Alliin

Chembox new
Name = Alliin
ImageFile = L-alliin-2D-skeletal.png ImageName = Alliin skeletal view
ImageFile1 = L-alliin-3D-balls.png ImageName1 = Alliin ball view
IUPACName = (2R)-2-amino-3- [(S)-prop-2-
enylsulfinyl] propanoic acid
OtherNames = 3-(2-Propenylsulfinyl)alanine
(S)-3-(2-Propenylsulfinyl)-L-alanine
3-((S)-Allylsulfinyl)-L-alanine
S-Allyl-L-cysteine sulfoxide
Section1 = Chembox Identifiers
SMILES = C=CCS(=O)CC(C(=O)O)N
CASNo = 556-27-4
Section2 = Chembox Properties
Formula = C₆H₁₁NO₃S
MolarMass = 177.22 g/mol
Appearance = White to off white crystalline powder
Solubility = Soluble
MeltingPt = 163-165 °C (325.4-329 °F)
Section7 = Chembox Hazards
ExternalMSDS = [http://www.mpbio.com/includes/msds/ansi/en/194125-en-ansi.pdf External MSDS]
NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0

Alliin (al'-ee-in) is a sulfoxide that is a natural constituent of fresh garlic. [cite journal
author = Iberl, B "et al"
title = Quantitative Determination of Allicin and Alliin from Garlic by HPLC
journal = Planta Med
volume = 56
issue =
pages = 320–326
date = 1990
doi = 10.1055/s-2006-960969 ] 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 primarily responsible for the aroma of fresh garlic. Garlic has been used since antiquity as a therapeutic remedy for oxygen toxicity, and when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical scavenging properties, possibly owing to the alliin contained within. [cite journal
author = Kourounakis, PN; Rekka, EA
title = Effect on active oxygen species of alliin and Allium sativum (garlic) powder
journal = Res Commun Chem Pathol Pharmacol.
volume = 74
issue = 2
pages = 249–252
date = Nov. 1991
pmid = 1667340 ]

When the effect of alliin is observed on blood cells in vitro, a noted increase in the engulfing capacity of phagocyting cells is seen. [cite journal
author = Salman, H "et al"
title = Effect of a garlic derivative (alliin) on peripheral blood cell immune responses
journal = Int J Immunopharmacol.
volume = 21
issue = 9
pages = 589–597
date = Sep. 1999
pmid = 10501628
doi = 10.1016/S0192-0561(99)00038-7 ]

References