**6. Legal status and patents**

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

β-cyclodextrin (**Figure 7**).

128 Cyclodextrin - A Versatile Ingredient

and statistically significant [12].

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

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

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

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

molecule.

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 Australia and New Zealand, the α and γ forms were classified as new ingredient since 2003 and 2004, respectively.

However, there was no information on the legal situation of β-cyclodextrin in this region of the globe. In Europe, since 1998, β-cyclodextrin was approved under the designation E-459 in the list of food additives. More recently, α-cyclodextrin and γ-cyclodextrin were approved as new ingredient in 2008 and 2012, respectively. In **Table 3**, the information is gathered about the legal status of native cyclodextrins worldwide [16–21].

In 2014, Deorsola et al. presented a research paper on patents involving cyclodextrins. These authors used free databases: Espacenet, USPTO, PATENT SCOPE, INPI, and DERWENT. The


30-year evaluation period was from 1981 to 2011, having found 14,572 records. The increased number of patents in three stages: (I) to 1990 followed by a slight decline; (II) a faster growth 2000–2005 and remained for 2 years; and (III) from 2008 to 2011 the number nearly doubled

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

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

131

Companies that recorded the highest number of cyclodextrin patents are Procter & Gamble Co. (>300), Kao Corp. (99), Schering AG (92), the Ensuiko Sugar Refining Co. (83), and Ono Pharm. Co. (79). The classification of patents allows an assessment of the topic of invention, and this analysis shows that the most selected classification relates to medicinal and/or food

Cyclodextrins passed the benches of research and development laboratories (R&D) for industrial-scale production, since they were discovered by Villers in 1891. This is due to the fact that CDs had a very special feature: the ability to include different types of molecules in the cavity

Currently, the global market for cyclodextrins is estimated above 10 tons per year, mainly applied to food systems, or related to them (*e.g.,* retardant product of fruit maturation,

patent (**Figure 9**).

**Figure 9.** Number of cyclodextrin patents [22].

preparations [23].

**7. Final notes**

of the molecular "donut."

SmartFresh® product from Agrofresh company).

1 WHO/FAO – World Health Organization /Food & Agriculture Organization of the United Nations. 2 GRAS in a wide range of intended use in food.

3 GRAS as flavor protectant.

4 State Mercosur – Argentina, Brazil, Paraguai, Uraguai & Venezuela.

5 FSANZ – Food Standards Australia and New Zealand.

**Table 3.** Cyclodextrins approval status as food ingredients/additives [ 15–20].

Room at the Top as well as at the Bottom: Structure of Functional Food Inclusion Compounds http://dx.doi.org/10.5772/intechopen.74162 131

**Figure 9.** Number of cyclodextrin patents [22].

30-year evaluation period was from 1981 to 2011, having found 14,572 records. The increased number of patents in three stages: (I) to 1990 followed by a slight decline; (II) a faster growth 2000–2005 and remained for 2 years; and (III) from 2008 to 2011 the number nearly doubled patent (**Figure 9**).

Companies that recorded the highest number of cyclodextrin patents are Procter & Gamble Co. (>300), Kao Corp. (99), Schering AG (92), the Ensuiko Sugar Refining Co. (83), and Ono Pharm. Co. (79). The classification of patents allows an assessment of the topic of invention, and this analysis shows that the most selected classification relates to medicinal and/or food preparations [23].
