6452. Neohesperidin Dihydrochalcone

Nomenclature

CAS number: 20702-77-6
1-[4-[[2-O-(6-Deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone; 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl-2-O-(6-deoxy-α-l-mannopyranosyl)-β-d-glucopyranoside; neohesperidin DHC; NHDC; Sukor (Calif. Aromatics & Flavor).
C28H36O15; mol wt 612.58.
C 54.90%, H 5.92%, O 39.18%.

Description and references

Prepn from naringen, a flavanone glycoside occurring naturally in grapefruit: Horowitz, Gentile, US 3087821 and US 3375242 (1963, 1968, both to U.S. Secy. Agr.); Robertson et al., Ind. Eng. Chem. Prod. Res. Dev. 13, 125 (1974). Sweetening effect: Inglett et al., J. Food Sci. 34, 101 (1969). Chromatography: Gentile, Horowitz, J. Chromatogr. 63, 467 (1971); J. F. Fisher, J. Agric. Food Chem. 25, 682 (1977). Subchronic oral toxicity study: B. A. R. Lina et al., Food Chem. Toxicol. 28, 507 (1990). Review: P. J. Pratter, Perfum. Flavor. 5, 12-18 (1981).

Chemical structure

Properties

Crystals from acetone, mp 156-158°. 1000 to 1500 times sweeter than sucrose; 20 times sweeter than saccharin.

Use

Sweetening agent, especially in chewing gum and dentifrices.