View source for Chemistry:Diallyl disulfide

{{short description|Chemical compound}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443633922
| Name = Diallyl disulfide
| ImageFile = 1,2-diallyldisulfane 200.svg
| ImageName = Diallyl disulfide
| ImageFileL1 = Diallyl-disulfide-from-xtal-3D-bs.png
| ImageFileR1 = Diallyl-disulfide-from-xtal-3D-sf.png
| ImageSizeR1 = 150
| PIN = 3-[(Prop-2-en-1-yl)disulfanyl]prop-1-ene
| OtherNames = Diallyl disulfide<br />Garlicin<br />1,2-Diallyldisulfane (not recommended)<br />4,5-Dithia-1,7-octadiene
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 15730
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C08369
| InChI = 1/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
| InChIKey = PFRGXCVKLLPLIP-UHFFFAOYAX
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 366603
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PFRGXCVKLLPLIP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 2179-57-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5HI47O6OA7
| PubChem = 16590
| Beilstein = 1699241
| Gmelin = 217847
| EC_number = 218-548-6
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4488
| SMILES = S(SC\C=C)C\C=C
}}
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>10</sub>S<sub>2</sub>
| Appearance = yellowish clear liquid with an intense garlic smell<ref name="gsc">[http://www.thegoodscentscompany.com/data/rw1002791.html allyl disulfide]</ref>
| MolarMass = 146.28 g/mol
| Density = 1.01 g/cm<sup>3</sup><ref name="sa">[http://www.sigmaaldrich.com/catalog/search/ProductDetail/sigma/smb00378 Diallyl disulfide at Sigma Aldrich]</ref>
| MeltingPt = 
| BoilingPtC = 180
| Solubility = soluble in [[Chemistry:Ethanol|ethanol]] and oils<ref name="gsc" />
 }} 
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|301|315|317|319}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|272|280|301+310|302+352|303+361+353|305+351+338|321|330|332+313|333+313|337+313|362|363|370+378|403+235|405|501}}
}}
}}
'''Diallyl disulfide''' ('''DADS''' or '''4,5-dithia-1,7-octadiene''') is an organosulfur compound derived from [[Biology:Garlic|garlic]] and a few other genus ''[[Biology:Allium|Allium]]'' plants.<ref Name="Block">{{cite book |last1=Block |first1=Eric |year=2010 |title=Garlic and Other Alliums: The Lore and the Science |url={{Google books|6AB89RHV9ucC|plainurl=yes}} |publisher=Royal Society of Chemistry |isbn=9780854041909 }}{{page needed|date=September 2018}}</ref> Along with [[Chemistry:Diallyl trisulfide|diallyl trisulfide]] and diallyl tetrasulfide, it is one of the principal components of the distilled [[Chemistry:Oil|oil]] of [[Biology:Garlic|garlic]]. It is a yellowish liquid which is insoluble in water and has a strong garlic odour. It is produced during the decomposition of [[Chemistry:Allicin|allicin]], which is released upon crushing [[Biology:Garlic|garlic]] and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an [[Biology:Allergen|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 [[Chemistry:Allyl methyl sulfide|allyl methyl sulfide]].

== History ==
In 1844, Theodor Wertheim separated by [[Chemistry:Steam distillation|steam distillation]] a pungent-smelling substance from garlic and named it "[[Chemistry:Allyl|allyl]] [[Chemistry:Sulfur|sulfur]]." However, only in 1892 could Friedrich Wilhelm Semmler identify diallyl disulfide as one of the components of distilled [[Chemistry:Garlic oil|garlic oil]]. The natural precursor of diallyl disulfide, [[Chemistry:Allicin|allicin]], was discovered in 1944 by Chester J. Cavallito and John Hays Bailey. In 1947, A. Stoll and E. Seebeck found that [[Chemistry:Allicin|allicin]] in turn can be produced from the [[Chemistry:Cysteine|cysteine]] derivative [[Chemistry:Alliin|alliin]] using the enzyme [[Biology:Alliinase|alliinase]].<ref Name="Block"/><ref Name="omar">{{cite journal |first1=Syed Haris |last1=Omar |first2=Ahmed |last2=Hasan |first3=Nashat |last3=Hunjul |first4=Javed |last4=Ali |first5=M |last5=Aqil |url=http://www.phcogrev.com/article.asp?issn=0973-7847;year=2007;volume=1;issue=1;spage=80;epage=87;aulast=Omar;type=0 |title=Historical, chemical and cardiovascular perspectives on garlic: A review |journal=Pharmacognosy Reviews |volume=1 |year=2007 |pages=80–87 |issue=1 |access-date=2010-05-28 |archive-url=https://web.archive.org/web/20120307003643/http://www.phcogrev.com/article.asp?issn=0973-7847;year=2007;volume=1;issue=1;spage=80;epage=87;aulast=Omar;type=0 |archive-date=2012-03-07 |url-status=dead }}</ref>

==Occurrence==
Diallyl disulfide and trisulfide are produced by decomposition of [[Chemistry:Allicin|allicin]], which is released upon breaking the cells of the Alliaceae plants, especially [[Biology:Garlic|garlic]]. The diallyl disulfide yield is the highest for the [[Chemistry:Steam distillation|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.%.<ref>{{cite journal |doi=10.1055/s-2006-960119 |title=Identification and HPLC Quantitation of the Sulfides and Dialk(en)yl Thiosulfinates in Commercial Garlic Products |year=2007 |last1=Lawson |first1=L |last2=Wang |first2=Z |last3=Hughes |first3=B |journal=Planta Medica |volume=57 |pages=363–370 |pmid=1775579 |issue=4 }}</ref><ref>{{cite journal |doi=10.1007/s00217-001-0429-2 |title=Investigation of the volatile aroma components of garlic leaves essential oil. Possibility of utilization to enrich garlic bulb oil |year=2002 |last1=Edris |first1=A |last2=Fadel |first2=H |journal=European Food Research and Technology |volume=214 |pages=105–107 |issue=2 |s2cid=95448926 }}</ref>

==Extraction and representation==
On an industrial scale, diallyl disulfide is produced from sodium disulfide and [[Chemistry:Allyl bromide|allyl bromide]] or [[Chemistry:Allyl chloride|allyl chloride]] at temperatures of 40–60&nbsp;°C in an [[Physics:Inert gas|inert gas]] atmosphere; sodium disulfide is generated ''in situ'' by reacting [[Chemistry:Sodium sulfide|sodium sulfide]] with [[Chemistry:Sulfur|sulfur]]. The reaction is exothermic and its theoretical efficiency of 88% has been achieved in practice.<ref>{{cite patent
| country = WO
| number = 2006016881
|title=PROCESS FOR PRODUCING DIALLYL DISULFIDE
|pubdate=16-02-2006
|fdate=09-07-2004
}}</ref>

:[[File:Diallyldisulfid formation.png|left|500px]]{{clear|left}}

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%.<ref>{{cite journal |doi=10.1007/s11771-006-0079-4 |title=Synthesis, characterization and bioactivity evaluation of diallyl disulfide |year=2006 |last1=Yuan |first1=X |last2=Chen |first2=X |last3=Jiang |first3=X |last4=Nie |first4=Y |journal=Journal of Central South University of Technology |volume=13 |pages=515–518 |issue=5 |s2cid=97570822 }}</ref> 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&nbsp;°C.<ref>{{cite journal |doi=10.1021/jf00057a004 |title=Garlic Chemistry: Stability of S-(2-Propenyl)-2-Propene-1-sulfinothioate (Allicin) in Blood, Solvents, and Simulated Physiological Fluids |year=1995 |last1=Freeman |first1=F |last2=Kodera |first2=Y |journal=Journal of Agricultural and Food Chemistry |volume=43 |pages=2332–2338 |issue=9 }}</ref>

== Properties ==

===Physical characteristics ===
Diallyl disulfide has a strong garlic smell. It is a clear, yellowish liquid which boils at 138–139&nbsp;°C (for the typical 80% purity) and has its [[Physics:Flash point|flash point]] at 50&nbsp;°C, a [[Physics:Density|density]] of about 1.0 g/mL and a [[Physics:Vapor pressure|vapor pressure]] of 1 mmHg at 20&nbsp;°C. It is non-polar; therefore, diallyl disulfide is insoluble in water and is soluble in fats, oils, [[Chemistry:Lipid|lipid]]s, and non-polar solvents such as [[Chemistry:Hexane|hexane]] or [[Chemistry:Toluene|toluene]].<ref Name="gsc" /><ref name="sa" />

===Chemical reactions===
Diallyl disulfide can be readily oxidized to [[Chemistry:Allicin|allicin]] with [[Chemistry:Hydrogen peroxide|hydrogen peroxide]] or [[Chemistry:Peracetic acid|peracetic acid]]. [[Chemistry:Allicin|Allicin]] in turn can hydrolyze giving diallyl disulfide and trisulfide. Reaction of diallyl disulfide with liquid [[Chemistry:Sulfur|sulfur]] gives a mixture containing diallyl [[Chemistry:Polysulfide|polysulfide]]s with as many as 22 [[Chemistry:Sulfur|sulfur]] atoms in a continuous chain identified.<ref Name=Block/><ref>{{cite journal |doi=10.1080/17415993.2012.721368 |title=Liquid sulfur as a reagent: Synthesis of polysulfanes with 20 or more sulfur atoms with characterization by UPLC-(Ag+)-coordination ion spray-MS |journal=Journal of Sulfur Chemistry |volume=34 |issue=1–2 |pages=55–66 |year=2013 |last1=Wang |first1=Kai |last2=Groom |first2=Murree |last3=Sheridan |first3=Robert |last4=Zhang |first4=Shaozhong |last5=Block |first5=Eric |s2cid=95562164 }}</ref>  When diallyl disulfide is heated it decomposes giving a complex mixture. The carbon-sulfur bond of diallyl disulfide is 16 kcal mol<sup>−1</sup> weaker than the sulfur-sulfur bond (46 kcal mol<sup>−1</sup> versus 62 kcal mol<sup>−1</sup>, 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.<ref Name=Block/><ref>{{cite journal |doi=10.1021/ja00231a037 |title=Lipoxygenase inhibitors from the essential oil of garlic. Markovnikov addition of the allyldithio radical to olefins |journal=Journal of the American Chemical Society |volume=110 |issue=23 |pages=7813–7827 |year=1988 |last1=Block |first1=Eric |last2=Iyer |first2=Rajeshwari |last3=Grisoni |first3=Serge |last4=Saha |first4=Chantu |last5=Belman |first5=Sidney |last6=Lossing |first6=Fred P }}</ref> 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.<ref>{{cite journal |last1=Amosova |first1=S.V. |last2=Nosyreva |first2=V.V. |last3=Musorin |first3=G.K. |last4=Sigalov |first4=M.V. |last5=Sinegovskaya |first5=L.M. |last6=Trofimov |first6=B.A. |year=1986 |title=Synthesis of 1-alkylthio-3-allylthio-1-propenes by the reaction of dialllyl disulfide with allyl halides in the alkali-metal hydroxide-DMSO superbasic system |journal=Journal of Organic Chemistry of the USSR |volume=22 |issue=5 |pages=856–61 |oclc=4434235280 |osti=6388212 }}</ref>

== Applications ==
In the presence of iron chloride or copper chloride catalyst, or of liquid [[Chemistry:Sulfur|sulfur]] at 120&nbsp;°C<ref Name="Block"/><ref>{{US Patent|8101802}}</ref> 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 [[Chemistry:Nematicide|nematicide]]s.<ref Name="Block"/> Diallyl disulfide is also a starting material for the synthesis of [[Chemistry:Allicin|allicin]]. In the food industry, diallyl disulfide is used to improve the taste of meat, vegetables and fruits.<ref Name="gsc"/><ref>{{US Patent|5231114}}</ref>

==Biological importance==

=== Smell and taste===
The unpleasant smell of diallyl disulfide is perceived through the transient receptor potential cation channel, member A1 (TRPA1). This [[Biology:Ion channel|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.<ref Name="stink">{{cite journal |doi=10.1073/pnas.0505356102 |pmid=16103371 |pmc=1189336 |title=Pungent products from garlic activate the sensory ion channel TRPA1 |journal=Proceedings of the National Academy of Sciences |volume=102 |issue=34 |pages=12248–12252 |year=2005 |last1=Bautista |first1=D. M |last2=Movahed |first2=P |last3=Hinman |first3=A |last4=Axelsson |first4=H. E |last5=Sterner |first5=O |last6=Hogestatt |first6=E. D |last7=Julius |first7=D |last8=Jordt |first8=S.-E |last9=Zygmunt |first9=P. M |bibcode=2005PNAS..10212248B |doi-access=free }}</ref><ref>{{cite journal |doi=10.1021/jf035181d |pmid=15080619 |title=Aversion of European Starlings (Sturnus vulgaris) to Garlic Oil Treated Granules: Garlic Oil as an Avian Repellent. Garlic Oil Analysis by Nuclear Magnetic Resonance Spectroscopy |journal=Journal of Agricultural and Food Chemistry |volume=52 |issue=8 |pages=2192–2196 |year=2004 |last1=Hile |first1=Arla G |last2=Shan |first2=Zhixing |last3=Zhang |first3=Shao-Zhong |last4=Block |first4=Eric }}</ref>

===Poisoning and detoxification===
Diallyl disulfide is an efficient agent for detoxication of the cells. It significantly increases the production of the enzyme [[Biology:Glutathione S-transferase|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''.<ref Name="germ">{{cite journal |doi=10.1080/00498250310001636840 |pmid=14742141 |title=Hepatic metabolism of diallyl disulphide in rat and man |journal=Xenobiotica |volume=33 |issue=12 |pages=1185–1199 |year=2008 |last1=Germain |first1=E |last2=Chevalier |first2=J |last3=Siess |first3=M.-H |last4=Teyssier |first4=C |s2cid=20421070 |url=https://hal.inrae.fr/hal-02678545/file/16149_20081024022736808_1.pdf }}</ref><ref>{{cite journal |doi=10.1093/jn/135.11.2560 |pmid=16251611 |title=Garlic Organosulfur Compounds Upregulate the Expression of the π Class of Glutathione S-Transferase in Rat Primary Hepatocytes |journal=The Journal of Nutrition |volume=135 |issue=11 |pages=2560–2565 |year=2005 |last1=Tsai |first1=Chia-Wen |last2=Yang |first2=Jaw-Ji |last3=Chen |first3=Haw-Wen |last4=Sheen |first4=Lee-Yan |last5=Lii |first5=Chong-Kuei |doi-access=free }}</ref><ref>{{cite journal |doi=10.1021/jf010937z |pmid=11782211 |year=2002 |last1=Wu |first1=CC |last2=Sheen |first2=LY |last3=Chen |first3=HW |last4=Kuo |first4=WW |last5=Tsai |first5=SJ |last6=Lii |first6=CK |title=Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats |volume=50 |issue=2 |pages=378–83 |journal=Journal of Agricultural and Food Chemistry|url=http://ntur.lib.ntu.edu.tw/bitstream/246246/190076/1/24.pdf }}</ref><ref>{{cite journal |doi=10.1016/j.fct.2003.12.010 |pmid=15046820 |title=The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride |journal=Food and Chemical Toxicology |volume=42 |issue=5 |pages=743–749 |year=2004 |last1=Fukao |first1=T |last2=Hosono |first2=T |last3=Misawa |first3=S |last4=Seki |first4=T |last5=Ariga |first5=T }}</ref><ref name="lemar">{{cite journal |doi=10.1002/yea.1503 |pmid=17534841 |pmc=2292485 |title=Diallyl disulphide depletes glutathione in ''Candida'' albicans: Oxidative stress-mediated cell death studied by two-photon microscopy |journal=Yeast |volume=24 |issue=8 |pages=695–706 |year=2007 |last1=Lemar |first1=Katey M |last2=Aon |first2=Miguel A |last3=Cortassa |first3=Sonia |last4=O'Rourke |first4=Brian |last5=Müller |first5=Carsten T |last6=Lloyd |first6=David }}</ref><ref>{{cite journal |doi=10.1515/BC.2007.135 |pmid=17937621 |title=Glutathione- and thioredoxin-related enzymes are modulated by sulfur-containing chemopreventive agents |journal=Biological Chemistry |volume=388 |issue=10 |pages=1069–81 |year=2007 |last1=Hu |first1=Ying |last2=Urig |first2=Sabine |last3=Koncarevic |first3=Sasa |last4=Wu |first4=Xinjiang |last5=Fischer |first5=Marina |last6=Rahlfs |first6=Stefan |last7=Mersch-Sundermann |first7=Volker |last8=Becker |first8=Katja |s2cid=6384362 |url=https://zenodo.org/record/894094 }}</ref><ref>{{cite journal |doi=10.1016/j.molbrainres.2004.10.006 |pmid=15710234 |title=Protective effect of diallyl disulfide on oxidative stress-injured neuronally differentiated PC12 cells |journal=Molecular Brain Research |volume=133 |issue=2 |pages=176–186 |year=2005 |last1=Koh |first1=Seong-Ho |last2=Kwon |first2=Hyugsung |last3=Park |first3=Kee Hyung |last4=Ko |first4=Jin Kyung |last5=Kim |first5=Joo Hwan |last6=Hwang |first6=Myung Sil |last7=Yum |first7=Young Na |last8=Kim |first8=Ok-Hee |last9=Kim |first9=Juhan |last10=Kim |first10=Hee-Tae |last11=Do |first11=Byung-Rok |last12=Kim |first12=Kyung Suk |last13=Kim |first13=Haekwon |last14=Roh |first14=Hakjae |last15=Yu |first15=Hyun-Jeung |last16=Jung |first16=Hai Kwan |last17=Kim |first17=Seung Hyun }}</ref><ref>{{cite journal |doi=10.1016/j.tox.2005.02.011 |pmid=15863251 |title=Differential effects of diallyl disulfide on neuronal cells depend on its concentration |journal=Toxicology |volume=211 |issue=1–2 |pages=86–96 |year=2005 |last1=Kim |first1=Jun-Gyou |last2=Koh |first2=Seong-Ho |last3=Lee |first3=Young Joo |last4=Lee |first4=Kyu-Young |last5=Kim |first5=Youngchul |last6=Kim |first6=Sunyoun |last7=Lee |first7=Myung-Koo |last8=Kim |first8=Seung Hyun }}</ref> 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.<ref>{{cite journal |doi=10.1016/j.taap.2005.08.008 |pmid=16274720 |title=Effects of garlic oil and two of its major organosulfur compounds, diallyl disulfide and diallyl trisulfide, on intestinal damage in rats injected with endotoxin |journal=Toxicology and Applied Pharmacology |volume=213 |issue=1 |pages=46–54 |year=2006 |last1=Chiang |first1=Yi-Hsuan |last2=Jen |first2=Lin-Ni |last3=Su |first3=Hsiau-Yuan |last4=Lii |first4=Chong-Kuei |last5=Sheen |first5=Lee-Yan |last6=Liu |first6=Cheng-Tzu }}</ref> By supporting the detoxification activity in the liver, diallyl disulfide might offer liver protection during the [[Medicine:Chemotherapy|chemotherapy]], e.g. against [[Chemistry:Cyanide|cyanide]] detoxification.<ref>{{cite journal |doi=10.1016/j.ejphar.2007.04.055 |pmid=17560567 |title=Selective effects of diallyl disulfide, a sulfane sulfur precursor, in the liver and Ehrlich ascites tumor cells |journal=European Journal of Pharmacology |volume=569 |issue=1–2 |pages=1–7 |year=2007 |last1=Iciek |first1=Małgorzata |last2=Marcinek |first2=Joanna |last3=Mleczko |first3=Urszula |last4=Włodek |first4=Lidia }}</ref><ref>{{cite journal |pmid=15886420 |url=http://www.if-pan.krakow.pl/pjp/pdf/2005/2_212.pdf |year=2005 |last1=Iciek |first1=M |last2=Bilska |first2=A |last3=Ksiazek |first3=L |last4=Srebro |first4=Z |last5=Włodek |first5=L |title=Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues |volume=57 |issue=2 |pages=212–8 |journal=Pharmacological Reports }}</ref>

===Antimicrobial effect===
The release of organosulfur compounds upon destruction of Alliaceae plant cells has great importance, because of the antimicrobial, [[Biology:Insecticide|insecticidal]] and [[Biology:Larvicide|larvicidal]] properties of those compounds.<ref>{{cite journal |doi=10.1126/science.174.4016.1343 |title=Isolation and Characterization of Larvicidal Principle of Garlic |journal=Science |volume=174 |issue=4016 |pages=1343–1344 |year=1971 |last1=Amonkar |first1=S. V |last2=Banerji |first2=A |pmid=5135721 |bibcode=1971Sci...174.1343A |s2cid=43748340 }}</ref> 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.<ref>{{cite journal |doi=10.1016/s0944-7113(00)80010-0 |title=Allylsulfide constituents of garlic volatile oil as antimicrobial agents |journal=Phytomedicine |volume=7 |issue=3 |pages=239–243 |year=2000 |last1=Avato |first1=P |last2=Tursi |first2=F |last3=Vitali |first3=C |last4=Miccolis |first4=V |last5=Candido |first5=V |pmid=11185736 }}</ref><ref>{{cite journal |doi=10.1128/AEM.66.5.2269-2273.2000 |pmid=10788416 |year=2000 |last1=O'Gara |first1=EA |last2=Hill |first2=DJ |last3=Maslin |first3=DJ |title=Activities of garlic oil, garlic powder, and their diallyl constituents against Helicobacter pylori |volume=66 |issue=5 |pages=2269–73 |pmc=101489 |journal=Applied and Environmental Microbiology|bibcode=2000ApEnM..66.2269O }}</ref> Because of its antimicrobial effects, diallyl disulfide, together with [[Chemistry:Tobramycin|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.<ref>{{cite journal |pmid=17535634 |year=2007 |last1=Yu |first1=J |last2=Xiao |first2=YB |last3=Wang |first3=XY |title=Effects of preoperatively selected gut decontamination on cardiopulmonary bypass-induced endotoxemia |volume=10 |issue=3 |pages=131–7 |journal=Chinese Journal of Traumatology}}</ref>

===Protection against colon cancer===
Garlic can prevent [[Medicine:Colorectal cancer|colorectal cancer]],<ref>World Cancer Research Fund/American Institute for Cancer Research: Food, Nutrition, Physical Activity and the Prevention of Cancer. 2nd Edition, 2007 ({{ISBN|0-97225222-3}}) S. [http://www.dietandcancerreport.org/downloads/Second_Expert_Report.pdf pp.93–94] {{Webarchive|url=https://web.archive.org/web/20090325235446/http://www.dietandcancerreport.org/downloads/Second_Expert_Report.pdf |date=2009-03-25 }} (PDF, 12 MB)</ref> and several studies revealed that diallyl disulfide is a major component responsible for this action. The effect is dose dependent as demonstrated on mice.<ref>{{cite journal |doi=10.1093/jn/136.3.727S |pmid=16484574 |title=Preclinical Perspectives on Garlic and Cancer |journal=The Journal of Nutrition |volume=136 |issue=3 |pages=827S–831S |year=2006 |last1=Milner |first1=John A |doi-access=free }}</ref><ref>{{cite journal |pmid=16475702 |year=2006 |last1=Yang |first1=JS |last2=Kok |first2=LF |last3=Lin |first3=YH |last4=Kuo |first4=TC |last5=Yang |first5=JL |last6=Lin |first6=CC |last7=Chen |first7=GW |last8=Huang |first8=WW |last9=Ho |first9=HC |last10=Chung |first10=J. G. |title=Diallyl disulfide inhibits WEHI-3 leukemia cells in vivo |volume=26 |issue=1A |pages=219–25 |journal=Anticancer Research|display-authors=8 }}</ref> Diallyl disulfide affects cancer cells much more strongly than normal cells.<ref>{{cite journal |doi=10.1111/j.1745-7270.2007.00356.x |pmid=17989874 |year=2007 |last1=Huang |first1=Z |last2=Lei |first2=X |last3=Zhong |first3=M |last4=Zhu |first4=B |last5=Tang |first5=S |last6=Liao |first6=D |title=Bcl-2 small interfering RNA sensitizes cisplatin-resistant human lung adenocarcinoma A549/DDP cell to cisplatin and diallyl disulfide |volume=39 |issue=11 |pages=835–43 |journal=Acta Biochimica et Biophysica Sinica|doi-access= }}</ref> 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.<ref>{{cite journal |doi=10.3892/or.19.1.275 |title=Diallyl disulfide induces reversible G2/M phase arrest on a p53-independent mechanism in human colon cancer HCT-116 cells |journal=Oncology Reports |year=2008 |last1=Jo |first1=Hong |last2=Song |first2=Ju |last3=Kim |first3=Kang |last4=Cho |first4=Yong |last5=Kim |first5=Ki |last6=Park |first6=Young |volume=19 |issue=1 |pages=275–80 |pmid=18097607 |doi-access=free }}</ref>

=== 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 [[Medicine:Atherosclerosis|atherosclerosis]] or coronary heart disease is [[Biology:Oxidative stress|oxidative stress]]. The latter is reduced by diallyl disulfide by assisting in the detoxification of the cell, as well as some other mechanisms.<ref Name="omar" /> By activating the TRPA1 ion channel, diallyl disulfide leads to a short-term lowering of blood pressure.<ref Name="stink" />

== Safety ==
Diallyl disulfide is a skin irritant and an [[Biology:Allergen|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.<ref>{{cite book |url=https://books.google.com/books?id=6AB89RHV9ucC&pg=PA288 |page=228 |title=Garlic and other alliums: the lore and the science |author=Block, E |publisher=Royal Society of Chemistry |year=2009 |isbn=978-0-85404-190-9}}</ref><ref>{{cite book |url=https://books.google.com/books?id=f2IwYiyh3YUC&pg=PT305 |page=305 |title=Dermatology, Volume 2 |author=Horn, TD |publisher=Elsevier Health Sciences |year=2003 |isbn=978-0-323-02578-2}}</ref><ref>[http://www.allallergy.net/fapaidfind.cfm?cdeoc=684 Garlic] {{webarchive|url=https://web.archive.org/web/20100615004222/http://allallergy.net/fapaidfind.cfm?cdeoc=684 |date=2010-06-15 }}</ref><ref>{{cite journal |doi=10.1111/j.1440-0960.2004.00102.x |pmid=15527433 |title=Use of gloves in protection from diallyl disulphide allergy |journal=Australasian Journal of Dermatology |volume=45 |issue=4 |pages=223–225 |year=2004 |last1=Moyle |first1=Mignon |last2=Frowen |first2=Kath |last3=Nixon |first3=Rosemary |s2cid=38878468 }}</ref>

The median [[Chemistry:Lethal dose|lethal dose]] (LD<sub>50</sub>) for oral intake in [[Biology:Rat|rat]]s is 260&nbsp;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.<ref Name="gsc"/><ref>[http://yosemite.epa.gov/oppts/epatscat8.nsf/ReportSearch?OpenAgent&CASNumber=2179-57-9 EPA documents]</ref>

Diallyl disulfide can be easily detected in the air or in the blood with [[Gas chromatography|gas chromatography]].<ref>[http://www.osha.gov/dts/chemicalsampling/data/CH_231730.html documents of the U.S. Department of Labor Occupational Safety & Health]</ref><ref>{{cite journal |pmid=17283653 |year=2006 |last1=Sun |first1=X |last2=Guo |first2=T |last3=He |first3=J |last4=Zhao |first4=M |last5=Yan |first5=M |last6=Cui |first6=F |last7=Deng |first7=Y |title=Simultaneous determination of diallyl trisulfide and diallyl disulfide in rat blood by gas chromatography with electron-capture detection |volume=61 |issue=12 |pages=985–8 |journal=Die Pharmazie}}</ref>

==See also==
* [[Chemistry:Allyl propyl disulfide|Allyl propyl disulfide]]

== References ==
{{Reflist|2}}

{{Allium}}
{{HDAC inhibitors}}
{{Transient receptor potential channel modulators}}

[[Category:Organic disulfides]]
[[Category:Allyl compounds]]
[[Category:Nematicides]]
[[Category:Histone deacetylase inhibitors]]

{{Sourceattribution|Diallyl disulfide}}