S-acetyl-L-glutathione

Base Information

• Chemical Name: S-acetyl-L-glutathione
• CAS No.: 3054-47-5
• Molecular Formula: C12H19 N3 O7 S
• Molecular Weight: 349.365
• Hs Code.: 2934999090
• European Community (EC) Number: 221-275-5
• DSSTox Substance ID: DTXSID60952839
• Mol file: 3054-47-5.mol

Synonyms:S-acetylglutathione

Chemical Property of S-acetyl-L-glutathione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.51E-26mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 770.2°Cat760mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 419.6°C
• PSA: 201.19000
• Density: 1.436g/cm³
• LogP: -0.37410
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 349.09437113
• Heavy Atom Count: 23
• Complexity: 483

Purity/Quality:

99%, ^*data from raw suppliers

S-Acetyl-L-glutathione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• Description: S-acetyl-L-glutathione is a glutathione derivative that can increase intracellular glutathione similar to a prodrug. It can be used to replenish the depletion of reduced glutathione occurring during HIV infection and to inhibit HIV replication. However, it was found to selectively induce apoptosis in human lymphoma cells, Daudi, Raji and Jurkat cells, by depleting the intracellular glutathione level rather than increase it.
• Uses: S-Acetyl L-Glutathione is used for treating cataracts, glaucoma, preventing aging, treating or preventing alcoholism, asthma, cancer, heart disease (atherosclerosis and hypercholesterolemia), hepatitis, liver disease, immunosuppression (including AIDS and Chronic Fatigue Syndrome), maintaining immune function, memory loss, Alzheimer’s disease, osteoarthritis, Parkinson’s disease, people with ASD, detoxifying metals and drugs, cystic fibrosis, for preventing toxicity of chemotherapy, for treating male infertility, for preventing anaemia in patients undergoing haemodialysis, preventing renal dysfunction after coronary bypass surgery, shown to selectively induce apoptosis (cell death) in human lymphoma cancer cells.
• Biological Functions: S-Acetyl L-Glutathione is the most effective glutathione variant currently on the market. Glutathione (Gluthathione) is one of the most potent antioxidants that is naturally produced by the body (and the only one that is intracellular) and it has been shown to neutralize free radicals, detoxify the liver, and to improve the functioning of the immune system. After age 45, the body begins to produce less and less Glutathione and supplementing it becomes an attractive idea. Unfortunately, most Glutathione supplements have nearly no bioavailability, as the molecule breaks down rapidly after oral ingestion. S-Acetyl L-Glutathione is an altered form with an attached acetyl function group. This greatly improves its ability to remain intact in the gut and allows a greater concentration to be absorbed into the bloodstream where it can take effect. Double Wood Supplement’s S-Acetyl Glutathione is manufactured in New York city and tested for purity right here in the USA.

Technology Process of S-acetyl-L-glutathione

There total 17 articles about S-acetyl-L-glutathione 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: 91.5%

GLUTATHIONE (70-18-8) + acetyl chloride (75-36-5) → N5-((R)-3-(acetylthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine (3054-47-5)

Guidance literature:

With cobalt(II) chloride; In N,N-dimethyl-formamide; trifluoroacetic acid; at 0 - 30 ℃; for 0.166667h; Reagent/catalyst; Solvent; Time; Large scale;

DOI:10.1021/acs.oprd.5b00081

Reference yield: 85.0%

→ N5-((R)-3-(acetylthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine (3054-47-5)

Guidance literature:

Reference yield: 59.0%

GLUTATHIONE (70-18-8) → N5-((R)-3-(acetylthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine (3054-47-5)

Guidance literature:

In water; ethyl acetate; acetone; trifluoroacetic acid;

upstream raw materials:

GLUTATHIONE

thioacetic acid

S-phenyl thioacetate

acetic anhydride

Refernces

• 1、 Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo. "Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis". supporting information. p. 14976 - 14980. Retrieved 2021/09/29.
• 2、 Maimon, Eric,Lerner, Ana,Samuni, Amram,Goldstein, Sara. "Direct Observation of Acyl Nitroso Compounds in Aqueous Solution and the Kinetics of Their Reactions with Amines, Thiols, and Hydroxamic Acids". . p. 7006 - 7013. Retrieved 2018/09/06.