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Article

Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone

Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470 Mülheim an der Ruhr, Germany
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Author to whom correspondence should be addressed.
Dedicated to Dr. Howard Flack (1943–2017).
Academic Editors: Catherine Housecroft and Katharina M. Fromm
Received: 30 March 2021 / Revised: 16 April 2021 / Accepted: 18 April 2021 / Published: 21 April 2021
Knowledge about the absolute configuration of small bioactive organic molecules is essential in pharmaceutical research because enantiomers can exhibit considerably different effects on living organisms. X-ray crystallography enables chemists to determine the absolute configuration of an enantiopure compound due to anomalous dispersion. Here, we present the determination of the absolute configuration of the flavoring agent (+)-γ-decalactone, which is liquid under ambient conditions. Single crystals were grown from the liquid in a glass capillary by in situ cryo-crystallization. Diffraction data collection was performed using Cu-Kα radiation. The absolute configuration was confirmed. The molecule consists of a linear aliphatic non-polar backbone and a polar lactone head. In the solid state, layers of polar and non-polar sections of the molecule alternating along the c-axis of the unit cell are observed. In favorable cases, this method of absolute configuration determination of pure liquid (bioactive) agents or liquid products from asymmetric catalysis is a convenient alternative to conventional methods of absolute structure determination, such as optical rotatory dispersion, vibrational circular dichroism, ultraviolet-visible spectroscopy, use of chiral shift reagents in proton NMR and Coulomb explosion imaging. View Full-Text
Keywords: γ-(+)-decalactone; absolute configuration; in situ cryo-crystallization; flavoring agent; lactone; hydrogen bonding; crystal structure; X-ray crystallography γ-(+)-decalactone; absolute configuration; in situ cryo-crystallization; flavoring agent; lactone; hydrogen bonding; crystal structure; X-ray crystallography
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MDPI and ACS Style

Patzer, M.; Nöthling, N.; Goddard, R.; Lehmann, C.W. Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone. Chemistry 2021, 3, 578-584. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3020040

AMA Style

Patzer M, Nöthling N, Goddard R, Lehmann CW. Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone. Chemistry. 2021; 3(2):578-584. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3020040

Chicago/Turabian Style

Patzer, Michael, Nils Nöthling, Richard Goddard, and Christian W. Lehmann 2021. "Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone" Chemistry 3, no. 2: 578-584. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3020040

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