Infoscience

Journal article

About the "physiological size" of fluorine substituents: comparison of sensorially active compounds with fluorine and methyl substituted analogs

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)]

    Keywords: Methyl group; Taste (organoleptic properties of fluorine- and methyl-substituted raspberry flavoring materials); Molecular structure-biological activity relationship (flavor ; of fluorine- and methyl-substituted raspberry flavoring materials); Flavoring ; raspberry taste fluorine methyl substituent; flavoring material raspberry fluorine methyl substituent

    Note:

    CAN 124:171569

    13-6

    Mammalian Biochemistry

    Inst. Chim. organique,l'Univ. Batiment Chim.,Lausanne-Dorigny,Switz.

    Journal

    0040-4020

    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)

    Reference

    • LSCO-ARTICLE-1996-019

    Record created on 2006-03-03, modified on 2016-08-08

Fulltext

  • There is no available fulltext. Please contact the lab or the authors.

Related material