E182 - Orcein

Orcein, also archil, orchil, lacmus and C.I. Natural Red 28, are names for dyes extracted from several species of lichen, commonly known as "orchella weeds", found in various parts of the world. A major source is the archil lichen, Roccella tinctoria. Orcinol is extracted from such lichens. It is then converted to orcein by ammonia and air. In traditional dye-making methods, urine was used as the ammonia source. If the conversion is carried out in the presence of potassium carbonate, calcium hydroxide, and calcium sulfate -in the form of potash, lime, and gypsum in traditional dye-making methods-, the result is litmus, a more complex molecule. The manufacture was described by Cocq in 1812 and in the UK in 1874. Roberts noted orchilla as a principal export of the Cape Verde islands, superior to the same kind of moss found in Italy or the Canaries, that in 1832 was yielding an annual revenue of $200‚000. Commercial archil is either a powder -called cudbear- or a paste. It is red in acidic pH and blue in alkaline pH. Orcein is not approved as a food dye -banned in Europe since January 1977-, with E number E121 before 1977 and E182 after., Its CAS number is 1400-62-0. Its chemical formula is C28H24N2O7. It forms dark brown crystals. It is a mixture of phenoxazone derivates - hydroxyorceins, aminoorceins, and aminoorceinimines. The chemical components of orcein were elucidated only in the 1950s by Hans Musso. The structures are shown below. A paper originally published in 1961, embodying most of Musso's work on components of orcein and litmus, was translated into English and published in 2003 in a special issue of the journal Biotechnic & Histochemistry -Vol 78, No. 6- devoted to the dye. A single alternative structural formula for orcein, possibly incorrect, is given by the National Library of Medicine [1] and Emolecules [2]. Orcein is a reddish-brown dye, orchil is a purple-blue dye. Orcein is also used as a stain in microscopy to visualize chromosomes, elastic fibers, Hepatitis B surface antigens, and copper-associated proteins. - Wikipedia