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
Differential effects of diallyl disulfide on neuronal cells depend on its concentration.	2005-07-01	15863251
Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells.	2005-07	15833378
A case-control study in Shanghai of fruit and vegetable intake and endometrial cancer.	2005-06-06	15886701
Garlic arrests MDA-MB-435 cancer cells in mitosis, phosphorylates the proapoptotic BH3-only protein BimEL and induces apoptosis.	2005-05-09	15827557
Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation.	2005-04-29	15862674
Modulation of cytokine secretion by garlic oil derivatives is associated with suppressed nitric oxide production in stimulated macrophages.	2005-04-06	15796590
Differential effects of organosulfur compounds from garlic oil on nitric oxide and prostaglandin E2 in stimulated macrophages.	2005-04	15811776
Growth suppressing effect of garlic compound diallyl disulfide on prostate cancer cell line (PC-3) in vitro.	2005-04	15802821
Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability.	2005-03-23	15769123
Garlic-fingered chefs.	2005-03	15811038
Protective effect of diallyl disulfide on oxidative stress-injured neuronally differentiated PC12 cells.	2005-02-18	15710234
Inhibition by allyl sulfides and crushed garlic of O6-methylguanine formation in liver DNA of dimethylnitrosamine-treated rats.	2005	15749632
Diallyldisulfide-induced calcium response of HL-60 human promyelocytes.	2004-12-14	15587801
[The experimental study of garlicin in treating Pneumocystis carinii pneumonia in rats].	2004-12	15830863
Repetitive treatments of colon HT-29 cells with diallyl disulfide induce a prolonged hyperacetylation of histone H3 K14.	2004-12	15659844
Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells.	2004-12	15500931
Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals.	2004-11-15	15477009
Diallyl disulfide, a chemopreventive agent in garlic, induces multidrug resistance-associated protein 2 expression.	2004-11-12	15474518
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	15476856
Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.	2004-11	15604822
Use of gloves in protection from diallyl disulphide allergy.	2004-11	15527433
Antioxidant effects of sulfur-containing amino acids.	2004-10-31	15515186
Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells.	2004-10	15304301
Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways.	2004-09-15	15309729
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	15341661
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.	2004-09	15234078
Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice.	2004-08	15301936
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	15184882
Enhancement of diallyl disulfide-induced apoptosis by inhibitors of MAPKs in human HepG2 hepatoma cells.	2004-07-15	15194004
Influence of organosulphur compounds from garlic on the secretion of matrix metalloproteinases and their inhibitor TIMP-1 by cultured HUVEC cells.	2004-07	15499972
Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell lines.	2004-07	14976134
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.	2004-06-02	15161248
Biological activity of volatile di-n-propyl disulfide from seeds of neem, Azadirachta indica (Meliaceae), to two species of stored grain pests, Sitophilus oryzae (L.) and Tribolium castaneum (Herbst).	2004-06	15279303
[Preventive effect and clinical significance of garlicin injection on mechanical ventilator-associated low respiratory tract deep-seated fungal infection].	2004-06	15250201
Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation.	2004-05-14	15139418
[The initiation of G2/M checkpoint by diallyl disulfide requires the activation of p38 MAP kinase in HL-60 cells].	2004-05	15182534
The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride.	2004-05	15046820
Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues.	2004-03-31	15886420
Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake.	2004-03-01	14980597
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	14991270
[Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways].	2004-02	14960237
Mechanism and kinetics of synthesis of allicin.	2004-01	14964414
Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats.	2004	15630193
Anticarcinogenic properties of garlic: a review.	2004	15615431
Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells.	2004	15523159
Conjugated docosahexaenoic acid suppresses KPL-1 human breast cancer cell growth in vitro and in vivo: potential mechanisms of action.	2004	15217495
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
Hepatic metabolism of diallyl disulphide in rat and man.	2003-12	14742141
Photocontact allergy to diallyl disulfide.	2003-09	14744409
A comparative study of allitin and garlic on lipid turnover in a teleost, Anabas testudineus (Bloch).	2003-03	15267155

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