Chromatographic and spectral characteristic of some esters of a common monoterpene alcohols

Bonikowski, Radosław; Paoli, Mathieu; Szymczak, Kamil; Krajewska, Agnieszka; Wajs-Bonikowska, Anna; Tomi, Félix; Kalemba, Danuta

doi:10.1002/ffj.3307

Cited by 9 publications

(10 citation statements)

References 23 publications

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“…Monoterpene alcohols (MAs) are primary, secondary or tertiary alcohols with a hydrocarbon backbone consisting of two isoprene units. They are isolated from plant essential oils or obtained by (bio)chemical synthesis methods and constitute a very important group of PRMs (Sato et al 2018;Bonikowski et al 2016). As the reports about the surface activity of MAs are scarce in the literature, the aim of this study was to investigate the influence of the molecular structure of monoterpene alcohols on their adsorption at the water-air interface.…”

Section: Introductionmentioning

confidence: 99%

Adsorption of monoterpene alcohols at the water–air interface

Lewandowski

2019

Adsorption

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The measurements of the surface tension of aqueous solutions of 10 monoterpene alcohols, MAs: (−)-β-citronellol, geraniol, tetrahydrolinalool, linalool, (−)-menthol, (−)-terpinen-4-ol, p-cymene-8-ol, α-terpineol, isoborneol and (−)-borneol were made at T = 293 K. On the basis of the obtained results the values of the adsorption constant, the excluded area per molecule at the interface and the interaction parameter were determined by fitting the experimental data to various adsorption models. Next the adsorption free energy of studied MAs was determined and discussed in terms of the preferred orientation of studied MAs at the water-air interface and molecular structure of MAs.

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Section: Introductionmentioning

confidence: 99%

Adsorption of monoterpene alcohols at the water–air interface

Lewandowski

2019

Adsorption

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“…Adams and Dev (2009) and Bonikowski et al . (2016) recognized the importance of untargeted SLs as a source of RI and MS data crucial for EO analysis, and, recently reported libraries of esters of tiglic and angelic acids or of selected monoterpenols (geraniol, borneol, isoborneol, linalool, nerol, thymol, carvacrol, lavandulol and citronellol), respectively . Despite the great amount of EO‐relevant MS and RI data provided within these studies, the information on analogous derivatives of diastereomeric endo‐ and exo ‐fenchols ( endo ‐1 and exo ‐1 , respectively) remained scarce.…”

Section: Resultsmentioning

confidence: 99%

“…Although previous applications of SLA were mainly targeted ones (libraries of compounds were designed to resolve problems related to a single EO sample), the possible benefits of a more general employment of SLA in EO chemistry was already recognized . In this more universal approach, chemical profiles of previously studied essential oils are used as ‘sources of the likely SL‐parent‐structures’ (SL‐synthetic library), Figure , route c, step 1.…”

Section: Introductionmentioning

confidence: 99%

“…In this more universal approach, chemical profiles of previously studied essential oils are used as ‘sources of the likely SL‐parent‐structures’ (SL‐synthetic library), Figure , route c, step 1. Such libraries were comprised of compounds (possibly new, previously unreported natural products) that were structurally and biosynthetically related to the already known secondary metabolites . Such EO‐tailored SLs are adequate sources of MS, RI and NMR data (the upgrades of existing MS/RI libraries) .…”

Section: Introductionmentioning

confidence: 99%

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Essential‐oil inspired synthetic libraries: synthesis, spectral and gas‐chromatographic properties of new fenchyl esters

Blagojević

Pešić

Radulović

2017

Flavour & Fragrance J

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Herein, the design, synthesis, and gas‐chromatographic and spectral characterization of a library of endo‐ and exo‐fenchyl esters (formate, acetate, propanoate, butanoate, isobutanoate, pentanoate, isopentanoate, 2‐methylbutanoate, hexanoate, heptanoate, octanoate, nonanoate, tiglate, angelate, senecioate and benzoate; 32 compounds in total) were described. 1D‐ and 2D–NMR experiments combined with 1H iterative full spin analysis and GIAO (gauge invariant atomic orbitals) computation of NMR chemical shifts and coupling constants for DFT‐calculated minimum energy conformations enabled a complete 1H–NMR assignment of the higher‐order signals of the fenchyl‐core protons. Library members, derivatives of a well‐known monoterpenol of economical importance, often encountered in essential oils (EOs), might potentially represent new (up to now undiscovered), or be classified as rare, natural products. The data summarized in this work should facilitate future EO analyses, especially those studies dealing with minor constituents. The benefits of the usage of (untargeted) metabolome‐inspired synthetic libraries in the analysis of EOs were discussed.

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“…Constituents of the essential oils were identified based on their MS spectra and their comparison with those from mass spectra libraries: NIST 2012, Wiley Registry of Mass Spectral Data 8th edition and MassFinder 4.1, along with the relative retention indices (RI) on DB-1 column (available from MassFinder 4.1) and on Rtx-1MS column found in the literature [35]. Isolated compounds were also identified by the comparison of their 1 H-NMR and 13 C-NMR spectral data with those of the compounds isolated previously in our laboratory or those from the literature.…”

Section: Methodsmentioning

confidence: 99%

Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland

2019

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Carpesium divaricatum Sieb. and Zucc. has long been used both as traditional medicine and seasonal food. The most extensively studied specialized metabolites synthesized by the plant are sesquiterpene lactones of germacrane-type. Low-molecular and volatile terpenoids produced by C. divaricatum, however, have never been explored. In this work, compositions of essential oils distilled from roots and shoots of C. divaricatum plants, cultivated either in the open field or in the glasshouse have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 145 compounds in all, 112 of which were localized in aerial parts and 80 in roots of the plants grown in the open field. Moreover, remarkable differences in composition of oils produced by aerial and underground parts of C. divaricatum have been observed. The major volatiles found in the shoots were: α-pinene (40%), nerol (4%) and neryl-isobutyrate (3%), whereas predominant components of the root oil were 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate (29%), thymyl-isobutyrate (6%) and 9-isobutyryloxythymyl-isobutyrate (6%). In the analyzed oils, seventeen thymol derivatives were identified. Among them eight compounds were specific for roots. Roots of the plants cultivated in the glasshouse were, in general, a poor source of essential oil in comparison with those of the plants grown in the open field. Chemophenetic relationships with other taxa of the Inuleae-Inulineae were also briefly discussed.

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Chromatographic and spectral characteristic of some esters of a common monoterpene alcohols

Cited by 9 publications

References 23 publications

Adsorption of monoterpene alcohols at the water–air interface

Adsorption of monoterpene alcohols at the water–air interface

Essential‐oil inspired synthetic libraries: synthesis, spectral and gas‐chromatographic properties of new fenchyl esters

Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland

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