alliin

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477317756

| Name = Alliin

| ImageFile = L-alliin-2D-skeletal.png

| ImageName = Alliin skeletal view

| ImageFile1 = L-alliin-3D-balls.png

| ImageName1 = Alliin ball view

| SystematicName = (2R)-2-Amino-3-[(S)-(prop-2-ene-1-sulfinyl)]propanoic acid

| OtherNames = 3-(2-Propenylsulfinyl)alanine
(S)-3-(2-Propenylsulfinyl)-{{small|L}}-alanine
3-[(S)-Allylsulfinyl]-{{small|L}}-alanine
S-Allyl-{{small|L}}-cysteine sulfoxide

|Section1={{Chembox Identifiers

| SMILES = C=CCS(=O)CC(C(=O)O)N

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 7850537

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 2596

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 464166

| PubChem = 9576089

| EC_number = 209-118-9

| UNII = 7I4L2D0E9G

| KEGG = C08265

| SMILES1 = N[C@H](C(=O)O)C[S@@](=O)CC=C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XUHLIQGRKRUKPH-DYEAUMGKSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 556-27-4

}}

|Section2={{Chembox Properties

| C=6 | H=11 | N=1 | O=3 | S=1

| Appearance = White to off white crystalline powder

| Solubility = Soluble

| MeltingPt = {{convert|163|-|165|C|F}}

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.mpbio.com/includes/msds/ansi/en/194125-en-ansi.pdf External MSDS]

| NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

}}

}}

Alliin {{IPAc-en|ˈ|æ|l|i|.|ɪ|n}} is a sulfoxide that is a natural constituent of fresh garlic.{{cite journal

| author = Iberl, B

| title = Quantitative Determination of Allicin and Alliin from Garlic by HPLC

| journal = Planta Med.

| volume = 56

| issue =3

| pages = 320–326

| year = 1990

| doi = 10.1055/s-2006-960969

| pmid = 17221429

| last2 = Winkler, G

| last3 = Müller, B

| last4 = Knobloch, K

| s2cid = 30268881

}} 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.{{cite journal | last1=Amagase | first1=Harunobu | last2=Petesch | first2=Brenda L. | last3=Matsuura | first3=Hiromichi | last4=Kasuga | first4=Shigeo | last5=Itakura | first5=Yoichi | title=Intake of Garlic and Its Bioactive Components | journal=The Journal of Nutrition | publisher=Oxford University Press (OUP) | volume=131 | issue=3 | year=2001 | issn=0022-3166 | doi=10.1093/jn/131.3.955s | pages=955S–962S| pmid=11238796 | doi-access=free }} 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.{{cite book |title= Garlic and Other Alliums: The lore and the science |author = Block, E |publisher= Royal Society of Chemistry |year= 2009 |pages= 100–106 }}