Purification of synthetic all- E lycophyll (ψ,ψ-carotene-16,16′-diol)

• Published in: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences Vol. 834; no. 1; pp. 208 - 212
• Main Authors: Braun, Cristi L., Jackson, Henry L., Lockwood, Samuel F., Nadolski, Geoff
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 13.04.2006; Elsevier Science
• Subjects: All- trans lycophyll; Analysis; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Carotenoids; Carotenoids - isolation & purification; Chemical Precipitation; Chromatography, High Pressure Liquid - methods; Fundamental and applied biological sciences. Psychology; General pharmacology; HPLC analysis; Lycophyll; Lycophyll isomers; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Pharmacology. Drug treatments; Semi-preparative chromatography; Semi-preparative chromatography; THF; Carotenoids; Lycophyll isomers; HPLC analysis; Lycophyll; All- trans lycophyll; DIBAL; HPLC; MTBE; TFA; DCM; Purification; Carotene; Preparative chromatography; HPLC chromatography; All-trans lycophyll; Carotenoid
• ISSN: 1570-0232; 1873-376X
• DOI: 10.1016/j.jchromb.2006.02.023

An efficient purification of synthetic all- trans (all- E) lycophyll is described. The synthetic preparation of the rare xanthophyll lycophyll produces a mixture of geometric isomers. Purification by HPLC using reverse-phase C30 silica affords milligram quantities of the desired all- trans isomer in >95% purity, as confirmed by 1H NMR and LC/MS. Most recently, a facile work-up of the geometric mixture formed during total synthesis was found to provide multigrams of the targeted all- E geometric isomer of lycophyll. The acquisition of modest quantities of this specific lycopene analog allows its therapeutic potential to be explored.