21593-77-1

Basic information

• Product Name: S-ALLYL-L-CYSTEINE
• Synonyms: S-ALLYL-L-CYSTEINE;(R)-ALLYLTHIO-2-AMINOPROPIONIC ACID;s-allylcysteine;CYSTEINE, S-ALLYL-L-;DEOXYALLIIN;L-DEOXYALLIIN;(L)-3-(ALLYLSULFENYL)-ALANINE;Allylcysteine
• CAS NO: 21593-77-1
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.22
• Product Categories: Amino acids methyl、ethyl、t-butyl series;Inhibitors
• Mol File: 21593-77-1.mol
• Article Data: 34

Chemical Properties

• Melting Point: 235-236℃
• Boiling Point: 300℃
• Flash Point: 135℃
• Appearance: white to beige/
• Density: 1.191
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• Solubility: H2O: >10mg/mL
• PKA: 2.07±0.10(Predicted)
• CAS DataBase Reference: S-ALLYL-L-CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: S-ALLYL-L-CYSTEINE(21593-77-1)
• EPA Substance Registry System: S-ALLYL-L-CYSTEINE(21593-77-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: HA2466200
• Hazardous Substances Data: 21593-77-1(Hazardous Substances Data)

Usage

Description

S-ALLYL-L-CYSTEINE, also known as L-Deoxyalliin, is a water-soluble organosulfur compound derived from garlic. It is the most abundant constituent of aged garlic extracts and has been found to exhibit antineoplastic activity. S-ALLYL-L-CYSTEINE possesses anti-inflammatory properties, inhibits prooxidant enzymes, chelates metals, and exhibits hypoglycemic and cholesterol-lowering effects. It also prevents apoptosis, lowers the activity of inducible nitric oxide synthase, and blocks nuclear factor kappa B activity.

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

• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 106-95-6 allyl bromide 
• 870-23-5 prop-2-ene-1-thiol 
• 407-41-0 L-phosphoserine 
• 124773-55-3 N-Boc 3-allylsulfanyl-2-aminopropionic acid 
• 52-90-4 L-Cysteine 
• 556-27-4 Alliin 
• 107-05-1 3-chloroprop-1-ene 
• 1609455-99-3 (R)-3-(allylthio)-2-((R)-3-(allylthio)-2-aminopropanamido)propanoic acid 
• 107-18-6 allyl alcohol 
• 232953-12-7 (R)-3-allylsulfanyl-2-tert-butoxycarbonylaminopropionic acid methyl ester 
• 49621-03-6 S-propenyl-L-cysteine 
• 23127-41-5 (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid 
• 2731-73-9 2-amino-3-chloropropanoic 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 

Relevant articles and documents

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.

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.

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.