Alliin

Alliin
Alliin skeletal 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).
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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.

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

  1. ^ Iberl, B; Winkler, G; Müller, B; Knobloch, K (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. S2CID 30268881.
  2. ^ Amagase, Harunobu; Petesch, Brenda L.; Matsuura, Hiromichi; Kasuga, Shigeo; Itakura, Yoichi (2001). "Intake of Garlic and Its Bioactive Components". The Journal of Nutrition. 131 (3). Oxford University Press (OUP): 955S–962S. doi:10.1093/jn/131.3.955s. ISSN 0022-3166. PMID 11238796.
  3. ^ Block, E (2009). Garlic and Other Alliums: The lore and the science. Royal Society of Chemistry. pp. 100–106.