| Identification | More | [Name]
(S)-3-(Allylsulphinyl)-L-alanine | [CAS]
556-27-4 | [Synonyms]
3-(2-PROPENYLSUFINYL)ALANINE
(+)-3-(2-PROPENYLSULFINYL) ALANINE
3-(2-PROPENYLSULFINYL)ALANINE
ALLIIN
L(+) ALLIIN
L(+/-) ALLIIN
(S)-3-(ALLYLSULFINYL)-L-ALANINE
(S)-S-ALLYL-L-CYSTEINE SULFOXIDE
(S)-3-(allylsulphinyl)-L-alanine
S-Allyl-L-cysteine Sulfoxide
ALLIIN(P)
ALLIIN hplc
(2R)-2-Amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid
ALLIIN WITH HPLC
L-Alliin 556-27-4
3-(Allylsulfinyl)-L-alanine, (S)-
L-Alanine, 3-[(S)-2-propenylsulfinyl]- | [EINECS(EC#)]
209-118-9 | [Molecular Formula]
C6H11NO3S | [MDL Number]
MFCD01311056 | [Molecular Weight]
177.22 | [MOL File]
556-27-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
164-166° (effervescence) | [alpha ]
D20 +63.5° (c = 2) | [Boiling point ]
416.1±45.0 °C(Predicted) | [density ]
1.205 (estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
solid | [pka]
1.88±0.10(Predicted) | [color ]
White to off-white | [Merck ]
13,259 | [InChI]
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-/s3 | [InChIKey]
XUHLIQGRKRUKPH-DYEAUMGKSA-N | [SMILES]
C(O)(=O)[C@H](C[S@](CC=C)=O)N |&1:3,5,r| | [LogP]
-0.478 (est) | [CAS DataBase Reference]
556-27-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
8-10 | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Description]
Alliin (S-allyl cysteine sulfoxide) is an organic sulfur-containing product derived from the amino acid cysteine. It is the precursor of thiosulfinates, which are responsible for the characteristic pungent flavours of Allium species. It is an L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allyl sulfinyl group. It has a role as a plant metabolite, an antioxidant, a cardioprotective agent, a neuroprotective agent and an antimicrobial agent. It is a non-proteinogenic alpha-amino acid, an L-cysteine derivative, an L-alanine derivative, a sulfoxide and an olefinic compound. It is a tautomer of an alliin zwitterion. | [Occurrence]
Alliin is a sulfoxide that is a natural constituent of fresh garlic. 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 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 with both carbon- and sulfur-centered stereochemistry[1].
| [Uses]
antibacterial, antioxidant | [Definition]
ChEBI: An L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allylsulfinyl group. | [benefits]
Different from allicin, which is quickly metabolized into diallyl disulfide and allyl mercaptan, alliin with bioavailability of 16.5% has nearly no first liver pass effect except that some are converted to diallyl disulfide. An extensive literature review discloses the nutraceutical and medicinal potential of alliin in several aspects. For example, alliin decreased fasting glucose levels and increased insulin levels to the same extent as glibenclamide, glyclazide or insulin in diabetic rats. Weeks’ administration of alliin modified the redox environment by decreasing reactive substances in organs and increasing the catalase and superoxide dismutase activities in nicotine-fed rats. Another study showed that alliin markedly depressed the increase of plasma and liver cholesterol levels in rats fed a hypercholesterolemic diet containing 10% hydrogenated coconut oil, 1% cholesterol and 0.2% cholic acid. Alliin was also found to possess anti-inflammatory activities for bowel diseases. These symptoms like diabetes, high radicals, hypercholesterolemia and inflammation are all associated with obesity and/or metabolic diseases. Supportively, a meta-analysis suggests that the single component intake of garlic may be effective for lowering plasma glucose concentration and body weight[1]. | [Synthesis]
General procedure for the synthesis of (R)-3-((S)-allyl sulfinyl)-2-aminopropionic acid from (R)-3-(allyl sulfinyl)-2-aminopropionic acid: Pure 2-PeCS (0.2 mol) obtained in step (2) was dissolved in 250 mL of distilled water, and 0.28 mol of a 30% hydrogen peroxide solution was added slowly with magnetic stirring, and the stirring was continued for 12 hours. After completion of the reaction, insoluble impurities in the solution were removed by filtration, followed by the addition of 2 L of anhydrous ethanol, and the mixture was allowed to stand at 4 °C for 6 h to induce the formation of 2-PeCSO crystals. The crystals were collected by filtration and dried at 40 °C to obtain 33.6 g of thioallyl cysteine sulfoxide (2-PeCSO). The 2-PeCSO crystals made in step (3) were dissolved in 150 mL of distilled water, heated to 50 °C and a pre-diluted acetone solution (consisting of 96 mL of distilled water with 492 mL of acetone) was slowly added at this temperature and subsequently cooled to room temperature. The mixture was allowed to stand at 4°C for 12 hours. Next, another diluted acetone solution (a mixture of 8.2 mL of distilled water with 112 mL of acetone) was added at 50°C, heat-filtered and cooled to room temperature. The solution was again allowed to stand at 4°C for 12 hours to promote crystallization. Finally, the solution was purified by thermal filtration, the crystals were collected and dried in 15 mL of distilled water to give about 3.3 g of (+)2-PeCSO in pure form. | [target]
PPAR | TNF-α | IL Receptor | NF-kB | SOD | NADPH-oxidase | ROS | [References]
[1] Baiqiang Zhai. “Hypoglycemic and hypolipidemic effect of S-allyl-cysteine sulfoxide (alliin) in DIO mice.” Scientific Reports (2018): 3527.
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