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SMB00378

Sigma-Aldrich

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
Beilstein:
1699241
EC Number:
218-548-6
MDL number:
MFCD00008656
UNSPSC Code:
12352200
PubChem Substance ID:
329824979
NACRES:
NA.25

biological source

Allium sativum L.

Quality Level

200

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

SMILES string

C=CCSSCC=C

InChI

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

InChI key

PFRGXCVKLLPLIP-UHFFFAOYSA-N

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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.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

Certificates of Analysis (COA)

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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.
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
Effects of drying time on the aroma of garlic (Allium sativum L.) seasoning powder
Li Kaixuan, et al.,
Flavour and Fragrance Journal, 36(1), 99-110 (2021)
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)
You Jeong Lee et al.
Artificial cells, nanomedicine, and biotechnology, 48(1), 948-960 (2020-06-05)
Onion (Allium cepa) extract was used for the green synthesis of gold and silver nanoparticles. Each colloidal solution exhibited surface plasmon resonance, with a peak at 532 nm for gold nanoparticles and 391 nm for silver nanoparticles. Microscopic results confirmed the presence
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