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Allicin



Allicin
IUPAC name 2-propene-1-sulfinothioic acid S-2-propenyl ester
Identifiers
CAS number 539-86-6
SMILES C=CCS(=O)SCC=C
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

Allicin compound obtained from garlic that has demonstrated potent antibacterial and anti-fungal properties that protect garlic from pathogens [1][2]. Allicin is also the chemical constituent primarily responsible for the hot, burning flavor of fresh garlic.[citation needed]

Additional recommended knowledge

Allicin is not present in garlic in its natural state. When garlic is chopped or otherwise damaged, the enzyme alliinase acts on the chemical alliin converting it into allicin.[3] Alliin is an amino acid that does not build proteins. Alliinase has been demonstrated to be 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][6] In light of this, Allicin is considered to be of very limited value as an oral antibiotic due to poor bioavailability.[7]

Allicin is not a very stable compound. It degrades slowly upon standing and is rapidly destroyed by cooking. Allicin can be used for some medicinal purposes: it helps fighting arteriosclerosis, it has the ability to dissolve fats and it can also be used as an antioxidant to some extent.[8][9] Other studies have shown a strong oxidative effect in the gut that can damage intestinal cells [10],[11] Vasodilative effect of garlic in physiological oxygen levels is possibly caused by catabolism of its allicin-like polysulfides to hydrogen sulfide, a reaction which could depend on reduction mediated by glutathione.[12]

See also


References

  1. ^ http://www.allicin.com/#refs
  2. ^ Cavalitto, C.J. et al. 1944. J. Am. Chem. Soc. 66: 1950
  3. ^ Eric Block (1985). "The chemistry of garlic and onions". Scientific American 252 (March): 114-119.
  4. ^ http://www.allicin.com/#refs
  5. ^ Brodnitz, M.H. Pascale, J.V., and Derslice, L.V. Flavor components of garlic extract. J. Agr. Food. Chem. 19(2):273-275, 1971
  6. ^ Yu. T-H, and Wu, C-M. Stability of allicin in garlic juice. J. Food Sci. 54(4): 977-981, 1989
  7. ^ 11. Amagase, H., Petesch, B., Matsuura, H., Kasuga, S. and Itakura, Y. Intake of garlic and its bioactive components. J. Nutr. 131(3S): 955S-962S, 2001.
  8. ^ 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.
  9. ^ 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.
  10. ^ http://www.allicin.com/#refs
  11. ^ 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.
  12. ^ Hydrogen sulfide mediates the vasoactivity of garlic.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Allicin". A list of authors is available in Wikipedia.
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