Crystal Structure of Zerumbone [(E, E, E)-2, 6, 9, 9-Tetramethylcycloundeca-2, 6, 10-trien-1-one]

Sydney R. Hall; Surachai Nimgirawath; Colin L. Raston; Amnard Sittatrakul; Somkiat Thadaniti; Narumol Thirasasana; Allan H. White

doi:10.1071/CH9812243

Crystal Structure of Zerumbone [(E, E, E)-2, 6, 9, 9-Tetramethylcycloundeca-2, 6, 10-trien-1-one]

Sydney R. Hall, Surachai Nimgirawath, Colin L. Raston, Amnard Sittatrakul, Somkiat Thadaniti, Narumol Thirasasana, Allan H. White

Research output: Contribution to journal › Article

25 Citations (Scopus)

Abstract

The crystal structure of zerumbone, C₁₅H₂₂O, extracted from the rhizomes of Zingiber zerumbet Smith, has been determined by single-crystal X-ray diffraction at 295(1) K and refined by least squares to a residual of 0.051 for 925 ‘observed’ reflections. Crystals are monoclinic, space group P 2₁c, a 9•036(3), b 9•712(5), c 15•643(6) Å, β 97•19(3)°, Z = 4. Although the molecule has no chiral centre, the presence of the three trans double bonds confers considerable distortion and rigidity on the eleven-membered ring and renders the whole molecule chiral and potentially resolvable.

Original language	English
Pages (from-to)	2243-2247
Number of pages	5
Journal	Australian Journal of Chemistry
Volume	34
Issue number	10
DOIs	https://doi.org/10.1071/CH9812243
Publication status	Published - 1981
Externally published	Yes

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10.1071/CH9812243Licence: In Copyright

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Hall, S. R., Nimgirawath, S., Raston, C. L., Sittatrakul, A., Thadaniti, S., Thirasasana, N., & White, A. H. (1981). Crystal Structure of Zerumbone [(E, E, E)-2, 6, 9, 9-Tetramethylcycloundeca-2, 6, 10-trien-1-one]. Australian Journal of Chemistry, 34(10), 2243-2247. https://doi.org/10.1071/CH9812243

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title = "Crystal Structure of Zerumbone [(E, E, E)-2, 6, 9, 9-Tetramethylcycloundeca-2, 6, 10-trien-1-one]",

abstract = "The crystal structure of zerumbone, C15H22O, extracted from the rhizomes of Zingiber zerumbet Smith, has been determined by single-crystal X-ray diffraction at 295(1) K and refined by least squares to a residual of 0.051 for 925 {\textquoteleft}observed{\textquoteright} reflections. Crystals are monoclinic, space group P 21c, a 9•036(3), b 9•712(5), c 15•643(6) {\AA}, β 97•19(3)°, Z = 4. Although the molecule has no chiral centre, the presence of the three trans double bonds confers considerable distortion and rigidity on the eleven-membered ring and renders the whole molecule chiral and potentially resolvable.",

author = "Hall, {Sydney R.} and Surachai Nimgirawath and Raston, {Colin L.} and Amnard Sittatrakul and Somkiat Thadaniti and Narumol Thirasasana and White, {Allan H.}",

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T1 - Crystal Structure of Zerumbone [(E, E, E)-2, 6, 9, 9-Tetramethylcycloundeca-2, 6, 10-trien-1-one]

AU - Hall, Sydney R.

AU - Nimgirawath, Surachai

AU - Raston, Colin L.

AU - Sittatrakul, Amnard

AU - Thadaniti, Somkiat

AU - Thirasasana, Narumol

AU - White, Allan H.

PY - 1981

Y1 - 1981

N2 - The crystal structure of zerumbone, C15H22O, extracted from the rhizomes of Zingiber zerumbet Smith, has been determined by single-crystal X-ray diffraction at 295(1) K and refined by least squares to a residual of 0.051 for 925 ‘observed’ reflections. Crystals are monoclinic, space group P 21c, a 9•036(3), b 9•712(5), c 15•643(6) Å, β 97•19(3)°, Z = 4. Although the molecule has no chiral centre, the presence of the three trans double bonds confers considerable distortion and rigidity on the eleven-membered ring and renders the whole molecule chiral and potentially resolvable.

AB - The crystal structure of zerumbone, C15H22O, extracted from the rhizomes of Zingiber zerumbet Smith, has been determined by single-crystal X-ray diffraction at 295(1) K and refined by least squares to a residual of 0.051 for 925 ‘observed’ reflections. Crystals are monoclinic, space group P 21c, a 9•036(3), b 9•712(5), c 15•643(6) Å, β 97•19(3)°, Z = 4. Although the molecule has no chiral centre, the presence of the three trans double bonds confers considerable distortion and rigidity on the eleven-membered ring and renders the whole molecule chiral and potentially resolvable.

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