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| ImageFile = Rubrocurcumin.png
| ImageFile = Rubrocurcumin.png
| ImageSize = 300px
| ImageSize = 300px
| IUPACName = 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
| IUPACName = 2-[(1''E'',3''Z'',6''E'')-1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-trien-3-yl]oxy-1,3,2-dioxaborolane-4,5-dione
| OtherNames = Rubrocurcumin
| OtherNames = Rubrocurcumin
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=23 | H=19 | B=1 | O=10
| Formula = C<sub>23</sub>H<sub>19</sub>BO<sub>10</sub>
| MolarMass = 466.19 g/mol
| Appearance = Red solid
| Appearance = red solid
| Density =
| Density =
| MeltingPt =
| MeltingPt =
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}}
}}


'''Rubrocurcumin''' is a red-colored dye that is formed by the reaction of [[curcumin]] and [[borate]]s.
'''Rubrocurcumin''' is a red-colored dye that is formed by the reaction of [[curcumin]] and [[boric acid]].<ref>{{ cite journal | last = Spicer | first = G. S. | last2 = Strickland | first2 = J. D. H. | title = Compounds of Curcumin and Boric Acid. Part II. The Structure of Rubrocurcumin | journal = Journal of the Chemical Society | location = London | date = 1952 | volume = 1952 | issue = art. 907 | pages = 4650–4653 | doi = 10.1039/JR9520004650 }}</ref>


== Synthesis ==
== Synthesis ==
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== Characteristics ==
== Characteristics ==
Rubrocurcumin produces a red colored solution.
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.
Rubrocurcumin is a neutral molecule, while [[rosocyanine]] is ionic. In rubrocurcumin, one molecule of curcumin is replaced with [[oxalate]] compared to rosocyanine.
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== References ==
== References ==
{{reflist}}
{{reflist}}

=== Further reading ===
{{refbegin}}
* {{ cite journal | last = Spicer | first = G. S. | last2 = Strickland | first2 = J. D. H. | title = Compounds of Curcumin and Boric Acid. Part II. The Structure of Rubrocurcumin | journal = Journal of the Chemical Society | location = London | date = 1952 | volume = 1952 | issue = art. 907 | pages = 4650–4653 | doi = 10.1039/JR9520004650 }}
{{refend}}
[[Category:Curcuminoid dyes]]
[[Category:Curcuminoid dyes]]
[[Category:Tetrahydroxyborate esters]]
[[Category:Tetrahydroxyborate esters]]

Latest revision as of 14:14, 2 April 2024

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
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 466.21 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).
☒N verify (what is checkY☒N ?)

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

Synthesis

[edit]

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

Characteristics

[edit]

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

[edit]
  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. ^ 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.