Alliin Chemical Properties

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. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

1.88±0.10(Predicted)

form 

solid

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

F 

8-10

HS Code 

29309090

MSDS

• Language:English Provider:Alliin
• Language:English Provider:SigmaAldrich

Alliin Usage And Synthesis

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 It is an L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allyl sulfinyl group.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.

Chemical Properties

Colorless block crystals, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from garlic.

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ChEBI: An L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allylsulfinyl group.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.

Alliin(556-27-4)Related Product Information

• ALTRENOGEST
• Allyl glycidyl ether
• Sodium allylsulfonate
• Quizalofop-ethyl
• Glycine
• Allyl bromide
• L-Alanine
• Allyl chloride
• 6-Aminocaproic acid
• Tris(hydroxymethyl)aminomethane
• S-ALLYL-L-CYSTEINE
• Allylamine
• 3-(allylsulphinyl)-L-alanine
• D-Alliin
• alliin lyase
• DL-Alliin
• S-ALLYL-L-CYSTEINE
• AMINO ACIDS