Curcumins solubility

The principal coloring matter in turmeric and its oleoresin is curcumin [458-37-7] (l,6-heptadiene-3,5-dione, l,7-bis[4-hydroxy-3-methoxy-phenyl] (45), an orange-yeUow, crystalline powder, insoluble in water and ether but soluble in ethanol and glacial acetic acid. It has a reported melting point of 180-183°C. 

The yellow dye curcumin, [458-37-7] (Cl Natural Ye//oii> 3 Cl 75300) (41), also known as tumeric, occurs in the roots of the plant Curcuma tinctoria found growing wild in Asia. The dye was well known to the ancient Romans and Greeks who used it to dye wool, cotton, and silk. The dye is an oil-soluble bright yellow material, and is the only natural yellow dye that requires no mordant. It finds use as a colorant for baked goods such as cakes. 

Tpnnesen, H.H, Masson, M., and Loftsson, T., Studies on curcumin and curcuminoids. XXVII. Cyclodextrin complexation solubility, chemical an photochemical stability, Int. J. Pharm., 244, 127, 2002. 

Curcumin is a bright yellow pigment that is oil soluble. It is sometimes produced in a water dispersible form. 

The pure oleoresin produced by solvents normally contains only pure curcumin, in a crystalline form. It is hardly soluble in liquid- and supercritical CO2- Even at an extraction pressure of 450 bar, and with 2 hours extraction time at 65°C, only 20% of the initial curcumin can be extracted. On the other hand, all the volatile oil and fatty oil is extracted, and a fat-free curcumin-starch mixture with a very low flavour-content can be produced. The total extraction yields are between 5 to 12%, with mostly fatty oil and volatile oil, and about 10% curcumin in the extract. 

The purified colour, curcumin, is not water-soluble, but water-dispersible systems are available... 

Chen J, Wanming D, Zhang D, Liu Q, Kang J. 2005. Water-soluble antioxidants improve the antioxidant and anticancer activity of low concentrations of curcumin in human leukemia cells. Pharmazie 60 57-61. 

It is insoluble in water but soluble in ethanol and acetone. The structure and synthesis of curcumin as a diferuloylmeth-ane was confirmed by the work of Lampe (1910), and also by Majeed et al. (1995). 

Baumann, W., Rodrigues, S.V. and Viana, L.M. (2000) Pigments and their solubility in and extractability by supercritical C02. Part 1. The case of curcumin. Brazilian journal of Chemical Engineering 1 7, 323-328. 

Curcumin is obtained from the spice turmeric which comes from the plant Curcuma longa, which itself is related to ginger. Curcumin is a bright yellow pigment which is obtained by extraction from the plant to give a deodorised product. It is oil soluble but is sometimes produced in a water dispersible form. 

Most carotenoids are fat-soluble although, like curcumin, preparations that allow them to be dispersed in water are made. The colours available from carotenoids vary between pale yellow and red. 

One example that can demonstrate the effectiveness and great promise of nanoencapsulation is the curcumin nanoemulsions. Curcumin is the major yellow pigment in turmeric Curcuma longa Linn). In South and Southeast Asia, curcumin preparation or turmeric has been used extensively to treat inflammatory conditions and chronic diseases (Reddy and Rao 2003). Orally administered curcumin usually has low systemic bioavailability. Only trace amounts of curcumin (or its metabolites) appear in the blood, and most of ingested curcumin is excreted in the feces. One reason is that curcumin has low solubility and does not disperse for absorption. The absorbed curcumin is rapidly metabolized in the intestine and liver to several reduction products (di-, tetra-, and hexa-hydrocurcumin and hexahydrocurcuminol) and... 

Jovanovic SV, Boone GW, Steenken S, Trinoga M, Kaskey RB. (2001) How curcumin works preferentially with water soluble antioxidants. J Am Chem Soc 123 3064-3068. 

Tonnesen HH. Studies on curcumin and curcuminoids. XXVIII. Solubility, chemical and photochemical stability of curcumin in surfactant solution. Pharmazie 2002 57 ... 

As it can be deduced from the description of the chemical structures of anthocyans and anthocyanidins, polyphenolic pigments are usually water soluble (Figure 1). Noticeable exceptions are the curcumin oils (yellow),... 

Because the cyclodextrin pigment complexes are much more soluble than the noncomplexed pigments, particular chromatographic methods should be used for their analysis (Cserhati and Forgacs, 2003). For instance, to analyze curcumin-cyclodextrin complexes, Tonnesen et al. (2002) used a C18-RP-HPLC (Nova Pack column). The mobile phase was citric acid and acetonitrile (60/40 v v). 

The pure colom is produced by further crystallisation of the oleoresin resulting in a product with minimum 90% curcumin and very little of the flavour compounds. It is insoluble in water and poorly soluble in other solvents. Typical products for use in the food industry have a curcumin content of 4 to 10% and are achieved by dispersing pure curcumin in a mixture of food-grade solvent and emulsifier, by dissolving in vegetable oil or by spraying onto starch. 

The use of natural pigments for food applications is gaining soil from day to day [95]. Curcumin, betaine, amarathine, anthocyanins and P-carotene are the most common and widely used pigments [95,96], Saffron s coloring properties attributed mainly to water-soluble carotenoids are used for coloring of foods. The stability of these saffron pigments in aqueous... 

We demonstrated that a naturally derived polysaccharide, chitosan, is capable of forming composite nanoparticles with silica. For encapsulated particles, we used silicification and biosilicification to encapsulate curcumin and analyzed the physicochemical properties of curcumin nanoparticles. It proved that encapsulated curcumin nanoparticles enhanced stability toward ultraviolet (UV) irradiation, antioxidation and antitumor activity, enhanced/added function, solubility, bioactivities/ bioavailability, and control release and overcame the immunobarrier. We present an in vitro study that examined the cytotoxicity of amorphous and composite silica nanoparticles to different cell lines. These bioactives include curcumin mdAntrodia cinnamomea. It is hoped that by examining the response of multiple cell lines to silica nanoparticles more basic information regarding the cytotoxicity as well as potential functions of silica in future oncological applications could become available. 

Curcumin is not water-soluble, but it is soluble in ethanol or in dimethylsulfoxide. The degradation kinetics of curcumin under various pH conditions and the stability of curcumin in physiological matrices have been established. When curcumin was incubated in O. IM phosphate buffer and semm-free medium (pH 7.2 at 37°C), about 90% decomposed within 30min. A series of pH conditions ranging from 3 to 10 were tested, and the results showed that decomposition was pH-dependent and occurred faster at neutral-basic conditions. It is more stable in cell culture medium containing 10% fetal calf seram and in human blood. Less than 20% of curcumin decomposed within Ih, and after incubation for 8h, about 50% of curcumin still remained. Trans-6-(4 -hydroxy-3 -methoxyphenyl)-2,4-dioxo-5-hexenal was predicted to be the major degradation product, and vanillin, feralic acid, and feraloyl methane were identified as minor degradation products. The amount of vanillin increased with incubation time. 

The solvent evaporation method can also be used to produce nanoparticles from polylactic polymers, mainly to improve the oral bioavailability of polyphenolics by the oral route. For example, curcumin, EGCG, or ellagic acid has been encapsulated in PLGA nanoparticles, and quercitrin or quercetin has been immobilized in polylactic acid (PLA) nanoparticles, to improve the aqueous solubility, to increase the intestinal absorption, and to increase globally the oral efficacy of these compounds. Ellagic acid in PLGA-PCL nanoparticles was shown to be more active against nephrotoxicity than the free molecule. ... 

Curcumin shows very interesting therapeutic properties in the fields of cancer, AIDS, or inflammation, but its use is limited by a low aqueous solubility and poor bioavailability. Nanocurc is a dispersion of curcumin, in micelles of synthetic block copolymer of N-isopropylacrylamide, N-vinylpyrrolidone, and poly(ethylene glycol)acrylate. Nanocurc is a water-soluble version of curcumin, with increased bioavailability and activity against tumor growth and metastases. The in vivo studies suggest that Nanocurc allows curcumin to cross the blood-brain barrier and exert an activity against inflammatory damages in the brain associated with Alzheimer s disease. ... 

Lapenna S, Bilia AR, Morris GA, Nilsson M. Novel artemisinin and curcumin micellar formulations Drug solubility studies by NMR spectroscopy. 7 Pharm Sci. 2009 98(10) 3666-3675. 

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