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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 Code

11 - Combustible Solids

WGK

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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Bioactive Nutraceuticals and Dietary Supplements in Neurological and Brain Disease: Prevention and Therapy (2014)
Hayate Javed et al.
Brain research, 1389, 133-142 (2011-03-08)
S-allyl cysteine (SAC), a sulfur containing amino acid derived from garlic, has been reported to have antioxidant, anti-cancer, antihepatotoxic and neurotrophic activity. This study was designed to examine the pre-treatment effects of SAC on cognitive deficits and oxidative damage in
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
J Yu et al.
Placenta, 33(6), 487-494 (2012-03-13)
Preeclampsia (PE) is a major cause of fetal growth restriction and perinatal mortality, which involves oxidative stress and vasodilator signaling disorder. S-allyl-L-cysteine (SAC) is one of the most abundant compounds in garlic extracts, and possesses several biological activities. This research
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
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