Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10S |
| Molecular Weight | 114.209 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CCSCC=C
InChI
InChIKey=UBJVUCKUDDKUJF-UHFFFAOYSA-N
InChI=1S/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2
| Molecular Formula | C6H10S |
| Molecular Weight | 114.209 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Allyl sulfide or diallyl sulfide, a natural organosulfur compound, which is mostly obtained from the genus Allium plants, exhibits anticancer activities. This compound also possesses a protective role in cisplatin-induced nephrotoxicity via suppressing NF-κB downstream inflammatory proteins and p53/Puma signaling pathway. Besides, diallyl sulfide exerts protective properties in experimental Inflammatory bowel disease (IBD), an incurable disease which affects millions of people. It was also discovered, that diallyl sulfide may be effective in reducing ethanol-induced injury of cells thereby suggesting its potential to be used in drug formulations.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Diallyl sulfide induces heme oxygenase-1 through MAPK pathway. | 2004-12-15 |
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| Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells. | 2004-12 |
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| Role of chemopreventive agents in cancer therapy. | 2004-11-25 |
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| Signal transduction pathways leading to cell cycle arrest and apoptosis induction in cancer cells by Allium vegetable-derived organosulfur compounds: a review. | 2004-11-02 |
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| Antioxidant effects of sulfur-containing amino acids. | 2004-10-31 |
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| Involvement of cytochrome P450 2E1 in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse model of Parkinson's disease. | 2004-10 |
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| Garlic's ability to prevent in vitro Cu2+-induced lipoprotein oxidation in human serum is preserved in heated garlic: effect unrelated to Cu2+-chelation. | 2004-09-01 |
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| Effect of garlic (Allium sativum) on lipid peroxidation in experimental myocardial infarction in rats. | 2004-09 |
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| Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis. | 2004-09 |
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| Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2. | 2004-07-22 |
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| Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. | 2004-06-02 |
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| Spice phenolics inhibit human PMNL 5-lipoxygenase. | 2004-06 |
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| Reversal of P-glycoprotein-mediated multidrug resistance by diallyl sulfide in K562 leukemic cells and in mouse liver. | 2004-06 |
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| Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation. | 2004-05-14 |
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| [Gladness and troubles for using garlic as an anti-oxidant]. | 2004-05 |
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| The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride. | 2004-05 |
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| Diallyl sulfide inhibits the oxidation and reduction reactions of stilbene estrogens catalyzed by microsomes, mitochondria and nuclei isolated from breast tissue of female ACI rats. | 2004-05 |
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| Aversion of European starlings (Sturnus vulgaris) to garlic oil treated granules: garlic oil as an avian repellent. Garlic oil analysis by nuclear magnetic resonance spectroscopy. | 2004-04-21 |
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| Organosulfur compounds from alliaceae in the prevention of human pathologies. | 2004-04 |
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| Role of cytochrome P4502E1 activation in proximal tubular cell injury induced by hydrogen peroxide. | 2004-03 |
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| Inhibitory activity of essential oils of garlic and onion against bacteria and yeasts. | 2004-03 |
|
| Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells. | 2004-02 |
|
| Inhibition of N-acetyltransferase activity and gene expression in human colon cancer cell lines by diallyl sulfide. | 2004-02 |
|
| Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells. | 2004 |
|
| Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. | 2004 |
|
| Protective effect of diallyl sulfide on oxidative stress and nephrotoxicity induced by gentamicin in rats. | 2003-12 |
|
| Garlic extract and two diallyl sulphides inhibit methicillin-resistant Staphylococcus aureus infection in BALB/cA mice. | 2003-12 |
|
| Induction of multidrug resistance protein 3 (mrp3) in vivo is independent of constitutive androstane receptor. | 2003-11 |
|
| Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry. | 2003-10 |
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| Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. | 2003-09 |
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| Neuroprotective effect of antioxidants on ischaemia and reperfusion-induced cerebral injury. | 2003-08 |
|
| Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer. | 2003-07-24 |
|
| Diallylsulfide attenuates asbestos-induced genotoxicity. | 2003-06-05 |
|
| The inhibition of superoxide production in EL4 lymphoma cells overexpressing growth hormone. | 2003-05 |
|
| Inhibition of DES-induced DNA adducts by diallyl sulfide: implications in liver cancer prevention. | 2003-04-10 |
|
| Diallyl sulfide inhibits diethylstilbestrol-induced lipid peroxidation in breast tissue of female ACI rats: implications in breast cancer prevention. | 2003-04-10 |
|
| Short-term acetaldehyde exposure depresses ventricular myocyte contraction: role of cytochrome P450 oxidase, xanthine oxidase, and lipid peroxidation. | 2003-04 |
|
| Mechanism-based in vitro screening of potential cancer chemopreventive agents. | 2003-03-12 |
|
| Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic. | 2003-03 |
|
| Interactions of herbs with cytochrome P450. | 2003-02 |
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| The combined effects of garlic oil and fish oil on the hepatic antioxidant and drug-metabolizing enzymes of rats. | 2003-02 |
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| Prevention of chemical carcinogen DNA binding and inhibition of nuclear RNA polymerase activity by organosulfur compounds as the possible mechanisms for their anticancer initiation and proliferation effects. | 2003 |
|
| Enhancement of glutathione and g-glutamylcysteine synthetase, the rate limiting enzyme of glutathione synthesis, by chemoprotective plant-derived food and beverage components in the human hepatoma cell line HepG2. | 2003 |
|
| Antigenotoxic potential of certain dietary constituents. | 2003 |
|
| Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregation. | 2002-12-15 |
|
| Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds. | 2002-12 |
|
| Effect of garlic on cardiovascular disorders: a review. | 2002-11-19 |
|
| Induction of apoptosis by diallyl sulfide in DMBA-induced mouse skin tumors. | 2002 |
|
| [Status of and prospect on experimental studies of single Chinese herb inducing tumor cell apoptosis]. | 2001-01 |
|
| A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat. Effects of chemicals of varied structure. | 1992-03-03 |
Sample Use Guides
cisplatin-induced nephrotoxicity in rats: diallyl sulfide (DAS) was given at two dose levels; 50 and 100 mg/kg, orally for 4 consecutive days, starting one hour after administration of single dose of cisplatin (3.5 mg/kg, i.p.).
Route of Administration:
Oral
Diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS) at 25 μM for 24-h and 48-h incubations promoted expression of drug resistant genes in colo 205 human colon cancer cells. Cells were treated with 25 uM DAS, DADS and DATS for 24 and 48 h and gene expression levels in colo 205 cells were determined for MRP1, MRP3, MRP4 and MRP6. Results indicated that DAS and DADS enhanced Mdr3 gene expression at the 48-h treatment, but did not affect MRP1, MRP4 and MRP6 gene expression in colo 205 cells. However, DAS and DADS inhibited the gene expressions of MRPs at 24 and 48-h treatment, and both inhibited MRP3 at 24-h treatment and inhibited MRP4 at 48 h treatment in colo 205 cells.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:35:55 GMT 2025
by
admin
on
Mon Mar 31 19:35:55 GMT 2025
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| Record UNII |
60G7CF7CWZ
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68520
Created by
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JECFA EVALUATION |
ALLYL SULFIDE
Created by
admin on Mon Mar 31 19:35:55 GMT 2025 , Edited by admin on Mon Mar 31 19:35:55 GMT 2025
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CFR |
21 CFR 172.515
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admin on Mon Mar 31 19:35:55 GMT 2025 , Edited by admin on Mon Mar 31 19:35:55 GMT 2025
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209-775-1
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17376
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60G7CF7CWZ
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1636800
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DTXSID6060470
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m1558
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C038491
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592-88-1
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20947
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105
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7333
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11617
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C68524
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT | |||
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METABOLIC ENZYME -> INHIBITOR |
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METABOLITE -> PARENT |
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