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S-allyl-laevo-cysteine

Chemical Structure

General Material Information

Preferred name S-allyl-laevo-cysteine
Trivial Name (+)-S-Allylcysteine
Short Description S-allyl-L-cysteine
Formula C6 H11 N O2 S
CAS Number 21593-77-1
FEMA Number 4322
Flavis Number 17.036
FDA UNII 81R3X99M15
Nikkaji Number J490.173H
MDL MFCD00151975
xLogP3-AA -2.10 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1710 S-allyl-L-cysteine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 21593-77-1 ; S-ALLYL-L-CYSTEINE
Synonyms
  • S- allyl cysteine
  • S- allyl L-cysteine
  • allyl laevo-cysteine
  • (2R)-3-( allyl thio)-2-aminopropanoic acid
  • S- allyl-L-cysteine
  • S- allylcysteine
  • (2R)-2-amino-3-(prop-2-en-1-yl sulfanyl) propanoic acid
  • (2R)-2-amino-3-prop-2-enylsulfanylpropanoic acid
  • cysteine, S-2-propen-1-yl-
  • L- cysteine,S-2-propen-1-yl-
  • L- deoxyalliin
  • S- prop-2-en-1-ylcysteine
  • S-2-propenyl-L-cysteine
  • S-2-propenyl-laevo-cysteine
  • L-Cysteine, S-2-propen-1-yl-
  • Alanine, 3-(allylthio)-, L-
  • L-Cysteine, S-2-propenyl-
  • Alanine, 3-(allylthio)-
  • S-2-Propen-1-yl-L-cysteine
  • S-Allyl-L-cysteine
  • 3-(Allylthio)-L-alanine
  • S-Allylcysteine
  • S-2-Propenylcysteine
  • S-(2-Propenyl)-L-cysteine
  • Deoxyalliin
  • (+)-S-Allylcysteine
  • NSC 96449
  • PMK-S 005
  • (2R)-2-Amino-3-(prop-2-en-1-ylsulfanyl)propanoic acid
  • (2R)-2-Azaniumyl-3-prop-2-enylsulfanylpropanoate
  • S-1-Propenylmercaptocysteine

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Literature & References

(2R)-2-amino-3-prop-2-enylsulfanylpropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9793905
Pubchem (cas):21593-77-1
Publications by PubMed
Oral Administration of (S)-Allyl-l-Cysteine and Aged Garlic Extract to Rats: Determination of Metabolites and Their Pharmacokinetics.
EGFR gene regulation in colorectal cancer cells by garlic phytocompounds with special emphasis on S-Allyl-L-Cysteine Sulfoxide.
Thermolysis kinetics and thermal degradation compounds of alliin.
Evaluation of the Effects of S-Allyl-L-cysteine, S-Methyl-L-cysteine, trans-S-1-Propenyl-L-cysteine, and Their N-Acetylated and S-Oxidized Metabolites on Human CYP Activities.
Alliin Attenuated RANKL-Induced Osteoclastogenesis by Scavenging Reactive Oxygen Species through Inhibiting Nox1.
Molecular detection and in vitro antioxidant activity of S-allyl-L-cysteine (SAC) extracted from Allium sativum.
Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum).
Protective Effects of AGE and Its Components on Neuroinflammation and Neurodegeneration.
PMK-S005 Alleviates Age-Related Gastric Acid Secretion, Inflammation, and Oxidative Status in the Rat Stomach.
Neuroprotective effect of S-allyl-l-cysteine derivatives against endoplasmic reticulum stress-induced cytotoxicity is independent of calpain inhibition.
Downregulation of importin-9 protects MCF-7 cells against apoptosis induced by the combination of garlic-derived alliin and paclitaxel.
Pharmacokinetics of S-Allyl-l-cysteine in Rats Is Characterized by High Oral Absorption and Extensive Renal Reabsorption.
S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress.
Gastroprotective Effects of PMK-S005 against Ethanol-Induced Acute Gastric Damage in Rats.
Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic.
Enzymatic synthesis of γ-L-glutamyl-S-allyl-L-cysteine, a naturally occurring organosulfur compound from garlic, by Bacillus licheniformis γ-glutamyltranspeptidase.
Effective production of S-allyl-L-cysteine through a homogeneous reaction with activated endogenous γ-glutamyltranspeptidase in garlic (Allium Sativum).
Metabolism, excretion, and pharmacokinetics of S-allyl-L-cysteine in rats and dogs.
Garlic γ-glutamyl transpeptidases that catalyze deglutamylation of biosynthetic intermediate of alliin.
Protective effects of garlic extract, PMK-S005, against nonsteroidal anti-inflammatory drugs-induced acute gastric damage in rats.
S-allyl L-cysteine protects the retina against kainate excitotoxicity in the rat.
Development and validation of S-allyl-L-cysteine in rat plasma using a mixed-mode reversed-phase and cation-exchange LC-ESI-MS/MS method: application to pharmacokinetic studies.
Protective effect of S-allyl-L-cysteine against endoplasmic reticulum stress-induced neuronal death is mediated by inhibition of calpain.
Retraction. S-Allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells.
Effect of processing and storage time on the contents of organosulfur compounds in pickled blanched garlic.
Effects of SAC on oxidative stress and NO availability in placenta: potential benefits to preeclampsia.
The effects and underlying mechanisms of S-allyl l-cysteine treatment of the retina after ischemia/reperfusion.
Alliinase from Ensifer adhaerens and Its Use for Generation of Fungicidal Activity.
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).
[Effect of S-allyl-L-cysteine on isolate heart subject to ischemia/reperfusion].
Effects of s-allyl-L-cysteine on cell proliferation and neuroblast differentiation in the mouse dentate gyrus.
Oxidative insults to neurons and synapse are prevented by aged garlic extract and S-allyl-L-cysteine treatment in the neuronal culture and APP-Tg mouse model.
Palladium(II) complex with S-allyl-L-cysteine: new solid-state NMR spectroscopic measurements, molecular modeling and antibacterial assays.
Garlic flavonoids and organosulfur compounds: impact on the hepatic pharmacokinetics of saquinavir and darunavir.
3-(allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic.
S-allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells.
Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H(2)S production.
S-allyl L-cysteine diminishes cerebral ischemia-induced mitochondrial dysfunctions in hippocampus.
Purification and characterization of flavin-containing monooxygenase isoform 3 from rat kidney microsomes.
Unusual cystine lyase activity of the enzyme alliinase: direct formation of polysulphides.
Anti-amyloidogenic activity of S-allyl-L-cysteine and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro.
Amyloid beta-protein potentiates tunicamycin-induced neuronal death in organotypic hippocampal slice cultures.
Role of caspase-12 in amyloid beta-peptide-induced toxicity in organotypic hippocampal slices cultured for long periods.
Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor.
S-Allyl-L-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase.
Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds.
Dietary S-allyl-L-cysteine reduces mortality with decreased incidence of stroke and behavioral changes in stroke-prone spontaneously hypertensive rats.
Changes in organosulfur compounds in garlic cloves during storage.
N-acetylcysteine selectively protects cerebellar granule cells from 4-hydroxynonenal-induced cell death.
Comparative study of endoplasmic reticulum stress-induced neuronal death in rat cultured hippocampal and cerebellar granule neurons.
Redox-sensitive proteins are potential targets of garlic-derived mercaptocysteine derivatives.
In vitro interactions of water-soluble garlic components with human cytochromes p450.
Aged garlic extract and its constituents inhibit platelet aggregation through multiple mechanisms.
1H-15N NMR studies of the complex bis(S-allyl-L-cysteinate)palladium(II).
Model studies on precursor system generating blue pigment in onion and garlic.
Aminotransferase, L-amino acid oxidase and beta-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity?
Inhibition of tumor growth by a novel approach: in situ allicin generation using targeted alliinase delivery.
S-allyl-L-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death.
Neurotoxicity induced by amyloid beta-peptide and ibotenic acid in organotypic hippocampal cultures: protection by S-allyl-L-cysteine, a garlic compound.
Protective effect of S-allyl-L-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated PC12 cells.
High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection.
Sulfoxides as urinary metabolites of S-allyl-L-cysteine in rats: evidence for the involvement of flavin-containing monooxygenases.
Biomonitoring the intake of garlic via urinary excretion of allyl mercapturic acid.
N alpha-(1-deoxy-D-fructos-1-yl)-L-arginine, an antioxidant compound identified in aged garlic extract.
Methionine S-oxidation in human and rabbit liver microsomes: evidence for a high-affinity methionine S-oxidase activity that is distinct from flavin-containing monooxygenase 3.
Allyl-containing sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats.
Species and sex differences in expression of flavin-containing monooxygenase form 3 in liver and kidney microsomes.
The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins.
Neurotrophic activity of organosulfur compounds having a thioallyl group on cultured rat hippocampal neurons.
Cysteine-S-conjugate beta-lyase activity and pyridoxal phosphate binding site of onion alliin lyase.
Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin-containing mono-oxygenases: studies with S-(1,2-dichlorovinyl)-L-cysteine, S-(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L-cysteine, and S-benzyl-L-cysteine.
New agents for cancer chemoprevention.
Urinary excretion of N-acetyl-S-allyl-L-cysteine upon garlic consumption by human volunteers.
On the Isolation and Characterization of a C-S-Lyase Preparation from Leek,Allium porrum.
A novel amino acid glycoside and three amino acids from Allium sativum.
Interspecific hybrid between Allium cepa and Allium sativum.
The acute effects of S-(1,2-dichlorovinyl)-L-cysteine and related chemicals on renal function and ultrastructure in the pentobarbital-anesthetized dog: structure-activity relationships, biotransformation, and unique site-specific nephrotoxicity.
HPLC of S-Alk(en)yl-L-cysteine Derivatives in Garlic including Quantitative Determination of (+)-S-Allyl-L-cysteine Sulfoxide (Alliin).
Studies on the antimutagenic activities of garlic extract.
The C-S lyases of higher plants: preparation and properties of homogeneous alliin lyase from garlic (Allium sativum).
Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein.
Purification of the alliin lyase of garlic, Allium sativum L.
gama-L-Glutamyl-S-allyl-L-cysteine, a new gama-glutamyl peptide in garlic.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C16759
HMDB (The Human Metabolome Database):HMDB34323
FooDB:FDB012675
Export Tariff Code:2930.90.9190
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 161.22407531738
Specific gravity @ 25 °C
Pounds per Gallon
Melting Point 214 to 216°C @ 760 mm Hg
Boiling Point 300 to 301°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 135 °C TCC
logP (o/w) 1.31
Shelf life 12 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
water, slightly Yes
water, 3.291e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Roasted
cooked, roasted
General comment At 0.10 % in propylene glycol. cooked roasted

Occurrences

Potential Uses

Applications
Flavoring purposes Garlic, Onion, Roasted

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
IFRA Purity Specification:
Recommendation for S-allyl-laevo-cysteine usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 30.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): ND (μg/person/day)
NOEL (No Observed Effect Level): 250 (mg/kg bw per day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 23
Click here to view publication 23
average usual ppmaverage maximum ppm
baked goods: 2.0000025.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 2.0000025.00000
cheese: 2.0000025.00000
chewing gum: --
condiments / relishes: 2.0000025.00000
confectionery froastings: --
egg products: --
fats / oils: 2.0000025.00000
fish products: 2.0000025.00000
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: 2.0000025.00000
hard candy: --
imitation dairy: 2.0000025.00000
instant coffee / tea: 2.0000025.00000
jams / jellies: --
meat products: 2.0000025.00000
milk products: --
nut products: 2.0000025.00000
other grains: --
poultry: 2.0000025.00000
processed fruits: --
processed vegetables: 2.0000025.00000
reconstituted vegetables: 2.0000025.00000
seasonings / flavors: 2.0000025.00000
snack foods: 2.0000025.00000
soft candy: --
soups: 2.0000025.00000
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 91, Revision 1 (FGE.91Rev1): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev3 (2011)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 91, Revision 2 (FGE.91Rev2): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by the JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev5 (2012)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 91, Revision 3 (FGE.91Rev3): consideration of aliphatic, aromatic and a,ß-unsaturated sulfides and thiols evaluated by JECFA (53rd, 61st, 68th and 76th meetings), structurally related to substances in FGE.08Rev5
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9793905
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R)-2-amino-3-prop-2-enylsulfanylpropanoic acid
Chemidplus:0021593771
RTECS:HA2466200 for cas# 21593-77-1