SMB00378

Diallyl disulfide

≥98% (HPLC)

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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H315,H319,H335
• pcodes: P301 + P310 + P330 - P302 + P352 - P305 + P351 + P338
• 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_germany: WGK 3
• flash_point_f: 143.6 °F - closed cup
• flash_point_c: 62 °C - closed cup