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Issue 20, 2012
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Insights into the crystal structure, polymorphism and thermal behavior of menthol optical isomers and racemates

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Abstract

The physico-chemical properties of the levo- and dextrorotatory menthol isomers as well as the corresponding racemic compound were studied using X-ray single-crystal or powder diffraction and differential scanning calorimetry experiments. As a result, the not yet determined crystal structure of DL-menthol was solved. Moreover, the stable and metastable experimental temperature-composition phase diagrams of the L-menthol/D-menthol binary system were determined. The thermodynamic relative stability of the different menthol polymorphs was also established. The present paper provides new physical, chemical and thermodynamic data of L-, D- and DL-menthol and offers new insight into their polymorphism as well as into the levorotatory–dextrorotatory menthol interactions. Both the thermodynamic and crystallographic approaches demonstrate unambiguously that racemic menthol is a racemate.

Graphical abstract: Insights into the crystal structure, polymorphism and thermal behavior of menthol optical isomers and racemates

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Supplementary files

Article information


Submitted
27 Jun 2012
Accepted
27 Jul 2012
First published
01 Aug 2012

CrystEngComm, 2012,14, 7055-7064
Article type
Paper

Insights into the crystal structure, polymorphism and thermal behavior of menthol optical isomers and racemates

Y. Corvis, P. Négrier, S. Massip, J. Leger and P. Espeau, CrystEngComm, 2012, 14, 7055
DOI: 10.1039/C2CE26025E

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