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| Allicin | |
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| IUPAC name | 2-propene-1-sulfinothioic acid S-2-propenyl ester |
| Identifiers | |
| CAS number | [539-86-6] |
| SMILES |
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| Properties | |
| Molecular formula | C6H10OS2 |
| Molar mass | 162.28 g/mol |
| Density | 1.112 g/cm³ |
| Melting point |
<25 °C |
| Boiling point |
dec. |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Allicin is an organic compound obtained from garlic. This colourless liquid has a distinctively pungent smell. This compound exhibits antibacterial and anti-fungal properties.[1]
Contents |
Structure and occurrence
Allicin is formed by the action of the enzyme alliinase on alliin.[2] It can also be prepared in racemic form by oxidation of diallyldisulfide:[3]
- (SCH2CH=CH2)2 + RCO3H → CH2=CHCH2SS(O)CH2CH=CH2 + RCO2H
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.[4][5] 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.[6][7], normalize the lipoprotein balance, decrease blood pressure[8][9], have anti-thrombotic[10] and anti-inflammatory activities, and function as an antioxidant to some extent [11][12][13]. Other studies have shown a strong oxidative effect in the gut that can damage intestinal cells.[14]
See also
- Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish and wasabi
- Capsaicin, the active piquant chemical in chile peppers
- Piperine, the active piquant chemical in black pepper
- Syn-propanethial-S-oxide, the chemical found in onions
- List of phytochemicals in food
References
- ^ 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}}
- ^ Eric Block (1985). "The chemistry of garlic and onions". Scientific American 252 (March): 114–119.
- ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4.
- ^ Brodnitz, M.H. Pascale, J.V., and Derslice, L.V. Flavor components of garlic extract. J. Agr. Food. Chem. 19(2):273-275, 1971
- ^ Yu. T-H, and Wu, C-M. Stability of allicin in garlic juice. J. Food Sci. 54(4): 977-981, 1989
- ^ S. Eilat, Y. Oestraicher, A. Rabinkov, D. Ohad, D. Mirelman, A. Battler, M. Eldar and Z. Vered (1995). "Alteration of lipid profile in hyperlipidemic rabbits by allicin, an active constituent of garlic". Coron. Artery Dis. 6: 985–990.
- ^ D. Abramovitz, S. Gavri, D. Harats, H. Levkovitz, D. Mirelman, T. Miron, S. Eilat-Adar, A. Rabinkov, M. Wilchek, M. Eldar and Z. Vered, (1999). "Allicin-induced decrease in formation of fatty streaks (atherosclerosis) in mice fed a cholesterol-rich diet". Coron. Artery Dis. 10: 515–519. doi:.
- ^ Silagy CA, Neil HA (1994). "A meta-analysis of the effect of garlic on blood pressure". J Hypertens 12(4): 463-468.
- ^ A. Elkayam, D. Mirelman, E. Peleg, M. Wilchek, T. Miron, A. Rabinkov, M. Oron-Herman and T. Rosenthal (2003). "The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats". Am. J. Hypertens 16: 1053–1056. doi:.
- ^ Srivastava KC (1986). "Evidence for the mechanism by which garlic inhibits platelet aggregation.". Prostaglandins Leukot Med 22(3): 313-321.
- ^ U. Sela, S. Ganor, I. Hecht, A. Brill, T. Miron, A. Rabinkov, M. Wilchek, D. Mirelman, O. Lider and R. Hershkoviz (2004). "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". Immunology 111: 391–399. doi:.
- ^ Lindsey J. Macpherson, Bernhard H. Geierstanger, Veena Viswanath, Michael Bandell, Samer R. Eid, SunWook Hwang, and Ardem Patapoutian (2005). "The pungency of garlic: Activation of TRPA1 and TRPV1 in response to allicin". Current Biology 15 (May 24): 929–934.
- ^ Bautista DM, Movahed P, Hinman A, Axelsson HE, Sterner O, Hogestatt ED, Julius D, Jordt SE and Zygmunt PM (2005). "Pungent products from garlic activate the sensory ion channel TRPA1". Proc Natl Acad Sci U S A 102 (34): 12248–52. doi:. PMID 16103371.
- ^ 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.
External links
- Investigation of allicin use against superbugs, MRSA & VRE
- Antimicrobial properties of allicin from garlic
