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 |
|---|---|---|
| A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat. Effects of chemicals of varied structure. | 1992 Mar 3 |
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| [Status of and prospect on experimental studies of single Chinese herb inducing tumor cell apoptosis]. | 2001 Jan |
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| Induction of apoptosis by diallyl sulfide in DMBA-induced mouse skin tumors. | 2002 |
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| Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds. | 2002 Dec |
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| Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregation. | 2002 Dec 15 |
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| Effect of garlic on cardiovascular disorders: a review. | 2002 Nov 19 |
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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 |
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| 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 |
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| Antigenotoxic potential of certain dietary constituents. | 2003 |
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| Short-term acetaldehyde exposure depresses ventricular myocyte contraction: role of cytochrome P450 oxidase, xanthine oxidase, and lipid peroxidation. | 2003 Apr |
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| Neuroprotective effect of antioxidants on ischaemia and reperfusion-induced cerebral injury. | 2003 Aug |
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| Protective effect of diallyl sulfide on oxidative stress and nephrotoxicity induced by gentamicin in rats. | 2003 Dec |
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| Garlic extract and two diallyl sulphides inhibit methicillin-resistant Staphylococcus aureus infection in BALB/cA mice. | 2003 Dec |
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| Interactions of herbs with cytochrome P450. | 2003 Feb |
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| The combined effects of garlic oil and fish oil on the hepatic antioxidant and drug-metabolizing enzymes of rats. | 2003 Feb |
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| Mechanism-based in vitro screening of potential cancer chemopreventive agents. | 2003 Feb-Mar |
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| Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer. | 2003 Jul 24 |
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| Diallylsulfide attenuates asbestos-induced genotoxicity. | 2003 Jun 5 |
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| Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic. | 2003 Mar |
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| The inhibition of superoxide production in EL4 lymphoma cells overexpressing growth hormone. | 2003 May |
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| Inhibition of DES-induced DNA adducts by diallyl sulfide: implications in liver cancer prevention. | 2003 May-Jun |
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| Diallyl sulfide inhibits diethylstilbestrol-induced lipid peroxidation in breast tissue of female ACI rats: implications in breast cancer prevention. | 2003 May-Jun |
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| Induction of multidrug resistance protein 3 (mrp3) in vivo is independent of constitutive androstane receptor. | 2003 Nov |
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| Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry. | 2003 Oct |
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| Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. | 2003 Sep |
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| Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells. | 2004 |
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| Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. | 2004 |
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| Organosulfur compounds from alliaceae in the prevention of human pathologies. | 2004 Apr |
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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 Apr 21 |
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| Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells. | 2004 Dec |
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| Diallyl sulfide induces heme oxygenase-1 through MAPK pathway. | 2004 Dec 15 |
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| 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 Feb |
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| Inhibition of N-acetyltransferase activity and gene expression in human colon cancer cell lines by diallyl sulfide. | 2004 Feb |
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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 Jul 22 |
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| Spice phenolics inhibit human PMNL 5-lipoxygenase. | 2004 Jun |
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| Reversal of P-glycoprotein-mediated multidrug resistance by diallyl sulfide in K562 leukemic cells and in mouse liver. | 2004 Jun |
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| Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. | 2004 Jun 2 |
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| Role of cytochrome P4502E1 activation in proximal tubular cell injury induced by hydrogen peroxide. | 2004 Mar |
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| Inhibitory activity of essential oils of garlic and onion against bacteria and yeasts. | 2004 Mar |
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| [Gladness and troubles for using garlic as an anti-oxidant]. | 2004 May |
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| The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride. | 2004 May |
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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 May |
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| Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation. | 2004 May 14 |
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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 Nov 2 |
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| Role of chemopreventive agents in cancer therapy. | 2004 Nov 25 |
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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 Oct |
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| Antioxidant effects of sulfur-containing amino acids. | 2004 Oct 31 |
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| Effect of garlic (Allium sativum) on lipid peroxidation in experimental myocardial infarction in rats. | 2004 Sep |
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| Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis. | 2004 Sep |
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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 Sep 1 |
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
Fri Dec 15 19:12:51 GMT 2023
by
admin
on
Fri Dec 15 19:12:51 GMT 2023
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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 Fri Dec 15 19:12:51 GMT 2023 , Edited by admin on Fri Dec 15 19:12:51 GMT 2023
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CFR |
21 CFR 172.515
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admin on Fri Dec 15 19:12:51 GMT 2023 , Edited by admin on Fri Dec 15 19:12:51 GMT 2023
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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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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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