Crocins

The coloring principles of saffron are crocin [42553-65-1] and crocetin [27876-94-4J. Crocin is the gentiobiose diester of crocetin (44)... 

Crocin is a yellow-orange glycoside that is freely soluble in hot water, slightly soluble in absolute alcohol, glycerol, and propylene glycol, and insoluble in vegetable oils. Crocin melts with decomposition at about 186°C and has absorption maxima in methanol at about 464 nm and 434 nm. 

Crocetin [27876-94-4] Cl Natural Yellow 6 Cl 75100) occurs in saffron as crocin [42553-65-1] (46), the digentiobiose ester of crocetin (47). 

Crocus sativus petals Crocin, crocetin (saffron) Food colouring... 

Watanabe, T. et al., Separation and determination of yellow and red Safflower pigments in food by capillary electrophoresis, Biosci. Biotech. Biochem., 61, 1179, 1997. Fekrat, H., The application of crocin and saffron ethanol-extractable components in formulation of health care and beauty care products. Proceedings of International Symposium on Saffron Biology and Biotechnology, Fernandez, J.A. and Abdullaev, R, Eds., Albacete, Spain, 2004, p. 650. 

Crocin, from stigmas of crocus (saffron) or fruits of cape jasmine Gardenia Jasminoides... 

FIGURE 3.4 UV-VIS spectra of crocin 3.7 monomers (low concentration of crocin in water, A.=445 nm) and crocin aggregates (high concentration of crocin 3.7 in water, A,=410nm). Monomer-aggregate equilibrium concentration c= 1 mg/mL, cf. cM=0.8mg/mL from tensiometric determination. (Reprinted from Nalum Naess, S. et al., Helv. Chim. Acta, 89, 45, 2006. With permission.)... 

The size of carotenoid aggregates have been determined by dynamic light scattering (DLS), a noninvasive method (Santos and Castanho 1996). DLS also allows distinguishing between spherical or cylindrical aggregates. The hydrodynamic radii rH of hydrophilic carotenoids in water are given in Table 3.1. Size and molecular structure of the bolaamphiphiles crocin, 3.7, and Cardax,... 

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). 

Nalum Naess S, Elgsaeter A, Foss BJ, Li BJ, Sliwka HR, Partali V, Mel0 TB, and Naqvi KR. 2006. Hydrophilic carotenoids Surface properties and aggregation of crocin as a biosurfactant. Helvetica Chimica Acta 89(1) 45-53. 

Greek saffron Picrocrocin, safranal, crocins, kaempferol diglucoside Me0H/H20 A MeOH B H20 with AcOH 250, 308, 440 nm/ ESI (+) ESI interface 22... 

These assays measure the level of protection provided to the naturally occurring carotenoid derivative crocin from bleaching by the radical generator AAPH. The assay was originally suggested by Bors and others (1984) and modified by Tubaro and others (1998), who used it to show that plasma antioxidant capacity is deeply influenced by the consumption of wine. The addition of a sample containing chain-breaking antioxidants results in the decrease in the rate of crocin decay. The sample is monitored for 10 min at 443 nm. 

Bors W, Michel C and Saran M. 1984. Inhibition of the bleaching of the carotenoid crocin. A rapid test for quantifying antioxidant activity. Biochim Biophys Acta Lipids Lipid Metab 796(3) 312-319. 

Ordoudi SA and Tsimidou MZ. 2006. Crocin bleaching assay (CBA) in structure-radical scavenging activity studies of selected phenolic compounds. J Agric Food Chem 54(25) 9347-9356. 

Perjesi P, Kuzmaa M, Fodora K and Rozmera, Z. 2007. Application of crocin bleaching and deoxyribose degradation tests to assess antioxidant capacity of capsaicinoids and some selected flavonoids. Eur J Pharm Sci 32 39. 

Crocin. Crocin is found in saffron and in gardenias. Extracting crocin from saffron is not economically viable. Saffron is obtained from Crocus sativus. Seventy thousand plants are needed to produce 500 g of saffron, which would contain 70 g of crocin. The commercial source of crocin is the gardenia bush. The town of Saffron Walden in Essex, UK, takes its name because saffron used to be produced there. 

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