The Reaction of Methanesulfenyl Chloride with Alkoxides and Alcohols. Preparation of Aliphatic Sulfenate and Sulfinate Esters

Moore, T. L.; O’Connor, Daniel

doi:10.1021/jo01349a027

Cited by 39 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reference compounds hydrogen sulfide and methanethiol were gaseous standards at 5.06 ppm and 5.20 ppm, respectively, diluted in nitrogen (BOC, Surrey, UK). Dimethyl, dipropyl and diallyl thiosulfinate were synthesized by oxidation of the corresponding disulfide with peracetic acid according to the method of Moore and O’Connor [24]. The thiosulfinates were stored at −80 °C until analysis 6 days later.…”

Section: Methodsmentioning

confidence: 99%

Investigation of Volatiles Emitted from Freshly Cut Onions (Allium cepa L.) by Real Time Proton-Transfer Reaction-Mass Spectrometry (PTR-MS)

Løkke

Edelenbos

Larsen

et al. 2012

Sensors

View full text Add to dashboard Cite

Volatile organic compounds (VOCs) in cut onions (Allium cepa L.) were continuously measured by PTR-MS during the first 120 min after cutting. The headspace composition changed rapidly due to the very reactive volatile sulfurous compounds emitted from onion tissue after cell disruption. Mass spectral signals corresponding to propanethial S-oxide (the lachrymatory factor) and breakdown products of this compound dominated 0–10 min after cutting. Subsequently, propanethiol and dipropyl disulfide predominantly appeared, together with traces of thiosulfinates. The concentrations of these compounds reached a maximum at 60 min after cutting. Propanethiol was present in highest concentrations and had an odor activity value 20 times higher than dipropyl disulfide. Thus, propanethiol is suggested to be the main source of the characteristic onion odor. Monitoring the rapid changes of VOCs in the headspace of cut onion necessitates a high time resolution, and PTR-MS is demonstrated to be a very suitable method for monitoring the headspace of freshly cut onions directly after cutting without extraction or pre-concentration.

show abstract

Section: Methodsmentioning

confidence: 99%

Investigation of Volatiles Emitted from Freshly Cut Onions (Allium cepa L.) by Real Time Proton-Transfer Reaction-Mass Spectrometry (PTR-MS)

Løkke

Edelenbos

Larsen

et al. 2012

Sensors

View full text Add to dashboard Cite

show abstract

“…MMTSO was synthesized by oxidizing dimetbyl disulfide with peracetic acid according to the method of Moore and O'Connor (1966). It was purified by vacuum distillation at 2 mm Hg, and the fraction boiling at 65°C was collected (Chin and Lindsay, 1993a).…”

Section: Mmtso Preparationmentioning

confidence: 99%

S‐Methyl‐L‐Cysteine Sulf oxide as the Precursor of Methyl Methanethiolsulfinate, the Principal Antibacterial Compound in Cabbage

Kyung

Fleming

1994

Journal of Food Science

View full text Add to dashboard Cite

S-Methyl-L-cysteine sulfoxide (SMCSO) was present in several cultivars of cabbage (Brussicn oleracea) at 690-1,120 ppm. SMCSO was not inhibitory to Leuconostoc mesenreroides, but its hydrolysis product, methyl methanethiolsulfinate (MMTSO), was inhibitory. MMTSO was formed in fresh cabbage juice (CJ) and in a model system containing SMCSO and fresh cabbage (pH 4.0) precipitate, perhaps by cysteine sulfoxide lyase. Growth inhibition by 1 mM MMTSO was reversed by 5 mM dithiothreitol, cysteine, or reduced glutathione, but not by oxidized glutathione or thiamine.

show abstract

“…In connection with our recent preparation of ''symmetric'' thiosulfonate S-esters (R 1 ASO 2 ASAR 2 , R 1 =R 2 ) by microwave supported permanganate oxidation of the corresponding symmetric disulfides (R 1 ASASAR 2 , R 1 =R 2 ) [4], the products were characterized by spectroscopic methods, including IR spectroscopy. However, a comprehensive search for comparative background information on IR data for thiosulfonate S-esters resulted in surprisingly few hits [5][6][7][8][9][10][11]. The published IR absorption data were primarily reported (always together with NMR data) for the purpose of spectroscopic documentation with respect to structural identity and purity of the thiosulfonate S-esters synthesized.…”

Section: Introductionmentioning

confidence: 99%

Molecular and vibrational structure of thiosulfonate S-esters

Luu

Duus

Spanget‐Larsen

2013

Journal of Molecular Structure

View full text Add to dashboard Cite

The Reaction of Methanesulfenyl Chloride with Alkoxides and Alcohols. Preparation of Aliphatic Sulfenate and Sulfinate Esters

Cited by 39 publications

References 0 publications

Investigation of Volatiles Emitted from Freshly Cut Onions (Allium cepa L.) by Real Time Proton-Transfer Reaction-Mass Spectrometry (PTR-MS)

Investigation of Volatiles Emitted from Freshly Cut Onions (Allium cepa L.) by Real Time Proton-Transfer Reaction-Mass Spectrometry (PTR-MS)

S‐Methyl‐L‐Cysteine Sulf oxide as the Precursor of Methyl Methanethiolsulfinate, the Principal Antibacterial Compound in Cabbage

Molecular and vibrational structure of thiosulfonate S-esters

Contact Info

Product

Resources

About