Crystal structure of (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanol, (-)-menthol

P. Bombicz, J. Buschmann, P. Luger, Nguyen Xuan Dung, Chu Ba Nam

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

In spite of the fact that menthol is commonly known and widely used in confectionery, cosmetics, medicine and pharmacy its crystal structure has not been determined and published. The reason might be its high vapour pressure that makes the crystal handling difficult. Crystals sublimate in a few minutes in open air at room temperature. The investigated sample crystal was extracted from the plant Mentha arvensis Linner. The essential oil of the plant was steam distilled and esterifìed to menthyl acetate. Menthol crystals were obtained after hydrolysis. Single crystal X-ray diffraction measurement was carried out at low temperature (143 K) using MoKα radiation. Qualitative optical rotation measurement proves the (-) or (1R,2S,5R) absolute configuration, one of the eight possible optically active stereoisomers. (-)-Menthol crystallises in the trigonal crystal system, space group P31, with three independent molecules in the asymmetric unit. Each molecule generates an infinite column of hydrogen bonded molecules related by the 31 screw axis.

Original languageEnglish
Pages (from-to)420-423
Number of pages4
JournalZeitschrift fur Kristallographie - New Crystal Structures
Volume214
Issue number7
DOIs
Publication statusPublished - Jan 1 1999

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Inorganic Chemistry

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