Diallyl disulfide
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Names | |||
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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 ) |
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1699241 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.016.862 | ||
EC Number |
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217847 | |||
KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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: | |||
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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Diallyl disulfide (DADS or 4,5-dithia-1,7-octadiene) is an
History
In 1844,
Occurrence
Diallyl disulfide and trisulfide are produced by decomposition of
Extraction and representation
On an industrial scale, diallyl disulfide is produced from sodium disulfide and
Smaller quantities can be synthesized from the same starting materials, but in air and using
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
Applications
In the presence of
Biological importance
Smell and taste
The unpleasant smell of diallyl disulfide is perceived through the
Poisoning and detoxification
Diallyl disulfide is an efficient agent for detoxication of the cells. It significantly increases the production of the enzyme
Antimicrobial effect
The release of
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
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
- ^ a b c d e allyl disulfide
- ^ a b Diallyl disulfide at Sigma Aldrich
- ^ ISBN 9780854041909.[page needed]
- ^ a b Omar, Syed Haris; Hasan, Ahmed; Hunjul, Nashat; Ali, Javed; Aqil, M (2007). "Historical, chemical and cardiovascular perspectives on garlic: A review". Pharmacognosy Reviews. 1 (1): 80–87. Archived from the original on 2012-03-07. Retrieved 2010-05-28.
- PMID 1775579.
- S2CID 95448926.
- ^ WO 2006016881, "PROCESS FOR PRODUCING DIALLYL DISULFIDE", published 16-02-2006
- S2CID 97570822.
- .
- S2CID 95562164.
- .
- OSTI 6388212.
- ^ U.S. patent 8,101,802
- ^ U.S. patent 5,231,114
- ^ PMID 16103371.
- PMID 15080619.
- S2CID 20421070.
- PMID 16251611.
- PMID 11782211.
- PMID 15046820.
- PMID 17534841.
- S2CID 6384362.
- PMID 15710234.
- PMID 15863251.
- PMID 16274720.
- PMID 17560567.
- PMID 15886420.
- S2CID 43748340.
- PMID 11185736.
- PMID 10788416.
- PMID 17535634.
- (PDF, 12 MB)
- PMID 16484574.
- PMID 16475702.
- PMID 17989874.
- PMID 18097607.
- ISBN 978-0-85404-190-9.
- ISBN 978-0-323-02578-2.
- ^ Garlic Archived 2010-06-15 at the Wayback Machine
- S2CID 38878468.
- ^ EPA documents
- ^ documents of the U.S. Department of Labor Occupational Safety & Health
- PMID 17283653.