The taste of four fluoro substituted derivs. is almost indistinguishable from that of the parent compd. 4-(4-hydroxyphenyl)butan-2-one, the main flavor component of raspberries. The same holds for the comparison between the corresponding acetate, another raspberry ingredient, and its 1-fluoro analog. In contrast, Me substituents profoundly alter the organoleptic properties. The prepn. of the fluorinated derivs, involved the three principal options existing for the incorporation of fluorine into org. mol. skeletons: the use of prefabricates (i.e., of fluoroarom. building blocks), the formation of chlorofluorocarbene cycloadducts followed by their solvolytic ring opening and the addn. of fluoride to olefinic double bonds. [on SciFinder (R)]
Title
About the "physiological size" of fluorine substituents: comparison of sensorially active compounds with fluorine and methyl substituted analogs
Published in
Tetrahedron
Volume
52
Issue
1
Pages
99-108
Date
1996
ISSN
0040-4020
Note
CAN 124:171569
13-6
Mammalian Biochemistry
Inst. Chim. organique,l'Univ. Batiment Chim.,Lausanne-Dorigny,Switz.
Journal
written in English.
135981-59-8 Role: RCT (Reactant), RACT (Reactant or reagent) (acetylation of); 91060-98-9 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), FFD (Food or feed use), RCT (Reactant), BIOL (Biological study), USES (Uses), RACT (Reactant or reagent) (organoleptic properties and oxobutylphenyl acetate prepn. from); 37904-78-2 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), FFD (Food or feed use), BIOL (Biological study), USES (Uses) (organoleptic properties of); 173852-01-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromination of); 173851-98-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cyclization of); 173851-97-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and isomerization of); 3572-06-3P; 91969-86-7P; 125101-98-6P; 173851-92-8P; 173851-93-9P; 173851-94-0P; 173851-95-1P; 173851-96-2P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), FFD (Food or feed use), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn. and organoleptic properties of); 173851-99-5P; 173852-00-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of)
Record creation date
2006-03-03
