Thietane, tetrahydrothiophene and tetrahydrothiopyran formation in reaction of methylene-interrupted dienoates with dimethyl disulfide

Carballeira, Néstor M.; Shalabi, Fathi; Cruz, Clarisa

doi:10.1016/s0040-4039(00)77250-9

Cited by 27 publications

(18 citation statements)

References 6 publications

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“…This fraction gave a low relative abundance of cardol (2b), and it was not possible to determine the position of the double bonds in this experiment. According to other reports [14,[22][23], if the double bonds are interrupted with more than four carbon atoms, an independent derivation of the alkenes occurs. When the double bonds are closer together, (such as in cardol, and alkene units interrupted by one methylene group) a complex product mixture is formed.…”

Section: Resultsmentioning

confidence: 96%

“…The position of the double bonds of unsaturated hydrocarbons was determined by iodinecatalyzed methylthiolation using dimethyl disulphide -DMDS [12][13][14][22][23]. Approximately 50 mg of the phenolic fraction was kept dehydrated using anhydrous calcium chloride for 24 hours and then incubated with 0.3 mL of DMDS containing 10 mg/mL in ethyl ether of I 2 at 25 o C, for 4 hours.…”

Section: Alkylthiolation Reactionmentioning

confidence: 99%

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Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

et al. 2008

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Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by ¹H and 13C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), monoene anacardic acid (3), a-amirine (4), b-amirine (5), cycloartenol (6), 24-methylene-cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp.

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Section: Resultsmentioning

confidence: 96%

Section: Alkylthiolation Reactionmentioning

confidence: 99%

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

et al. 2008

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“…In addition when the two double bonds are in close proximity, complications can arise in the reaction with dimethyl disulphide. When higher temperatures (up to 60°C) and longer reaction times (40 hours) were employed, a second mole of dimethyl disulphide was added, and cyclisation occurred giving heterocyclic compounds with thietane, tetrahydrothiophene and tetrahydrothiopyran structures (4-, 5-and 6membered rings) (42,205]. When the double bonds are closer together a variety of products is possible.…”

Section: Dimethyl Disulphuje Derivativesmentioning

confidence: 99%

Structural Analysis of Fatty Acids

Christie

2012

Advances in Lipid Methodology

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“…Dienoic fatty acids present more of a problem for the technique, partly because comparatively high temperatures are required for GC analysis, but mainly from complications in the reaction with dimethyl disulfide. There is no problem when double bonds are separated by more than four carbon atoms, but methylene-interrupted double bonds give products with thietane, tetrahydrothiophene, and tetrahydrothiopyran structures (4-, 5-, and 6-membered rings) (49,50). However, such compounds can give characteristic and diagnostic spectra, so that the technique continues to have some practical value.…”

Section: Some Ancillary Mass Spectrometric Techniquesmentioning

confidence: 99%

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

Christie

1998

Lipids

329

246

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Procedures for structural analysis of fatty acids are reviewed. The emphasis is on methods that involve gas chromatography-mass spectrometry and, in particular, the use of picolinyl ester and dimethyloxazoline derivatives. These should be considered as complementing each other, not simply as alternatives. However, additional derivatization procedures can be of value, including hydrogenation and deuteration, and preparation of dimethyl disulfide and 4-methyl-1,2,4-triazoline-3,5-dione adducts. Sometimes complex mixtures must be separated into simpler fractions prior to analysis by gas chromatography-mass spectrometry. Silver ion and reversed-phase high-performance liquid chromatography are then of special value. In particular, a novel application of the latter technique, involving a base-deactivated stationary phase and acetonitrile as mobile phase, is described that is suited to the separation of fatty acids in the form of picolinyl ester and dimethyloxazoline derivatives, as well as methyl esters.

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Thietane, tetrahydrothiophene and tetrahydrothiopyran formation in reaction of methylene-interrupted dienoates with dimethyl disulfide

Cited by 27 publications

References 6 publications

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

Structural Analysis of Fatty Acids

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

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