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Lett Org Chem. 2012 Dec 1;9(10):762-766.

A Practical Synthesis and X-ray Crystallographic Analysis of Dithymoquinone, a Photodimer of Thymoquinone.

Author information

1
Department of Pharmacy Research, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA.
2
Department of Experimental Therapeutics, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA.
3
Department of Gastrointestinal Medical Oncology, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA.
4
Department of General Oncology, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA.
5
Department of Pharmacy Research, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA ; Department of Thoracic Head and Neck Medical Oncology, The University of Texas M.D. Anderson Cancer Center, Houston, Texas, USA.

Abstract

An updated and practical approach to the synthesis of dithymoquinone via one-step photoirradiation of thymoquinone (2-methyl-5-isopropyl-1,4-benzoquinone) is described. Synthesis resulted in a 55% yield of one structural isomer (trans-anti derivative), as confirmed by HPLC, NMR spectroscopy and first ever single-crystal X-ray diffraction analyses.

KEYWORDS:

X-ray structure; dithymoquinone; photodimerization; thymoquinone

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