Allyl sulfides Disulfide

Nishimura and coworkers57-59 studied the y-radiolysis of aqueous solutions of sulfoxide amino acids. Sulfoxide amino acids are the precursors of the flavors of onions (S-propyl-L-cysteine sulfoxide, S-methyl-L-cysteine sulfoxide and S-(l-propenyl)-L-cysteine sulfoxide) and garlic (S-allyl-L-cysteine sulfoxide). In studies on sprout inhibition of onion by /-irradiation it was found that the characteristic flavor of onions became milder. In the y-radiolysis of an aqueous solution of S-propyl-L-cysteine sulfoxide (PCSO)57,58 they identified as the main products alanine, cysteic acid, dipropyl disulfide and dipropyl sulfide. In the radiolysis of S-allyl-L-cysteine sulfoxide (ACSO) they found that the main products are S-allyl-L-cysteine, cysteic acid, cystine, allyl alcohol, propyl allyl sulfide and diallyl sulfide. The mechanisms of formation of the products were partly elucidated by the study of the radiolysis in the presence of N20 and Br- as eaq - and OH radicals scavengers, respectively. 

Propyl sulfide o-Propyl sulfide (/i-n-Propyl sulfide Ethyl methyl sulfide Dimethyl disulfide Butyl sulfide Dibuytyl sulfide Trimethylene sulfide Ethylene sulfide Propylene sulfide Allyl sulfide... 

Disulfide Cyclic Allylic Sulfide cr-Oxyacrylate Vinylsulfone... 

Cyclic allylic disulfide readily underwent the R-ROP due to the facile cleavage of the bond between allylic carbon and sulfur atom, resulting in the production of polysuffides with exo-methylene groups (3, 41, 42). Acrylate-based cyclic allylic sulfide also showed a high radical polymerizability (3, 43). The copolymerization of acrylate-based cyclic allylic sulfide with MMA and styrene produced the corresponding copolymers bearing sulfide and ester moieties in the polymer backbone (43). 

Among the main garlic-related compounds detected in the breath by GC-AED were allyl methyl sulfide, allyl metfiyl disulfide, diallyl sulfide, diallyl disulfide, 2-propenethiol, dimethyl disulfide, and diallyl trisulfide [54]. Measurements taken shortly after Ae ingestion of garlic and at four hourly intervals thereafter, indicating a more rapid decrease with time of diallyl disulfide than allyl methyl sulfide. Allyl methyl disulfide, diallyl sulfide, and diallyl trisulfide were reported to decrease slowly, while 2-propenethiol vanished rapidly. 

The breath of a test person was analyzed over a time period of about 30 hours by means of proton-transfer-reaction mass spectrometry [55]. After ingestion of cut raw garlic, tiie components allyl metfiyl sulfide, allyl methyl disulfide, diallyl sulfide, diallyl disulfide, diallyl trisulfide, dimethyl sulfide, and acetone were detected. While the concentrations of allyl mediyl disulfide, diallyl sulfide, diallyl disulfide, and diallyl trisulfide reached maximum concentration shortly after ingestion of garlic and declined to baseline values within the next 2-3 h, concentrations of allyl methyl sulfide, dimethyl sulfide, and acetone increased much more slowly... 

Known active constituents of garlic (there are at least 35 other constituents whose actions are unknown) ajoene, allicin, aliin, allixin, allyl mercaptan, allyl methyl thiosulfmate, allyl methyl trisulfide, allyl propyl disulfide, diallyl disulfide, diallyl hepta sulfide, diallyl hexa sulfide, diallyl penta sulfide, diallyl sulfide, diallyl tetra sulfide, diallyl tri sulfide, dimethyl disulfide, dimethyl trisulfide, dirpopyl disulfide, methyl ajoene, methyl allyl thiosulfmate, propyline sulfide, 2-vinyl-4H-l, 3-tithiin, 3-vinyl-4H-1, 2dithiin, S-allyl cysteine sulfoxide, S-allyl mercapto, cysteine. 

Fourteen members of this group of flavouring substances, ethane-1,1 -dithiol (No. 1660), 4-mercapto-2-pentanone (No. 1670), diisopentyl thiomalate (No. 1672), cis- and frans-mercapto-p-menthan-3-one (No. 1673), 2,4,6-trithiaheptane (No. 1684), ( )-2,8-epithio-c/s-p-menthane (No. 1685), mixture of 3,6-diethyl-1,2,4,5-tetrathiane and 3,5-diethyl-1,2,4-trithiolane (No. 1687), ( )-3-(methylthio)heptanal (No. 1692), ethyl methyl disulfide (No. 1693), ethyl propyl trisulfide (No. 1695), methyl isopentyl disulfide (No. 1696), butyl ethyl disulfide (No. 1698), allyl propyl disulfide (No. 1700) and bis(1-mercaptopropyl)sulfide (No. 1709), have assay values of <95%. Information on the safety of the secondary components of these 14 compounds is summarized in Annex 5 (Summary of the safety evaluation of secondary components for flavouring agents with minimum assay values of less than 95%). The secondary component of diisopentyl thiomalate, diisopentyl thiotartronate, is expected to share the same metabolic fate as the primary substance. The secondary components of frans-mercapto-p-menthan-3-one, piperitone (No. 435) and a-terpineol (No. 366), are expected to undergo rapid absorption, distribution, metabolism and excretion and were evaluated at previous... 

Allyl phenylacetate Allyl propionate Allyl propyl disulfide Allyl sorbate Allyl sulfide Allyl tiglate Allyl 10-undecenoate Ambrettolide Ammonium isovalerate Ammonium sulfide... 

Allyl caproate Allyl cinnamate Allyl cyclohexaneacetate Allyl cyclohexanebutyrate Allyl cyclohexanehexanoate Allyl cyclohexanepropionate Allyl cyclohexanevalerate Allyl disulfide Allyl 2-ethy I butyrate Allyl heptanoate Allyl a-ionone Allyl isothiocyanate Allyl isovalerate Allyl mercaptan Allyl nonanoate Allyl octanoate Allyl phenoxyacetate Allyl phenylacetate Allyl propionate Allyl sorbate Allyl sulfide Allyl tiglate Allyl 10-undecenoate Ambrettolide Ammonium isovalerate Ammonium sulfide Amyl acetate n-Amyl alcohol Amyl butyrate o-Amylcinnamaldehyde a-Amylcinnamaldehyde dimethyl acetal a-Amylcinnamyl acetate o-Amylcinnamyl alcohol a-Amylcinnamyl formate a-Amylcinnamyl isovalerate Amyl formate Amyl 2-furoate Amyl heptanoate Amyl hexanoate Amyl octanoate Amyl salicylate p-Anisaldehyde Anisole p-Anisyl acetate p-Anisyl alcohol Anisyl butyrate Anisyl formate Anisyl phenylacetate Anisyl propionate Benzaidehyde... 

Potassium acid saccharate CeHioS Allyl sulfide C6H10S2 Allyl disulfide CeHioSe Diallyl trisulfide CeHiiCIHgOe... 

A series of trisubstituted alkenes containing (Z)-allylthio moieties as the key structural units, that is, sodium (Z)-allyl thiosulfates 338, symmetrical di[(Z)-allyl] sulfides 343 and di[(Z)-allyl] disulfides 339 and unsymmetrical diallyl sulfides 341 have been prepared in moderate to good yields via chemical transformations from the acetates of MBH adducts. In addition, it was found that the Sm and a trace amount of I2 could be used for the selective cleavage of the S-S or C-S bonds in sodium (Z)-allyl thiosulfates 338, depending on the substituents (alkyl or aryl group), to give the corresponding... 

Various organic sulfides present in Allium have been found to have anticar-cinogenic activity. For example, allyl sulfide, a constituent of garlic oil, inhibited colon cancer in mice exposed to 1,2-dimethylhydrazine, and allyl methyl trisulfide, allyl methyl disulfide, aUyl trisulfide, and allyl sulfide all inhibited benzo[a]pyrene-induced neoplasma of the forestomach and lung in female mice (55). Lam et al. (Chapter 22) investigated the ability of 2-n-butyl thiophene, a constituent of roast beef aroma, to inhibit chemically induced carcinogenesis in three different tumor systems. This compound was found to be effective in the forestomach, lung, and colon models. 

The earlier studies and the competition experiments [5b] with equivalent molar, enal, or enone 9-BBN (3-5% excess) reveal that enals or enones are selectively reduced to allylic alcohols (Eq. 25.9) in the presence of other organic functional groups such as nitro, halogen, epoxide, carboxylic acid, amide, ester, nitrile, sulfide, disulfide, sulfoxide, sulfone, tosylate, azo, etc. 

Allyl disulfides Allyl sulfides Allyl trisulfides... 

The volatile oil contains allicin (diallyldi-sulfide-5-oxide diallyl thiosulfinate), allyl-propyl disulfide, diallyl disulfide, and diallyl trisulfide as the major components, with lesser amounts of dimethyl sulfide, dimethyl disulfide dimethyl trisulfide, allylmethyl sulfide, 2,3,4-trithiapentane, bis-2-propenyl... 

Treatments tested inclnded combinations of whole plants, leaves, and leaf extracts. Valencia orange. Citrus sinensis L., plants were grown in 3.78-L pots in a temperature-controlled greenhouse. Plant samples were composed of 10-week-old whole plants or 2-g samples of fresh leaves. DMDS ( 98% purity), DMTS ( 98.5% purity), and allyl methyl sulfide (AMS) ( 98% purity) were obtained from Sigma-Aldrich, St. Louis, Missouri. Allyl methyl disulfide (AMDS) ( 98% purity) and allyl disulfide (ADS) ( 80.0% purity) were obtained from Frutarom Ltd., Billingham, United Kingdom, and Penta Chemical Company, United States. 

Figure 16.8 Responses of female adult Diaphorina citri presented with sulfur volatiles at (a) 0.25%, (b) 0.5%, or (c) 1.0% concentrations with or without citrus odors. Allyl methyl sulfide (AMS), allyl disulfide (ADS), allyl methyl disulfide (AMDS), dimethyl disulfide (DMDS), and dimethyl trisulfide (DMTS). Black bars followed by same letters are not significantly different (Tukey s honest significant difference, p <.05).

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