Rubrocurcumin

Rubrocurcumin is a red-colored dye that is formed by the reaction of curcumin and borates.

Rubrocurcumin

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
CAS Number	12098-66-7
3D model (JSmol)	Interactive image
ChemSpider	24751750 Non-charged form 24751749 Charged form
PubChem CID	57461353
CompTox Dashboard (EPA)	DTXSID90726681
InChI 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- Key: CSMMVHRUFPYHCS-YRLHZMKXSA-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
SMILES 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
Chemical formula	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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Infobox references

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. 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.