556-27-4

Basic information

• Product Name: (S)-3-(Allylsulphinyl)-L-alanine
• Synonyms: L-Alanine, 3-(2-propenylsulfinyl)-, (S)-;S-Allyl-L-cystein-S-oxid;Alliin (25 mg);(S)-3-(Allylsulphiny;L(+)Alliin / 3-(2-Propenylsulfinyl) alanine;(+)-3-(2-PROPENYLSULFINYL) ALANINE (+/-)-L-ALLIIN (2S)-3-(ALLYLSULFINYL)-2-AMINOPROPANOIC ACID;Alliin:(S)-3-(Allylsulphinyl)-L-alanine;Allylsulphinyl-L-alanine
• CAS NO: 556-27-4
• Molecular Formula: C₆H₁₁NO₃S
• Molecular Weight: 177.22
• EINECS: 209-118-9
• Product Categories: Sulphur Derivatives;Miscellaneous Natural Products
• Mol File: 556-27-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 164-166° (effervescence)
• Boiling Point: 416.1 °C at 760 mmHg
• Flash Point: 205.5 °C
• Appearance: /solid
• Density: 1.205 (estimate)
• Vapor Pressure: 4.32E-08mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: −20°C
• PKA: 1.88±0.10(Predicted)
• Merck: 13,259
• CAS DataBase Reference: (S)-3-(Allylsulphinyl)-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(Allylsulphinyl)-L-alanine(556-27-4)
• EPA Substance Registry System: (S)-3-(Allylsulphinyl)-L-alanine(556-27-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 556-27-4(Hazardous Substances Data)

Usage

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ChEBI: An L-alanine derivative in which one of the methyl hydrogens of L-alanine has been replaced by an (S)-allylsulfinyl group.

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?/m0/s1

Synthetic route

(Rc,Ss)-S-allyl-L-cysteine sulfoxide methyl ester → Alliin (556-27-4)

Conditions	Yield
With sodium methylate In methanol; water at -20℃; for 2h;	28.2%

S-allyl cysteine (21593-77-1, 49621-03-6) → (2R)-2-amino-3-[(R)-prop-2-enylsulfinyl]propanoic acid + Alliin (556-27-4)

Conditions	Yield
With dihydrogen peroxide for 0.5h; Ambient temperature;
With dihydrogen peroxide for 0.75h; Ambient temperature;
With tris buffer pH 9.0; NADPH at 25℃; for 3h; cyclohexanone oxygenase (EC 1.14.13.22); Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With DL-dithiothreitol; iron(II) sulfate In aq. buffer at 28℃; for 16h; pH=6; Enzymatic reaction; diastereoselective reaction;	A n/a B n/a
With dihydrogen peroxide In water at 25℃; for 48h;

N-tert-butoxycarbonyl-S-(2-propenyl)-L-cysteine fluoren-9-ylmethyl ester S-oxide → (2R)-2-amino-3-[(R)-prop-2-enylsulfinyl]propanoic acid + Alliin (556-27-4)

Conditions	Yield
With diethylamine; trifluoroacetic acid 1) r.t., 2 h, 2) CH2Cl2, r.t., 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(2R)-3-allylsulfanyl-2-amino-propionic acid methyl ester (328975-04-8) → Alliin (556-27-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide / water; acetonitrile / 26 h / 20 °C 2: sodium methylate / methanol; water / 2 h / -20 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) + Alliin (556-27-4) → C11H19NO5S

Conditions	Yield
With triethylamine In water; acetone at 10 - 45℃; under 1520.1 Torr; for 5h;	94%

Alliin (556-27-4) → allicin (539-86-6) + bis-2-propenyl thiosulfonate (29418-05-1) + 2-oxo-propionic acid (127-17-3)

Conditions	Yield
With nitrogen(II) oxide; trifluoroacetic acid In water for 6h; Mechanism; Ambient temperature; other time; also in absence of CF3COOH;

Alliin (556-27-4) → allicin (539-86-6)

Conditions	Yield
With immobilized alliinase
Immobilized alliinase column;
With alliinase In water at 25 - 35℃; for 0.5h; pH=6.5 - 8.5; Time; Enzymatic reaction; Inert atmosphere;

2-methylpropan-2-thiol (75-66-1) + Alliin (556-27-4) + o-phthalic dicarboxaldehyde (643-79-8) → C18H23NO3S2

Conditions	Yield
In methanol at 20℃; for 0.5h; Darkness; aq. buffer;

L-Cysteine (52-90-4) + Alliin (556-27-4) → S-allyl cysteine (21593-77-1, 49621-03-6)

Conditions	Yield
In water at 80℃; for 24h; Sealed tube;	2.1 mg

Alliin (556-27-4) → C23H35N3O6S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C View Scheme

Alliin (556-27-4) → tapentadol-3-(N-methyl-N-((S)-3-(allylsulfinyl)-L-alanyl(methyl)amino))ethyl carbamate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 7 h / 20 °C View Scheme

Alliin (556-27-4) → C15H29N3O4S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C View Scheme

Alliin (556-27-4) → C30H50N4O6S

Conditions

Yield

Multi-step reaction with 4 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C View Scheme

Alliin (556-27-4) → C25H42N4O4S*ClH

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 7 h / 20 °C 6.1: hydrogenchloride / water; methanol / 1 h / 40 - 45 °C / pH 1 - 2 View Scheme

Upstream product

• 328975-04-8 (2R)-3-allylsulfanyl-2-amino-propionic acid methyl ester 
• 52467-58-0 S-allyl-N-formyl-DL-cysteine 
• 49621-03-6 S-propenyl-L-cysteine 
• 21593-77-1 S-allyl cysteine 
• 770742-93-3 (S)-3-(allylthio)-2-aminopropanoic acid 

Downstream Products

• 23127-41-5 (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid 
• 21593-77-1 S-allyl cysteine 
• 17795-24-3 (+/-)-S-propyl-L-cysteine sulfoxide 
• 539-86-6 allicin 
• 127-17-3 2-oxo-propionic acid 
• 29418-05-1 bis-2-propenyl thiosulfonate 

Relevant articles and documents

A Simple Synthesis of Alliin and allo-Alliin: X-ray Diffraction Analysis and Determination of Their Absolute Configurations

A simple method for the isolation of the bioactive compound alliin from garlic, as well as a method for the synthesis of diastereomerically pure alliin and allo-alliin on a preparative laboratory scale, was developed. The absolute configuration of the sulfur atom in alliin and allo-alliin was assigned on the basis of enzyme reactivity, optical rotatory dispersion, and circular dichroism analyses. A comparison of the results from these analyses, in combination with an X-ray diffraction study on a protected allo-alliin derivative, revealed S and R configurations of the sulfur atoms in alliin and allo-alliin, respectively. In addition, the same 1H NMR spectrum was observed for synthetic and natural alliin. The absolute configuration of natural alliin was assigned for the first time on the basis of the NMR spectrum and X-ray coordinates.

Type of complex-BSA binding forces affected by different coordination modes of alliin in novel water-soluble ruthenium complexes

Three novel water-soluble ruthenium complexes having differently bound alliin ligands were prepared by solution synthesis and characterized by chemical analysis, and infrared, mass, nuclear magnetic resonance and electron paramagnetic resonance spectrosco

Changes of S-Allylmercaptocysteine and γ-Glutamyl- S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process

γ-Glutamyl-S-allylmercaptocysteine (GSAMC), a putative precursor compound of S-allylmercaptocysteine (SAMC), was isolated and identified from aged garlic extract (AGE). We analyzed the change of their contents in AGE during the aging process, chronologica