21593-77-1

Usage

Uses

Used in Pharmaceutical Industry:
S-ALLYL-L-CYSTEINE is used as an antineoplastic agent for its potential to inhibit tumor growth and progression. It is also used as a neuroprotective and antioxidative agent, reducing edema formation in the ischemic brain and preventing neuronal cell death in cerebral ischemic insult.
Used in Nutraceutical Industry:
S-ALLYL-L-CYSTEINE is used as a supplement for its hypoglycemic and cholesterol-lowering effects, making it beneficial for individuals with diabetes and those looking to maintain healthy cholesterol levels.
Used in Food Industry:
S-ALLYL-L-CYSTEINE is used as a flavoring agent due to its cooked roasted brown aroma. It is recommended to smell in a 0.10% solution or less due to its high strength odor.
Used in Cosmetic Industry:
S-ALLYL-L-CYSTEINE can be used as an ingredient in anti-inflammatory and antioxidant skincare products, potentially benefiting individuals with inflammatory skin conditions or those looking to improve their skin's overall health.

As a flavor ingredient

Identification ▼▲ CAS.No.:? 21593-77-1? FL.No.:? 15.055 FEMA.No.:? 4322 NAS.No.:? n/a? CoE.No.:? n/a? EINECS.No.? n/a? JECFA.No.:? 1710 　 　 Description: White powder; cooked roasted brown aroma. Regulatory Status: CoE: n/a FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2007). Reported uses (ppm): (FEMA, 2007) ▼▲ Food Category? Usual? Max.? Baked goods? 2 25 Breakfast cereal? 2 25 Cheese? 2 25 Condiments, relishes? 2 25 Fats, oils? 2 25 Fish products? 2 25 Gravies? 2 25 Imitation dairy? 2 25 Instant coffee, tea? 2 25 Meat products? 2 25 Nut products? 2 25 Poultry? 2 25 Processed vegetables? 2 25 Reconstituted vegetables? 2 25 Seasonings/flavors? 2 25 Snack foods? 2 25 Soups? 2 25 ? Natural occurrence: Reported found in garlic.

Biochem/physiol Actions

S-allyl-L-cysteine is a sulfur containing amino acid found in garlic with antioxidant, anti-cancer, antihepatotoxic, neuroprotective and neurotrophic activity. S-allyl-L-cysteine has potent activity in several animal models of ischemic injury and Alzhemer′s disease.

InChI:InChI=1/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

Upstream product

• 556-27-4 S-allyl-L-cysteine sulfoxide 
• 52-90-4 L-Cysteine 
• 106-95-6 allyl bromide 
• 52-89-1 l-cysteine hydrochloride 
• 870-23-5 prop-2-ene-1-thiol 
• 5147-00-2 O-acetyl-L-serine 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 23127-41-5 (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid 
• 49621-03-6 S-propenyl-L-cysteine 
• 232953-12-7 (R)-3-allylsulfanyl-2-tert-butoxycarbonylaminopropionic acid methyl ester 
• 107-18-6 allyl alcohol 
• 1609455-99-3 (R)-3-(allylthio)-2-((R)-3-(allylthio)-2-aminopropanamido)propanoic acid 
• 556-27-4 Alliin 
• 124773-55-3 N-Boc 3-allylsulfanyl-2-aminopropionic acid 

Downstream Products

• 23127-41-5 (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid 
• 556-27-4 S-allyl-L-cysteine sulfoxide 
• 2179-57-9 diallyl disulphide 
• 539-86-6 allicin 
• 29418-05-1 bis-2-propenyl thiosulfonate 
• 113-24-6 sodium pyruvate 
• 127-17-3 2-oxo-propionic acid 
• 556-27-4 Alliin 
• 1187-84-4 S-methyl-L-cysteine 
• 52-90-4 L-Cysteine 
• 857638-18-7 (2R)-3-allylsulfanyl-2-(2,4,6-trimethoxybenzylamino)-propionic acid 
• 857638-17-6 (2R)-3-allylsulfanyl-2-(2,4-dimethoxybenzylamino)-propionic acid 
• 857638-21-2 (2R)-3-allylsulfanyl-2-(2,4-dimethoxybenzylamino)-propionic acid methyl ester 
• 857638-22-3 (2R)-3-allylsulfanyl-2-(2,4,6-trimethoxybenzylamino)-propionic acid methyl ester 

Relevant academic research and scientific papers

Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols

Incorporation of structurally novel noncanonical amino acids (ncAAs) into proteins is valuable for both scientific and biomedical applications. To expand the structural diversity of available ncAAs and to reduce the burden of chemically synthesizing them, we have developed a general and simple biosynthetic method for genetically encoding novel ncAAs into recombinant proteins by feeding cells with economical commercially available or synthetically accessible aromatic thiols. We demonstrate that nearly 50 ncAAs with a diverse array of structures can be biosynthesized from these simple small-molecule precursors by hijacking the cysteine biosynthetic enzymes, and the resulting ncAAs can subsequently be incorporated into proteins via an expanded genetic code. Moreover, we demonstrate that bioorthogonal reactive groups such as aromatic azides and aromatic ketones can be incorporated into green fluorescent protein or a therapeutic antibody with high yields, allowing for subsequent chemical conjugation.

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.

Composition for promoting differentiation of skin keratinocyte comprising a SAC derivatives or a SMC derivatives

The present invention relates to a composition for promoting keratinocyte differentiation. More specifically, SAC derivative or SMC derivatives as an active ingredient promotes differentiation of keratinocytes to promote skin keratinocyte differentiation, has excellent anti-wrinkling effect, skin barrier recovery effect, and is applicable to pharmaceutical, cosmetic, soap, body, shampoo and pack.

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

Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam3CSK4-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 ± 2.60 μM. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam3CSK4 triggered TNF-α cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam3CSK4 ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-α, to realize its anti-inflammatory activity.

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.

Derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, preparation method and use thereof

The invention relates to a derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, a preparation method and use thereof. The compound has a structure shown as a general formula (I). According to the invention, an alkyl group, an aryl group, a heteroaryl group, an alkoxycarbonylalkyl group, an acyl group, a sulfonate group, an antioxidant group such as a lipoic acid group,a H2S donor group such as a cysteine group, and a NO donor group such as a nitrate group are introduced to JJA-D0, and a series of structurally novel compounds can be synthesized and disclosed. The compounds inhibit NADPH oxidase and have superior anti-oxidation and anti-inflammatory pharmacological mechanisms by comparing with Kutkin, the compounds also have donor groups that provide NO and H2S,can further enhance pharmacological activity, and can be a new class of multifunctional compounds. The disclosed JJA-D0 derivative can be used for preparing health products or drugs for prevention ortreatment of diseases associated with NADPH oxidase, diseases associated with free radicals, diseases associated with inflammation, diseases associated with NO, and diseases associated with H2S.

Unnatural amino acid synthesis by thermostable O-phospho-L-serine sulfhydrylase from hyperthermophilic archaeon Aeropyrum pernix K1

O-Acetyl-L-serine sulfhydrylase (OASS) from plants and bacteria synthesizes cysteine and unnatural amino acids that are important building blocks for active pharmaceuticals and agrochemicals. A thermostable O-phospho-L-serine sulfhydrylase from hyperthermophilic archaeon Aeropyrum pernix K1 (OPSSAp) exhibits a function similar to OASS. In the present study, we examined the synthesis of various unnatural amino acids using OPSSAp and demonstrated OPSSAp could efficiently synthesize various sulfur-containing amino acids. OPSSAp would be useful for industrial production of biologically important unnatural amino acids.

NEW COMPOUNDS WITH ANTIOXIDANT AND ANTIAGING ACTIVITY

The present invention describes new derivatives of S-allyicysteine with antioxidant and antiaging activity. Said derivatives can be used alone or in a combined formulation with other compounds with known activity.

Tacrine-allyl/propargylcysteine-benzothiazole trihybrids as potential anti-Alzheimer's drug candidates

On continuing our research into new drug candidates for Alzheimer's disease (AD), we have designed, synthesized and evaluated a series of multifunctional trihybrid agents. The design strategy was based on the incorporation of a benzothiazole (BTA) moiety on a series of very recently reported bihybrids, resulting from the conjugation of a tacrine (TAC) with natural based moieties, namely S-allylcysteine (SAC) (garlic constituent) and S-propargylcysteine (SPRC). Thus, in addition to the acetylcholinesterase inhibition (AChEI) and anti-ROS capacity of the bihybrids (TAC-SAC/SPRC), the new trihybrids (TAC-SAC/SPRC-BTA) appeared endowed with a 5-fold capacity for inhibition of amyloid beta-peptide (Aβ) aggregation. The BTA moiety led also to considerable enhancement of the AChEI on the trihybrids, which molecular modeling suggested as being due to simultaneous binding to the catalytic active site and peripheral anionic site of AChE. The trihybrids were also assessed for MAO inhibition, but resulted in lower activity than expected, ascribed to the low accessibility of the propargyl groups to the enzyme active site. Finally, the effects of the compounds on the viability of neuroblastome cells stressed with Aβ42 and H2O2 showed moderate cell protection. Overall, the performed studies illustrate the importance (and limitations) of enclosing several molecular scaffolds in one molecular entity to allow the modulation of multiple AD targets.