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

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

1. Used in Pharmaceutical Industry:
(S)-3-(Allylsulphinyl)-L-alanine is used as a pharmaceutical compound for its potential antibacterial properties. The presence of the (S)-allylsulfinyl group may contribute to its ability to inhibit bacterial growth, making it a candidate for the development of new antibiotics.
2. Used in Food Industry:
(S)-3-(Allylsulphinyl)-L-alanine is used as a natural antioxidant in the food industry. Its antioxidant properties can help preserve the freshness and quality of various food products, extending their shelf life and maintaining their nutritional value.
3. Used in Cosmetics Industry:
(S)-3-(Allylsulphinyl)-L-alanine can be used as an ingredient in the cosmetics industry, where its antioxidant properties may provide benefits for skin health and protection against environmental stressors.
4. Used in Research and Development:
(S)-3-(Allylsulphinyl)-L-alanine is also used in research and development for its potential applications in various fields, including pharmaceuticals, food science, and cosmetics. Its unique structure and properties make it an interesting compound for further study and potential development of new products and applications.

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

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

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 
• 29418-05-1 bis-2-propenyl thiosulfonate 
• 127-17-3 2-oxo-propionic acid 

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.

Effect of physicochemical parameters on the stability and activity of garlic alliinase and its use for in-situ allicin synthesis

Garlic is a well-known example of natural self-defence system consisting of an inactive substrate (alliin) and enzyme (alliinase) which, when combined, produce highly antimicrobial allicin. Increase of alliinase stability and its activity are of paramount importance in various applications relying on its use for in-situ synthesis of allicin or its analogues, e.g., pulmonary drug delivery, treatment of superficial injuries, or urease inhibitors in fertilizers. Here, we discuss the effect of temperature, pH, buffers, salts, and additives, i.e. antioxidants, chelating agents, reducing agents and cosolvents, on the stability and the activity of alliinase extracted from garlic. The effects of the storage temperature and relative humidity on the stability of lyophilized alliinase was demonstrated. A combination of the short half-life, high reactivity and non-specificity to particular proteins are reasons most bacteria cannot deal with allicin's mode of action and develop effective defence mechanism, which could be the key to sustainable drug design addressing serious problems with escalating emergence of multidrug-resistant (MDR) bacterial strains.

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

S-allyl-L-cysteine sulfoxide, a garlic odor precursor, suppresses elevation in blood ethanol concentration by accelerating ethanol metabolism and preventing ethanol absorption from gut

Alcoholic beverages are enjoyed together with meals worldwide, but their excessive intake is associated with an increased risk of various diseases. We investigated whether S-allyl-L-cysteine sulfoxide (ACSO), a sulfuric odor precursor of garlic, suppresses elevation in plasma ethanol concentration by accelerating ethanol metabolism and preventing ethanol absorption from the gut in rats. ACSO and garlic extract with a high ACSO content (Garlic-H) suppressed elevation in concentrations of ethanol and acetaldehyde in plasma and promoted the activities of alcohol dehydrogenase and aldehyde dehydrogenase. However, ACSO and Garlic-H did not affect plasma acetate so much. Furthermore, we examined the change in plasma ethanol concentration by injecting ACSO or Garlic-H into the ligated stomach or jejunum together with ethanol solution. ACSO and Garlic-H suppressed the absorption of ethanol from the stomach and jejunum, but suppression in the jejunum was less than in the stomach. In conclusion, ACSO inhibits ethanol absorption and accelerates ethanol metabolism.

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

A step-by-step crystallization for preparing thio alkyl/alkenyl cysteine sulfoxide method

The invention discloses a method for preparing thioalkyl/alkenyl cysteine sulfoxide by fractional crystallization, belonging to the technical field of compound preparation. The method comprises the following steps: adding cysteine or cysteine salts, a sodium hydroxide solution and an R group (alkyl or alkenyl)-derived material into absolute ethanol in sequence for reaction to synthesize coarse ACSs, re-crystallizing ACSs, purifying, oxidizing to form ACSOs, and fractionally crystallizing to obtain natural dextrorotatory ACSOs, wherein the R group-derived material is replaced to synthesize different types of ACSOs in allium; enantiomers in racemes are separated by adopting the fractional crystallization method to obtain natural dextrorotatory ACSOs with optical activity. Compared with a conventional extraction method, the method has the characteristics that the yield and the purity are high, a conventional complicated extraction process is avoided, the product has the optical activity, and the physical property is close to that of natural extract; the product is used in the fields of health products, pharmaceuticals and the like, the effects of resisting bacteria and cancers, reducing blood fat and the like of ACSOs are brought into play, or the product serves as an intermediate such as an active ingredient-diallyl thiosulfinate for synthesizing allium.

IMPROVEMENTS IN OR RELATING TO ALLIUM EXTRACTS

The present invention relates to improvements in or relating to Allium extracts. In particular, it relates to improvements in or relating to extending the therapeutic half- life or duration of Allium extracts. The invention also relates to the synthesis of certain thiosulfinate compounds, especially to the synthesis of methyl allyl thiosulfinate and allyl methyl thiosulfinate, in particular from either methiin or alliin alone or a mixture of both. The invention further relates to the synthesis of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allicin, and methyl methyl thiosulfinate in a mixture with varying molar or mass ratios depending on the reaction conditions, in particular from either methiin or alliin alone or a mixture of both. A high yielding, optimized synthesis of allicin starts from alliin, whereas methyl methyl thiosulfinate is advantageously obtained from methiin. Also provided is a kit comprising methiin in a first container and/or alliin in a second container and an allinase source, in particular garlic powder in a third container. Finally, the invention provides a method of preparing a mixture of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allyl allyl thiosulfinate (allicin) and methyl methyl thiosulfinate from methiin and pieces of an Allium species.

Enzymatic synthesis of chiral amino acid sulfoxides by Fe(II)/α- ketoglutarate-dependent dioxygenase

Asymmetric sulfoxidation of sulfur-containing l-amino acids was successfully achieved through bioconversion using IDO, which is an Fe(II)/α-ketoglutarate-dependent dioxygenase previously found in Bacillus thuringiensis strain 2e2. The IDO catalyzed sulfoxidation of l-methionine, l-ethionine, S-methyl-l-cysteine, S-ethyl-l-cysteine, and S-allyl-l-cysteine into the corresponding (S)-configured sulfoxides such as (+)-methiin and (+)-alliin, which are responsible for valuable physiological activities in mammals, and have high stereoselectivity. Herein we have established an effective preparative laboratory scale production method to obtain enantiomerically pure chiral sulfoxides using an IDO biocatalyst.

Synthesis, spectroscopic characterization, DFT studies, and antibacterial and antitumor activities of a novel water soluble Pd(II) complex with l-alliin

A new water soluble Pd(II) complex with l-alliin (S-allyl-l-cysteine sulfoxide) was obtained and characterized by a set of chemical and spectroscopic measurements. Elemental and mass spectrometric data are consistent with the formula [Pd(C6Hsu

Antiviral composition derived from allium CEPA and therapeutic use thereof

Novel medicinal extracts derived from Allium species, preferablyAllium cepaare provided. These extracts have broad medicinal properties, especially for treatment of AIDS and other viral infections.