Dihydrochalcone neohesperidin

Neohesperidin dihydrochalcone (NeoDHC) is a phenolic compound prepared from the bitter citrus flavanones naringin and neohesperidin (Horowitz Gentili, 1985). NeoDHC is a white solid with solubility in water of 0.5 g/1, which increases with temperature, but as use level is low, sufficient for most applications. 

The relative sweetness of NeoDHC is quoted at 250-1300 depending on concentration (Horowitz Gentili, 1985). Its taste is characterised by a slow onset time and a lingering liquorice aftertaste. This is a major limitation on its use in soft drinks applications. However, NeoDHC has some interesting taste-masking properties and has been used at very low levels (6-12 ppm) to mask bitterness in fruit juices (Horowitz and Gentili, 1985). 

The stability of NeoDHC is good under many of the process and storage conditions that exist in soft drinks production. In the European Union it is permitted via the 1994 Sweetener in Food Regulation, with a maximum use level in soft drinks of 30 mg/1. It is assigned E-number 959. It is not permitted for use in the United States. Use in soft drinks is limited by its taste profile. 

Citrosa 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinna-moyl)phenyl-2-0-(6-deoxy-a-L-mannopyranosyl)-P-D-gluco-pyranoside 3,5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl) propionyl]phenyl-2-0-(6-deoxy-a-L-mannopyranosyl)-P-D-glucopyranoside E959 neohesperidin DC neohesperidin DHC neohesperidine dihydrochalcone NHDC 1-propanone, l-[4-[[2-0-6-deoxy-a-L-mannopyranosyl)-P-D-glycopyranosyl ]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl) Sukor. 

The typical level used in foods is 1-5 ppm although much higher levels may be used in certain applications such as chewing gum. Synergistic effects occur with other intense and bulk sweeteners such as acesulfame K, aspartame, polyols, and saccharin.  

In pharmaceutical applications, neohesperidin dihydrochalcone is useful in masking the unpleasant bitter taste of a number of drugs such as antacids, antibiotics, and vitamins. In antacid preparations levels of 10-30 ppm result in improved palat-ability. 

Neohesperidin dihydrochalcone occurs as a white or yellowish-white powder with an intensely sweet taste. 

Hygroscopicity slightly hygroscopic absorbs up to 15% of water. Melting point 156-158°C Solubility see Table II.  

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Finally, some amphiphilic sweeteners, eg, aspartame, saccharin, and neohesperidin dihydrochalcone, have been shown to be capable of stimulating a purified G-protein direcdy in an in vitro assay (136). This suggests some sweeteners may be able to cross the plasma membrane and stimulate the G-protein without first binding to a receptor. This type of action could explain the relatively longer response times and the lingering of taste associated with many high potency sweeteners. 

Neohesperidin dihydrochalcone 2-O-a-L-rhamnosyl- -D-glucopyranoside substituted phloroglucinol, -QH, substituted phloroglucinol, -C2H4 phenyl OH and —OMe... 

See also Nd YAG entries Neodymium oxide, for oxidizing iron in glass, 7 343 Neoflon, 7 641 Neoflon AP, 7 641 Neoglaziovia variegata, 11 296 Neohesperidin dihydrochalcones (DHC), 12 42 24 240-241... 

Intense and bulk sweeteners are endorsed by international agencies and approved in a large number of countries. Acesulfame K, aspartame and saccharin are available as sweeteners in the EU and Europe while sucralose is approved in the USA and due for approval in Europe and cyclamate, neohesperidin dihydrochalcone and thaumatin are available in Europe. As bulk sweeteners isomalt, lactitol, maltitol, mannitol, sorbitol and xylitol are commonly available. 

Naphthaleneacetic acid, 296 Narrow bore columns, 33, 34 Natural products, analysis by RPC, 293 Neohesperidin dihydrochalcone, 295 Netilmicin, 282 Niacin, 260, 263, 296 Niacinamide, 263... 

Malpezzi, L. et al., Crystal architecture and conformational properties of the inclusion complex, neohesperidin dihydrochalcone-cyclomaltoheptaose (p-cyclodextrin), by x-ray diffraction, Carbo-hydr. Res., 339, 2117, 2004. 

Fig-1 Chemical structures of the intense sweeteners saccharin, sodium cyclamate, acesulfame-K, aspartame, alitame, dulcin, sucralose, and neohesperidin dihydrochalcone. 

Neohesperidin dihydrochalcone has also been determined by ion-pair chromatography on LiChrospher 60 with a gradient of 15-95% methanol in 10 mM tetrabutylammonium hydrogen sulfate. No interference was observed from acesulfame-K, aspartame, and saccharin (66). 

F Borrego, I Canales, MG Lindley. Neohesperidin dihydrochalcone state of knowledge review. Z Lebensm Unters Forsch 200 32-37, 1995. 

M Hausch. Simultaneous determination of neohesperidin-dihydrochalcone and other sweeteners by HPLC. Lebensmittelschemie 50(2) 31-32, 1996. 

I Canales, F Borrego, MG Lindley. Neohesperidin dihydrochalcone stability in aqueous buffer solutions. J Food Sci 57(3) 589-591, 643, 1992. 

FA Tomas-Barberan, F Borrego, F Ferreres, MG Lindley. Stability of the intense sweetener neohesperidin dihydrochalcone in blackcurrant jams. Food Chem 52(3) 263 -265, 1995. 

MR Castellar, JL Iborra, I Canales. Analysis of commercial neohesperidin dihydrochalcone by high performance liquid chromatography. J Liq Chrom Rel Technol 20(13) 2063-2073, 1997. 

R Schwartzenbach. Liquid chromatography of neohesperidin dihydrochalcone. J Chromatogr 129 31-39, 1976. 

JF Fisher. A high-pressure liquid chromatographic method for the quantitation of neohesperidin dihydrochalcone. J Agric Food Chem 25(3) 682-683, 1977. 

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