Assembly of New vic-Dihydroxyoctadecanoic Acid Methyl Esters at the Air−Water Interface

Overs, Michael; Fix, Marina; Jacobi, S.; Li, Feng; Sieber, Manfred; Schäfer, Hans‐Jürgen; Fuchs, and Harald; Galla, Hans‐Joachim

doi:10.1021/la990655h

Cited by 26 publications

(23 citation statements)

References 18 publications

(44 reference statements)

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“…Peak assignments were confirmed by 2D correlation and, for 13 C NMR, an approach described here using a symmetrical bis(alkylthio) alkane as well as DEPT. As briefly discussed below, the erythro/threo diastereomers of other disubstituted fatty esters have been reported in previous literature with similar evaluations, which include vicinal methyl dihydroxyoctadecanoates [32][33][34], vicinal dimethoxy methyl esters and diacetoxy methyl esters [35] and also the diastereomers of 1,4-disubstituted fatty acid methyl esters [36,37].…”

Section: Nuclear Magnetic Resonancesupporting

confidence: 61%

Fatty Acid Methyl Esters with Two Vicinal Alkylthio Side Chains and Their NMR Characterization

Knothe

Steidley

2017

J Americ Oil Chem Soc

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IntroductionNumerous useful procedures have been developed for determining the location of double bonds in unsaturated fatty acid methyl esters (FAME) or alkenes using mass spectrometry (MS) as the analytical method [1][2][3][4][5][6][7]. Besides various methods involving different ionization procedures, several derivatization reactions have been developed which can largely be categorized as belonging to one of two types. One reaction type is derivatization directly at the double bond by addition of suitable molecules while the other type is substitution of the acid or methyl (alkyl) ester moiety at C1 with a different functionality to induce remote fragmentation. The objective of both types of reactions is to synthesize derivatives that produce fragments in mass spectrometry that are more facile to interpret and, therefore, provide unambiguous information regarding the position of the double bond.Among the first type of the aforementioned derivatization reactions is methylthiolation, usually catalyzed by iodine. The application of this reaction to yield compounds for facile mass spectrometric analysis was, likely, first extensively reported in 1981 [8,9], although an earlier report noted the usefulness of gas chromatography-mass spectrometry for the analysis of the methylthio adducts of 1-dodecene [10]. As its name implies, this reaction consists of the addition of methylthio moieties to the double bond using dimethyl disulfide (DMDS; CH 3 S-SCH 3 ) in the Abstract The addition reaction of dimethyl disulfide (DMDS) to double bonds in alkenes and monounsaturated fatty acid esters in the presence of iodine or other catalysts to give bis(methylthio) derivatives has largely served analytical purposes in mass spectrometry with scattered reports on the addition of other disulfides to alkenes also existing. In this work, this iodine-catalyzed reaction was expanded to include the addition of other dialkyl disulfides (RSSR; R=ethyl, propyl, butyl, iso-propyl) besides DMDS to the double bonds in monounsaturated fatty acid methyl esters with 16, 18, 20, and 22 carbon atoms in the fatty acid chain to give the corresponding methyl 1,2-bis(alkylthio) alkanoates. The products are obtained in high to moderate yield after a facile purification procedure and are analytically characterized not only by mass spectrometry but also 1 H and 13 C NMR. The threo and erythro diastereomers obtained from (Z) and (E) fatty acid methyl esters, respectively, can be easily distinguished by the NMR shifts of the protons and carbons in and close to the 1,2-bis(alkylthio) moiety. Various other effects in the NMR spectra are discussed. The 1,2-bis(alkylthio) derivatives of a symmetrical alkene, 7(E)-tetradecene, serve to confirm the NMR assignments besides NMR techniques such as 2D correlations Disclaimer Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture. USDA is an equal opportunity prov...

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Section: Nuclear Magnetic Resonancesupporting

confidence: 61%

Fatty Acid Methyl Esters with Two Vicinal Alkylthio Side Chains and Their NMR Characterization

Knothe

Steidley

2017

J Americ Oil Chem Soc

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“…51 Formylation of (2) yields asymmetrically functionalized 1-formyl-1'bromoferrocene (3), which was then subjected to a Wittig reaction with hexyltriphenylphosphonium bromide to provide 1-(Z)-heptenyl-1'-bromoferrocene (4). [52][53][54] Subsequent conversion with Eschenmoser's salt to 1-(Z)-heptenyl-1'-dimethylaminomethylferrocene (5) was performed under Mannich-like conditions. 55 Quaternization with 1,3propanesultone finally yielded 1-(Z)-heptenyl-1'-dimethylammoniummethyl-(3-sulfopropyl)ferrocene (FcNMe2SO3Heptene, 6).…”

Section: Resultsmentioning

confidence: 99%

Ferro-Self-Assembly: Magnetic and Electrochemical Adaptation of a Multiresponsive Zwitterionic Metalloamphiphile Showing a Shape-Hysteresis Effect

Bitter¹,

Schlötter²,

Schilling³

et al. 2020

Preprint

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We report on a novel multi-stimuli-responsive amphiphile, 1-(Z)-heptenyl-1’-dimethylammonium-methyl-(3-sulfopropyl)ferrocene (6), whose self-assembly properties can be altered by three different stimuli, namely: (i) the addition of external salts which serve to unfold the sultone headgroup, thus triggering self-assembly of 6 into vesicles; (ii) oxidation to 6+, which changes the lipophilic ferrocene to a hydrophilic ferrocenium entity, thereby broadening the size-distribution of the aggregates; and (iii) exposition of 6+ to an external magnetic field of 0.8 T. Under thease conditions and at sufficient concentration, 6+ forms large, tubular aggregates with lengths of up to 15 µm, which persist for over 5 min after the field is switched off again. 6+ is thus the first amphiphile to exhibit a shape-hysteresis effect. The self-assembly/disassembly processes and their dynamics were studied live and in situ by optical birefringence measurements coupled to light scattering.

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“…A series of methyl and ethyl esters of enantioenriched syn-2,3-dihydroxy fatty acids with different chain lengths was designed and synthesized [18][19][20][21], abbreviated as M-DHH, E-DHH, M-DHO, etc. (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

“…In our previous works, we had studied monolayers of different methyl vic-dihydroxyoctadecanoates in racemic and enantioenriched forms at the air-water interface [18][19][20][21][22][23][24][25][26]. Effects of positions of the two hydroxy groups on phase behaviors were studied in detail.…”

Section: Introductionmentioning

confidence: 99%

Anisotropic aggregation and phase transition in Langmuir monolayers of methyl/ethyl esters of 2,3-dihydroxy fatty acids

Wang

Jacobi

Sun

et al. 2005

Journal of Colloid and Interface Science

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Assembly of New vic-Dihydroxyoctadecanoic Acid Methyl Esters at the Air−Water Interface

Cited by 26 publications

References 18 publications

Fatty Acid Methyl Esters with Two Vicinal Alkylthio Side Chains and Their NMR Characterization

Fatty Acid Methyl Esters with Two Vicinal Alkylthio Side Chains and Their NMR Characterization

Ferro-Self-Assembly: Magnetic and Electrochemical Adaptation of a Multiresponsive Zwitterionic Metalloamphiphile Showing a Shape-Hysteresis Effect

Anisotropic aggregation and phase transition in Langmuir monolayers of methyl/ethyl esters of 2,3-dihydroxy fatty acids

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