Chemistry: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 N
3D model (JSmol)	Interactive image
ChemSpider	24751750 Non-charged form N 24751749 Charged form Y
PubChem CID	57461353
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- 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
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).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

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.

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.

References

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.