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Details

Stereochemistry ACHIRAL
Molecular Formula C6H10S
Molecular Weight 114.2099
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIALLYL SULFIDE

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

HIDE SMILES / InChI

Molecular Formula C6H10S
Molecular Weight 114.2099
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: p53/Puma signaling pathway
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of carcinogenesis and toxicity by dietary constituents.
2001
Sodium salicylate increases CYP2E1 levels and enhances arachidonic acid toxicity in HepG2 cells and cultured rat hepatocytes.
2001 Apr
Effect of garlic oil on the levels of various enzymes in the serum and tissue of streptozotocin diabetic rats.
2001 Feb
Ethanol enhances retinoic acid metabolism into polar metabolites in rat liver via induction of cytochrome P4502E1.
2001 Jan
Diallyl sulfide--a flavour component from garlic (Allium sativum) attenuates lipid peroxidation in mice infected with Trichinella spiralis.
2001 May
Effect of diallyl sulfide and diallyl disulfide, the active principles of garlic, on the aflatoxin B(1)-induced DNA damage in primary rat hepatocytes.
2001 May 31
Etiology and chemoprevention of esophageal squamous cell carcinoma.
2001 Nov
Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells.
2001 Oct
Effects of garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity and 2-aminofluorene-DNA adducts in human promyelocytic leukemia cells.
2002
Mechanisms of protection against aflatoxin B(1) genotoxicity in rats treated by organosulfur compounds from garlic.
2002 Aug
Spontaneous oxidative stress and liver tumors in mice lacking methionine adenosyltransferase 1A.
2002 Aug
Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds.
2002 Dec
Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregation.
2002 Dec 15
Mechanisms of circadian rhythmicity of carbon tetrachloride hepatotoxicity.
2002 Jan
Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats.
2002 Jan
Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.
2002 Nov
Antigenotoxic potential of certain dietary constituents.
2003
Short-term acetaldehyde exposure depresses ventricular myocyte contraction: role of cytochrome P450 oxidase, xanthine oxidase, and lipid peroxidation.
2003 Apr
Protective effect of diallyl sulfide on oxidative stress and nephrotoxicity induced by gentamicin in rats.
2003 Dec
Mechanism-based in vitro screening of potential cancer chemopreventive agents.
2003 Feb-Mar
Diallylsulfide attenuates asbestos-induced genotoxicity.
2003 Jun 5
Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic.
2003 Mar
The inhibition of superoxide production in EL4 lymphoma cells overexpressing growth hormone.
2003 May
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
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
Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells.
2004 Dec
Diallyl sulfide induces heme oxygenase-1 through MAPK pathway.
2004 Dec 15
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
Inhibition of N-acetyltransferase activity and gene expression in human colon cancer cell lines by diallyl sulfide.
2004 Feb
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
Spice phenolics inhibit human PMNL 5-lipoxygenase.
2004 Jun
Reversal of P-glycoprotein-mediated multidrug resistance by diallyl sulfide in K562 leukemic cells and in mouse liver.
2004 Jun
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.
2004 Jun 2
Role of cytochrome P4502E1 activation in proximal tubular cell injury induced by hydrogen peroxide.
2004 Mar
Inhibitory activity of essential oils of garlic and onion against bacteria and yeasts.
2004 Mar
[Gladness and troubles for using garlic as an anti-oxidant].
2004 May
The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride.
2004 May
Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation.
2004 May 14
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
Role of chemopreventive agents in cancer therapy.
2004 Nov 25
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
Antioxidant effects of sulfur-containing amino acids.
2004 Oct 31
Effect of garlic (Allium sativum) on lipid peroxidation in experimental myocardial infarction in rats.
2004 Sep
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.
2004 Sep
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
Patents

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 Sat Jun 26 02:40:18 UTC 2021
Edited
by admin
on Sat Jun 26 02:40:18 UTC 2021
Record UNII
60G7CF7CWZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIALLYL SULFIDE
Systematic Name English
DIALLYL SULPHIDE
Systematic Name English
ALLYL SULFIDE [FHFI]
Common Name English
DIALLYL MONOSULPHIDE
Common Name English
ALLYL SULPHIDE
Systematic Name English
ALLYL SULFIDE [MI]
Common Name English
NSC-20947
Code English
ALLYL SULFIDE [USP-RS]
Common Name English
BIS(2-PROPENYL) SULPHIDE
Systematic Name English
ALLYL SULFIDE
FHFI   HSDB   MI   USP-RS  
Systematic Name English
1-PROPENE, 3,3'-THIOBIS-
Systematic Name English
DIALLYL MONOSULFIDE
Common Name English
DI(2-PROPENYL) SULPHIDE
Systematic Name English
DIALLYL THIOETHER
Systematic Name English
BIS(2-PROPENYL) SULFIDE
Systematic Name English
ALLYL SULFIDE [HSDB]
Common Name English
FEMA NO. 2042
Code English
DI(2-PROPENYL) SULFIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C68520
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
JECFA EVALUATION ALLYL SULFIDE
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
CFR 21 CFR 172.515
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
209-775-1
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
RXCUI
17376
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY RxNorm
FDA UNII
60G7CF7CWZ
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
EPA CompTox
592-88-1
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
MERCK INDEX
M1558
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY Merck Index
MESH
C038491
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
CAS
592-88-1
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
USP_CATALOG
1636800
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY USP-RS
HSDB
7333
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
PUBCHEM
11617
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
NCI_THESAURUS
C68524
Created by admin on Sat Jun 26 02:40:18 UTC 2021 , Edited by admin on Sat Jun 26 02:40:18 UTC 2021
PRIMARY
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