Rubrocurcumin

Last updated
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
PubChem CID
  • 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- X mark.svgN
    Key: CSMMVHRUFPYHCS-YRLHZMKXSA-N X mark.svgN
  • 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 466.21 g·mol−1
AppearanceRed solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Rubrocurcumin is a red-colored dye that is formed by the reaction of curcumin and boric acid. [1]

Contents

Synthesis

The reaction of curcumin with borates in presence of oxalic acid produces rubrocurcumin. [2]

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. [2]

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<span class="mw-page-title-main">Boron</span> Chemical element, symbol B and atomic number 5

Boron is a chemical element; it has symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the boron group it has three valence electrons for forming covalent bonds, resulting in many compounds such as boric acid, the mineral sodium borate, and the ultra-hard crystals of boron carbide and boron nitride.

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References

  1. 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 (art. 907). London: 4650–4653. doi:10.1039/JR9520004650.
  2. 1 2 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.