S-Allylcysteine

Base Information

• Chemical Name: S-Allylcysteine
• CAS No.: 21593-77-1
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.225
• Hs Code.: 2930909090
• European Community (EC) Number: 639-018-4
• UNII: 81R3X99M15
• DSSTox Substance ID: DTXSID20894862
• Nikkaji Number: J490.173H
• Wikipedia: S-Allylcysteine
• Wikidata: Q7387047
• NCI Thesaurus Code: C63658
• ChEMBL ID: CHEMBL2048654
• Mol file: 21593-77-1.mol

Synonyms:allyl cysteine;S-2-propenyl-L-cysteine;S-allylcysteine

Chemical Property of S-Allylcysteine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235-236℃
• Refractive Index: 1.543
• Boiling Point: 300.331 °C at 760 mmHg
• PKA: 2.07±0.10(Predicted)
• Flash Point: 135.435 °C
• PSA: 88.62000
• Density: 1.191g/cm³
• LogP: 1.01780
• Storage Temp.: 2-8°C
• Solubility.: H2O: >10mg/mL
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 161.05104977
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

L-Deoxyalliin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCSCC(C(=O)O)N
• Isomeric SMILES: C=CCSC[C@@H](C(=O)O)N
• Description: L-Deoxyalliin is a water soluble organosulfur compound derived from garlic and is the most abundant constituent of aged garlic extracts. It has neuroprotective and antioxidative activities, reducing edema formation in the ischemic brain by inhibiting free radical-mediated lipid peroxidation and preventing neuronal cell death in cerebral ischemic insult by specifically scavenging peroxynitrite at concentrations up to 100 μM. L-Deoxyalliin also demonstrates various anti-amyloidogenic properties in experimental models of Alzheimer’s disease.
• Uses: A water-soluble organosulfur antineoplastic L-Deoxyalliin is a organosulfur compound that naturally occurs in garlic. L-Deoxyalliin is known to exhibit neuroprotective and antioxidative properties.

Technology Process of S-Allylcysteine

There total 17 articles about S-Allylcysteine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

L-Cysteine (52-90-4) + allyl alcohol (107-18-6) → S-allyl cysteine (21593-77-1,49621-03-6)

Guidance literature:

With ruthenium(1+), (?(5)-2,4-cyclopentadien-1-yl)(?(3)-2-propen-1-yl)(2-quinolinecarboxylato-N1,O2)-, hexafluorophosphate(1-); In methanol; at 27 ℃; for 6h; aq. acetate buffer;

DOI:10.1021/jo102278m

Reference yield: 93.0%

→ S-allyl cysteine (21593-77-1,49621-03-6)

Guidance literature:

With ammonium hydroxide; for 3h;

Reference yield: 86.0%

L-Cysteine (52-90-4) + allyl bromide (106-95-6) → S-allyl cysteine (21593-77-1,49621-03-6)

Guidance literature:

With sodium ethanolate; In ethanol; at 25 ℃;

upstream raw materials:

S-allyl-L-cysteine sulfoxide

L-Cysteine

allyl bromide

l-cysteine hydrochloride

Downstream raw materials:

(2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid

S-methyl-L-cysteine

N-tert-butoxycarbonyl-S-(2-propenyl)-L-cysteine fluoren-9-ylmethyl ester

methyl 2-allylthiomethyl-4-(3'-hydroxy-5'-hydroxymethyl-2'-methyl-4'-pyridyl)-7-phenyl-6,8-dioxo-3,7-diazabicyclo(3.3.0)octane-2-carboxylate

Refernces

• 1、 Wang, Yong,Chen, Xiaoxu,Cai, Wenkang,Tan, Linzhi,Yu, Yutong,Han, Boyang,Li, Yuxuan,Xie, Yuanzhe,Su, Yeyu,Luo, Xiaozhou,Liu, Tao. "Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols". supporting information. p. 10040 - 10048. Retrieved 2021/03/26.
• 2、 Zahirovi?, Adnan,?ili?, Dijana,Paveli?, Sandra Kraljevi?,Huki?, Mirsada,Muratovi?, Senada,Harej, Anja,Kahrovi?, Emira. "Type of complex-BSA binding forces affected by different coordination modes of alliin in novel water-soluble ruthenium complexes". . p. 5791 - 5804. Retrieved 2019/04/17.