Diallyl disulfide

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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
3D model (
JSmol
)
1699241
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.016.862 Edit this at Wikidata
EC Number
  • 218-548-6
217847
KEGG
UNII
  • InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2 checkY
    Key: PFRGXCVKLLPLIP-UHFFFAOYSA-N checkY
  • InChI=1/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
    Key: PFRGXCVKLLPLIP-UHFFFAOYAX
  • S(SC\C=C)C\C=C
Properties
C6H10S2
Molar mass 146.28 g/mol
Appearance yellowish clear liquid with an intense garlic smell[1]
Density 1.01 g/cm3[2]
Boiling point 180 °C (356 °F; 453 K)
soluble in ethanol and oils[1]
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)

Diallyl disulfide (DADS or 4,5-dithia-1,7-octadiene) is an

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
.

History

In 1844,

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.[3][4]

Occurrence

Diallyl disulfide and trisulfide are produced by decomposition of

Alliaceae plants, especially garlic. The diallyl disulfide yield is the highest for the steam distillation of garlic bulbs which contain about 2 wt.% of diallyl disulfide-rich oil. Diallyl disulfide can also be extracted from garlic leaves, but their oil content is significantly lower at 0.06 wt.%.[5][6]

Extraction and representation

On an industrial scale, diallyl disulfide is produced from sodium disulfide and

exothermic and its theoretical efficiency of 88% has been achieved in practice.[7]

Smaller quantities can be synthesized from the same starting materials, but in air and using

DATS), etc.). They have very similar physical properties and therefore, a typical commercial product contains only 80% of diallyl disulfide. The conversion of allicin to diallyl disulfide and trisulfide takes place particularly rapidly above 37 °C.[9]

Properties

Physical characteristics

Diallyl disulfide has a strong garlic smell. It is a clear, yellowish liquid which boils at 138–139 °C (for the typical 80% purity) and has its flash point at 50 °C, a density of about 1.0 g/mL and a vapor pressure of 1 mmHg at 20 °C. It is non-polar; therefore, diallyl disulfide is insoluble in water and is soluble in fats, oils, lipids, and non-polar solvents such as hexane or toluene.[1][2]

Chemical reactions

Diallyl disulfide can be readily oxidized to

alkyl halides forming 1-alkylthio-3-allylthio-1-propene and 1,3-di(alkylthio)propene.[12]

Applications

In the presence of

polysulfides (polysulfanes). In agriculture, diallyl disulfide and related diallyl polysulfides show useful activity as environmentally-benign nematicides.[3] Diallyl disulfide is also a starting material for the synthesis of allicin. In the food industry, diallyl disulfide is used to improve the taste of meat, vegetables and fruits.[1][14]

Biological importance

Smell and taste

The unpleasant smell of diallyl disulfide is perceived through the

Alliaceae plants have likely developed the diallyl disulfide-TRPA1 protection mechanism against predators at the early stages of the evolution.[15][16]

Poisoning and detoxification

Diallyl disulfide is an efficient agent for detoxication of the cells. It significantly increases the production of the enzyme

electrophilic toxins in the cell. Garlic therefore supports, for example, the detoxification function of liver cells in vitro and protects nerve cells from oxidative stress, also in vitro.[17][18][19][20][21][22][23][24] The detoxification effect may prevent symptoms of inflammation. This was confirmed in a study on rats where prolonged administration of diallyl disulfide protected poisoning of their intestinal cells. This study also showed that certain side effects of high doses of garlic oil are not attributable to the diallyl disulfide.[25] By supporting the detoxification activity in the liver, diallyl disulfide might offer liver protection during the chemotherapy, e.g. against cyanide detoxification.[26][27]

Antimicrobial effect

The release of

endotoxemia in heart valve operations.[31]

Protection against colon cancer

Garlic can prevent colorectal cancer,[32] and several studies revealed that diallyl disulfide is a major component responsible for this action. The effect is dose dependent as demonstrated on mice.[33][34] Diallyl disulfide affects cancer cells much more strongly than normal cells.[35] It also results in a strong and dose-dependent accumulation of several agents, such as reactive oxygen species, which activate enzyme and lead to destruction of cancer cells.[36]

Protection against cardiovascular disease

There is evidence that garlic may prevent the development of cardiovascular diseases. A possible reason for some of these diseases, such as

coronary heart disease is oxidative stress. The latter is reduced by diallyl disulfide by assisting in the detoxification of the cell, as well as some other mechanisms.[4] By activating the TRPA1 ion channel, diallyl disulfide leads to a short-term lowering of blood pressure.[15]

Safety

Diallyl disulfide is a skin irritant and an allergen. In particular, it is the main cause of garlic allergy (allergic contact dermatitis to garlic). The allergy usually starts at the fingertips and cannot be prevented by wearing gloves because diallyl disulfide penetrates through most commercial glove types.[37][38][39][40]

The median lethal dose (LD50) for oral intake in rats is 260 mg per kg of body weight and it is 3.6 g/kg for dermal intake. High doses of 5 g/kg placed on the skin of cats cause death through hemolytic anemia.[1][41]

Diallyl disulfide can be easily detected in the air or in the blood with gas chromatography.[42][43]

See also

References