**5. Inclusion compounds based on cyclodextrins: applications in food and food processing**

The three-dimensional nature of native CDs makes these molecules very important, since these starch derivatives are ingredients that do not have toxic characteristics; they are not absorbed in the digestive tract and are completely metabolized by the intestinal microflora. These CDs have the necessary requirements to be neutral in terms of aroma and flavor, although they are made from glucose units; the α-CD and β-CD have no sweet taste, while the γform only has a slight sweet taste. Since the CDs are occurring in the form of a colorless powder, it makes them easier to process [4, 11].

with spices, the CDs can help stabilize emulsions (mayonnaises and salad dressings). Cyclodextrins may act as sweetener by aspartame encapsulation to make it more water

Room at the Top as well as at the Bottom: Structure of Functional Food Inclusion Compounds

http://dx.doi.org/10.5772/intechopen.74162

127

In beverages, the CDs allow the use of aromas, control the dissolution of aspartame preventing its breakage, maintain the color of fruit juices, and also allow the encapsulating of carbon

In Japan, CDs are considered a natural product, used to deodorize meats and fish, improving the defrosting properties through water and red pigments retention and reduction of undesir-

Some of the foods that contain plant extracts have undesirable bitter flavors. The CD molecules are suitable to encapsulate these components. For example, grapefruit juice can be treated during preparation CD are to remove the bitter taste caused by naringin and the limonene (**Figure 6**). The other grapefruit aromas are encapsulated in a small extent, and the treat-

The polymers of cyclodextrins are used to prevent the juice to precipitate. The polymer molecules are synthesized using a bifunctional crosslinking agent (*e.g.* glutaraldehyde). The CD loaded polymer naringin, adding sodium hydroxide and subsequent washing regenerate

ment does not alter the contents acid or vitamin C [11].

**Brand Type of food CD'S function** Natural<sup>a</sup> Cheese Cholesterol removal

Balade <sup>c</sup> Butter Cholesterol removal Simply eggs<sup>d</sup> Eggs Cholesterol removal FlavorAktiv Standard Kit <sup>e</sup> Patterns of beer aromas Preserve the flavor Flavono f Chewing gum Estabilize the flavor

Choco bar <sup>f</sup> Chocolate Emulsifier Poder tea <sup>f</sup> Instant tea Preserve color Gymet f Dietary fiber drink Mask flavor Stick lemon f Instant tea Preserve the flavor

**Table 2.** Foods that include cyclodextrins in their formulation.

Cyroma-line<sup>b</sup> Flavored sugar for baking Preserve the flavor after heating

soluble (**Table 2**).

dioxide.

able aromas.

limonene.

a France. b Hungary. c Bélgium. <sup>d</sup>USA. e

f Japan.

Great Britain.

The molecular inclusion phenomenon is one chemistry field also called supramolecular chemistry. Jean-Marie Lehn, Nobel Prize in 1997, is one of the creators of this area of chemistry that deals with complex entities resulting from the association of two or more chemical species held together by non-covalent intramolecular bonds. Lehn, paraphrasing Richard Feynman (and his well-known speech on nanotechnology "There is plenty of room on the bottom") with the expression "There's even more room at the top", has indicated that chemistry not only has to look toward the extremely small but can also go beyond the molecular size, studying the supramolecular complexity.

The main advantage of using CDs in food systems lies summarized in **Table 1**. The prolongation of the shelf-life of the compositions and standardization and ease in dosing and transport of inclusion compounds are very important features of this inclusion nanotechnology.

Cyclodextrins can encapsulate biocides that can be applied to food packaging materials. By changing humidity conditions, there is controlled release of the biocide thus preventing, for example, the proliferation of microorganisms (bacteria, fungi, and yeasts). The CDs are good carriers for flavors and fragrances. In bakery products, it can be reduced to one-third the amount of aroma needed, if they are CD encapsulated. The CDs can also improve the bread dough and the crispy effect of rice crackers. The aroma of fresh vegetables can also be preserved by reduction of the degradation rate and preventing discoloration. Mixed


**Table 1.** Summary of some beneficial effects of the use of cyclodextrins in food systems.

with spices, the CDs can help stabilize emulsions (mayonnaises and salad dressings). Cyclodextrins may act as sweetener by aspartame encapsulation to make it more water soluble (**Table 2**).

although they are made from glucose units; the α-CD and β-CD have no sweet taste, while the γform only has a slight sweet taste. Since the CDs are occurring in the form of a colorless

The molecular inclusion phenomenon is one chemistry field also called supramolecular chemistry. Jean-Marie Lehn, Nobel Prize in 1997, is one of the creators of this area of chemistry that deals with complex entities resulting from the association of two or more chemical species held together by non-covalent intramolecular bonds. Lehn, paraphrasing Richard Feynman (and his well-known speech on nanotechnology "There is plenty of room on the bottom") with the expression "There's even more room at the top", has indicated that chemistry not only has to look toward the extremely small but can also go beyond the molecular size, study-

The main advantage of using CDs in food systems lies summarized in **Table 1**. The prolongation of the shelf-life of the compositions and standardization and ease in dosing and transport

Cyclodextrins can encapsulate biocides that can be applied to food packaging materials. By changing humidity conditions, there is controlled release of the biocide thus preventing, for example, the proliferation of microorganisms (bacteria, fungi, and yeasts). The CDs are good carriers for flavors and fragrances. In bakery products, it can be reduced to one-third the amount of aroma needed, if they are CD encapsulated. The CDs can also improve the bread dough and the crispy effect of rice crackers. The aroma of fresh vegetables can also be preserved by reduction of the degradation rate and preventing discoloration. Mixed

> • Terpenos • Flavors

• Butter

• Curcumin

• Dairy products

• Smell of Vitamin B1

• Removal of bitter taste in grapefruit juices

of inclusion compounds are very important features of this inclusion nanotechnology.

**Benefit Food system**

Protection against deterioration of sensitive substances • Fats,

Selective cholesterol removal • Cheese

Improvement of the solubility of lipophilic ingredients • Carotenes

Improvement of emulsion stability • Mayonnaise

Improvement in the uniformity of content • Standard flavors

**Table 1.** Summary of some beneficial effects of the use of cyclodextrins in food systems.

powder, it makes them easier to process [4, 11].

ing the supramolecular complexity.

126 Cyclodextrin - A Versatile Ingredient

Stabilization effect

Elimination or reduction Unpleasant flavors/aromas

Microbial contamination; Hygroscopicity

In beverages, the CDs allow the use of aromas, control the dissolution of aspartame preventing its breakage, maintain the color of fruit juices, and also allow the encapsulating of carbon dioxide.

In Japan, CDs are considered a natural product, used to deodorize meats and fish, improving the defrosting properties through water and red pigments retention and reduction of undesirable aromas.

Some of the foods that contain plant extracts have undesirable bitter flavors. The CD molecules are suitable to encapsulate these components. For example, grapefruit juice can be treated during preparation CD are to remove the bitter taste caused by naringin and the limonene (**Figure 6**). The other grapefruit aromas are encapsulated in a small extent, and the treatment does not alter the contents acid or vitamin C [11].

The polymers of cyclodextrins are used to prevent the juice to precipitate. The polymer molecules are synthesized using a bifunctional crosslinking agent (*e.g.* glutaraldehyde). The CD loaded polymer naringin, adding sodium hydroxide and subsequent washing regenerate limonene.


**Table 2.** Foods that include cyclodextrins in their formulation.

**Figure 6.** Naringin (a) and Limonene (b) give a bitter taste to grapefruit juice.

The ability to form inclusion complexes is also used for the production of cholesterol-free food due to the cholesterol molecule is retained in the cavity of seven glucose units from β-cyclodextrin (**Figure 7**).

the inclusion of these molecules is the protection against oxidation, sublimation, and evaporation. The complexation may also be used to mask unpleasant flavors and odors. One of the advantages of cyclodextrins nanoencapsulation is exploited in the case of omega 3 (ω3

**Figure 8.** (a) Fatty acids ω3 and ω6 complexed with several cyclodextrin molecules; (b) The product contains OmegaDry®

Cranberry inclusion compounds with components obtained from cranberry essential oil [13].

blood plasma, with a consequent reduction in the risk of cardiovascular diseases. Although the

have an unpleasant taste and aroma. Therefore, the encapsulation via CD is necessary to obtain a white odorless powder, which is easily processable, preventing also the oxidation reactions. Currently, there is a product on the market, registered under the name OmegaDry® *Cranberry*, which contains several cranberry oil components encapsulated in γ-CD (**Figure 8 (a)**) [13]. There are also formulations with isomeric vitamin E with functional tocotrienols (**Figure 8 (b)**) and myricetin (3,5,7-trihydroxy-2- (3,4,5-trihidroxifenil) - 4-chromenona) and quercetin [14, 15]. Considerable interest in these formulations results of whether they are lipophilic substances with antioxidant properties, enabling the cell protection from oxidative degradation of lipid membrane structures of the molecules, preventing premature aging of the skin, caused by damage from ultraviolet radiation. Thus, the complexes with tocopherol and tocotrienol can

From very early stages, cyclodextrins were used by the food industry. In Japan, cyclodextrins were considered natural products, and its use occurred in the late 70s of last century after the development of industrial manufacturing processes. In 1987, there were already 88 Japanese patents, making Japan the first country to functionalize food with CDs. Since 2000, the three native cyclodextrins can be used as food additives in the United States of America (USA). In

) fatty acids because they have proven positive effects in reducing fat levels in the

Room at the Top as well as at the Bottom: Structure of Functional Food Inclusion Compounds

http://dx.doi.org/10.5772/intechopen.74162

fatty acids are mostly derived from fish oils and algae extracts that in the native state

omega 6 (ω6

be used in food systems and also in cosmetics.

**6. Legal status and patents**

ω3 and ω6 ) and

129

The results of the preliminary study on the effect of β-cyclodextrin in removing red wine unpleasant smells have also been promising. This study was conducted triangle sensory analysis by 14 untrained panelists using a red wine enriched with 4-ethylphenol (5000 g/L) or a mixture of 4-ethylphenol (750 g/L) + 4-ethylguaiacol (75 g/L) and different levels of β-CD concentration. According to the sensory panel, the concentration of 11.52 g/l CD-β (ratio 2:1) was sufficient to reduce the perception of red wine unpleasant odors. Additionally, an increase of colour intensity and the total polyphenol content of red wine treated with β-CD was measure and statistically significant [12].

β-cyclodextrin and γ-cyclodextrin are the most commonly used forms, because its size is usually more favorable. The complex formation facilitates controlled release of the encapsulated molecules, since the dissociation of the complex requires low humidity. For example, the flavors may be stored and released in a chewing gum, when it is chewed. An additional advantage of

**Figure 7.** Cholesterol free butter is obtained by treatment with cyclodextrin to sequester (encapsulate) the cholesterol molecule.

Room at the Top as well as at the Bottom: Structure of Functional Food Inclusion Compounds http://dx.doi.org/10.5772/intechopen.74162 129

**Figure 8.** (a) Fatty acids ω3 and ω6 complexed with several cyclodextrin molecules; (b) The product contains OmegaDry® Cranberry inclusion compounds with components obtained from cranberry essential oil [13].

the inclusion of these molecules is the protection against oxidation, sublimation, and evaporation. The complexation may also be used to mask unpleasant flavors and odors. One of the advantages of cyclodextrins nanoencapsulation is exploited in the case of omega 3 (ω3 ) and omega 6 (ω6 ) fatty acids because they have proven positive effects in reducing fat levels in the blood plasma, with a consequent reduction in the risk of cardiovascular diseases. Although the ω3 and ω6 fatty acids are mostly derived from fish oils and algae extracts that in the native state have an unpleasant taste and aroma. Therefore, the encapsulation via CD is necessary to obtain a white odorless powder, which is easily processable, preventing also the oxidation reactions.

Currently, there is a product on the market, registered under the name OmegaDry® *Cranberry*, which contains several cranberry oil components encapsulated in γ-CD (**Figure 8 (a)**) [13]. There are also formulations with isomeric vitamin E with functional tocotrienols (**Figure 8 (b)**) and myricetin (3,5,7-trihydroxy-2- (3,4,5-trihidroxifenil) - 4-chromenona) and quercetin [14, 15]. Considerable interest in these formulations results of whether they are lipophilic substances with antioxidant properties, enabling the cell protection from oxidative degradation of lipid membrane structures of the molecules, preventing premature aging of the skin, caused by damage from ultraviolet radiation. Thus, the complexes with tocopherol and tocotrienol can be used in food systems and also in cosmetics.
