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S-methyl-laevo-cysteine
alanine, 3-(methylthio)-, L- (8CI)

Supplier Sponsors

Name:(2R)-2-amino-3-methylsulfanylpropanoic acid
CAS Number: 1187-84-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:214-701-6
FDA UNII: A34I1H07YM
Nikkaji Web:J55.191K
Beilstein Number:1721675
MDL:MFCD00002612
XlogP3-AA:-2.70 (est)
Molecular Weight:135.18613000
Formula:C4 H9 N O2 S
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 300.30 °C. @ 760.00 mm Hg (est)
Flash Point: 276.00 °F. TCC ( 135.40 °C. ) (est)
logP (o/w): 0.380 (est)
Soluble in:
 water, 2.252e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
S-Methyl-L-cysteine 98%
ExtraSynthese
For experimental / research use only.
S-Methyl-L-cysteine
Glentham Life Sciences
S-Methyl-L-cysteine
sds
Santa Cruz Biotechnology
For experimental / research use only.
S-Methyl-L-cysteine ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
S-Methyl-L-cysteine substrate for methionine sulfoxide reductase A
sds
TCI AMERICA
For experimental / research use only.
S-Methyl-L-cysteine >98.0%(T)
sds
 
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:
natural substances and extractives
Recommendation for S-methyl-laevo-cysteine usage levels up to:
 not for fragrance use.
 
Recommendation for S-methyl-laevo-cysteine flavor usage levels up to:
 not for flavor use.
 
Safety References:
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 :24417
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R)-2-amino-3-methylsulfanylpropanoic acid
Chemidplus:0001187844
RTECS:AY7175000 for cas# 1187-84-4
 
References:
 (2R)-2-amino-3-methylsulfanylpropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):24417
Pubchem (sid):135028761
 
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
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):HMDB02108
FooDB:FDB012676
Export Tariff Code:2930.90.9190
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean butter bean plant
Search Trop Picture
 garlic bulb
Search Trop Picture
 onion bulb
Search Trop Picture
 
Synonyms:
 alanine, 3-(methylthio)-, L- (8CI)
S-methyl-L-cysteine
L-cysteine, S-methyl- (9CI)
S-methylcysteine
(2R)-2-amino-3-methylsulfanylpropanoic acid
 

Articles:

PubMed:Transcriptome Profiling Identifies Candidate Genes Associated with the Accumulation of Distinct Sulfur γ-Glutamyl Dipeptides in Phaseolus vulgaris and Vigna mungo Seeds.
PubMed:Transcripts of sulphur metabolic genes are co-ordinately regulated in developing seeds of common bean lacking phaseolin and major lectins.
PubMed:Precursors and formation of pyrithione and other pyridyl-containing sulfur compounds in drumstick onion, Allium stipitatum.
PubMed:Effect of genetic characteristics and environmental factors on organosulfur compounds in garlic ( Allium sativum L.) grown in Andalusia, Spain.
PubMed:Applications of direct analysis in real time-mass spectrometry (DART-MS) in Allium chemistry. (Z)-butanethial S-oxide and 1-butenyl thiosulfinates and their S-(E)-1-butenylcysteine S-oxide precursor from Allium siculum.
PubMed:Characterization of shortday onion cultivars of 3 pungency levels with flavor precursor, free amino acid, sulfur, and sugar contents.
PubMed:The antidiabetic effect of onion and garlic in experimental diabetic rats: meta-analysis.
PubMed:Seed storage protein deficiency improves sulfur amino acid content in common bean (Phaseolus vulgaris L.): redirection of sulfur from gamma-glutamyl-S-methyl-cysteine.
PubMed:Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation.
PubMed:Antiinflammatory and antifibrogenic effects of s-ethyl cysteine and s-methyl cysteine in the kidney of diabetic mice.
PubMed:Determination of seven organosulfur compounds in garlic by high-performance liquid chromatography.
PubMed:Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.
PubMed:Antioxidative activity of sulfur-containing compounds in Allium species for human low-density lipoprotein (LDL) oxidation in vitro.
PubMed:Kale carotenoids remain stable while flavor compounds respond to changes in sulfur fertility.
PubMed:Determination of S-methyl-, S-propyl-, and S-propenyl-L-cysteine sulfoxides by gas chromatography-mass spectrometry after tert-butyldimethylsilylation.
PubMed:Characterization of some Allium hybrids by aroma precursors, aroma profiles, and alliinase activity.
PubMed:3-methylthiopropionaldehyde as precursor of dimethyl trisulfide in aged beers.
PubMed:Chemopreventive effects of S-methylcysteine on rat hepatocarcinogenesis induced by concurrent administration of sodium nitrite and morpholine.
PubMed:Cysteine sulfoxides and alliinase activity of some Allium species.
PubMed:Antimicrobial activity of sulfur compounds derived from cabbage.
PubMed:The utilization and safety of isomeric sulfur-containing amino acids in mice.
PubMed:The nutritional role of S-Methyl-L-cysteine.
PubMed:Inhibition of nitrosation of amines by thiols, alcohols and carbohydrates.
PubMed:A simple method for the approximate determination of S-methylcysteine sulphoxide (kale anaemia factor).
PubMed:Estimation of S-methylcysteine sulphoxide (kale anaemia factor) and its distribution among brassica forage and root crops.
 
Notes:
Occurs in all members of the genus Allium, at least two genera of Brassicaceae family (Brassica and Raphanus) and sporadically in the families Compositae, Leguminosae and Umbelliferae. Found in kidney bean seeds (Phaseolus vulgaris) Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble. (PMID 16484549); It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases. (PMID 15161248); It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined. (PMID 9591199)
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