Diallylsulfid

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Diallyl sulfide (DAS) and diallyl disulfide (DADS) at 25 ug/mL decreased the benzo[a]pyrene (B[a]P)-induced colony growth inhibition of human epidermal keratinocytes. DAS and DADS decreased B[a]P-DNA and B[a]P-protein adducts by 65% and 49-55%, respectively. The B[a]P-induced ethoxyresorufin O-deethylase activity, a marker enzyme for cytochrome P450 1, was decreased from 3 to 1.7-1.9 nmol/min/mg microsomal protein by DAS and DADS treatments. The activity of glutathione S-transferase, a detoxifying enzyme for B[a]P, ... was decreased by DADS, but was unaffected by DAS

... /The authors/ investigated the mutation preventive properties of ellagic acid, green tea, and diallyl sulfide (DAS) against the mutagenicity of the nitrosamine N-nitrosomethylbenzylamine (NMBA) in the esophagus of the rat. ... The type of mutations induced by two 2-mg/kg sc injections of NMBA in the lacI gene of "Big Blue" rats is consistent with that found previously for nitrosamines in other systems and consists of G:C-->A:T transitions. .... the addition of ellagic acid to the feed, replacing drinking water with green tea, and gavage with DAS significantly reduced the mutagenicity of NMBA. ...

Diallyl sulphide (DAS) is a sulphur-containing volatile compound present in garlic (Allium sativum). It has been shown to inhibit a number of chemically induced forms of cancer in experimental animals. The present study demonstrates the inhibitory effect of DAS on the development of diethylnitrosamine (DEN) initiated and 2-acetyl-aminofluorene (2-AAF) promoted preneoplastic altered hepatic foci (AHF) in Wistar rats. AHF were scored and analysed by quantitative stereology using the Image Analysis system from frozen liver sections stained for biological markers, namely glutathione S-transferase, placental form (GST-P), gamma-glutamyl transpeptidase (GGT), adenosine triphosphatase (ATPase), glucose-6-phosphatase (G6 Pase) and alkaline phosphatase (AlkPase). DAS-supplemented rats were found to restore the near-normal levels of enzymes GST-P and GGT when exposed to DEN and 2-AAF. DAS administration following DEN and 2-AAF exposure led to the restoration of enzymic activity of ATPase, G6 Pase and AlkPase, as evident by number and area of the foci. These findings suggest the protective role of DAS in rat hepatocarcinogenesis ...

Gentamicin (GM) is an antibiotic whose clinical use is limited by its nephrotoxicity. Experimental evidences suggest a role of reactive oxygen species in GM-induced nephrotoxicity. ...This work ... explored the effect of diallyl sulfide (DAS) ... on GM-induced nephrotoxicity. Four groups of rats were studied: (1) Control, treated intragastrically with olive oil as a vehicle, (2) GM, treated subcutaneously with GM (125 mg/kg/day for 4 days), (3) DAS, treated intragastrically with DAS (50 mg/kg/day for 4 days), and (4) GM + DAS. Nephrotoxicity was made evident by: (1) the increase in creatinine and blood urea nitrogen in serum, (2) the increase in urinary excretion of N-acetyl-beta-D-glucosaminidase and total protein, and (3) necrosis of proximal tubular cells. These functional and structural alterations were prevented or ameliorated by DAS treatment. In addition, GM increased levels of renal oxidative stress markers nitrotyrosine and protein carbonyl groups which were also ameliorated by DAS in GM + DAS group. The mechanism by which DAS has a protective effect on GM-induced nephrotoxicity may be related, at least in part, to the decrease in oxidative stress in renal cortex.

For more Interactions (Complete) data for ALLYL SULFIDE (12 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 270(SRC), determined from a structure estimation method(2), indicates that allyl sulfide is expected to have moderate mobility in soil(SRC). Volatilization of allyl sulfide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Allyl sulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.22 mm Hg(4). Biodegradation data were not avilable(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 270(SRC), determined from a structure estimation method(2), indicates that allyl sulfide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 20(SRC), from an estimated log Kow of 2.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegadation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl sulfide, which has a vapor pressure of 9.22 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl sulfide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 6.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Allyl sulfide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Allyl sulfide was identified as one of the volatile compounds from stir-fried garlic, at the following concentrations (mg/100 g garlic, % composition): raw garlic, distilled without soybean oil - 1.04 (0.64); raw garlic, distilled with soybean oil - 0.12 (0.10); stir-fired garlic, 0.12 (0.80)(1). The compound has been identified as a beef volatile(2).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of allyl sulfide can be estimated to be 270(SRC). According to a classification scheme(2), this estimated Koc value suggests that allyl sulfide is expected to have moderate mobility in soil.

URBAN/SUBURBAN: Allyl sulfide was detected in the ambient air of a beech forest with Allium ursinum (broad-leaved garlic) ground cover at a concentration of not detected (detection limit <1.0 ppbC) to 370 parts per trillion, average 120 parts per trillion, sampled in a suburban forest park of Vienna Austria, May 13, 1994(1). The Allium plants were shown to be the source of the organic sulfur compounds(1).

/OTHER TOXICITY INFORMATION/ Two components of garlic, diallyl sulfide (DAS) and diallyl disulfide (DADS), inhibited arylamine N-acetyltransferase (NAT) activity and 2-aminofluorene-DNA adduct in human promyelocytic leukemia cells (HL-60). The NAT activity was measured by high performance liquid chromatography assaying for amounts of N-acetyl-2-aminofluorene (2-AAF) and remaining 2-aminofluorene (2-AF). Cellular cytosols and intact cell suspensions were assayed. The inhibition of NAT activity and 2-AF-DNA adduct formation in human leukemia cells by DAS and DADS were dose-dependent and were directly proportional. The data also indicated that DAS and DADS decrease the apparent values of Km and Vmax from human leukemia cells in both assays. This is the first report of garlic components affecting human leukemia cell NAT activity and 2-AF-DNA adduct formation.

An estimated BCF of 20 was calculated for allyl sulfide(SRC), using an estimated log Kow of 2.6(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for allyl sulfide is estimated as 1.3X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that allyl sulfide is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). Allyl sulfide's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Allyl sulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.22 mm Hg(3).

Allyl sulfide is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

A component of artificial oil of garlic; [Hawley] Used in flavor manufacturing; [Merck Index] Constitutes 8.9% of diallyl disulfides (DADs) which is 90% active ingredient of biopesticide used to control white rot (fungal pathogen) in onions, garlic, and leeks; DADs are volatile sulfur compounds found in garlic, onions, and other members of Allium species; [EPA]

Farming (Pesticides) [Category: Industry]

Manufacture flavors.

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

1-Propene, 3,3'-thiobis-: ACTIVE

Component of artificial oil of garlic