Chemistry:Rubrocurcumin

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Rubrocurcumin
Rubrocurcumin.png
Names
IUPAC name
2-[(1E,3Z,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-trien-3-yl]oxy-1,3,2-dioxaborolane-4,5-dione
Other names
Rubrocurcumin
Identifiers
3D model (JSmol)
ChemSpider
Properties
C23H19BO10
Molar mass 466.19 g/mol
Appearance red solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rubrocurcumin is a red-colored dye that is formed by the reaction of curcumin and borates.

Synthesis

The reaction of curcumin with borates in presence of oxalic acid produces rubrocurcumin.[1]

Characteristics

Rubrocurcumin produces a red colored solution.

Rubrocurcumin is a neutral molecule, while rosocyanine is ionic. In rubrocurcumin, one molecule of curcumin is replaced with oxalate compared to rosocyanine.

Complexes with boron such as rubrocurcumin are called 1,3,2-dioxaborines.[1]

References

  1. 1.0 1.1 Rohde, D. (2002). Darstellung und Eigenschaftsuntersuchungen an 1,3,2-Dioxaborinen mit variablen Coliganden am Boratom [Presentation and characterization of 1,3,2-dioxaborins with variable coligands on the boron atom] (Dissertation). University Halle.

Further reading

  • Spicer, G. S.; Strickland, J. D. H. (1952). "Compounds of Curcumin and Boric Acid. Part II. The Structure of Rubrocurcumin". Journal of the Chemical Society (London) 1952 (art. 907): 4650–4653. doi:10.1039/JR9520004650.