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Merck

SMB00378

Sigma-Aldrich

Diallyldisulfid

≥98% (HPLC)

Synonym(e):

Diallyldisulfid

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About This Item

Lineare Formel:
CH2=CHCH2SSCH2CH=CH2
CAS-Nummer:
Molekulargewicht:
146.27
Beilstein:
1699241
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.25

Biologische Quelle

Allium sativum L.

Qualitätsniveau

Dampfdichte

>5 (vs air)

Dampfdruck

1 mmHg ( 20 °C)

Assay

≥98% (HPLC)

Form

oil

Farbe

colorless to yellow

Brechungsindex

n20/D 1.541 (lit.)

bp

180-195 °C (lit.)

Dichte

1.008 g/mL at 25 °C (lit.)

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

−20°C

SMILES String

C=CCSSCC=C

InChI

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

InChIKey

PFRGXCVKLLPLIP-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Piktogramme

Skull and crossbones

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

143.6 °F - closed cup

Flammpunkt (°C)

62 °C - closed cup


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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
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
Lan Yi et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 57, 362-370 (2013-04-16)
Considerable evidence in recent years suggests that garlic has anti-proliferative effects against various types of cancer. Garlic contains water-soluble and oil-soluble sulfur compounds. Oil-soluble compounds such as diallyl sulfide (DAS), diallyl disulfide (DADS), diallyl trisulfide (DATS) and ajoene are more

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