Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties. 1985

G E DuBois, and R A Stephenson

Congeneric series of stevioside (1) and rebaudioside A (3) analogues have been prepared. It was found that the bitter-taste component endogenous in the natural compounds 1 and 3 may be eliminated by increase in molecular hydrophilic character. Through the series of compounds prepared, bitter-taste character was correlated with k', a chromatographic indicator of gross hydrophilicity. An analogue (11) of stevioside, shown chromatographically to be of increased hydrophilicity, was prepared and found to exhibit no bitter-taste character. Similarly an analogue (13) of rebaudioside A, having increased polarity, was prepared and found not to exhibit any bitter taste. The rebaudioside A analogue 13 was determined to have higher potency than 11 is suggested as a potential non-nutritive sweetener for food applications.

UI MeSH Term Description Entries
D004224 Diterpenes Twenty-carbon compounds derived from MEVALONIC ACID or deoxyxylulose phosphate. Diterpene,Diterpenes, Cembrane,Diterpenes, Labdane,Diterpenoid,Labdane Diterpene,Norditerpene,Norditerpenes,Norditerpenoid,Cembranes,Diterpenoids,Labdanes,Norditerpenoids,Cembrane Diterpenes,Diterpene, Labdane,Labdane Diterpenes
D005960 Glucosides A GLYCOSIDE that is derived from GLUCOSE. Glucoside
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013549 Sweetening Agents Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) Artificial Sweeteners,Sugar Substitutes,Sweeteners,Agent, Sweetening,Agents, Sweetening,Artificial Sweetener,Substitute, Sugar,Substitutes, Sugar,Sugar Substitute,Sweetener,Sweetener, Artificial,Sweeteners, Artificial,Sweetening Agent
D013649 Taste The ability to detect chemicals through gustatory receptors in the mouth, including those on the TONGUE; the PALATE; the PHARYNX; and the EPIGLOTTIS. Gustation,Taste Sense,Gustations,Sense, Taste,Senses, Taste,Taste Senses,Tastes
D013729 Terpenes A class of compounds composed of repeating 5-carbon units of HEMITERPENES. Isoprenoid,Terpene,Terpenoid,Isoprenoids,Terpenoids
D045786 Diterpenes, Kaurane A group of DITERPENES cyclized into four rings. Ent-Kaurane,Ent-Kaurene,Kaurane,Kaurane Diterpenoid,Kaurane Diterpenoids,Ent-Kauranes,Ent-Kaurenes,Kauranes,Diterpenoid, Kaurane,Diterpenoids, Kaurane,Ent Kaurane,Ent Kaurene,Kaurane Diterpenes

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