Rubrocurcumin

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	466.21 g·mol−1
Appearance	Red solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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]

References

^ 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.
^ ^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.

[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.

[rohde-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.

[1]

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