The Testament of Solomon could be the oldest of all classical grimoires. The work is one of the so called Pseudepigrapha and should therefore be dated somewhere before the middle of the first century AD, according to the latest research. The book was written in Greek, but most likely the Greek version is a translation of an older version in Hebrew.
Testament of Solomon sums up a list of demonic decan rulers of the Zodiac and provides the method or the invoked angel they can be countered by. This relation between decans and demons or their angelic counterforce is emphasized. Interesting is the relation between the decans and physical complaints. Especially if we compare this text with those of contemporary medical astrology. See Reinhold Ebertin, Enzo Venosta or H.L. Cornell.
The document was translated and first published by F.C. Conybeare in the Jewish Quaterly Review of October 1889. Possibly it is the first text that mentions the use of the pentagram (pentalpha) for protection against the evil forces.