Diallyl sulfide
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Diallyl sulfide
structure -
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CAS No:
592-88-1
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Formula:
C6H10S
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Chemical Name:
Diallyl sulfide
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Synonyms:
1-Propene,3,3′-thiobis-;Allyl sulfide;3,3′-Thiobis[1-propene];Allyl monosulfide;Diallyl sulfide;Thioallyl ether;Diallyl monosulfide;Oil garlic;Diallyl thioether;Di(2-propenyl) sulfide;Bis(2-propenyl) sulfide;NSC 20947;132879-26-6
- Categories:
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CAS No:
Description
clear colorless liquid A colorless liquid with characteristic garlic odor. Oil-soluble component of garlic
Liquid|colourless to pale yellow liquid with garlic odour
Diallyl sulfide is an organic sulfide.
Diallyl sulfide Basic Attributes
114.21
114.21
1736016
209-775-1
60G7CF7CWZ
20947
DTXSID6060470
Colorless liquid
2930909090
Characteristics
25.3
2.61 (est)
Clear colorless Liquid
0.888 at 27 deg C/4 deg C
-85 °C
138.6 °C
115 °F
1.478
soluble in alcohol, chloroform, ether, and carbon tetrachloride. Insoluble in water.
2-8°C
7 mm Hg ( 20 °C)
3.9 (vs air)
Oral-rat LD50: 2980 mg/kg
Open flame is flammable; burning emits toxic sulfur oxide fumes; emits toxic hydrogen sulfide vapor in case of heat or water vapor
1.1%(V)
Garlic odor
Garlic
Henry's Law constant = 1.3X10-3 atm-cu m/mol at 25 °C(est)
Hydroxyl radical reaction rate constant = 6.9X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
III
3
UN 1993 3/PG 3
2
10-36/37/38
26-36-37/39-23-16
BC4900000
Xi
The warehouse is ventilated, low-temperature and dry; stored and transported separately from food, oxidants, acids and water
Explosive reaction with N-bromosuccinamide
Stable under normal temperatures and pressures.
P261-P305 + P351 + P338
H226-H315-H319-H335
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.
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.
UN 1993
|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 1595 companies from 5 notifications to the ECHA C&L Inventory.
Emission rates of allyl sulfide from Allium ursinum (broad-leaved garlic) ground cover sampled in a suburban forest park of Vienna, Austria on May 13, 1994 was 10 ug/sq m-hr(1).
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).
Toxicity
moderately toxic
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.
Allyl sulfide is a volatile from Allium ursinum (broad-leaved garlic), a ground cover(1).
Allyl sulfide's production and use as a flavoring(1), specifically as a component of artificial oil of garlic may result in its release to the environment through various waste streams(SRC).
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).
The rate constant for the vapor-phase reaction of allyl sulfide with photochemically-produced hydroxyl radicals has been estimated as 6.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of allyl sulfide with ozone has been estimated as 2.4X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). Allyl sulfide is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4). 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).
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).
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.
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 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).
Occupational exposure to allyl sulfide may occur through inhalation and dermal contact with this compound at workplaces where allyl sulfide is produced or used. Monitoring data indicate that the general population may be exposed to allyl sulfide via inhalation of ambient air, ingestion of garlic, and dermal contact with this compound and other consumer products containing allyl sulfide. (SRC)
| Name | Type of Test | Exposure Route | Species Observed | Dose/Duration | Toxic Effects | Reference |
|---|---|---|---|---|---|---|
| ACUTE TOXICITY DATA | LD50 - Lethal dose, 50 percent kill | Oral | Rodent - rat | 2980 mg/kg | Details of toxic effects not reported other than lethal dose value-- | Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,299,1988 |
| ACUTE TOXICITY DATA | LD50 - Lethal dose, 50 percent kill | Administration onto the skin | Rodent - rabbit | >5 gm/kg | Details of toxic effects not reported other than lethal dose value-- | Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,299,1988 |
| ACUTE TOXICITY DATA | LDLo - Lowest published lethal dose | Intravenous | Rodent - rabbit | 330 mg/kg | Behavioral--muscle contraction or spasticity Lungs, Thorax, or Respiration--other changes Nutritional and Gross Metabolic--body temperature decrease |
Biochemical Journal. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1906- Volume(issue)/page/year: 4,107,1909 |
Drug Information
/Exptl Ther:/ The present study was conducted to elucidate the antioxidant role of garlic oil in isoproterenol (IPL)-induced myocardial infarction in rats. In myocardial necrosis induced by isoproterenol, a significant increase in serum iron content with a significant decrease in plasma iron binding capacity, ceruloplasmin activity and glutathione (GSH) level were observed. There was also a significant increase in lipid peroxides levels on isoproterenol administration. Activities of antioxidant enzymes like superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPX), glutathione-S-transferase (GST) and glutathione reductase (GRD) were decreased significantly in heart with isoproterenol-induced myocardial necrosis. Garlic oil produced a marked reversal of these metabolic changes related to myocardial infarction induced by isoproterenol. In conclusion, garlic oil exerts its effects by modulating lipid peroxidation and enhancing antioxidant and detoxifying enzyme system /Garlic oil/|/Exptl Ther:/ Low-density lipoprotein (LDL) and plasma were isolated from patients with non-insulin-dependent diabetes. The protective effects of six organosulfur compounds (DAS, diallyl sulfide; DADS, diallyl disulfide; SAC, S-allylcysteine; SEC, S-ethylcysteine; SMC, S-methylcysteine; SPC, S-propylcysteine) against further oxidation and glycation in these already partially oxidized and glycated samples were studied. DAS and DADS showed significantly greater oxidative-delaying effects than four cysteine-containing compounds in both partially oxidized LDL and plasma samples (P < 0.05). However, cysteine-containing agents were superior to DAS and DADS in delaying glycative deterioration in already partially glycated LDL (P < 0.05). The observed delays of oxidative and glycative effects from each agent were significantly concentration-dependent (P < 0.05). Furthermore, six organosulfur agents significantly decreased the loss of catalase and glutathione peroxidase activities in plasma and increased alpha-tocopherol retention in LDL and plasma (P < 0.05). These results suggested that the use of these organosulfur agents derived from garlic at these concentrations could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases. /Organosulfur compounds/|/Exptl Ther:/ The inhibitory effect of garlic extract, diallyl sulphide and diallyl disulphide against methicillin-resistant Staphylococcus aureus (MRSA) infection in BALB/cA mice was studied. The influence of these agents upon the levels of fibronectin, interleukin-6 and lipid oxidation in MRSA-infected mice was examined. ... Garlic extract at 100% and 50%; diallyl sulphide (DAS) at 10% and 5%; diallyl disulphide (DADS) at 1% and 0.5% were used in this study. Sixteen clinical MRSA isolates obtained from infected patients were used in this study (n=16). Mice were infected by injecting 200 microL MRSA-PBS solution, which contained 10(7) cfu, via the tail vein. At 16 hr post-infection (pi), garlic extract, DAS or DADS at 200 uL was administrated orally. At 24 hr pi, mice were killed and blood, liver, kidney and spleen of each mouse were collected. Plasma and the filtrate from each organ and serial dilutions were used to determine colony count. Plasma fibronectin level was determined by rabbit anti-rat fibronectin antibody and quantified by ELISA. Interleukin-6 levels were determined by commercial kit. Lipid oxidation was determined by measuring malondialdehyde levels. ... The oral administration of these agents significantly decreased the viability of MRSA, in plasma, liver, kidney and spleen (P<0.05). MRSA infection significantly increased fibronectin and interleukin-6 levels in plasma of MRSA-infected mice (P<0.05); however, the oral administration of garlic extract and two diallyl sulphides significantly reduced both fibronectin and interleukin-6 levels (P<0.05). MRSA infection also significantly enhanced lipid oxidation in plasma and three organs (P<0.05). The treatments of garlic extract and two diallyl sulphides significantly decreased the malondialdehyde level and showed antioxidant protection (P<0.05)... These data strongly supported the conclusion that garlic extract, diallyl sulphide and diallyl disulphide possessed multiple protective functions against MRSA infection, in which diallyl sulphide and diallyl disulphide could be considered as novel therapeutic agents for the treatment of MRSA infection.|/Exptl Ther:/ Multidrug resistance (MDR) mediated by the overexpression of drug efflux protein P-glycoprotein (P-gp) is one of the major obstacles to successful cancer chemotherapy. P-gp acts as an energy-dependent drug efflux pump, reducing the intracellular concentration of structurally unrelated drugs. Modulators of P-gp function can restore the sensitivity of multidrug-resistant cells to such drugs. ... The present study ... evaluated the P-gp modulatory potential of diallyl sulfide (DAS), a volatile organosulfur compound present in garlic, known to possess many medicinal properties, including antimutagenic and anticarcinogenic activities. For in vitro studies, K562 leukemic cells were made resistant (K562/R) to the cytotoxicity of vinblastine (VBL) by progressive adaptation of the sensitive K562 parental cells to VBL. Cross-resistance of K562/R was found between vincristine (VCR), doxorubicin and other antineoplastic agents. A non-toxic concentration of DAS (8.75 x 10(-3) M) enhanced the cytotoxic effects of VBL and another vinca alkaloid, VCR, time dependently in VBL-resistant human leukemia (K562/R10) cells but had no effect on the parent (K562/S) cells. The results show that DAS decreased the induced levels of P-gp in resistant cells back to the normal levels as analyzed both qualitatively and quantitatively by western blotting and immunocytochemistry. Furthermore, in vivo combination studies showed that DAS effectively inhibited vinca alkaloid-induced P-gp overexpression in mouse hepatocytes. Quantitation of immunostained tissue sections with image analysis showed that the reduction in P-gp levels was up to 73% for VBL- and 65% for VCR-induced drug resistance. The above features thus indicate that DAS can serve as a novel, non-toxic modulator of MDR and can be used as a dietary adjuvant.|For more Therapeutic Uses (Complete) data for ALLYL SULFIDE (7 total), please visit the HSDB record page.
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES. (See all compounds classified as Cytochrome P-450 Enzyme Inhibitors.)
Diallyl sulfide (DAS) ... is sequentially converted to diallyl sulfoxide (DASO) and diallyl sulfone (DASO2) by cytochrome P450 2E1 (CYP2E1).
Diallyl sulfide (DAS) ... Can induce the expression of heme oxygenase-1 (HO-1), which plays a critical role in the cell defense system against oxidative stress. DAS causes a dose- and time-dependent increase of HO-1 protein and mRNA level without toxicity in HepG2 cells. DAS-induced HO-1 protein expression is dependent on newly synthesized mRNA and newly synthesized protein. DAS increases Nrf2 protein expression, nuclear translocation, and DNA-binding activity. The MAP kinase ERK is activated by DAS. Both ERK and p38 pathways play an important role in DAS-induced Nrf2 nuclear translocation and ho-1 gene activation. DAS stimulates a transient increase of reactive oxygen species (ROS). N-Acetyl-cysteine blocked this increase of ROS production as well as DAS-induced ERK activation, Nrf2 protein expression and nuclear translocation, and ho-1 gene activation. The increase in HO-1 produced by DAS protected the HepG2 cells against toxicity by hydrogen peroxide or arachidonic acid. These results suggest that DAS induces ho-1 through production of ROS, and Nrf2 and MAPK (ERK and p38) mediate this induction. Induction of ho-1 may play a role in the protective effects of DAS.|... The pharmacologic role of /diallyl sulfide/ DAS in prevention and treatment of cancer is well documented in the literature, but its molecular mechanism of action is not yet well defined. In the present study, modulation in p53 expression by topical application of DAS was recorded in 7,12-dimethylbenz[a]anthracene (DMBA)-induced skin tumors in Swiss albino mice. Western blot analysis and immunohistochemical protein detection, combined with multivariable flow cytometry, show that DAS application induces the expression of the wild-type (wt) p53 and down-regulates the expression of mutant (mut) p53. Immunoblotting analysis of tumors showed significant increase in levels of wtp53 by DAS application, whereas for mutp53 the DMBA-induced levels of protein were found to reduce to near normal levels with DAS application. The quantitative analysis of immunostained skin/tumor sections using image analysis and quantitative stereology showed 66.6% and 54.2% increases in wtp53 levels and 53.4% and 44.3% decreases in mutp53 levels in animals where DAS was applied 1 hour prior to or 1 hour after DMBA application, respectively. Flow cytometric analysis further confirmed modulation of wtp53 and mutp53 protein in DAS-supplemented tumors. The increase in the expression of wt tumor suppressor gene protein p53 was accompanied by elevation of the levels of cyclin-dependent kinase inhibitor p21/waf1. The percentage increase in the levels of p21/waf1 was found to be 72.9% and 61.3%, respectively, in DAS-supplemented groups before and after administration. These results thus show that DAS is a potential chemopreventive agent capable of modulating and regulating the tumor suppressor p53 along with its downstream effective molecule, p21/waf1. Thus, DAS can be a potential chemopreventive agent against skin tumor development.|... Oxidation of LDL (Ox-LDL) promotes vascular dysfunction, enhances the production and release of inflammatory mediators such as reactive oxygen species and contribute to the initiation and progression of atherosclerosis. In addition, Ox-LDL enhances the production and release of tumor necrosis factor (TNF-alpha), interleukin (IL)-6, arachidonic acid metabolites and nitric oxide (NO) that are responsible for various human pathologies including cancer. Organosulfur compounds (OSC) from alliaceae modulate the glutathione (GSH) redox cycle and inhibits NFkappa-B activation in human T cells. ...|Diallyl sulfide (DAS) ... is sequentially converted to diallyl sulfoxide (DASO) and diallyl sulfone (DASO2) by cytochrome P450 2E1 (CYP2E1). These compounds have been shown to reduce the incidence of a multitude of chemically induced tumors in animal models. The impediment of phase I activation of these carcinogens is hypothesized to be accountable for the reduction in tumor incidence. Indeed, DAS, DASO and DASO2 are competitive inhibitors of CYP2E1. DASO2, in addition, is a suicide inhibitor of CYP2E1. These compounds have been shown to reduce carbon tetrachloride-, N-nitrosodimethylamine- and acetaminophen-induced toxicity in rodents. All three chemicals are substrates for CYP2E1. The protective effect was observed when the organosulfur compounds were given before, during or soon after chemical treatment. DAS and DASO2 inhibited the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and related lung tumorigenesis in A/J mice. Because CYP2E1 does not play a key role in NNK activation, the inhibition of other CYP enzymes active in NNK metabolism is likely. DAS also has been shown to induce other CYP and phase II enzymes as well as decrease hepatic catalase activity. All of these effects are observed at concentrations much higher than what is normally ingested by humans.|For more Mechanism of Action (Complete) data for ALLYL SULFIDE (7 total), please visit the HSDB record page.
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/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.
allyl sulfide
Diallyl sulfide Use and Manufacturing
Prepared from allyl bromide and sulfur in solution of Na in liquid NH3.
manufacture of flavors.
1-Propene, 3,3'-thiobis-: ACTIVE|Component of artificial oil of garlic
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index
Flavoring Agents
Computed Properties
Molecular Weight:114.21
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:114.05032149
Monoisotopic Mass:114.05032149
Topological Polar Surface Area:25.3
Heavy Atom Count:7
Complexity:49.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Synthesis Route
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