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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
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 114.209
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

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
Mechanisms by which garlic and allyl sulfur compounds suppress carcinogen bioactivation. Garlic and carcinogenesis.
2001
Removal of glutathione produces apoptosis and necrosis in HepG2 cells overexpressing CYP2E1.
2001 Apr
Plant foods and risk of gastric cancer: a case-control study in Uruguay.
2001 Aug
Effects of the garlic compound diallyl disulfide on the metabolism, adherence and cell cycle of HT-29 colon carcinoma cells: evidence of sensitive and resistant sub-populations.
2001 Aug
The effects of alcohol and diallyl sulphide on CYP2E1 activity in humans: a phenotyping study using chlorzoxazone.
2001 Jul
In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils.
2001 Jul
Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?
2001 Jun 15
In vitro activity of garlic oil and four diallyl sulphides against antibiotic-resistant Pseudomonas aeruginosa and Klebsiella pneumoniae.
2001 May
Diallyl sulfide inhibition of CYP2E1 does not rescue diabetic rats from thioacetamide-induced mortality.
2001 May 15
Etiology and chemoprevention of esophageal squamous cell carcinoma.
2001 Nov
Chemopreventive allylthiopyridazine derivatives induce apoptosis in SK-Hep-1 hepatocarcinoma cells through a caspase-3-dependent mechanism.
2001 Nov
Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells.
2001 Oct
A pilot study to determine the effectiveness of garlic oil capsules in the treatment of dyspeptic patients with Helicobacter pylori.
2001 Sep
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
In vivo effect of diallyl sulfide and cimetidine on phenacetin metabolism and bioavailability in rat.
2002
Role of endotoxin in NF-kappaB activation by ethanol in rat hepatocytes.
2002 Aug
Mechanisms of protection against aflatoxin B(1) genotoxicity in rats treated by organosulfur compounds from garlic.
2002 Aug
Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats.
2002 Jan 16
Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity.
2002 Jul 1
Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages.
2002 Jun 14
Effects of food materials on removal of Allium-specific volatile sulfur compounds.
2002 Jun 19
Antitumorigenic potential of diallyl sulfide in Ehrlich ascites tumor bearing mice.
2002 Mar
Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.
2002 Nov
Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic.
2002 Oct 9
Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans.
2002 Sep
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
Short-term acetaldehyde exposure depresses ventricular myocyte contraction: role of cytochrome P450 oxidase, xanthine oxidase, and lipid peroxidation.
2003 Apr
Cytochrome P450 2E1 responsiveness in the promoter of glutamate-cysteine ligase catalytic subunit.
2003 Jan
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 DES-induced DNA adducts by diallyl sulfide: implications in liver cancer prevention.
2003 May-Jun
Induction of multidrug resistance protein 3 (mrp3) in vivo is independent of constitutive androstane receptor.
2003 Nov
Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells.
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
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
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
Antioxidant effects of sulfur-containing amino acids.
2004 Oct 31
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 Dec 17 02:13:44 UTC 2022
Edited
by admin
on Sat Dec 17 02:13:44 UTC 2022
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 Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
JECFA EVALUATION ALLYL SULFIDE
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
CFR 21 CFR 172.515
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
209-775-1
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
RXCUI
17376
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY RxNorm
FDA UNII
60G7CF7CWZ
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
RS_ITEM_NUM
1636800
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
EPA CompTox
DTXSID6060470
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
MERCK INDEX
M1558
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY Merck Index
MESH
C038491
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
CAS
592-88-1
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
NSC
20947
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
HSDB
7333
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
PUBCHEM
11617
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
NCI_THESAURUS
C68524
Created by admin on Sat Dec 17 02:13:44 UTC 2022 , Edited by admin on Sat Dec 17 02:13:44 UTC 2022
PRIMARY
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