Diallyl disulfide

Diallyl disulfide (DADS or 4,5-dithia-1,7-octadiene) is an organosulfur compound derived from garlic and a few other genus Allium plants. Along with diallyl trisulfide and diallyl tetrasulfide, it is one of the principal components of the distilled oil of garlic. It is a yellowish liquid which is insoluble in water and has a strong garlic odour. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an allergen causing garlic allergy. Highly diluted, it is used as a flavoring in food. It decomposes in the human body into other compounds such as allyl methyl sulfide.

Diallyl disulfide
Names
Preferred IUPAC name
3-[(Prop-2-en-1-yl)disulfanyl]prop-1-ene
Other names
Diallyl disulfide
Garlicin
1,2-Diallyldisulfane (not recommended)
4,5-Dithia-1,7-octadiene
Identifiers
3D model (JSmol)
1699241
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.862
EC Number
  • 218-548-6
217847
KEGG
PubChem CID
UNII
  • InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2 Y
    Key: PFRGXCVKLLPLIP-UHFFFAOYSA-N Y
  • InChI=1/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
    Key: PFRGXCVKLLPLIP-UHFFFAOYAX
SMILES
  • S(SC\C=C)C\C=C
Properties
C6H10S2
Molar mass 146.28 g/mol
Appearance yellowish clear liquid with an intense garlic smell
Density 1.01 g/cm3
Boiling point 180 °C (356 °F; 453 K)
soluble in ethanol and oils
Hazards
GHS labelling:
Danger
H226, H301, H315, H317, H319
P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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