Alliin

Alliin
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
CAS Number	556-27-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:2596 ;
ChEMBL	ChEMBL464166 ;
ChemSpider	7850537 ;
ECHA InfoCard	100.008.291
EC Number	209-118-9;
KEGG	C08265;
PubChem CID	9576089;
UNII	7I4L2D0E9G;
CompTox Dashboard (EPA)	DTXSID801020639 ;
	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 Key: XUHLIQGRKRUKPH-DYEAUMGKSA-N ;
	SMILES C=CCS(=O)CC(C(=O)O)N; N[C@H](C(=O)O)C[S@@](=O)CC=C;
Properties
Chemical formula	C6H11NO3S
Molar mass	177.22 g·mol−1
Appearance	White to off white crystalline powder
Melting point	163–165 °C (325–329 °F)
Solubility in water	Soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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)	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). verify (what is ?) 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. 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]

^ 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.
^ 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.
^ Block, E (2009). Garlic and Other Alliums: The lore and the science. Royal Society of Chemistry. pp. 100–106.

[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.

[Amagase-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.

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