GC and NMR enantiodiscrimination of 2‐methyl substituted aliphatic acids via diastereomeric esterification with (R)‐pantolactone | Zendy

Barbeni Massimo | Zendy; Allegrone Gianna | Zendy; Cisero Marco | Zendy; Guarda Pier Antonio | Zendy

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GC and NMR enantiodiscrimination of 2‐methyl substituted aliphatic acids via diastereomeric esterification with (R)‐pantolactone

Author(s) -

Barbeni Massimo,

Allegrone Gianna,

Cisero Marco,

Guarda Pier Antonio

Publication year - 1992

Publication title -

flavour and fragrance journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.393

H-Index - 70

eISSN - 1099-1026

pISSN - 0882-5734

DOI - 10.1002/ffj.2730070313

Subject(s) - chemistry , diastereomer , enantiomer , derivatization , chromatography , wax , organic chemistry , resolution (logic) , high performance liquid chromatography , artificial intelligence , computer science

The chiral differentiation of the enantiomers of 2‐methylbutanoic acid, 2‐methylpentanoic acid and 2‐methylhexanoic acid was achieved by diastereomeric derivatization with (R) ‐( – )‐pantolactone. GC separation on achiral DB‐1, DB‐1701 and DB‐WAX capillary columns as well as 1 H‐ and 13 C‐NMR enantiodiscrimination were obtained, affording good resolution and quantitative evaluation of enantiomer composition. The method applied to 2‐methylbutanoic acid present in the aromatic fraction extracted from cultivated strawberry ( Fragaria vesca ) indicated a high enantiomeric excess of the (S) ‐isomer.

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