Review Article

Melanins: Skin Pigments and Much More—Types, Structural Models, Biological Functions, and Formation Routes

Figure 2

Model for eumelanin structure. This polymer is dark, from brown to black depending on the size and electronic conjugation. (a) The tetrone simplified model to account for empirical composition C18H10O4N2. (b) The classical model. Most units are indolic units. The most abundant units are DHI (5,6-dihydroxyindole, U1, U4, and U6) although some units of the 2-carboxylated analogue DHICA (5,6-dihydroxyindole-2-carboxylic acid, U2, and U5) are also found. The ratio DHI/DHICA depends on the dopachrome tautomerase activity and other conditions during the eumelanin formation. Oxidized units of IQ (5,6-indolequinone, U3), unaltered L-dopa units (U7), and carboxylated pyrroles due to partial degradation of indoles during the polymerization (U8) can also be incorporated during the polymerization. The units are linked by a variety of bonds involving positions 4, 7, 2, and 3. Arrows indicate some possible points for polymer growth.
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