Structural analogues of homoeriodictyol as flavor modifiers. Part III: short chain gingerdione derivatives.
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.
Ley
Jakob P
JP
Symrise GmbH & Co. KG, Flavor & Nutrition Research & Innovation, P.O. Box 1253, 37601 Holzminden, Germany. jakob.ley@symrise.com
Paetz
Susanne
S
Blings
Maria
M
Hoffmann-Lücke
Petra
P
Bertram
Heinz-Jürgen
HJ
Krammer
Gerhard E
GE
D001592:Benzyl Alcohols; D002110:Caffeine; D002241:Carbohydrates; D047309:Flavones / Q000737:chemistry*; D005421:Flavoring Agents / Q000737:chemistry* / Q000494:pharmacology; D005960:Glucosides; D006139:Guaiacol / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D011803:Quinine; D013329:Structure-Activity Relationship; D013649:Taste / Q000187:drug effects*
D001592:Benzyl Alcohols; D002241:Carbohydrates; D047309:Flavones; D005421:Flavoring Agents; D005960:Glucosides; D002110:Caffeine; C005696:salicin; D006139:Guaiacol; D011803:Quinine; C503231:homoeriodictyol; C050872:gingerdione