Analytical resolution of 4(5)-alkylated γ(δ)-lactones by high-performance liquid chromatography on a silica-bonded chiral polyacrylamide sorbent

Huffer, Manfred; Schreier, Peter

doi:10.1016/s0021-9673(01)96448-9

Cited by 29 publications

(7 citation statements)

References 8 publications

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“…The ChiraSpher column is stable under aqueous RP and apolar normal phase (NP) conditions; it has been used for resolution of homologous chiral lactones [11,12] and flavanones [13] under NP conditions with a hexane-2-propanol-dioxane mixture as mobile phase. Methanol was added to the eluent to coat the flee OH groups of the ChiraSpher silica gel support [12].…”

Section: Introductionmentioning

confidence: 99%

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Contribution of the lipophilic buffer to chiral recognition under reversed-phase conditions

et al. 1997

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SummaryA lipophilic buffered aqueous mobile phase, without organic modifier, was used for the high performance liquid chromatographic enantioseparation of D,L-lactic acid on a Merck ChiraSpher (250 mm x 4 mm i.d.) column in which the chiral selector is poly(N-acryloyl-S-phenylalanine ethyl ester) bonded to a spherical silica particle. The lipophilicity of the buffer was achieved by addition of triethylammonium phosphate, the 'ethyl' apolar chains of which dynamically modified the ChiraSpher stationary phase and increased its hydrophobic character. The ion-paired (cethyltrimethylammonium bromide) analyte enantioseparation was realized by hydrogen-bonding and dipole-dipole complexation on the ChiraSpher stationary phase, superimposed on simultaneous reversed-phase partitioning.

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Section: Introductionmentioning

confidence: 99%

“…Methanol was added to the eluent to coat the flee OH groups of the ChiraSpher silica gel support [12]. Benzoic acid amide derivatives have been successfully resolved under NP conditions on ChiraSpher, the effect of residual silanol groups being minimized by addition of 0.1% v/v diethylamine to the heptane-dioxane mobile phase [14].…”

Section: Introductionmentioning

confidence: 99%

Contribution of the lipophilic buffer to chiral recognition under reversed-phase conditions

et al. 1997

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“…Pure (1s) and (1R) enantiomers of 1 (500 mg each) were obtained by preparative HPLC of the product mixture on silica gel (Lichrospher SI 100; 5 pm; 250 x 16 mm; Knauer, Berlin, Germany) using cyc1ohexane:tert-butyl methyl ether (1: 1) as eluent (7.5 mL/min) and UV detection (254 nm). The determination of the optical rotation of the optical antipodes of 1 was achieved by on-line HPLC/ChiraMonitor detection (ACS ChiraMonitor, Zinsser, Frankfurt, Germany) on Hibar Chiraspher (RT 250-4mm; 250X4mm; 5pm; Merck, Darmstadt, Germany) using n-hexane as eluent (0.8 mL/min) (Huffer and Schreier, 1989;Bernreuther et al, 1990).…”

Section: Methodsmentioning

confidence: 99%

Multidimensional gas chromatography/mass spectrometry (MDGC/MS): A powerful tool for the direct chiral evaluation of aroma compounds in plant tissues. III. (1S)‐(–‐)‐2‐endo‐Acetoxy‐3‐exo‐hydroxybornane (vulgarole) in mugwort (Artemisia vulgaris L.) herb

Wörner

Schreier

1991

Phytochemical Analysis

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“…The run times are often long, reaching up to 1 h. The herein CCC method could be developed for industrial purpose, and it is therefore important for industries to have at their disposal convenient and fast methods to check the purity of massoia lactone. The few HPLC methods used to analyse such lactones are mainly based on chiral analysis, and use specific expensive phases [25,26]. A new, simple and ultra-fast method was developed for the analysis and separation of the three target massoia lactones, using UHPLC.…”

Section: Uhplc-uv/dad-hrms Analysis Of Massoia Lactonesmentioning

confidence: 99%

Hydrostatic countercurrent chromatography and ultra high pressure LC: Two fast complementary separation methods for the preparative isolation and the analysis of the fragrant massoia lactones

Urbain¹,

Corbeiller²,

Aligiannis³

et al. 2010

J of Separation Science

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Using a one-step preparative hydrostatic countercurrent chromatography method, the fragrant massoia lactones were purified from the crude massoia bark oil, in less than 3 h. The fractionation was performed with the biphasic solvent system c-hexane-methanol-water (10:9:1, v/v/v), leading to target compounds with purity over 96%, as determined by GC-MS and ultra high pressure LC-MS analyses. Together with C-10, C-12 and C-14 massoia lactones, two other aromatic compounds used in perfumes, benzyl benzoate and benzyl salicylate, were also obtained as pure compounds. In parallel, an easy and efficient ultra high pressure LC method was developed for the ultra-fast analysis of massoia lactones, as an alternative to long GC-MS methods.

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Analytical resolution of 4(5)-alkylated γ(δ)-lactones by high-performance liquid chromatography on a silica-bonded chiral polyacrylamide sorbent

Cited by 29 publications

References 8 publications

Contribution of the lipophilic buffer to chiral recognition under reversed-phase conditions

Contribution of the lipophilic buffer to chiral recognition under reversed-phase conditions

Multidimensional gas chromatography/mass spectrometry (MDGC/MS): A powerful tool for the direct chiral evaluation of aroma compounds in plant tissues. III. (1S)‐(–‐)‐2‐endo‐Acetoxy‐3‐exo‐hydroxybornane (vulgarole) in mugwort (Artemisia vulgaris L.) herb

Hydrostatic countercurrent chromatography and ultra high pressure LC: Two fast complementary separation methods for the preparative isolation and the analysis of the fragrant massoia lactones

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