Gas-Phase Infrared Spectroscopy for Determination of Double Bond Configuration of Monounsaturated Compounds

Attygalle, Athula B.; Svatoš, Aleš; Wilcox, Charles F.; Voerman, S.

doi:10.1021/ac00082a016

Cited by 32 publications

(20 citation statements)

References 20 publications

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“…The peaks at 2350 cm À1 are due to ambient CO 2 . The spectra of C C stretching band are apparent at about 1630 cm À1 [17][18][19]. Additionally, symmetric and asymmetric bands of CH 2 and CH 3 are at 2850 and 2920 cm À1 , respectively [20].…”

Section: Resultsmentioning

confidence: 99%

A comparative study on properties of multi-walled carbon nanotubes (MWCNTs) modified with acids and oxyfluorination

Kim

et al. 2007

Journal of Fluorine Chemistry

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Section: Resultsmentioning

confidence: 99%

A comparative study on properties of multi-walled carbon nanotubes (MWCNTs) modified with acids and oxyfluorination

Kim

et al. 2007

Journal of Fluorine Chemistry

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“…Unsaturated dienoic compounds with at least one (E)-double bond provide a characteristic strong band at 990-965 cm -1 assigned to the =C-H out-of-plane deformation vibration [15]. Compounds with a (Z)-double bond do not provide a signal in this area, but show a typical band from =C-H stretch absorption at 3,028-3,011 cm -1 [16]. The IR spectrum of 9,19-hexacosadienoic acid methyl ester (Fig.…”

Section: Identification Of Fatty Acidsmentioning

confidence: 99%

Unusual Fatty Acids in the Fat Body of the Early Nesting Bumblebee, Bombus pratorum

Cvačka¹,

Kofroňová²,

Vašíčková³

et al. 2008

Lipids

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Unusual fatty acids with 24, 26, and 28 carbon atoms were found in triacylglycerols (TAGs) isolated from fat body tissue of bumblebee Bombus pratorum. The most abundant one was (Z,Z)-9,19-hexacosadienoic acid. Its structure was determined by mass spectrometry after derivatization with dimethyl disulfide and by infrared spectroscopy. ECL (equivalent chain length) values of its methyl ester were determined on both DB-1 and DB-WAX capillary columns. (Z,Z)-9,19-Hexacosadienoic acid is quite rare in nature. So far it has been identified only in marine sponges, and this work is the first evidence of its occurrence in a terrestrial organism. HPLC/MS analysis of the bumblebee TAGs showed that (Z,Z)-9,19-hexacosadienoic acid is present in one third of all TAG molecular species. As it was found in all sn-TAG positions, it is likely that (Z,Z)-9,19-hexacosadienoic acid is transported to tissues. Interestingly, labial gland secretion of B. pratorum was found to contain (Z,Z)-7,17-pentacosadiene, a hydrocarbon with markedly similar double bond positions and geometry. Possible biosynthetic relationships between these two compounds are discussed.

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“…The (Z)-configuration can be determined by weak but useful bands above 3000 cm which are absent in (E)-configured compounds [25]. Because the unsaturated methyl ketones showed this absorption, the configuration of the CC bonds must be (Z).…”

mentioning

confidence: 99%

Volatile Organic Compounds from Arctic Bacteria of the Cytophaga‐Flavobacterium‐Bacteroides Group: A Retrobiosynthetic Approach in Chemotaxonomic Investigations

Dickschat

Helmke

Schulz

2005

Chemistry & Biodiversity

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Volatile organic compounds emitted by different marine arctic strains of the Cytophaga-Flavobacterium-Bacteroides group were investigated by using a modified closed-loop stripping apparatus (CLSA). Seven of nine strains emitted volatiles, dominated by methyl ketones, in specific patterns. The methyl ketones were aliphatic saturated, or unsaturated, and comprised 12 to 18 C-atoms, sometimes with terminal Me branches. They were identified by GC/MS, retention-index calculations, derivatization with dimethyl disulfide for C=C bond location, and GC/FTIR to elucidate their uniform (Z)-configuration. The proposed structures of all methyl ketones were subsequently confirmed by synthesis, while the absolute configuration of chiral volatiles was elucidated by stereoselective synthesis. From retrobiosynthetic considerations, it was found that strain ARK10267 uses mainly valine, and strain ARK10063 mainly isoleucine for formation of starters for the ketone biosynthesis, which is correlated to fatty acid biosynthesis. Four strains (ARK10223, ARK10044, ARK10141, and ARK10146) use leucine. These separations are supported by phylogenetic affiliations based on 16S rRNA. Strain ARK10255b, in the course of this study found to be not a member of the Cytophaga-Flavobacterium-Bacteroides phylum, did not emit aliphatic ketones of medium chain length, but methionine-derived 4-(methylsulfanyl)butan-2-one and corresponding 4-(methylsulfanyl)butan-2-ol. Most of the compounds described have not been reported previously from nature.

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Gas-Phase Infrared Spectroscopy for Determination of Double Bond Configuration of Monounsaturated Compounds

Cited by 32 publications

References 20 publications

A comparative study on properties of multi-walled carbon nanotubes (MWCNTs) modified with acids and oxyfluorination

A comparative study on properties of multi-walled carbon nanotubes (MWCNTs) modified with acids and oxyfluorination

Unusual Fatty Acids in the Fat Body of the Early Nesting Bumblebee, Bombus pratorum

Volatile Organic Compounds from Arctic Bacteria of the Cytophaga‐Flavobacterium‐Bacteroides Group: A Retrobiosynthetic Approach in Chemotaxonomic Investigations

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