Rubrocurcumin

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Rubrocurcumin
Names
Other names
Rubrocurcumin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C23H19BO10/c1-30-20-11-14(5-9-18(20)26)3-7-16(25)13-17(32-24-33-22(28)23(29)34-24)8-4-15-6-10-19(27)21(12-15)31-2/h3-13,26-27H,1-2H3/b7-3+,8-4+,17-13- ☒N
    Key: CSMMVHRUFPYHCS-YRLHZMKXSA-N ☒N
  • Charged form: InChI=1S/C23H19BO10/c1-29-20-11-14(5-9-18(20)25)3-7-16-13-17(32-24(31-16)33-22(27)23(28)34-24)8-4-15-6-10-19(26)21(12-15)30-2/h3-13,25-26H,1-2H3/b7-3+,8-4+
    Key: YIFZXJZUXMHJJG-FCXRPNKRSA-N
  • B1(OC(=O)C(=O)O1)O/C(=C\C(=O)/C=C/c2ccc(c(c2)OC)O)/C=C/c3ccc(c(c3)OC)O
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 neutrally charged composition, while rosocyanine is produced from ions. 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]

Literature

  • 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. 1952 (article 907). London: 4650–4653. doi:10.1039/JR9520004650.

References