S-Allyl-L-cysteine

Names

[ Name ]:
S-Allyl-L-cysteine

[Synonym ]:
(R)-Allylthio-2-aminopropanoic acid
L-DEOXYALLIIN
L-Cysteine, S-2-propen-1-yl
DEOXYALLIIN
MFCD00151975
s-allylcysteine
S-Allyl-D-cysteine
S-allylcysteine zwitterion
(2R)-3-(Allylthio)-2-aminopropanoic acid
(R)-Allylthio-2-aminopropionic Acid
S-allyl cysteine
CYSTEINE,S-ALLYL-L
3-(Allylthio)-L-alanine
L-Deoxyalliin S-allyl-cysteine S-allylcysteine SAC
3-allylsulfanyl-2-amino-propionic acid
(R)-3-(Allylthio)-2-aminopropanoic acid
S-2-Propenylcysteine
L-3-(Allylthio)-alanine
(2R)-3-allylsulfanyl-2-amino-propionic acid
Allylcysteine
D-Cysteine, S-2-propen-1-yl-
L-Cysteine, S-2-propen-1-yl-

Biological Activity

[Description]:

S-Allyl-L-cysteine, one of the organosulfur compounds found in AGE, possess various biological effects including neurotrophic activity, anti-cancer activity, anti-inflammatory activity.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Research Areas >> Neurological Disease

Natural Products >> Others

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Research Areas >> Others

[In Vitro]

It is found that S-Allyl-L-cysteine could protect against amyloid-protein (A)-and tunicamycin-induced cell death in differentiated PC12 cells. Simultaneously applied S-Allyl-L-cysteine (1 μM) suppresses the cell death induced by Aβ25-35 and Aβ1-40 in a concentration-dependent manner, and neuronal integrity is almost completely retained. Simultaneously applied S-Allyl-L-cysteine significantly decreases the Aβ-induced level of ROS. The TEAC value of S-Allyl-L-cysteine is lower than that of oxidized GSH, and no antioxidant activity is observed. Intracellular GSH levels remains unaffected by treatment of neurons with S-Allyl-L-cysteine for 24 h. Furthermore, the increase in caspase-12 protein expression is suppressed by simultaneously adding 1 μM S-Allyl-L-cysteine [1]. S-Allyl-L-cysteine up to a concentration 1.0 mM does not exhibit any cytotoxic impact on morphology of myoblast and myotubes in culture observed under bright field microscope. TNF treatment leads to a significant decrease in the intracellular CK activity while S-Allyl-L-cysteine pre-treatment to TNF treated myotubes decreases the release of CK in media. S-Allyl-L-cysteine pre-treatment decreases the level of active form of this enzyme in S-Allyl-L-cysteine+TNF group. Similar observations are recorded at mRNA level for caspase-3. These results illustrate that S-Allyl-L-cysteine regulates apoptotic signals via suppressing the transcription and thus protein expression of caspase-3[2].

[References]

[1]. Kosuge Y, et al. S-allyl-L-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. Neuroscience. 2003;122(4):885-95.

[2]. Dutt V, et al. S-allyl cysteine inhibits TNFα-induced skeletal muscle wasting through suppressing proteolysis and expression of inflammatory molecules. Biochim Biophys Acta. 2018 Apr;1862(4):895-906.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.191

[ Boiling Point ]:
300 ºC

[ Melting Point ]:
235-236 ºC

[ Molecular Formula ]:
C₆H₁₁NO₂S

[ Molecular Weight ]:
161.222

[ Flash Point ]:
135 ºC

[ Exact Mass ]:
161.051056

[ PSA ]:
88.62000

[ LogP ]:
1.31

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.543

[ Storage condition ]:
2-8°C

[ Stability ]:
稳定

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
F,C

[ Risk Phrases ]:
R11:Highly Flammable. R22:Harmful if swallowed. R34:Causes burns. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S16-S26-S36/37/39-S45

[ RIDADR ]:
UN 2379 3/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
EO4460000

[ Packaging Group ]:
II

[ Hazard Class ]:
3.1

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Berberine and S allyl cysteine mediated amelioration of DEN+CCl4 induced hepatocarcinoma.

Biochim. Biophys. Acta 1840(1) , 219-44, (2014)

Diethylnitrosamine (DEN) and carbon tetrachloride (CCl4) have been used as initiator and promoter respectively to establish an animal model for investigating molecular events appear to be involved in ...

The "aged garlic extract:" (AGE) and one of its active ingredients S-allyl-L-cysteine (SAC) as potential preventive and therapeutic agents for Alzheimer's disease (AD).

Curr. Med. Chem. 18 , 3306-3313, (2011)

Alzheimer's disease (AD) is the most common form of dementia in the older people and 7(th) leading cause of death in the United States. Deposition of amyloid-beta (Aβ) plaques, hyperphosphorylation of...

S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress.

Food Chem. 194 , 843-8, (2015)

Oxidative and nitrosative stress resulting in mitochondrial dysfunction are an early event in the pathogenesis of Alzheimer's disease (AD). Nuclear factor erythroid-2-related factor 2 (Nrf2) is a key ...