Allicin
311596
226110883
2008-07-16T21:32:37Z
128.173.74.100
/* Structure and occurrence */
{{Chembox new
| Name = '''Allicin'''
| ImageFile = R-allicin-2D-skeletal.png
| ImageSize = 250px
| ImageName = Allicin
| ImageFile1 = R-alllicin-3D-balls.png
| ImageSize1 = 220px
| ImageName1 = S-allicin
| IUPACName = 2-propene-1-sulfinothioic acid S-2-propenyl ester
| Section1 = {{Chembox Identifiers
| CASNo = 539-86-6
| pubchem = 65036
| CID = 65036
| SMILES = C=CCS(=O)SCC=C
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>10</sub>OS<sub>2</sub>
| MolarMass = 162.28 g/mol
| Density = 1.112 g/cm³
| MeltingPt =<25 °C
| BoilingPt = dec.
}}
}}
'''Allicin''' is an [[organic compound]] obtained from [[garlic]]. This colourless liquid has a distinctively pungent smell. This compound exhibits [[antibacterial]] and [[antifungal|anti-fungal]] properties.<ref>Chester J. Cavallito, John Hays Bailey "Allicin, the Antibacterial Principle of ''Allium sativum''. I. Isolation, Physical Properties and Antibacterial Action" Journal of the American Chemical Society, 1944, volume 66, pp 1950 - 1951. {DOI|10.1021/ja01239a048}}</ref>
==Structure and occurrence==
Allicin is formed by the action of the enzyme [[alliinase]] on [[alliin]].<ref>{{cite journal | author=Eric Block | title= The chemistry of garlic and onions | journal=Scientific American | volume=252 | issue=March | year=1985 | pages=114–119}}</ref> It can also be prepared in racemic form by oxidation of diallyl[[disulfide]]:<ref>R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4.</ref>
:(SCH<sub>2</sub>CH=CH<sub>2</sub>)<sub>2</sub> + [[meta-Chloroperoxybenzoic acid|RCO<sub>3</sub>H]] → CH<sub>2</sub>=CHCH<sub>2</sub>SS(O)CH<sub>2</sub>CH=CH<sub>2</sub> + RCO<sub>2</sub>H
===Instability of allicin===
Alliinase is irreversibly deactivated below a pH of 3; as such, allicin is generally not produced in the body from consumed fresh or powdered garlic.<ref>Brodnitz, M.H. Pascale, J.V., and Derslice, L.V. Flavor components of garlic extract. J. Agr. Food. Chem. 19(2):273-275, 1971</ref><ref>Yu. T-H, and Wu, C-M. Stability of allicin in garlic juice. J. Food Sci. 54(4): 977-981, 1989</ref> Furthermore, allicin is unstable, degrading slowly upon standing at room temperature and rapidly with heat (e.g., by cooking).
==Potential health benefits==
Several animal studies published between 1995 and 2005 indicate that allicin may: reduce [[atherosclerosis]] and fat deposition.<ref>{{cite journal | author= S. Eilat, Y. Oestraicher, A. Rabinkov, D. Ohad, D. Mirelman, A. Battler, M. Eldar and Z. Vered | title= Alteration of lipid profile in hyperlipidemic rabbits by allicin, an active constituent of garlic | journal= Coron. Artery Dis. | volume=6| year=1995| pages=985–990}}</ref><ref>{{cite journal | author= D. Abramovitz, S. Gavri, D. Harats, H. Levkovitz, D. Mirelman, T. Miron, S. Eilat-Adar, A. Rabinkov, M. [[Meir Wilchek|Wilchek]], M. Eldar and Z. Vered, | title= Allicin-induced decrease in formation of fatty streaks (atherosclerosis) in mice fed a cholesterol-rich diet | journal= Coron. Artery Dis. | volume=10 | year=1999| pages=515–519 | doi= 10.1097/00019501-199910000-00012}}</ref>, normalize the [[lipoprotein]] balance, decrease [[blood pressure]]<ref>{{cite journal | author= A. Elkayam, D. Mirelman, E. Peleg, M. [[Meir Wilchek|Wilchek]], T. Miron, A. Rabinkov, M. Oron-Herman and T. Rosenthal | title= The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats | journal= Am. J. Hypertens | volume=16 | year=2003| pages=1053–1056 | doi= 10.1016/j.amjhyper.2003.07.011}}</ref>, have anti-[[thrombosis|thrombotic]] and anti-[[inflammation|inflammatory]] activities, and function as an [[antioxidant]] to some extent <ref>{{cite journal | author= U. Sela, S. Ganor, I. Hecht, A. Brill, T. Miron, A. Rabinkov, M. [[Meir Wilchek|Wilchek]], D. Mirelman, O. Lider and R. Hershkoviz | title= Allicin inhibits SDF-1alpha-induced T cell interactions with fibronectin and endothelial cells by down-regulating cytoskeleton rearrangement, Pyk-2 phosphorylation and VLA-4 expression | journal= Immunology | volume=111 | year=2004| pages=391–399 | doi= 10.1111/j.0019-2805.2004.01841.x}}</ref><ref>{{cite journal | author=Lindsey J. Macpherson, Bernhard H. Geierstanger, Veena Viswanath, Michael Bandell, Samer R. Eid, SunWook Hwang, and Ardem Patapoutian | title=[http://www.current-biology.com/content/article/fulltext?uid=PIIS096098220500391X The pungency of garlic: Activation of TRPA1 and TRPV1 in response to allicin] | journal=Current Biology | volume=15 | issue=May 24 | year=2005 | pages=929–934}}</ref><ref>{{cite journal | author=Bautista DM, Movahed P, Hinman A, Axelsson HE, Sterner O, Hogestatt ED, Julius D, Jordt SE and Zygmunt PM | title=Pungent products from garlic activate the sensory ion channel TRPA1| journal=Proc Natl Acad Sci U S A | volume=102 | issue=34 | year=2005 | pages=12248–52 | doi=10.1073/pnas.0505356102 | pmid=16103371}}</ref>. Other studies have shown a strong oxidative effect in the gut that can damage intestinal cells.<ref>Lawson, L. D., Ransom, D. K. and Hughes, B. G. Inhibition of whole blood platelet-aggregation by compounds in garlic clove extracts and commercial garlic products. Throm. Res. 65: 141-156, 1992.</ref>
==See also==
* [[Allyl isothiocyanate]], the active piquant chemical in [[mustard plant|mustard]], [[radish]]es, [[horseradish]] and [[wasabi]]
* [[Capsaicin]], the active piquant chemical in [[chile pepper]]s
* [[Piperine]], the active piquant chemical in [[black pepper]]<!--why is this here?-->
* [[Syn-propanethial-S-oxide]], the chemical found in [[onion]]s
* [[List of phytochemicals in food]]
{{commonscat|allicin}}
==References==
<references/>
==External links==
*[http://pubs.acs.org/subscribe/journals/mdd/v05/i04/html/04news4.html Investigation of allicin use against superbugs, MRSA & VRE]
*[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=10594976&dopt=AbstractPlus Antimicrobial properties of allicin from garlic]
[[Category:Organosulfur compounds]]
[[Category:Alkenes]]
[[Category:Antibiotics]]
[[Category:Pungent flavors]]
[[Category:Garlic]]
[[Category:Nutrition]]
[[bg:Алицин]]
[[de:Allicin]]
[[es:Alicina]]
[[it:Allicina]]
[[he:אליצין]]
[[nl:Allicine]]
[[ja:アリシン]]
[[pl:Allicyna]]
[[ru:Аллицин]]
[[fi:Allisiini]]
[[sv:Allicin]]