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A new phenomenon of various polarity observed in p-menthane-1,2,4-triol

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Abstract

A new phenomenon was observed for p-menthane-1,2,4-triol, i.e., the substance with the same molecular structure occurs in two forms with different polarity. The form with a lower polarity is eluted with ethyl acetate in column chromatography; the form with a higher polarity is eluted with methanol. The crystals isolated by ethyl acetate elution exhibit polymorphism; whereas no polymorphism was observed for the crystals isolated by methanol elution. The crystals isolated differed in melting temperature and optical rotation. The structure of p-menthane-1,2,4-triol was confirmed by two independent methods, i.e., by the single-crystal X-ray diffraction and NMR spectra.

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Acknowledgments

The financial support from the Slovak Research and Development Agency under the contract no. APVV-0202-10, and the Slovak Scientific Grant Agency (VEGA Projects 1/0617/15 and 1/0592/15) is greatly acknowledged.

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Authors and Affiliations

  1. Faculty of Chemical and Food Technology, Institute of Biochemistry, Nutrition and Health Protection, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Peter Fodran, Andrea Marko & Lukáš Žemlička

  2. Faculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Jozef Kožíšek & Tibor Dubaj

  3. Faculty of Chemical and Food Technology, Institute of Analytical Chemistry, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Tibor Liptaj & Ivan Špánik

  4. Faculty of Chemical and Food Technology, Institute of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Tibor Gracza

  5. Food Research Institute, Priemyselná 4, 258 24, Bratislava, Slovakia

    Emil Kolek

  6. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, 842 15, Bratislava, Slovakia

    Marcel Ehn

Authors
  1. Peter Fodran
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  2. Andrea Marko
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  3. Lukáš Žemlička
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  4. Jozef Kožíšek
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  5. Tibor Liptaj
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  6. Tibor Gracza
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  7. Tibor Dubaj
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  8. Ivan Špánik
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  9. Emil Kolek
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  10. Marcel Ehn
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Corresponding author

Correspondence to Tibor Dubaj.

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Fodran, P., Marko, A., Žemlička, L. et al. A new phenomenon of various polarity observed in p-menthane-1,2,4-triol. Monatsh Chem 146, 1283–1289 (2015). https://doi.org/10.1007/s00706-015-1455-2

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  • DOI: https://doi.org/10.1007/s00706-015-1455-2

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