Enoxolone

Glycyrrhetinic acid is a pentacyclic triterpenoid amyrin derivative and obtained from hydrolysis of glycyrrhizic acid [1]. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and as an expectorant.

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In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 ^{[1] demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH₂)CO₂K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 nanometers (13 angstroms) available for docking with the sweetener molecule (lock-and-key model). In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity.}

References

• ^{[1] Molecular Design of Sweet Tasting Compounds Based on 3β-Amino-3β-deoxy-18β-glycyrrhetinic Acid: Amido Functionality Eliciting Tremendous Sweetness So Ijichi Seizo Tamagaki Chemistry Letters Vol. 34 (2005) , No. 3 p.356 Abstract}