Journal of the American Oil Chemists' Society

, Volume 88, Issue 8, pp 1143–1151 | Cite as

Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods

  • Naoki Kaze
  • Hirofumi Sato
  • Hiroshi Yamamoto
  • Yomi Watanabe
Original Paper


NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by 1H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step.


3-Monochloropropane-1,2-diol (3-MCPD) DFG standard method Glycidol Glycidyl ester NaCl 


  1. 1.
    Food Advisory Committee (2000) Genotoxicity of 3-monochloropropane-1,2-diol, FdAC/Contaminants/48. Paper for Discussion. UK Food Standards Agency, London. Accessed Oct 2010
  2. 2.
    FAO/WHO (2001) Joint FAO/WHO Expert Committee on Food Additives (JECFA) Fifty-Seventh Meeting, Rome, 2001, Summary and conclusions (Rome: Food and Agriculture Organization of the United Nations/World Health Organization). Accessed Oct 2010
  3. 3.
    (2009) Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and glycidol (glycidol esters). Deutsche Gesellschaft fuer Fettwissenschaft: DGF Standard Methods (14. Supplement) C-III 18 Google Scholar
  4. 4.
    Masukawa Y, Shiro H, Nakamura S, Kondo N, Jin N, Suzuki N, Ooi N, Kudo N (2010) A new analytical method for the quantification of glycidol fatty acid esters in edible oils. J Oleo Sci 59:81–88CrossRefGoogle Scholar
  5. 5.
    Shimizu M, Kudo N, Shiro H, Yasunaga K, Masukawa Y, Katsuragi Y, Yasumasu T (2010) Comparison of indirect and direct quantification of glycidol fatty acid ester in edible oils. J Oleo Sci 539:535–539CrossRefGoogle Scholar
  6. 6.
    Weisshaar R (2008) Determination of total 3-chloropropane-1, 2-diol (3-MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. Eur J Lipid Sci Technol 110:183–186CrossRefGoogle Scholar
  7. 7.
    Yan J, Springsteen G, Deeter S, Wang B (2004) The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols. Tetrahedron 60:11205–11209CrossRefGoogle Scholar
  8. 8.
    Weisshaar R, Perz R (2010) Fatty acid esters of glycidol in refined fats and oils. Eur J Lipid Sci Technol 112:158–165CrossRefGoogle Scholar
  9. 9.
    Kaze N, Sato H, Yamamoto H, Watanabe Y Improvement of accuracy in quantification of 3-monochloropropane-1,2-diol and its esters by DGF standard methods C-III 18 (in submission)Google Scholar

Copyright information

© AOCS 2011

Authors and Affiliations

  • Naoki Kaze
    • 1
  • Hirofumi Sato
    • 2
  • Hiroshi Yamamoto
    • 1
  • Yomi Watanabe
    • 2
  1. 1.Ueda Oils and Fats MFG Co. LtdKobeJapan
  2. 2.Osaka Municipal Technical Research InstituteOsakaJapan

Personalised recommendations