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A possible ethanol-catalyzed rearrangement of vitamin K-1 detected by gas chromatography/mass spectrometry
Linköping University, Department of Clinical and Experimental Medicine, Clinical Chemistry. Linköping University, Faculty of Health Sciences. Östergötlands Läns Landsting, Centre for Laboratory Medicine, Department of Clinical Chemistry.
Linköping University, Faculty of Health Sciences. Linköping University, Department of Clinical and Experimental Medicine, Clinical Chemistry.
2008 (English)In: Rapid Communications in Mass Spectrometry, ISSN 0951-4198, Vol. 22, no 23, 3861-3866 p.Article in journal (Refereed) Published
Abstract [en]

We studied vitamin K-1(20), vitamin K-1(25), and vitamin K, epoxide in n-hexane and ethanol solutions by gas chromatography/mass spectrometry (GC/MS) utilizing a DB-5 MS fused-silica capillary column. In ethanol solutions of K-1, we observed an extra peak eluting from the GC column with somewhat longer retention time than K-1(20). A similar peak following K-1(25) was also found. These peaks were not found in n-hexane solutions of K-1. A close examination of the mass spectra of these peaks indicated that they were vitamin K-1 variants containing a base peak at m/z 225 characteristic of the methylnaphthoquinone ring with a four-carbon side chain. In addition, they contained the molecular ions of K-1(20) and K-1(25), respectively. We conclude that K-1(20) and K-1(25), but not K-1 epoxide, might undergo rearrangements in ethanol involving an intramolecular proton transfer and a shift of the beta,gamma-double bond on the phytyl side chain toward the ring. The conjugation of the phytyl double bond with the quinone ring is probably the driving force of the rearrangement. We emphasize, however, that our conclusion is based only on mass spectral analysis and would require further investigation by other spectroscopic methods.

Place, publisher, year, edition, pages
2008. Vol. 22, no 23, 3861-3866 p.
National Category
Medical and Health Sciences
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URN: urn:nbn:se:liu:diva-16210DOI: 10.1002/rcm.3807OAI: oai:DiVA.org:liu-16210DiVA: diva2:133457
Available from: 2009-01-12 Created: 2009-01-09 Last updated: 2009-12-18

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Osman, AbdimajidHannestad, Ulf

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