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
  • 12098-66-7 ☒N
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).
☒N  (what is checkY☒N ?)
Infobox references

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]

References[]

  1. ^ a b 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.
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