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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

Quality Level

100

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.

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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Julio César Tobón-Velasco et al.
Free radical biology & medicine, 53(5), 1024-1040 (2012-07-12)
Pharmacological activation at the basal ganglia of the transcription factor Nrf2, guardian of redox homeostasis, holds a strong promise for the slow progression of Parkinson's disease (PD). However, a potent Nrf2 activator in the brain still must be found. In
Mei-chin Mong et al.
Journal of agricultural and food chemistry, 60(12), 3158-3165 (2012-03-08)
Renal protection of s-allyl cysteine (SAC) and s-propyl cysteine (SPC) in diabetic mice against inflammatory injury was examined. Each agent at 0.5 and 1 g/L was added to the drinking water for 10 weeks. SAC or SPC intake significantly reduced
Kevin T P Ng et al.
PloS one, 7(2), e31655-e31655 (2012-03-06)
Hepatocellular carcinoma (HCC) is highly malignant and metastatic. Currently, there is no effective chemotherapy for patients with advanced HCC leading to an urgent need to seek for novel therapeutic options. We aimed to investigate the effect of a garlic derivative
Bioactive Nutraceuticals and Dietary Supplements in Neurological and Brain Disease: Prevention and Therapy (2014)
Patricia Rojas et al.
The Journal of nutritional biochemistry, 22(10), 937-944 (2010-12-31)
S-Allylcysteine (SAC), the most abundant organosulfur compound in aged garlic extract, has multifunctional activity via different mechanisms and neuroprotective effects that are exerted probably via its antioxidant or free radical scavenger action. The 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated mouse has been the most widely
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