech Republic; Central Science Laboratory, Sand Hutton, York, Great Britain2 Czech Republic; Central Science Laboratory, Sand Hutton, York, Great Britain2 Czech Republic; Central Science Laboratory, Sand Hutton, York, Great BritainProtein hydrolysates produced by hydrochloric acid hydrolysis were analysed for 3-chloropropane-1,2-diol and its enantiomers. It was found that (R)-3-chloropropane-1,2-diol and (S)-3-chloropropane-1,2-diol were present in the hydrolysates in equimolar concentrations. Model experiments with glycerol, triolein and soy lecithin heated with hydrochloric acid in solution showed that these materials were precursors of 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol and, as expected, yielded racemic 3-chloropropane-1,2-diol. Yields of 3-chloropropane-1,2-diols decreased in the order triolein > lecithin > glycerol. The mechanisms of 3-chloropropane-1,2-diol enantiomers formation during the production of protein hydrolysates are presented and discussed as well as the reaction pathways of their decomposition in alkaline media via the corresponding intermediates, (R)- and (S)-glycidol, respectively. Both epoxides are hydrolysed to glycerol and form a variety of products with hydrolysate constituents.https://cjfs.agriculturejournals.cz/artkey/cjf-200205-0001_optical-isomers-of-chloropropanediols-mechanisms-of-their-formation-and-decomposition-in-protein-hydrolysates.phpchloropropanediolschloropropanols3-chloropropane-1,2-diol2-chloropropane-1,3-diolglycidolmcpdenantiomersprotein hydrolysates |
| spellingShingle | J. Velíšek M. Doležal C. Crews T. Dvořák Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates Czech Journal of Food Sciences chloropropanediols chloropropanols 3-chloropropane-1,2-diol 2-chloropropane-1,3-diol glycidol mcpd enantiomers protein hydrolysates |
| title | Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates |
| title_full | Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates |
| title_fullStr | Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates |
| title_full_unstemmed | Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates |
| title_short | Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates |
| title_sort | optical isomers of chloropropanediols mechanisms of their formation and decomposition in protein hydrolysates |
| topic | chloropropanediols chloropropanols 3-chloropropane-1,2-diol 2-chloropropane-1,3-diol glycidol mcpd enantiomers protein hydrolysates |
| url | https://cjfs.agriculturejournals.cz/artkey/cjf-200205-0001_optical-isomers-of-chloropropanediols-mechanisms-of-their-formation-and-decomposition-in-protein-hydrolysates.php |
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