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Alliin

Alliin


IUPAC name (2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid
Other names 3-(2-Propenylsulfinyl)alanine (S)-3-(2-Propenylsulfinyl)-L-alanine 3-((S)-Allylsulfinyl)-L-alanine S-Allyl-L-cysteine sulfoxide
Identifiers
CAS number	556-27-4^N
ChemSpider	7850537^Y
ChEMBL	CHEMBL464166^N
Jmol-3D images	Image 1 Image 2
SMILES C=CCS(=O)CC(C(=O)O)N O=S(CC=C)C[C@@H](C(=O)O)N
InChI InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11-/m0/s1^Y Key: XUHLIQGRKRUKPH-DYEAUMGKSA-N^Y InChI=1/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11-/m0/s1 Key: XUHLIQGRKRUKPH-DYEAUMGKBA
Properties
Molecular formula	C₆H₁₁NO₃S
Molar mass	177.22 g/mol
Appearance	White to off white crystalline powder
Melting point	163–165 °C (325–329 °F)
Solubility in water	Soluble
Hazards
MSDS	External MSDS
NFPA 704	1 1 0
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Alliin (/ˈæli.ɪn/) is a sulfoxide that is a natural constituent of fresh garlic.^[1] 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 responsible for the aroma of fresh garlic. Garlic has been used since antiquity as a therapeutic remedy for certain conditions now associated with oxygen toxicity, and, when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical-scavenging properties, it is presumed owing to the alliin contained within.^[2]

Alliin has been found to affect immune responses in blood.^[3]

Alliin was the first natural product found to have both carbon- and sulfur-centered stereochemistry.^[4]

References

^ Iberl, B et al. (1990). "Quantitative Determination of Allicin and Alliin from Garlic by HPLC". Planta Med 56 (3): 320–326. DOI:10.1055/s-2006-960969. PMID 17221429.
^ Kourounakis, PN; Rekka, EA (November 1991). "Effect on active oxygen species of alliin and Allium sativum (garlic) powder". Res Commun Chem Pathol Pharmacol. 74 (2): 249–252. PMID 1667340.
^ Salman, H et al. (September 1999). "Effect of a garlic derivative (alliin) on peripheral blood cell immune responses". Int J Immunopharmacol. 21 (9): 589–597. DOI:10.1016/S0192-0561(99)00038-7. PMID 10501628.
^ Eric Block (2009). Garlic and other alliums: the lore and the science. Royal Society of Chemistry. pp. 100–106.

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Alliin

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