680. Trisulphides and tetrasulphides from Bunte salts

Milligan, Brian; Saville, B.; Swan, JM

doi:10.1039/jr9630003608

Cited by 44 publications

(17 citation statements)

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“…The following isotopically substituted standards were synthesized according to the literature cited: ( 2 H 4 )- 7 , ( 13 C 5 )- 8 , ( 2 H 3 )- 11 , ( 13 C 2 )- 49 , ( 2 H 3 )-3-(methylthio)propan-1-ol, ( 2 H 3 )-5-methylthiophene-2-carbaldehyde, ( 13 C 2 )- 40 , ( 2 H 6 )- 9 , ( 2 H 3 )- 55 , and ( 2 H 4 )- 38 . ( 2 H 3 )- 6 was purchased from aromaLAB (Martinsried, Germany), ( 2 H 8 )naphthalene and ( 13 C 2 )- 54 were obtained from Merck, and ( 2 H 3 )- 26 was purchased from CDN Isotopes (Pointe-Claire, Quebec, Canada).…”

Section: Materials and Methodsmentioning

confidence: 99%

Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

Marcinkowska

Frank

Steinhaus

et al. 2021

J. Agric. Food Chem.

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Volatile compounds of raw and cooked green kohlrabi were investigated using a sensomics approach. A total of 55 odor-active compounds were detected and identified in raw and cooked green kohlrabi using GC-O. Twenty-eight odor-active compounds with high flavor dilution (FD) factors ranging from 64 to 1024 were quantitated, and odor activity values (OAVs) were determined. Eight compounds showed high OAVs in raw and cooked kohlrabi: five sulfur compounds (dimethyl trisulfide, methyl 2-methyl-3-furyl disulfide, and three isothiocyanates (1-isothiocyanato-3-(methylsulfanyl)propane, benzyl isothiocyanate, and 1-isothiocyanato-4-(methylsulfanyl)butane)), two lipid oxidation products (1-octen-3-one and trans-4,5-epoxy-(2E)-dec-2-enal), and 2-isopropyl-3-methoxypyrazine. Among these, the sulfur compounds contributed most to the overall smell of the raw and cooked vegetables. The quantitation analysis indicates that the eight odorants are the backbone compounds for raw and cooked kohlrabi. The OAVs for the backbone compounds and also for minor odorants are clearly higher in raw kohlrabi than in the cooked one. Differences can be explained by the influence of the cooking process.

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Section: Materials and Methodsmentioning

confidence: 99%

Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

Marcinkowska

Frank

Steinhaus

et al. 2021

J. Agric. Food Chem.

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“…Seminal work by Brian Milligan and John Swan in the early 1960s 19,20 established the first examples of trisulfane synthesis using methodology B, in which a Bunte salt (an Salkyl or S-arylthiosulfate salt as RSSO 3 -M + ) was used as the sulfenylating agent of sodium sulfide (Na 2 S), which is the most reliable of all the sulfide salts in regards to purity and constitution. In cases involving a reactive RSLg, H 2 S can be used as the monosulfur nucleophilic source, and once again, earlier reviews on polysulfanes 1 give an extensive coverage of this approach.…”

Section: Methodology B: M(s) N M (N = 1 2) + 2 × Rslgmentioning

confidence: 99%

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

Ali

Amer

Petersen

et al. 2021

SynOpen

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It has been ten years since the last comprehensive review on polysulfanes, and during the intervening period, organodi-, organotri- and organotetrasulfanes have featured prominently in both the chemistry and biology literature. This timely update presents both a mechanistic and historical account of synthesis methodology available for organotri- and organotetrasulfanes involving heterolytic S–S bond formation.

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“…The following reference standards were obtained from commercial suppliers (given in parentheses): 1 – 10 , 12 – 18 , 20 , 22 – 27 , 30 – 34 , 36 – 48 , and n ‐pentadecane‐d 32 (Sigma‐Aldrich, St. Louis, MO, USA); 28 (Penta Manufacturing Company, Livingston, NJ, USA). Compounds 11 , 19 , 21 , 29 , and 35 were synthesized according to the corresponding literature. The purity of the synthesized chemical standards was >90%.…”

Section: Methodsmentioning

confidence: 99%

Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)

Chiang

Munafo

2018

Flavour & Fragrance J

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Lily bulbs (Lilium longiflorum Thunb.), known as ‘Bai He’ in Chinese, are a popular ingredient used in Asian cooking. Despite their popularity, little is known about the odorants responsible for their distinct aroma. The key aroma‐active compounds present in both raw and roasted lily bulbs were isolated by solvent extraction followed by solvent‐assisted flavour evaporation (SAFE) and gas chromatography–olfactometery (GC/O) analysis. A comparative aroma extract dilution analysis (cAEDA) in the flavour dilution (FD) factor range from ≥1 to 1024 resulted in 48 aroma‐active compounds reported in L. longiflorum bulbs for the first time. The highest FD factors in raw lily bulbs were determined for (E)‐hex‐3‐enal (green, FD 1024) and 3‐methylsulfanylpropanal (cooked potato‐like, FD 1024), followed by 2,2,4‐trimethyl‐3‐oxabicyclo[2.2.2]octane (eucalyptus‐like, FD 256) and 2‐phenyl acetaldehyde (floral, FD 256). Following roasting, odorants with high FD values in raw lily bulbs decreased in intensity. The thermal treatment resulted in the generation of 34 aroma‐active compounds. Aroma‐active compounds with FD factors of ≥1024 in roasted lily bulbs were identified as 1‐(3,4‐dihydro‐2H‐pyrrol‐5‐yl)ethan‐1‐one (roasty), 3‐methylsulfanylpropanal (cooked potato‐like), 2‐ethyl‐3,5‐dimethylpyrazine (earthy), 2,3‐diethyl‐5‐methylpyrazine (earthy), 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (maple‐like), 2‐ethyl‐4‐hydroxy‐3‐methyl‐2H‐furan‐5‐one (maple‐like), and 2‐methoxy‐4‐[(E)‐prop‐1‐enyl]phenol (clove‐like). In summary, the aroma‐active compounds with high FD factors in raw lily bulbs decreased significantly as a result of roasting, and a new pool of aroma‐active compounds were formed during the roasting process.

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680. Trisulphides and tetrasulphides from Bunte salts

Abstract: Support for this mechanism has now been obtained by allowing dimethyl trisulphide to react with sulphite ion at pH 8; considerable amounts of dimethyl disulphide were formed.

Cited by 44 publications

References 0 publications

Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)

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