IDEAS home Printed from https://ideas.repec.org/a/caa/jnlcjf/v20y2002i5id3527-cjfs.html
   My bibliography  Save this article

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

Author

Listed:
  • J. Velíšek

    (Department of Food Chemistry and Analysis - Institute of Chemical Technology, Prague; Central Science Laboratory, Sand Hutton, York, Great Britain)

  • M. Doležal

    (Department of Food Chemistry and Analysis - Institute of Chemical Technology, Prague; Central Science Laboratory, Sand Hutton, York, Great Britain)

  • C. Crews

    (Department of Food Chemistry and Analysis - Institute of Chemical Technology, Prague; Central Science Laboratory, Sand Hutton, York, Great Britain)

  • T. Dvořák

    (Department of Food Chemistry and Analysis - Institute of Chemical Technology, Prague; Central Science Laboratory, Sand Hutton, York, Great Britain)

Abstract

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.

Suggested Citation

  • J. Velíšek & M. Doležal & C. Crews & T. Dvořák, 2002. "Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates," Czech Journal of Food Sciences, Czech Academy of Agricultural Sciences, vol. 20(5), pages 161-170.
    • Handle: RePEc:caa:jnlcjf:v:20:y:2002:i:5:id:3527-cjfs
    DOI: 10.17221/3527-CJFS
    as

    Download full text from publisher

    File URL: http://cjfs.agriculturejournals.cz/doi/10.17221/3527-CJFS.html
    Download Restriction: free of charge
    File URL: http://cjfs.agriculturejournals.cz/doi/10.17221/3527-CJFS.pdf
    Download Restriction: free of charge
    File URL: https://libkey.io/10.17221/3527-CJFS?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    As the access to this document is restricted, you may want to search for a different version of it.

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Vojtěch Ilko & Zuzana Zelinková & Marek Doležal & Jan Velíšek, 2011. "3-Chloropropane-1,2-diol fatty acid esters in potato products," Czech Journal of Food Sciences, Czech Academy of Agricultural Sciences, vol. 29(4), pages 411-419.
    2. Veronika Divinová & Marek Doležal & Jan Velíšek, 2007. "Free and bound 3-chloropropane-1,2-diol in coffee surrogates and malts," Czech Journal of Food Sciences, Czech Academy of Agricultural Sciences, vol. 25(1), pages 39-47.

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:caa:jnlcjf:v:20:y:2002:i:5:id:3527-cjfs. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Ivo Andrle (email available below). General contact details of provider: https://www.cazv.cz/en/home/ .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.