Alliin

Chemical compound From Wikipedia, the free encyclopedia

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. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene.[2] Garlic powder is not a source of alliin, nor is fresh garlic upon maceration, since the enzymatic conversion to allicin takes place in the order of seconds.

Quick facts Names, Identifiers ...
Alliin
Alliin skeletal view
Alliin skeletal view
Alliin ball view
Alliin ball view
Names
Systematic IUPAC name
(2R)-2-Amino-3-[(S)-(prop-2-ene-1-sulfinyl)]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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.291 Edit this at Wikidata
EC Number
  • 209-118-9
KEGG
UNII
  • 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 checkY
    Key: XUHLIQGRKRUKPH-DYEAUMGKSA-N checkY
  • C=CCS(=O)CC(C(=O)O)N
  • N[C@H](C(=O)O)C[S@@](=O)CC=C
Properties
C6H11NO3S
Molar mass 177.22 g·mol−1
Appearance White to off white crystalline powder
Melting point 163–165 °C (325–329 °F)
Soluble
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Close

Alliin was the first natural product found to have both carbon- and sulfur-centered stereochemistry.[3]

Chemical synthesis

The first reported synthesis, by Stoll and Seebeck in 1951,[4] begins the alkylation of L-cysteine with allyl bromide to form deoxyalliin. Oxidation of this sulfide with hydrogen peroxide gives both diastereomers of L-alliin, differing in the orientation of the oxygen atom on the sulfur stereocenter.

A newer route, reported by Koch and Keusgen in 1998,[5] allows stereospecific oxidation using conditions similar to the Sharpless asymmetric epoxidation. The chiral catalyst is produced from diethyl tartrate and titanium isopropoxide.

Medical exploration

Garlic has been used since antiquity for conditions now associated with oxidative stress (production and accumulation of reactive oxygen species (ROS)).[citation needed] In an in vitro test, garlic powder showed antioxidant properties, and alliin showed good hydroxyl radical-scavenging effect.[6] Alliin has also been found to affect immune responses in blood cells in vitro.[7]

References

Related Articles

Wikiwand AI