Structural Analogues of Homoeriodictyol as Flavor Modifiers. Part III: Short Chain Gingerdione Derivatives

• Published in: Journal of agricultural and food chemistry 2008-08, Vol.56 (15), p.6656-6664
• Main Authors: Ley, Jakob P., Paetz, Susanne, Blings, Maria, Hoffmann-Lücke, Petra, Bertram, Heinz-Jürgen, Krammer, Gerhard E.
• Format: Article
• Language: English
• Subjects: Benzyl Alcohols; Biological and medical sciences; bitter masking; Caffeine; Carbohydrates; Confectionery products and chocolate industries, honey; Flavones - chemistry; Flavoring Agents - chemistry; Flavoring Agents - pharmacology; Flavors and Aromas/Chemosensory Perception; Food industries; Fundamental and applied biological sciences. Psychology; gingerdiones; Glucosides; Guaiacol - analogs & derivatives; Guaiacol - chemistry; Guaiacol - pharmacology; Quinine; Structure-Activity Relationship; sweet enhancing; Taste - drug effects; Taste modifying
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf8006536

In order to find new flavor modifiers, various short chain gingerdione derivatives were synthesized as structural analogues of the known bitter masker homoeriodictyol and evaluated by a sensory panel for masking and sweetness enhancing activities. 1-(4-Hydroxy-3-methoxyphenyl)hexa-3,5-dione ([2]-gingerdione) and the homologue 1-(4-hydroxy-3-methoxyphenyl)hepta-3,5-dione ([3]-gingerdione) at concentration ranges 50−500 mg kg−1 showed the most promising masking activity of 20−30% against bitterness of a 500 mg kg−1 aqueous caffeine solution. Additionally, both compounds were able to reduce the bitterness of a 5 mg kg−1 quinine solution by about 20%; however, the bitter tastes of salicine, the model peptide H-Leu-Trp-OH, and KCl solutions were not reduced. Whereas for bitter masking activity a vanillyl moiety seems to be important, some of the tested isovanillyl isomers showed an interesting sweet enhancing effect without exhibiting a significant intrinsic sweetness. The isomer 1-(3-hydroxy-4-methoxyphenyl)hexa-3,5-dione ([2]-isogingerdione) at 100 mg kg−1 caused a significant and synergistic increase of 27% of sweet taste of a 5% sucrose solution.