Allyl sulfides Trisulfide

Allyl methyl trisulfide (alkene sulfide) Allium cepa (onion), A. sativum (garlic) (Liliaceae) [bulb] SLOX (competitive)... 

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. 

Diallyl sulfide Diallylthioether. See Allyl sulfide Diallyl trisulfide CAS 2050-87-5... 

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

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. 

Allyl disulfides Allyl sulfides Allyl trisulfides... 

Examination of 37 basidiomycetous yeasts indicated formation of several sulfur volatiles 3-(methylthio)-l-propanol, methanethiol (MT), S-methyl thio-acetate, dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), allyl methyl sulfide and 4,5-dihydro-3(2//)-thiophenone. The component produced in the largest amounts, 40 100 mg L-1, was 3-(methylthio)-l-propanol29 Cheeseripening yeasts are considered later (Section 11.1.2.4.5). 

See also ALKANETHIOLS, ALKENEBIS(SULFONIUM PERCHLORATES) allyl trifluo-ROMETHANESULFONATES, ARENEDIAZO ARYL SULFIDES BIS(ARENEDIAZO) sulfides, BIS(SULFURDIIMIDES DIAZONIUM SULFATES, DIAZONIUM SULFIDES AND DERIVATIVES METAL AMIDOSULFATES, METAL PHOSPHORUS TRISULFIDES METAL SULFATES, METAL SULFIDES, NON-METAL SULFIDES SULFONIC ACID ESTERS, SULFUR BLACK, SULFUR ESTERS THIOPHENOXIDES, XANTHATES ... 

Garlic contains various sulfur-containing compounds, all of which are derived from allicin, which is formed from alliin by the action of allinase, which is released when garlic is chopped (Srivastava and Tyagi, 1993). Allicin then produces diallyl sulfide, diallyl disulfide, diallyl trisulfide, ajoenes, methyl allyl trisulfides, vinyl dithiins, and other sulfur compounds, depending on how the garlic is prepared. 

The transformation products of allicin and odier thiosulfinates present in crushed garlic is greatly accelerated and expanded upon heating such as during steam distillation or cooking. As many as 20 different sulfides have been identified in the steam distillate and include diallyl mono to hexasulfides, allyl methyl mono to hexasulfides dimethyl mono to hexasulfides, and allyl 1-propenyl di and trisulfides [38]. 

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... 

Several of the lipid- and water-soluble organosulfur compounds have been examined for their antiproliferative efficacy [72, 117-128]. Table 4 provides a list of some of the human tumor cells that have been found to be inhibited by garlic and/or its allyl sulfur compounds some of the more commonly used lipid-soluble allyl sulfur compounds in tumorigenesis research are ajoene, diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS). A breakdown of allicin appears to be necessary for achieving maximum tumor inhibition. Studies by Scharfenberg et al. [117] found that the ED50 for lymphoma cells was two times lower for ajoene than for allicin. 

A mixture of thiophene and isomeric thienothiophenes (total yield of 85%) was prepared by the gas-phase reaction of dimethyl sulfide, diethyl disulfide, diethyl trisulfide and diethyl tetrasulfide with acetylene (89ZOR2588). It was also found that gaseous allyl 2-thienyl sulfide is transformed into a mixture of thiophene-2-thiol, bis(2-thienyl) sulfide and 2-methylthieno[2,3-i]thiophene at 350-410 °C in the presence of acetylene, the reaction gives these products along with thieno[2,3-i]thiophene (91KGS1312). Thermolysis (at 540 °C) of a mixture of di(prop-l-enyl) sulfide and 2-chloro(or bromo)thiophene affords a mixture of thieno[2,3-Z ]thiophene and thieno[3,2- )]thiophene (91ZOR354). 

The totai annuai voiume of production of the 51 simpie aiiphatic and aromatic suifides and thiois is approximateiy 182 kg in Europe (European Fiavour and Fragrance Association, 2005), 80 kg in the United States of America (USA) (Flavor and Extract Manufacturers Association, 2006) and 3 kg in Japan (Japanese Flavor and Fragrance Manufacturers Association, 2002). in Europe, approximately 72% of the total volume is accounted for solely by diethyl trisulfide (No. 1701), whereas in the USA, (S)-1-methoxy-3-heptanethiol (No. 1671), ( )-isobutyl 3-methylthiobutyrate (No. 1677), methyl (methylthio)acetate (No. 1691), bis(1-mercaptopropyl)sulfide (No. 1709) and S-allyl-L-cysteine (No. 1710) account for 84% of the total volume of production. The daily per capita intake of each agent is reported in Table 1. Annual volumes of production of this group of flavouring agents are summarized in Table 2. 

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... 

Garlic essential oil Diallyl disulfide (DADS), diallyl sulfide (DAS), diallyl trisulfide (DTS), methyl allyl disulfide, methyl allyl trisulfide, vinyldithiins, and ajoenes Steam distillation or ether extracted Most potent source of garlic odor and causes body odor, used in perfumery and cosmetic industry... 

Allyl chloride refluxed with Na-thiosulfate in ethanol-water until homogeneous, the mixture containing sodium S-allylthiosulfate distilled at reduced pressure to remove most of the ethanol, cooled, extracted with light petroleum (b. p. 30-40 ), treated with aq. Na-sulfide, and the product extracted with light petroleum diallyl trisulfide. Y 65-70%. F. e., also with isolation of the intermediate, and limitations s. B. Milligan, B. Saville, and J. M. Swan, Soc. 1961, 4850. 

The main products of alliin transformation in polar media are sulfides. At room temperature or on heating, allicin is converted by water into diaUyl disulfide, diaUyl trisulfide and diallyl polysulfides, which are the principal components of garlic essential oil and aged garlic (Figure 8.62). Other reaction products are allyl alcohol, sulfur dioxide and propene. Disproportionation of thiosulfinates in aqueous (polar) solutions also leads to disulfides and thiosuhonates of general formula R-SO2-S-R. For example. 

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... 

Behavioral bioassays with synthetic compounds. Allyl methyl trisulflde, diallyl trisulfide, DMTS, ADS, AMDS, DMDS, diallyl sulfide, and AMS were evaluated for their effect on Diaphorina citri behavior at 0.25%, 0.5%, and 1.0% concentrations, both individually and in combination with citrus leaves. The chemical samples were dissolved in 1 mL ethylene glycol (EG), to slow the release rate of the volatile sulfur compounds during the bioassays," " and pipetted onto a 5-cm Richmond cotton wick (Petty John Packaging Inc., Concord, North Carolina). The treated wick was then wrapped in laboratory tissue and placed in SPME chambers. The control treatment contained cotton wicks impregnated with 1 mL EG only. For evaluations of chemicals in the presence of citrus odors, approximately 2 g of fresh citrus leaves were placed in both chemical treatment and control arms of the olfactometer. 

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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