ALLYL DISULFIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10S2
Molecular Weight	146.274
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=CCSSCC=C

InChI

InChIKey=PFRGXCVKLLPLIP-UHFFFAOYSA-N

InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2

HIDE SMILES / InChI

Molecular Formula	C6H10S2
Molecular Weight	146.274
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122 | https://www.ncbi.nlm.nih.gov/pubmed/29329251 | https://www.ncbi.nlm.nih.gov/pubmed/28847761

Diallyl disulfide (DADS) or allyl disulfide is the main organosulfur ingredient in garlic, with known antioxidant and anti-inflammatory activities. It has been shown to have multi-targeted antitumor activities in a variety of cancer cells Experiments in vitro have revealed, that diallyl disulfide inhibits the metastasis of type Ⅱ esophageal-gastric junction adenocarcinoma cells via NF-κB and PI3K/AKT signaling pathways. At the same time, was shown the drug suppresses cell stemness, proliferation, metastasis and glucose metabolism in breast cancer stem cells partly through the inhibition of CD44/PKM2/AMPK. Besides diallyl disulfide can be a promising agent for the treatment of emphysema, this was discovered in experiments on rats. And also drug shows protective effects against acetaminophen (AAP)-induced acute hepatotoxicity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
PI3K-Akt signaling pathway 25 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Inhibitor 8504
CD44 antigen 1 Target ID: P16070\|\|\|Q13419\|\|\|Q13980\|\|\|Q86Z27\|\|\|Q9UCB0 Gene ID: 960.0 Gene Symbol: CD44 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8504
Pyruvate kinase PKM 1 Target ID: P14618\|\|\|Q96E76 Gene ID: 5315.0 Gene Symbol: PKM Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8504
AMPK signaling pathway 7 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Esophageal-gastric junction adenocarcinoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Primary	Basic research	Unknown Approved Use Unknown
Emphysema 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29329251	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Primary	Preclinical	Unknown Approved Use Unknown
Acetaminophen-induced hepatotoxicity 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28847761	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of CYP2E1 reverses CD4+ T-cell alterations in trichloroethylene-treated MRL+/+ mice.	2000 Apr	10774820
Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme induction.	2001 Aug 22	11448651
Screening of organosulfur compounds as inhibitors of human CYP2A6.	2001 Jul	11408364
Induction of histone acetylation in rat liver and hepatoma by organosulfur compounds including diallyl disulfide.	2001 Jul-Aug	11724364
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	11397556
Anti-tumour-promoting action of Allium constituents.	2002	12484213
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	12230020
Mechanisms of protection against aflatoxin B(1) genotoxicity in rats treated by organosulfur compounds from garlic.	2002 Aug	12151352
Eat your garlic!	2002 Dec	14696636
Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds.	2002 Dec	12636097
Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregation.	2002 Dec 15	12676192
Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages.	2002 Jun 14	12044841
Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.	2002 Nov	12430700
Effect of garlic on cardiovascular disorders: a review.	2002 Nov 19	12537594
Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic.	2002 Oct 9	12358493
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	14585324
Garlic extract and two diallyl sulphides inhibit methicillin-resistant Staphylococcus aureus infection in BALB/cA mice.	2003 Dec	14585852
Effects of garlic powders with varying alliin contents on hepatic drug metabolizing enzymes in rats.	2003 Dec 17	14664517
A comparative study of allitin and garlic on lipid turnover in a teleost, Anabas testudineus (Bloch).	2003 Mar	15267155
Prevention and therapy of fungal infection in severe acute pancreatitis: A prospective clinical study.	2003 Nov	14606111
Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry.	2003 Oct	12923610
Photocontact allergy to diallyl disulfide.	2003 Sep	14744409
Anticarcinogenic properties of garlic: a review.	2004	15615431
Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells.	2004	15523159
Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3.	2004	15203378
Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice.	2004 Aug	15301936
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	14991270
[Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways].	2004 Feb	14960237
Enhancement of diallyl disulfide-induced apoptosis by inhibitors of MAPKs in human HepG2 hepatoma cells.	2004 Jul 15	15194004
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	15184882
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.	2004 Jun 2	15161248
Selective expression of glutathione S-transferase genes in the murine gastrointestinal tract in response to dietary organosulfur compounds.	2004 Mar	14633659
[The initiation of G2/M checkpoint by diallyl disulfide requires the activation of p38 MAP kinase in HL-60 cells].	2004 May	15182534
The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride.	2004 May	15046820
Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.	2004 Nov	15604822
Diallyl disulfide, a chemopreventive agent in garlic, induces multidrug resistance-associated protein 2 expression.	2004 Nov 12	15474518
Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells.	2004 Oct	15304301
Antioxidant effects of sulfur-containing amino acids.	2004 Oct 31	15515186
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.	2004 Sep	15234078
Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation.	2005 Apr 29	15862674
Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells.	2005 Jul	15833378
Differential effects of diallyl disulfide on neuronal cells depend on its concentration.	2005 Jul 1	15863251
A case-control study in Shanghai of fruit and vegetable intake and endometrial cancer.	2005 Jun 6	15886701
Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues.	2005 Mar-Apr	15886420

Patents

Sample Use Guides

In Vivo Use Guide

Rat emphysema model: the rat emphysema model was established by intraperitoneal injection of cigarette smoke extract (CSE). Each rat in the CSE group was intraperitoneally injected with 1mL CSE-PBS solution on days 1, 8, and 15. Rats in the diallyl disulfide (DADS) and budesonide groups were intraperitoneally injected with 1 mL of CSE on Days 1, 8, and 15 along with the daily injection of DADS or budesonide. The doss of test groups were as follows: 100 and 10 mg/kg/day for DADS and budesonide, respectively.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Diallyl disulfide (DADS) inhibited cell viability of OE19 cells with low cytotoxicity to healthy hepatocytes, L02 cells, in vitro. Non-toxic doses of DADS were ≤10 µg/ml for a 24-h treatment. These non-toxic doses of DADS were found to block the metastasis of OE19 cells by suppressing MMPs, increasing u-PA and TIMPs, as well as altering the balance of MMPs/TIMPs, which at least in part resulted from the suppression of NF-κB and PI3K/AKT signaling pathways.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:56:18 GMT 2025` Edited by `admin` on `Mon Mar 31 18:56:18 GMT 2025`
Record UNII	5HI47O6OA7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIALLYL DISULFIDE

Preferred Name

English

ALLYL DISULFIDE

Systematic Name

English

ALLYL DISULPHIDE

Systematic Name

English

NSC-29228

Code

English

ALLYL DISULFIDE [FHFI]

Common Name

English

DIALLYL DISULPHIDE

Systematic Name

English

2-PROPENYL DISULFIDE

Systematic Name

English

FEMA NO. 2028

Code

English

DIALLYL DISULFIDE [HSDB]

Common Name

English

ALLYL DISULFIDE [USP-RS]

Common Name

English

DIALLYLDISULFIDE

Systematic Name

English

2-PROPENYL DISULPHIDE

Systematic Name

English

DISULFIDE, DI-2-PROPENYL

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

129087