Oleoresin, from paprika

Annato is a yellow oil or aqueous alkaline extract of fruit pulp of Raku or Orleans shrubs or brushwood Bixa orellana). The major pigments of annato are bixin (XVIII) and norbixin, both of which give dicarboxylic acids upon hydrolysis. Oleoresin from paprika is a red, oil extract containing about 50 different pigments. The aqueous extract of saffron (more accurately, from the pistils of the flower Crocus sativus) contains crocin (XVII) as its main constituent. It is used for coloring beverages and bakery products. 

Goda et al. (1995) separated capsanthin esters from oleoresin of paprika fruits from Spain and determined their chemical structures without saponification. The major monoesterified capsanthin was identified as 3 -0-myristoylcapsanthin. It is suggested that the rate of esterification of fatty acid to the hydroxyl group on the cyclopentane ring of capsanthin is different to that on the cyclohexene ring. 

Definition Coloring material derived from paprika oleoresin, consistg. predominantly of capsanthin and capsorubin... 

OLEOGUM resins. See gum resin OLEORESiNS. Mixtures of mostly resins and volatile oils. They either occur naturally or are prepared by solvent extraction of botanicals. Prepared oleoresins are made by extracting the oily and resinous materials from botanicals with fat solvents (hexane, acetone, ether, alcohol). The solvent is then removed under vacuum, leaving behind a viscous, semisolid extract that is an oleoresin. Examples of prepared oleoresins are paprika, ginger, and... 

Lipid fractions (oleoresins), in which the monoglyceride content is somewhat higher (up to 2-3 wt%), have been explored and used for some applications. Many of the oleoresins extracted from fruits, flowers, spices, leaves, etc. consist of various triglycerides, nonsaponifiable fats (waxes), and monoglyceride derivatives. These fractions are sometimes self-emulsifiable and can form in situ water-in-oil emulsions. Such oleoresins from tomato, rosemary, sage, paprika, etc. can provide other functional properties. 

Detailed information about carotenoids found in food or extracted from food and evaluated for their potential as food colorants appeared in Sections 4.2 and 6.2. We would like to mention some new data about the utilization of pure carotenoid molecules or extracts as allowed food additives. Looking to the list of E-coded natural colorants (Table 7.2.1), we can identify standardized colorants E160a through f, E 161a, and E161b as natural or semi-synthetic derivatives of carotenoids provided from carrots, annatto, tomatoes, paprika, and marigold. In addition, the extracts (powders or oleoresins) of saffron, - paprika, and marigold are considered more economical variants in the United States and European Union. 

Paprika contains capsombin and capsanthin (Fig. 8.3) which occur mainly as the lauric acid esters, and about 20 other carotenoid pigments. Paprika is produced in many countries which have developed their own specialties. Cayenne or cayenne pepper, produced from a different cultivar of C. annum, is usually more pungent. C. frutescens is the source of the very pungent Tabasco sauce. Paprika oleoresin is produced by solvent extraction of the ground powder. Obviously paprika supplies both flavor and color and its use is limited to those products compatible with the flavor. The recent rise in demand for tomato products in the form of pizza, salsa, etc., has increased the demand for paprika. Paprika is used in meat products, soups, sauces, salad dressings, processed cheese, snacks, confectionery and baked goods.1018... 

Exempt colors do not have to undergo formal FDA certification requirements, hut are monitored for purity. The colorants exempt from FD C certification are annatto extract, /i-carolene, beet powder, 0-apo—8 -carntenol. canlhaxanthin. caramel, carmine, carrot oil. cochineal extract, cottonseed Hour, ferrous gluconate, fruit juices, grape skin extract, paprika, paprika oleoresin. riboflavin, saffron, titanium dioxide, turmeric, turmeric oleoresin. ultramarine blue, and vegetable juices. See also Colorants (Foods). 

Figure 8. Sensory heat ratings versus concentration of oleoresin capsicum on paprika for a set of 15 artificial red peppers. Reproduced with permission from Ref. 4, copyright 1984, Institute of Food Technologists.

Figure 3.70 demonstrates impressively the extraordinary protecting power of rosemary extract [4]. A desodourized C02-extract from rosemary has been tested for the colour stabilization of carotenoids (i.e. paprika oleoresin). Fig. 3.70 shows the colour deterioration of stabilized versus unstabilized paprika oleoresin. For this test the carotenoids have been exposed to energetic radiation of 366 nm at ambient temperature. The colour units were measured as function of the radiation time. It is obvious that the colour reduction of the stabilized product (A) is almost 10 times slower compared to the unstabilized product (B). 

Paprika oleoresin (E 160(c)) is an orange-red oil-soluble extract from sweet red peppers Capsicum annum. The major coloring compounds are xanthophylls cap-santhin (Formula 9.8), capsorubin as their dilaurate esters, and P-carotene. The presence of characteristic flavoring and spicy pungency components limits application of this extract in foodstuffs. 

Pepper spray, oleoresin capsicum. Extracted from cayenne pepper and paprika proposed as a harassing agent in WWI. Used in pepper sprays. Irritant. Damages sensory nerve endings. 

Paprika and its oleoresin in the red and yellow varieties owe their colour to carotenoids such as capsanthin and capsorubin. They are obtained from the sweet red pepper by solvent extraction which affords an oleoresin containing mainly the two carotenoids. They are more important as flavour materials and illustrate, as do turmeric and its oleoresin, the feature that flavour is often the property of greater interest than colour alone. 

Capsanthin (16) and capsorubin (16a), the colourants in paprika oleoresin, although not produced by commercial synthesis have been prepared in the course of carotenoid studies (ref. 58). Capsanthin has been synthesised from p-citraurin ( 3-hydroxy-p-apo-8 -carotenal ) which is available from zeaxanthin (3R, 3R )-p-carotene-3,3 -diol), by oxidation with potassium permanganate (ref. 59). 

Some carotenoid pigments are used as fresh or dried plant parts or extracts (so-called oleoresins) to impart colour to food (e.g. carrots, orange peels, tomatoes, saffron, annatto and paprika, which is made from dried and ground fruits of various Capsicum species and cultivars). Palm oil containing carotenoid pigments is also used for the same purpose. 

Regulatory Status. Regulated in the United States as a dietary supplement. Capsicum (red pepper, cayenne pepper) and paprika are GRAS as natural seasonings and flavorings ( 182.10). Their essential oils, solvent-free oleoresins and natural extractives are also GRAS ( 182.20) paprika and paprika oleo-resin are also approved as color additives for food use exempt from certification ( 73.340 and 73.345). Capsaicin-containing topical products are approved in over-the-counter... 

The liposoluble nature of these compounds determines, a priori, the type of food in which they can be incorporated to dissolve efficientiy. 3-Carotene is added to fatty foods, such as butter, cheeses, and oils, although other pigments such as bixin and apocarotenals are also employed. Paprika and oleoresins industrially obtained from red pepper are used directly or as ingredient in the manufacture of sauces and meat products. Saffron, which contains crocin as a major pigment (a diester of crocetin with the disaccharide gentiobiose), is used as a hydrosoluble condiment for soups and to color foods and drinks. Other hydrosoluble preparations of 3-carotene and other pigments such as canthaxanthin and apocarotenoids are used to color drinks. Norbixin, a product derived from the saponification of bixin, is hydrosoluble, and used to color ice cream, cereals, and cheese. 

---