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Diallyl sulfide

Di-(2-propenyl) sulfide

Allyl sulfide · Thioallyl ether

Aliphatic alkene sulfide · C₆H₁₀S

Chemical structure of Diallyl sulfide
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
592-88-1
Molecular formula
C₆H₁₀S
Molecular weight
114.21 g/mol
Aroma
Garlic-like, less pungent than diallyl disulfide, slightly sweet.

Safety

Low concern · Chemopreventive

Diallyl sulfide occurs at low levels in garlic and mustard oils. It is less toxic than diallyl disulfide and shows pronounced protective activity.

Skin. A 0.5 percent patch test on 22 volunteers produced no irritation or sensitization. Undiluted, it was extremely irritating to rabbit skin. In garlic-sensitive patients it caused no sensitization reactions.

Oral. Acute oral LD50 in mice is 2.03 g/kg (male) and 1.81 g/kg (female), in rats 2.98 g/kg. Acute dermal LD50 in rabbits exceeds 5 g/kg.

Cardiovascular. Strong antiplatelet aggregation activity in vitro.

Liver. Protects against paracetamol- and aflatoxin B1-induced liver toxicity. Much less cytotoxic to hepatocytes than diallyl disulfide.

Cancer. Significant chemopreventive activity across multiple animal models, including colon, lung, skin, esophageal, liver and breast cancers.


Usage guidelines

Concern level
Low
Anticoagulant therapy
Caution due to antiplatelet activity
Oils with high content
Mustard 0 – 5.5 percent, Garlic 1.1 – 2.4 percent

Found in essential oils

Principal sources
Mustard0 – 5.5 %
Garlic1.1 – 2.4 %

Pharmacokinetics

Diallyl sulfide is mainly metabolized to allyl methyl sulfide in rat hepatocytes. The compound induces phase II detoxifying enzymes such as quinone reductase and glutathione S-transferase.


Notes

Diallyl sulfide shows more pronounced protective activity than diallyl disulfide, being both hepatoprotective and chemopreventive without significant hepatocyte toxicity.