Agnolo Bronzino's Portrait of a Young Man with a Book is set to lead Christie's January 28 sale of Renaissance art in London with an $8m-12m estimate.
Bronzino (1503-1572) was a key artist of the renaissance period best known for his distinctive portraits of the Medici family.
His love of the machinations and trappings of power are evident in his work.
Christie's comments: "Although there is no evidence of any knowledge of his work, there is a parallel between the portraiture of Bronzino and that of Andy Warhol, the most celebrated purveyor of 'iconic' images of the 20th century.
"Warhol, who became interested in Chairman Mao following Nixon's visit to China, painted him in part 'since fashion is art now and Chinese is in fashion'.
"Of course his interest was fired by Mao's power and celebrity, and his place in the select group of instantly recognizable people, like Jackie O and Liz Taylor, who defined his era and his culture."
A triptych by the Thuringian School depicting the Passion of Christ (circa 1400) is valued at $1.2m-1.8m.
The work is believed to have been presented by Charles VI of France to the Spanish statesman Don Pero during the early 15th century.
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