Names | |
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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 | |
CompTox Dashboard (EPA) | |
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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). |
Rubrocurcumin is a red-colored dye that is formed by the reaction of curcumin and boric acid. [1]
The reaction of curcumin with borates in presence of oxalic acid produces rubrocurcumin. [2]
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]
An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.
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.
Boric acid, more specifically orthoboric acid, is a compound of boron, oxygen, and hydrogen with formula B(OH)3. It may also be called hydrogen orthoborate, trihydroxidoboron or boracic acid. It is usually encountered as colorless crystals or a white powder, that dissolves in water, and occurs in nature as the mineral sassolite. It is a weak acid that yields various borate anions and salts, and can react with alcohols to form borate esters.
A borate is any of a range of boron oxyanions, anions containing boron and oxygen, such as orthoborate BO3−3, metaborate BO−2, or tetraborate B4O2−7; or any salt of such anions, such as sodium metaborate, Na+[BO2]− and borax (Na+)2[B4O7]2−. The name also refers to esters of such anions, such as trimethyl borate B(OCH3)3 but they are alkoxides.
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979.
Curcumin is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal curcuminoid of turmeric, a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmetics ingredient, food flavoring, and food coloring.
The aldol reaction is a reaction in organic chemistry that combines two carbonyl compounds to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:
Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds.
Boron trichloride is the inorganic compound with the formula BCl3. This colorless gas is a reagent in organic synthesis. It is highly reactive toward water.
Boron tribromide, BBr3, is a colorless, fuming liquid compound containing boron and bromine. Commercial samples usually are amber to red/brown, due to weak bromine contamination. It is decomposed by water and alcohols.
Rosocyanine and rubrocurcumin are two red colored materials, which are formed by the reaction between curcumin and borates.
A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.
Phenylboronic acid or benzeneboronic acid, abbreviated as PhB(OH)2 where Ph is the phenyl group C6H5-, is a boronic acid containing a phenyl substituent and two hydroxyl groups attached to boron. Phenylboronic acid is a white powder and is commonly used in organic synthesis. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.
Boron triiodide is a chemical compound of boron and iodine with chemical formula BI3. It has a trigonal planar molecular geometry.
A nuclear reactor coolant is a coolant in a nuclear reactor used to remove heat from the nuclear reactor core and transfer it to electrical generators and the environment. Frequently, a chain of two coolant loops are used because the primary coolant loop takes on short-term radioactivity from the reactor.
Trimethylborane (TMB) is a toxic, pyrophoric gas with the formula B(CH3)3 (which can also be written as Me3B, with Me representing methyl).
Metaboric acid is the name for a family of inorganic compounds with the same empirical formula HBO2 that differ in their molecular structure. They are colourless water-soluble solids formed by the dehydration or decomposition of boric acid.
Chromyl fluoride is an inorganic compound with the formula CrO2F2. It is a violet-red colored crystalline solid that melts to an orange-red liquid.
Boron phosphate is an inorganic compound with the chemical formula BPO4. The simplest way of producing it is the reaction of phosphoric acid and boric acid. It is a white infusible solid that evaporates above 1450 °C.
Boron monofluoride monoxide or oxoboryl fluoride or fluoroxoborane is an unstable inorganic molecular substance with formula FBO. It is also called boron fluoride oxide, fluoro(oxo)borane or fluoro-oxoborane. The molecule is stable at high temperatures, but below 1000 °C condenses to a trimer (BOF)3 called trifluoroboroxin. FBO can be isolated as a triatomic non-metallic molecule in an inert gas matrix, and has been condensed in solid neon and argon. When an attempt is made to condense the gas to a solid in bulk, a polymeric glass is formed, which is deficient in fluoride, and when heated forms a glassy froth like popcorn. Boron fluoride oxide has been studied because of its production in high energy rocket fuels that contain boron and fluorine, and in the form of an oxyfluoride glass. BOF glass is unusual in that it can condense directly from gas.