Diallyl disulfide

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
CAS Number	2179-57-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4488 Y
ChEMBL	ChEMBL366603 Y
ChemSpider	15730 Y
ECHA InfoCard	100.016.862
KEGG	C08369 Y
PubChem	16590
InChI 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
Chemical formula	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)
Solubility in water	soluble in ethanol and oils
Hazards
R-phrases	22-36/37/38
S-phrases	22-36/37/38
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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 odor. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the Alliaceae family. 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.

In 1844, Theodor Wertheim separated by steam distillation a pungent-smelling substance from garlic and named it "allyl sulfur." However, only in 1892 could Friedrich Wilhelm Semmler identify diallyl disulfide as one of the components of distilled garlic oil. The natural precursor of diallyl disulfide, allicin, was discovered in 1944 by Chester J. Cavallito and John Hays Bailey. In 1947, A. Stoll and E. Seebeck found that allicin in turn can be produced from the cysteine derivative alliin using the enzyme alliinase.