Norbixin

EEC No. E 160b), which is the monomethyl ester of the dicarboxyhc acid norhixin. The principal colorant ia alkaline aqueous extracts is norbixin [542-40-5] (36 R = H) (51,52). 

Annatto is a colored pigment that is extracted from the Central and South American plant Bixa orellana. The color comes from the resinous outer covering of the seeds of the plant, which is composed of the carotenoid pigments bixin and norbixin and their esters. The central portion of those molecules is the same as that of the molecule beta-carotene, and the yellow-orange color of annatto comes from the same physical chemistry origins as the orange color of beta-carotene. 

Bixa Orellana seeds Bixin, norbixin (annatto) Food colouring... 

Carotenoids are also present in animal products such as eggs, lobsters, greyflsh, and various types of hsh. In higher plants, they occur in photosynthetic tissues and choloroplasts where their color is masked by that of the more predominant green chlorophyll. The best known are P-carotene and lycopene but others are also used as food colorants a-carotene, y-carotene, bixin, norbixin, capsanthin, lycopene, and P-apo-8 -carotenal, the ethyl ester of P-apo-8-carotenic acid. These are Upid-soluble compounds, but the chemical industry manufactures water-dispersible preparations by formulating coUoid suspensions by emulsifying the carotenoids or by dispersing them in appropriate colloids. ... 

FIGURE 4.2.2 Structures of carotenoids found in paprika (capsanthin and capsombin), saffron and gardenia (crocetin derivatives), and annatto (bixin and norbixin). 

Annatto colors (C.I. 75120) E 100 2% norbixin Annatto extract, water, Yellow-orange Cheeses, ice cream, bakery products... 

Dried or freeze dried samples can be extracted with water-immiscible solvents such as EtOAc or diethyl ether. For quantitative extraction, dried samples are preferably rehydrated at different times for example, 5 to 10 min for dried mangoes, 30 min for lyophihzed red peppers and pasta. Rehydration is followed by extraction with acetone or MeOH. Bixin and norbixin from a mix dry powder of annatto and com can quantitatively be extracted with MeOH followed by acetone. In order to improve pigment recovery, extruded foods require pre-digestion with enzymes to liberate the pigment from the matrix. ... 

On the other hand, quantitative extraction requires complete and exhaustive extraction and no material can be lost. To assure complete extraction when a food is analyzed for the first time in a laboratory, it is useful to carry out two or three extractions, pool the solvents, and keep separate the next extracts to verify the presence of carotenoids. Usually four to six extractions are enough to remove the carotenoids completely from a sample. The extraction can be carried out in a blender, vortex, or with a mortar and pestle. Accelerated solvent extraction (ASE), an important extraction technique in residue analysis, currently attracts interest due to its short duration, low level of solvent use, and high extraction yield. The average recoveries for all carotenoids with the exception of norbixin ranged from 88.7 to 103.3% using manual extraction and from 91.0 to 99.6% by ASE (70 bar and temperature of 40°C) both extractions were carried out with a mixture of MeOH, EtOAc, and petroleum ether (1 1 1). ... 

More severe conditions, 35 ml of 35% methanolic KOH added to 10 mL extract in EtOAc and shaken for 20 min at 50°C, are necessary for the total conversion of bixin, an ester of a carotenoid acid, to norbixin in snacks. Since saponification yields the norbixin salt (K or Na, depending on the alkali) that is soluble in the aqueous phase, the pH should be decreased to 3.5 or even lower to allow extraction of the protonated norbixin by EtOAc and diethyl ether. ... 

Tocchini, L. and Mercadante, A.Z., Extraction and determination of bixin and norbixin, by HPLC, in annatto spice ( colorifico ), Cienc. Tecnol. Aliment., 21, 310, 2001. 

Lancaster, RE. and Lawrence, J.F., High-performance liquid chromatographic separation of carminic acid, and P-bixin, and a- and 13-norbixin, and the determination of carminic acid in foods, J. Chromatogr. A, 732, 394, 1996. 

Bixin, norbixin annato extracts E 160b Yes, 75120 Seeds of annatto (Bixa orellana) orange-red L>... 

As has been pointed out earlier in this chapter, the dietary consumption and historical medicinal use of carotenoids has been well documented. In the modern age, in addition to crocin, 3.7, and norbixin, 3.8, several carotenoids have become extremely important commercially. These include, in particular, astaxanthin, 3.6 (fish, swine, and poultry feed, and recently human nutritional supplements) lutein, 3.4, and zeaxanthin, 3.3 (animal feed and poultry egg production, human nutritional supplements) and lycopene, 3.2 (human nutritional supplements). The inherent lipophilicity of these compounds has limited their potential applications as hydrophilic additives without significant formulation efforts in the diet, the lipid content of the meal increases the absorption of these nutrients, however, parenteral administration to potentially effective therapeutic levels requires separate formulation that is sometimes ineffective or toxic (Lockwood et al. 2003). 

Breukers S, 0pstad CL, Sliwka HR, and Partali V. 2009. Hydrophilic carotenoids Surface properties and aggregation behaviour of the potassium salt of the highly unsaturated diacid norbixin. Helvetica Chimica Acta 92(9) 1741-1747. 

The photostability of the natural occurring 9 -cis carotenoids bixin and norbixin, Ligure 12.5, has received the attention of several research groups (Najar et al. 1988, Pimentel and Stringheta... 

FIGURE 12.5 Structures of bixin and norbixin, cis carotenoids from annatto. 

Silva, G. S., A. G. Souza, J. R. Botelho et al. 2007. Kinetics study of norbixin s first stage thermal decomposition, using dynamic method../. Thermal Anal. Calorim. 87 871-874. 

Figure 11.8 Structures of c/s-bixin and norbixin, apocarotenoid pigments in annatto.

Bixin is an oil soluble, highly stable coloring ingredient. The saponification of the methyl ester group to form the dicarboxylic acid yields the water-soluble form of bixin, sometimes called norbixin. Annatto colorants date back into antiquity. The colorant has been used for centuries in connection with various textiles, medicinals, cosmetics, and foods. Annatto colors have also been used to color cheese, butter, and other dairy products for over a century. See also Carotenoids. 

---