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SML0337

Sigma-Aldrich

S-Allyl-L-cysteine

≥98% (HPLC)

Synonym(s):

L-Deoxyalliin, S-allyl-cysteine, S-allylcysteine, SAC

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2S
CAS Number:
21593-77-1
Molecular Weight:
161.22
MDL number:
MFCD00151975
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329825342
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -8 to -15°, c = 1 in H2O

color

white to beige

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

N[C@@H](CSCC=C)C(O)=O

InChI

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

InChI key

ZFAHNWWNDFHPOH-YFKPBYRVSA-N

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General description

S-Allyl-L-cysteine has anti-inflammatory properties. It inhibits prooxidant enzymes and chelates metals. S-Allyl-L-cysteine exhibits hypoglycemic and cholesterol-lowering effects. It prevents apoptosis, lowers the activity of inducible nitric oxide synthase and blocks nuclear factor kappa B activity.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marcelle B M Spera et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 78(1), 313-318 (2010-11-06)
Nuclear magnetic resonance studies, molecular modeling and antibacterial assays of the palladium(II) complex with S-allyl-L-cysteine (deoxyalliin) are presented. Studies based on solid and solution 13C and 15N nuclear magnetic resonance (NMR) spectroscopy confirmed that the palladium(II) complex preserved the same
Man-Hui Pai et al.
The British journal of nutrition, 108(1), 28-38 (2011-10-21)
Oral cancer is prevalent worldwide. Studies have indicated that an increase in the osteopontin (OPN) plasma level is correlated with the progression of oral cancer. Our previous report showed that the aqueous garlic extract S-allylcysteine (SAC) inhibited the epithelial-mesenchymal transition
Samir Mandal et al.
Biochimica et biophysica acta, 1820(1), 9-23 (2011-10-29)
Chronic lead (Pb(2+)) exposure leads to the reduced lifespan of erythrocytes. Oxidative stress and K(+) loss accelerate Fas translocation into lipid raft microdomains inducing Fas mediated death signaling in these erythrocytes. Pathophysiological-based therapeutic strategies to combat against erythrocyte death were
K Ried et al.
European journal of clinical nutrition, 67(1), 64-70 (2012-11-22)
Hypertension affects about 30% of adults worldwide. Garlic has blood pressure-lowering properties and the mechanism of action is biologically plausible. Our trial assessed the effect, dose-response, tolerability and acceptability of different doses of aged garlic extract as an adjunct treatment
Ana L Colín-González et al.
Oxidative medicine and cellular longevity, 2012, 907162-907162 (2012-06-12)
Aged garlic extract (AGE) is an odorless garlic preparation containing S-allylcysteine (SAC) as its most abundant compound. A large number of studies have demonstrated the antioxidant activity of AGE and SAC in both in vivo--in diverse experimental animal models associated
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