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SMB00378

Sigma-Aldrich

Diallyl disulfide

≥98% (HPLC)

Synonyme(s) :

Allyl disulfide, Diallyl disulfide

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About This Item

Formule linéaire :
CH2=CHCH2SSCH2CH=CH2
Numéro CAS:
2179-57-9
Poids moléculaire :
146.27
Beilstein:
1699241
Numéro CE :
218-548-6
Numéro MDL:
MFCD00008656
Code UNSPSC :
12352200
ID de substance PubChem :
329824979
Nomenclature NACRES :
NA.25

Source biologique

Allium sativum L.

Niveau de qualité

200

Densité de vapeur

>5 (vs air)

Pression de vapeur

1 mmHg ( 20 °C)

Essai

≥98% (HPLC)

Forme

oil

Couleur

colorless to yellow

Indice de réfraction

n20/D 1.541 (lit.)

pb

180-195 °C (lit.)

Densité

1.008 g/mL at 25 °C (lit.)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

C=CCSSCC=C

InChI

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

Clé InChI

PFRGXCVKLLPLIP-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

143.6 °F - closed cup

Point d'éclair (°C)

62 °C - closed cup

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Certificats d'analyse (COA)

Lot/Batch Number
0000365355
0000350708
0000350708
0000365355
0000244221

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Supelco

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USP

USP

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Alliin

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.
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
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
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
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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