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Merck
CN

SMB00378

Diallyl disulfide

≥98% (HPLC)

Synonym(s):

Allyl disulfide, Diallyl disulfide

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About This Item

Linear Formula:
CH2=CHCH2SSCH2CH=CH2
CAS Number:
2179-57-9
Molecular Weight:
146.27
UNSPSC Code:
12352200
NACRES:
NA.25
PubChem Substance ID:
329824979
EC Number:
218-548-6
Beilstein/REAXYS Number:
1699241
MDL number:
MFCD00008656

Key Documents

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Product Name

Diallyl disulfide, ≥98% (HPLC)

biological source

Allium sativum L.

InChI

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

InChI key

PFRGXCVKLLPLIP-UHFFFAOYSA-N

SMILES string

C=CCSSCC=C

vapor density

>5 (vs air)

vapor pressure

1 mmHg ( 20 °C)

assay

≥98% (HPLC)

form

oil

color

colorless to yellow

refractive index

n20/D 1.541 (lit.)

bp

180-195 °C (lit.)

density

1.008 g/mL at 25 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

200

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Application

Diallyl disulfide has been used:
  • to study its effects in apoptosis induction and cell viability on different glioma cell lines
  • as a treatment and positive control to assess the anti-inflammatory regulation of nuclear factor erythroid-2 related factor-2 (Nrf2) in breast cancer cells
  • as a potential substrate compound to detect hydrogen sulfide (H2S) production via lead acetate/lead sulfide method

Biochem/physiol Actions

Diallyl disulfide is a potent anticancer agent. It can reduce carcinogen-induced cancers and shows anti-proliferative effects in both in vivo and in vitro models. DADS enhances the anti-obesity and anti-inflammatory effects of green tea in high-fat/high-sucrose (HF/HS) diet-fed mice. It also displays antioxidant, anti-microbial, cardiovascular protective, and neuroprotective activities. DADS elicits anti-mitotic and anti-neoplastic effects and arrests mitosis in colon neoplastic lesions in vivo and colon tumor cell growth in vitro experiments.
Organosulfur compound that is naturally found in garlic. Contributes to the pungent odor of crushed garlic. Anticancer agent and may provide protection against cardiovascular disease.

General description

Diallyl disulfide (DADS) is an oil-soluble volatile organosulfur compound that can be naturally found in Allium sativum (garlic). It has a simple chemical structure with two sulfur atoms attached with two allyl groups. This constitute of garlic contributes to its pungent aroma.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000485849
0000485850
0000485850
0000485849
0000438992

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Jaehoon Bae et al.
The Journal of nutritional biochemistry, 64, 152-161 (2018-12-06)
Obesity is a major problem in developed countries and a burden on social health care systems. Several epidemiological studies showed the protective effects of green tea against obesity-related diseases. Cyclic guanosine monophosphate (cGMP) acts as a mediator for the physiological
Xiuxiu Song et al.
Evidence-based complementary and alternative medicine : eCAM, 2021, 5103626-5103626 (2021-11-09)
Garlic is widely accepted as a functional food and an excellent source of pharmacologically active ingredients. Diallyl disulfide (DADS), a major bioactive component of garlic, has several beneficial biological functions, including anti-inflammatory, antioxidant, antimicrobial, cardiovascular protective, neuroprotective, and anticancer activities.
Anna Choromanska et al.
Biomedical reports, 13(4), 32-32 (2020-08-18)
Gliomas are a group of malignant brain tumors. Despite significant efforts to optimize treatment options for patients with high-grade glioma, the prognosis of the overwhelming majority of patients remain poor. This bleak prognosis despite treatment of the glioma, is partly
V Robert et al.
Carcinogenesis, 22(8), 1155-1161 (2001-07-27)
Diallyl disulfide (DADS) is a major organosulphur compound present in garlic with an anti-mitotic potential against colon neoplastic lesions in vivo and colon tumour cell growth in vitro. Using the human colon adenocarcinoma HT-29 Glc(-/+) cell line we identified sub-populations
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.
Robert V, et al.
Carcinogenesis, 22(8), 1155-1161 (2001)
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