Prediction of Gas Chromatographic Retention Indices of Coumarins

Soares, Míriam de Freitas; Monachè, Franco Delle; Heinzen, Vilma Edite Fonseca; Yunes, Rosendo A.

doi:10.1590/s0103-50531999000300006

Cited by 10 publications

(10 citation statements)

References 22 publications

(33 reference statements)

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“…The 1 H (including 1 H NMR spectra with homonuclear decoupling), 13 Fourier transforms were performed on a 512 × 512 data matrix. π/2 Shifted sine-squared window functions were used along F1 and F2 axes for all 2D spectra.…”

Section: Nmr Measurementsmentioning

confidence: 99%

“…(7), 94 (7), 93(11), 92 (7), 91(58), 90(4), 89 (7), 79 (12), 78(17), 77(54), 76(4), 66(9), 65(28), 64 (7), 63 (17), 62 (7), 55(12), 53(10), 52(8), 51(24), 50(11), 43(4), 41(6), 39 (25), 38(5). ], 149 (12), 133(6), 132(5), 131 (7), 121(3), 104(5), 103 (7), 91(10), 77(6), 65(4), 57(3), 55(9), 43 (19), 41 (13), 39(5). (6), 134 (7), 133 (15), 132 (15), 131(49), 122(5), 121(52), 115 (5) (11), 70(6), 69(13), 67(13), 66(10), 65(11), 63(9), 60(6), 57(39), 56(40), 55(16), 53(7), 51 (20), 44(14), 43(16), 42(13), 41(22), 39 (21).…”

Section: Nmr Measurementsunclassified

“…], 163 (7), 149 (21), 148(8), 147(10), 137(5), 135(29), 133(11), 131 (7), 121(10), 105 (7), 103 (11), 91 (15), 79 (6), 78(6), 77 (15), 71(21), 65(9), 55(5), 51 (7), 43(50), 41 (18), 39 (12). (9), 91 (7), 77 (7), 71 (8), 57(6), 55 (11), 43 (13), 41 (15).…”

Section: Nmr Measurementsunclassified

Section: Introductionmentioning

confidence: 99%

“…The choice of parameters, or among a certain type of parameters (for example, which topological index to use), is mostly intuitive and is quite frequently left to trial and error. 3 Up to now, a number of researchers have successfully used predicted retention data of an array of compound classes; branched alkanes and alkenes, substituted aromatics, 11 unsaturated esters, 12 coumarins, 13 and sulfur-containing compounds 14 are just a few examples, and such findings have been reviewed on several occasions. 3,4 Building on the already accumulated data on the esters of eugenol and its regioisomers, we were motivated to enlarge the existing library and explore the gas chromatographic behavior, that is, retention index trends on the column of the most widely employed polarity (5% phenylmethylsiloxane) within and between series of regioisomeric allylmethoxyphenyl esters.…”

Section: Introductionmentioning

confidence: 99%

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A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

Mladenović

Radulović

2019

Flavour & Fragrance J

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A recent identification of eugenyl (allylmethoxyphenyl) esters as Anthemis segetalis Ten. (Asteraceae) essential oil constituents, accomplished by means of organic synthesis, motivated us to expand the existing synthetic library with an aim to examine the generality of structure‐chromatographic property relationships within this series of volatiles. Herein, the design, synthesis, gas–chromatographic and spectral characterization of members of a library of 85 allylmethoxyphenyl esters (64 are completely new) were described. Analysis of experimentally obtained RI data showed that esters of the same acid and different allylmethoxyphenols always elute in the same order from an apolar gas chromatography (DB‐5MS) column: 2‐allyl‐6‐methoxyphenyl < 2‐allyl‐3‐methoxyphenyl < 2‐allyl‐5‐methoxyphenyl < 2‐allyl‐4‐methoxyphenyl < 4‐allyl‐2‐methoxyphenyl esters. Based on the obtained RI values, several quantitative structure–property relationship models were built up that correlated several easily available parameters (e.g. Wiener [WI], Balaban [BI], and molecular topological [MTI] indices) of the mentioned esters and their RI data. The generated various quantitative structure–property relationships models (equations that predict RIs of esters of different regioisomers of allylmethoxyphenols with the same acids and the ones that predict RIs of esters of different acids with the same allylmethoxyphenols) were tested on data of previously known related esters. RI data of esters of allylmethoxyphenol regioisomers could be successfully predicted based on 1D topological indices, such as the Balaban, Wiener, and molecular topological indices. Together with RI and MS data accumulated in this work, these models represent a new and simple tool for the identification of allylmethoxyphenyl esters that might potentially represent new or rare natural products.

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Section: Nmr Measurementsmentioning

confidence: 99%

Section: Nmr Measurementsunclassified

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

Mladenović

Radulović

2019

Flavour & Fragrance J

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Quantitative structure—Retention relationships (QSRR), using the optimum semi-empirical topological index, for methyl-branched alkanes produced by insects

et al. 2002

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SummaryTheoretical prediction of chromatographic retention couJd be used as a means of identification of organic compounds separated bygas chromatography.An optimum semi-empirical topological index, JET(opt), is proposed for prediction of the chromatographic retention of the methylbranched alkanes produced by insects. Our previously-developed semi-empirical topological index (lET) has been improved to make it possible to distinguish bel',,veen methylalkane isomers. The new topological index is based on the length of the chain, the positions of the methyl groups, and the number of methyl groups attached to the backbone. Simple linear regression belvveen chromatographic retention and the proposed optimum semi-empirical topological indexes, for 178 methylalkanes with nine to forty carbon atoms in the linear chain, was very satisfactory (r 2 = 0.9999 and SD = 3.20). The good predictive quality of the model is shown by the chromatographic retention indexes predicted for an external group of 30 methylalkanes.

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Natural coumarins: Methods of isolation and analysis

Lozhkin

Sakanyan

2006

Pharm Chem J

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With a view to optimizing of the quality control of sweetclover herbs and related preparations containing coumarins among the active substances, methods for the isolation and analysis of compounds of this class -in particular, coumarin and furocoumarin -are reviewed. The group of possible analytical methods includes gravimetric, titrimetric, photocolorimetric, and polarographic analysis, and the more recently developed spectroscopic (UV and IR), fluorimetric, and chromatographic (GC and HPLC) techniques.Psoralen: R 1 = H, R 2 = H; Xanthotoxin: R 1 = H, R 2 = OCH 3 ;Bergapten: R 1 = OCH 3 , R 2 = H; Isopimpinellin: R 1 = OCH 3 , R 2 = OCH 3 .

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Prediction of Gas Chromatographic Retention Indices of Coumarins

Cited by 10 publications

References 22 publications

A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

Quantitative structure—Retention relationships (QSRR), using the optimum semi-empirical topological index, for methyl-branched alkanes produced by insects

Natural coumarins: Methods of isolation and analysis

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