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

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

doi:10.1002/ffj.2730070313

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

Massimo Barbeni
, Gianna Allegrone
, Marco Cisero
, Pier Antonio Guarda

Research output: Contribution to journal › Article › peer-review

Abstract

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 ¹H‐ and ¹³C‐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.

Original language	English
Pages (from-to)	163-167
Number of pages	5
Journal	Flavour and Fragrance Journal
Volume	7
Issue number	3
DOIs	https://doi.org/10.1002/ffj.2730070313
Publication status	Published - Jun 1992
Externally published	Yes

Keywords

2‐Alkylated carboxylic acids
Chiral analysis
GC
NMR
Strawberry
S‐2‐Methylbutanoic acid

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10.1002/ffj.2730070313

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

abstract = "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 1H‐ and 13C‐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.",

keywords = "2‐Alkylated carboxylic acids, Chiral analysis, GC, NMR, Strawberry, S‐2‐Methylbutanoic acid",

author = "Massimo Barbeni and Gianna Allegrone and Marco Cisero and Guarda, \{Pier Antonio\}",

year = "1992",

month = jun,

doi = "10.1002/ffj.2730070313",

language = "English",

volume = "7",

pages = "163--167",

journal = "Flavour and Fragrance Journal",

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TY - JOUR

T1 - GC and NMR enantiodiscrimination of 2‐methyl substituted aliphatic acids via diastereomeric esterification with (R)‐pantolactone

AU - Barbeni, Massimo

AU - Allegrone, Gianna

AU - Cisero, Marco

AU - Guarda, Pier Antonio

PY - 1992/6

Y1 - 1992/6

N2 - 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 1H‐ and 13C‐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.

AB - 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 1H‐ and 13C‐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.

KW - 2‐Alkylated carboxylic acids

KW - Chiral analysis

KW - GC

KW - NMR

KW - Strawberry

KW - S‐2‐Methylbutanoic acid

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U2 - 10.1002/ffj.2730070313

DO - 10.1002/ffj.2730070313

M3 - Article

SN - 0882-5734

VL - 7

SP - 163

EP - 167

JO - Flavour and Fragrance Journal

JF - Flavour and Fragrance Journal

IS - 3

ER -

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

Abstract

Keywords

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