Structure-taste correlations for flavans and flavanones conformationally equivalent to phyllodulcin

Dick, Wolfgang

doi:10.1021/jf00104a022

Cited by 19 publications

(9 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…31 The extensive efforts to obtain phyllodulcin analogs with enhanced sensory characteristics have been reviewed by Dick. 215 One such compound (Figure 13-III), was found to be 3,000 times sweeter than sucrose but also proved io be very unstable, losing all of its sweetness when stored in solution at 25°C for 7 days. 216 …”

Section: Dihydroisocoumarinmentioning

confidence: 99%

Sweetening agents of plant origin*

Kinghora

Soejarto

Inglett

1986

Critical Reviews in Plant Sciences

View full text Add to dashboard Cite

Section: Dihydroisocoumarinmentioning

confidence: 99%

Sweetening agents of plant origin*

Kinghora

Soejarto

Inglett

1986

Critical Reviews in Plant Sciences

View full text Add to dashboard Cite

“…Another valuable flavan is (2 S )-7,3′-dihydroxy-4′-methoxyflavan ( 2 ). First synthesized in racemic fashion by Dick, it stood out among others because of its pleasant sweet taste even when considerably diluted. Later on, the enantiomer ( S )- 2 was isolated from various plants like Dracaena cinnabari, Hippeastrum x hortorum, Brosimum acutifolium, and Terminalia argenta .…”

mentioning

confidence: 99%

“…Especially as other sweetening agents such as Stevia rebaudiana are suspected to have adverse side effects on the male reproductive system, alternative substances are of growing importance . Although studied in the racemic series, no enantioselective route to flavan 2 has been described to date. , Herein we report the first enantioselective synthesis of the two flavans kazinol U ( 1 ) and (2 S )-7,3′-dihydroxy-4′-methoxyflavan ( 2 ).…”

mentioning

confidence: 99%

Enantioselective Synthesis of 2′- and 3′-Substituted Natural Flavans by Domino Asymmetric Transfer Hydrogenation/Deoxygenation

Keßberg

Metz

2016

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…Receptor Conformational requirements for Z among the flavanones and compounds related to phyllodulcin have been discussed by DiCK and others (28). In a compound such as 5 quite possibly there are two A-H--B fragments and the -CH2-CH2-phenyl moiety forming the right hand ring is the hydrophobic region.…”

mentioning

confidence: 99%

Some SAR studies on the sense of taste

Ferguson

Lang

Morga

et al. 1984

Carlsberg Res. Commun.

View full text Add to dashboard Cite

Using the Shallenberger-Kier model as a molecular requirement for the sweet taste, adsorption and spectroscopic measurements on sweet and nonsweel analogs are described. Additional exploratory experiments were made in search of a set of parameters which could be used to predict the taste (sweet or nonsweet) oftrisubstituted benzenes. INTRODUCTIONScientists of diverse disciplines are studying the sense of taste, essentially from three different perspectives. There are those, primarily organic chemists, who seek structure-taste relationships (SAR). A sub-group, "flavor chemists", analyze foods and examine the effects of flavor-enhancers, flavor-inhibitors, and flavor modifiers. A second category of interest is the mechanism of taste stimulation, being explored by biochemists, biophysicists and others. They are probing the mechanism of stimulus-receptor interaction, cell structure of the taste buds, and the triggering process of nerve transmission up to the brain. Thirdly, there are those interested in taste perception, especially psychologists. This includes the measurements of taste quality and intensity, taste preferences, and food flavors.Recent work has shown that for a clearer elucidation of the mechanism of taste stimulation by sweet or bitter substances, studies must be made of (1) structure-activity relationships of the stimulus,'{2) the rate of development (reaction time), intensity, and longevity of response to the stimulus Cpersistance'), (3) the nature of the stimulus-receptor interaction. (4) The influence of biosphere environment, i.e. ionic strength, viscosity, temperature, concentration of stimulus, etc., (5) biochemical factors affecting transduction of the nerve impulses to the brain, e.g. presence of critical enzymes, etc. As organic chemists, we have been particulary interested in the first and third factors above.With respect to the sweet taste, a widely used working hypothesis has been that sweet molecules have a triangular region, A-H, B, y, in which A-H is a proton-donor group, B a proton-acceptor function and y is a lipophilic moiety (46,70).

show abstract

Structure-taste correlations for flavans and flavanones conformationally equivalent to phyllodulcin

Cited by 19 publications

References 22 publications

Sweetening agents of plant origin*

Sweetening agents of plant origin*

Enantioselective Synthesis of 2′- and 3′-Substituted Natural Flavans by Domino Asymmetric Transfer Hydrogenation/Deoxygenation

Some SAR studies on the sense of taste

Contact Info

Product

Resources

About