Diallyl disulfide

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Diallyl disulfide
Diallyl disulfide.svg
Diallyl-disulfide-from-xtal-3D-bs.png
Diallyl-disulfide-from-xtal-3D-sf.png
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 OOjs UI icon edit-ltr-progressive.svg
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 Yes check.svgY
    Key: PFRGXCVKLLPLIP-UHFFFAOYSA-N Yes check.svgY
  • 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 146.27 g·mol−1
AppearanceYellowish clear liquid [1]
Odor 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:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diallyl disulfide (DADS or 4,5-dithia-1,7-octadiene) is an organosulfur compound derived from garlic and a few other plants in the genus Allium . [3] 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 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.

Contents

History

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. [3] [4]

Occurrence

Diallyl disulfide and the related trisulfide are produced by decomposition of allicin, which is released upon breaking the cells of the 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 allyl bromide or allyl chloride at temperatures of 40–60 °C in an inert gas atmosphere; sodium disulfide is generated in situ by reacting sodium sulfide with sulfur. The reaction is exothermic and its theoretical efficiency of 88% has been achieved in practice. [7]

Diallyldisulfid formation.png

Smaller quantities can be synthesized from the same starting materials, but in air and using tetrabutylammonium bromide as a catalyst. The corresponding yield is below 82%. [8] The major problem, both in the industrial synthesis and in the extraction from plants, is separation of diallyl disulfide from higher sulfides (diallyl trisulfide (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 allicin with hydrogen peroxide or peracetic acid. Allicin in turn can hydrolyze giving diallyl disulfide and trisulfide. Reaction of diallyl disulfide with liquid sulfur gives a mixture containing diallyl polysulfides with as many as 22 sulfur atoms in a continuous chain identified. [3] [10] When diallyl disulfide is heated it decomposes giving a complex mixture. The carbon-sulfur bond of diallyl disulfide is 16 kcal mol−1 weaker than the sulfur-sulfur bond (46 kcal mol−1 versus 62 kcal mol−1, respectively), with the consequence that on heating diallyl disulfide gives the allyldithio radical (AllSS•), which through addition to the double bonds in diallyl disulfide followed by fragmentation and subsequent reactions generates numerous organosulfur compounds, many of which are found in trace amounts in distilled garlic oil. [3] [11] In the presence of a catalyst, diallyl disulfide can combine with alkyl halides forming 1-alkylthio-3-allylthio-1-propene and 1,3-di(alkylthio)propene. [12]

Applications

In the presence of iron chloride or copper chloride catalyst, or of liquid sulfur at 120 °C [3] [13] Diallyl disulfide can be used as a precursor for the synthesis of higher diallyl 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 transient receptor potential cation channel, member A1 (TRPA1). This ion channel had long been present not only in humans and animals, but even in fungi. Thus, 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 glutathione S-transferase (GST), which binds 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 organosulfur compounds upon destruction of Alliaceae plant cells has great importance, because of the antimicrobial, insecticidal and larvicidal properties of those compounds. [28] In particular, diallyl disulfide is the main reason for inhibiting the growth of molds and bacteria by garlic oil. It is also acts against the stomach ulcer germ Helicobacter pylori , however not as efficiently as allicin. [29] [30] Because of its antimicrobial effects, diallyl disulfide, together with tobramycin, is included in preparations which are used for selective decontamination of the organs (e.g. gut) before surgical operations. A clinical study showed that such preparations prevent 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 atherosclerosis or 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

Related Research Articles

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Sulfur (also spelled sulphur in British English) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with the chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature.

<span class="mw-page-title-main">Garlic</span> Species of edible plant

Garlic is a species of bulbous flowering plant in the genus Allium. Its close relatives include the onion, shallot, leek, chive, Welsh onion, and Chinese onion. It is native to Central Asia, South Asia and northeastern Iran and has long been used as a seasoning worldwide, with a history of several thousand years of human consumption and use. It was known to ancient Egyptians and has been used as both a food flavoring and a traditional medicine. China produced 73% of the world's supply of garlic in 2021.

<span class="mw-page-title-main">Thiol</span> Any organic compound having a sulfanyl group (–SH)

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<span class="mw-page-title-main">Allicin</span> Chemical compound

Allicin is an organosulfur compound obtained from garlic. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is an antifeedant, i.e. the defense mechanism against attacks by pests on the garlic plant.

<span class="mw-page-title-main">Allyl isothiocyanate</span> Chemical compound

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but more soluble in most organic solvents.

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Alliin is a sulfoxide that is a natural constituent of fresh garlic. It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene. Garlic powder is not a source of alliin, nor is fresh garlic upon maceration, since the enzymatic conversion to allicin takes place in the order of seconds.

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References

  1. 1 2 3 4 5 6 allyl disulfide
  2. 1 2 Diallyl disulfide at Sigma Aldrich
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  33. ↑ Milner, John A (2006). "Preclinical Perspectives on Garlic and Cancer". The Journal of Nutrition. 136 (3): 827S–831S. doi: 10.1093/jn/136.3.727S . PMID   16484574.
  34. ↑ Yang, JS; Kok, LF; Lin, YH; Kuo, TC; Yang, JL; Lin, CC; Chen, GW; Huang, WW; et al. (2006). "Diallyl disulfide inhibits WEHI-3 leukemia cells in vivo". Anticancer Research. 26 (1A): 219–25. PMID   16475702.
  35. ↑ Huang, Z; Lei, X; Zhong, M; Zhu, B; Tang, S; Liao, D (2007). "Bcl-2 small interfering RNA sensitizes cisplatin-resistant human lung adenocarcinoma A549/DDP cell to cisplatin and diallyl disulfide". Acta Biochimica et Biophysica Sinica. 39 (11): 835–43. doi:10.1111/j.1745-7270.2007.00356.x. PMID   17989874.
  36. ↑ Jo, Hong; Song, Ju; Kim, Kang; Cho, Yong; Kim, Ki; Park, Young (2008). "Diallyl disulfide induces reversible G2/M phase arrest on a p53-independent mechanism in human colon cancer HCT-116 cells". Oncology Reports. 19 (1): 275–80. doi: 10.3892/or.19.1.275 . PMID   18097607.
  37. ↑ Block, E (2009). Garlic and other alliums: the lore and the science. Royal Society of Chemistry. p. 228. ISBN   978-0-85404-190-9.
  38. ↑ Horn, TD (2003). Dermatology, Volume 2. Elsevier Health Sciences. p. 305. ISBN   978-0-323-02578-2.
  39. ↑ Garlic Archived 2010-06-15 at the Wayback Machine
  40. ↑ Moyle, Mignon; Frowen, Kath; Nixon, Rosemary (2004). "Use of gloves in protection from diallyl disulphide allergy". Australasian Journal of Dermatology. 45 (4): 223–225. doi:10.1111/j.1440-0960.2004.00102.x. PMID   15527433. S2CID   38878468.
  41. ↑ EPA documents
  42. ↑ documents of the U.S. Department of Labor Occupational Safety & Health
  43. ↑ Sun, X; Guo, T; He, J; Zhao, M; Yan, M; Cui, F; Deng, Y (2006). "Simultaneous determination of diallyl trisulfide and diallyl disulfide in rat blood by gas chromatography with electron-capture detection". Die Pharmazie. 61 (12): 985–8. PMID   17283653.
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