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Dear Prof. Derome,
As our friend Francis Herbert has already pointed out in his previous message to this list, one of the most prominent examples, in 16th century cartography, of an effort to imagine, and to include in a map, a portrait considered as representing Ptolemy, is included in the famous map of 1507 by Martin Waldseemüller (the famous map bringing the name 'America', whose reproduction and reference can be found for instance as item number 26, studied in pages 28-29, of the wonderful work by our friend Rodney Shirley,
'The Mapping of the World', London: Holland Press, reed. 1987).
Today I scanned that particular part of the map (the detail with the Waldseemuller's tentative portrait of Ptolemy), and I am now sending it as an attachment in a message to our friend Peter van der Krogt, coordinator of the MapHist homepage, so that he can put it available in display at the MapHist illustrations page, if that is possible.
With best wishes for your project. Alfredo Pinheiro Marques