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Documenti fondamentali

SMB00378

Sigma-Aldrich

Diallyl disulfide

≥98% (HPLC)

Sinonimo/i:

Allyl disulfide, Diallyl disulfide

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About This Item

Formula condensata:
CH2=CHCH2SSCH2CH=CH2
Numero CAS:
Peso molecolare:
146.27
Beilstein:
1699241
Numero CE:
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.25

Origine biologica

Allium sativum L.

Livello qualitativo

Densità del vapore

>5 (vs air)

Tensione di vapore

1 mmHg ( 20 °C)

Saggio

≥98% (HPLC)

Stato

oil

Colore

colorless to yellow

Indice di rifrazione

n20/D 1.541 (lit.)

P. ebollizione

180-195 °C (lit.)

Densità

1.008 g/mL at 25 °C (lit.)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

−20°C

Stringa SMILE

C=CCSSCC=C

InChI

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

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbones

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

143.6 °F - closed cup

Punto d’infiammabilità (°C)

62 °C - closed cup


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(+)-L-Alliin analytical standard

Supelco

72805

(+)-L-Alliin

USP

USP

1012950

Alliin

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)
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.

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