17795-26-5

Usage

Uses

Used in Pharmaceutical Applications:
3-(Allylsulphinyl)-L-alanine is used as a therapeutic agent for its potential anticancer properties. It has been shown to exhibit anti-cancer activities, which can be beneficial in the development of new cancer treatments.
Used in Food Industry:
3-(Allylsulphinyl)-L-alanine is used as a flavor enhancer due to its allyl sulphinyl group, which contributes to the characteristic aroma and taste of certain foods.
Used in Antimicrobial Applications:
3-(Allylsulphinyl)-L-alanine is used as an antimicrobial agent, particularly against Clostridium jejuni, a bacterium that can cause food poisoning. It has been used in nutrient broth No. 2 (NB2) for determining the concentrations of garlic-derived products active against this bacterium.
Used in Cardioprotective Applications:
3-(Allylsulphinyl)-L-alanine is used as a cardioprotective agent, showing potential preventive effects on cardiac marker enzymes and lipids in isoproterenol-induced myocardial injury.
Used in Antihypertensive Applications:
3-(Allylsulphinyl)-L-alanine is used as an antihypertensive agent, which can help in the regulation of blood pressure.
Used in Antioxidant Applications:
3-(Allylsulphinyl)-L-alanine is used as an antioxidant, which can help in neutralizing free radicals and reducing oxidative stress in the body.

Biochem/physiol Actions

S-Allyl-L-cysteine ((±)-L-Alliin) (SAC) may be used to study its potential as an anti-Alzheimer′s factor. SAC has been shown to increase cell proliferation and neuroblast differentiation by increasing 5-HT(1A) and provide antioxidative benefit to neurons and synapses.

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

Upstream product

• 21593-77-1 S-allyl cysteine 
• 770742-93-3 (S)-3-(allylthio)-2-aminopropanoic acid 
• 49621-03-6 S-propenyl-L-cysteine 
• 52467-58-0 S-allyl-N-formyl-DL-cysteine 

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 

Relevant academic research and scientific papers

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.

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.

Differential inhibition of human platelet aggregation by selected Allium thiosulfinates

Thiosulfinates (TSs) have been implicated as a principle source of the antiplatelet property of raw onion and garlic juice. The in vitro responses of human platelets to dosages of four TSs were measured using whole blood aggregometry and compared by regression analysis. Of the compounds evaluated, methyl methane-TS (MMTS), propyl propane-TS (PPTS), and 2-propenyl 2-propene-TS (allicin) are present in freshly cut Allium vegetables, whereas ethyl ethane-TS (EETS) has not been detected. All TSs were synthesized using a model reaction system. PPTS and allicin had the strongest antiplatelet activity at 0.4 mM, inhibiting aggregation by 90 and 89%, respectively. At the same concentration, EETS and MMTS were significantly weaker, inhibiting 74 and 26%, respectively. Combinations of TSs were not additive in their inhibition of aggregation, indicating that the antiplatelet potential of Allium extracts cannot be easily predicted by quantifying organosulfur components. EETS, PPTS, and allicin were significantly more potent platelet inhibitors than aspirin at nearly equivalent concentrations.

In vitro biogeneration of pure thiosulfinates and propanethial-S-oxide

A model reaction system was developed for generating, pure thiosulfinates and propanethial-S-oxide (PTSO) using an isolated alliinase (EC 4.4.1.4) and isolated or synthetic alk(en)yl-L-cysteine sulfoxides (ACSO). Reaction yields ranged from 30 to 60% after 3 h at 21-23°C, and organosulfur reaction products were extracted into CHCl3 to yield product preparations of controlled composition. A pure thiosulfinate or PTSO was derived from a single ACSO, and a preparation containing a mixture of four thiosulfinate species was derived from reaction mixtures employing binary ACSO substrate systems. Identities of homologous thiosulfinates and PTSO were confirmed by 1H NMR. This approach has the potential to be used as a preparative tool for yielding pure thiosulfinates and PTSO to facilitate the study of chemical and biological properties of this group of compounds or as a means to study the dynamics of organosulfur chemistry in preparations from Allium spp.

Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA- expressed flavin-containing mono-oxygenases: Studies with S-(1,2- dichlorovinyl)-L-cysteine, S(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L- cysteine, and S-benzyl-L-cysteine

Rabbit liver microsomes catalyzed the highly stereoselective, NADPH- and time-dependent S-oxidation of S-benzyl-L-cysteine (SBC), S-allyl-L-cysteine (SAC), S-(1,2-dichlorovinyl)-L-cysteine (DCVC), and S-(1,2,2-trichlorovinyl)- L-cysteine (TCVC) to their r