N-Acetyl-S-allyl-L-cysteine

Base Information

• Chemical Name: N-Acetyl-S-allyl-L-cysteine
• CAS No.: 23127-41-5
• Molecular Formula: C8H13NO3S
• Molecular Weight: 203.262
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID20945803
• Nikkaji Number: J755.659D
• Wikidata: Q82923247
• Mol file: 23127-41-5.mol

Synonyms:N-acetyl-S-allyl-L-cysteine;N-acetyl-S-allylcysteine

Chemical Property of N-Acetyl-S-allyl-L-cysteine

Chemical Property:

• Vapor Pressure: 4.01E-09mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 444 °C at 760 mmHg
• Flash Point: 222.3 °C
• PSA: 91.70000
• Density: 1.191 g/cm³
• LogP: 0.88580
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 203.06161445
• Heavy Atom Count: 13
• Complexity: 206

Purity/Quality:

98%Min ^*data from raw suppliers

N-Acetyl-S-allyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CSCC=C)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CSCC=C)C(=O)O
• Uses: L-Deoxyalliin , also known as S-allyl-L-cysteine, is a water soluble organosulfur compound derived from garlic that has neuroprotective and antioxidative activities. N-Acetyl-S-allyl-L-cysteine is a principal metabolite of L-deoxyalliin in humans, mice, rats, and dogs. It is readily detected in plasma and urine. The conversion of L-deoxyalliin to N-acetyl-S-allyl-L-cysteine appears to be mediated by a family of flavin-containing monooxygenases.

Technology Process of N-Acetyl-S-allyl-L-cysteine

There total 12 articles about N-Acetyl-S-allyl-L-cysteine 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: 80.0%

prop-2-en-1-yl (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoate → (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid (23127-41-5,23127-20-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.6b00184

Reference yield: 60.0%

N-acetylcystein (616-91-1,7696-05-1) + allyl bromide (106-95-6) → (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid (23127-41-5,23127-20-0)

Guidance literature:

With zinc; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00268-2

Reference yield:

S-allyl cysteine (21593-77-1,49621-03-6) + acetic anhydride (108-24-7) → (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid (23127-41-5,23127-20-0)

Guidance literature:

With sodium hydroxide; at 0 ℃;

DOI:10.1002/hlca.19480310140

upstream raw materials:

S-allyl cysteine

thioacetic acid

S-allyl-L-cysteine sulfoxide

acetic anhydride

Downstream raw materials:

S-allyl cysteine

prop-2-ene-1-thiol

ammonia

acetic acid

Refernces

• 1、 Cacciatore, Ivana,Di Giulio, Mara,Fornasari, Erika,Di Stefano, Antonio,Cerasa, Laura Serafina,Marinelli, Lisa,Turkez, Hasan,Di Campli, Emanuela,Di Bartolomeo, Soraya,Robuffo, Iole,Cellini, Luigina. "Carvacrol codrugs: A new approach in the antimicrobial plan". . . Retrieved 2015/06/02.
• 2、 Chowdhury, Shantanu,Roy, Sujit. "Cobalt assisted cleavage of S-S bonds and a base-free synthesis of mercapturic acids". . p. 2149 - 2152. Retrieved 2007/10/03.