S-Acetyl-L-Glutathione (SAG / S-Acetylglutathione) is an advanced acetylated derivative of the endogenous master antioxidant tripeptide (γ-L-glutamyl-L-cysteinylglycine). Featuring an S-acetyl group attached to the active cysteine sulfur atom, S-Acetyl-L-Glutathione is lipid-permeable and highly resistant to extracellular peptidase degradation. Once inside target cells, intracellular esterases cleave the acetyl group, directly generating active reduced Glutathione (GSH) within cytoplasm and mitochondria.
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S-Acetyl-L-Glutathione (known chemically as SAG, S-Acetylglutathione, or S-acetyl-γ-L-glutamyl-L-cysteinylglycine) is a lipid-permeable, structurally modified form of the endogenous antioxidant tripeptide Glutathione. By attaching an acetyl functional group to the reactive sulfhydryl (thiol) moiety of the central cysteine residue, S-Acetyl-L-Glutathione forms a stable thioester complex that protects the molecule from premature oxidation and extracellular degradation by γ-glutamyltranspeptidase (γ-GT).
Because standard reduced Glutathione (GSH) exhibits low cell-membrane permeability, S-Acetyl-L-Glutathione serves as an efficient intracellular donor. Its lipophilic nature enables rapid passive diffusion across plasma and outer mitochondrial membranes. Once localized within the cytoplasm, ubiquitous cellular esterase enzymes cleave the acetyl bond, releasing fully active reduced GSH directly into intracellular pools.
Batch-verified for high analytical purity at Modern Aminos, S-Acetyl-L-Glutathione is offered as a standardized high-purity reference material for advanced laboratory research. Laboratories evaluating mitochondrial bioenergetics, phase II enzymatic conjugation, and free-radical neutralization evaluate S-Acetyl-L-Glutathione alongside complementary redox and tissue-repair standards available on the site, such as Reduced Glutathione (GSH), N-Acetyl Cysteine (NAC), GHK-Cu, and CoQ10.
| Compound Name | S-Acetyl-L-Glutathione (SAG) |
|---|---|
| Quantity / Formats Offered | High-Purity Dry Powder / Solid Unit Reference Standard |
| Chemical Structure | S-Acetylated Tripeptide (L-γ-glutamyl-S-acetyl-L-cysteinylglycine) |
| Synonyms / Alt Names | S-Acetylglutathione, SAG, SALG, S-acetyl-γ-L-glutamyl-L-cysteinylglycine |
| CAS Number | 3054-47-5 |
| Chemical Formula | C12H19N3O7S |
| Molecular Weight | 349.36 g/mol |
| IUPAC Name | (2S)-2-amino-5-[[(1R)-1-[(carboxymethyl)carbamoyl]-2-S-acetylethanethiol]amino]-5-oxopentanoic acid |
| InChIKey | InChIKey=VZUYBCXHMUWNEB-UHFFFAOYSA-N |
| SMILES Code | CC(=O)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N |
The biochemical pathways and cellular targets of S-Acetyl-L-Glutathione in laboratory research include:
When evaluating research efficacy and published scientific literature:
To evaluate cellular uptake dynamics, membrane permeability, and antioxidant activity, researchers compare S-Acetyl-L-Glutathione against alternative reference standards available at Modern Aminos:
| Compound / Reference | Chemical Structure & Form | Core Mechanism of Action | Research Focus & Profile |
|---|---|---|---|
| S-Acetyl-L-Glutathione (SAG) | Lipophilic S-Acetylated Tripeptide Thioester | Crosses cell membranes intact; cleaved intracellularly by esterases to elevate cytoplasmic and mitochondrial GSH | Focuses on enhanced cell permeability, intracellular GSH pool restoration, mitochondrial ROS suppression, and γ-GT resistance |
| Reduced Glutathione (GSH) | Un-Modified Endogenous Tripeptide | Direct substrate for GPx and GST enzymes; subject to extracellular cleavage by γ-GT | Standard baseline reference compound for extracellular free-radical neutralization and direct enzymatic cofactor assays |
| N-Acetyl Cysteine (NAC) | Acetylated Cysteine Amino Acid Precursor | Provides L-cysteine to support rate-limiting endogenous de novo GSH biosynthesis via glutamate-cysteine ligase | Focuses on upstream enzymatic glutathione synthesis, mucolytic cysteine signaling, and precursor rate-limiting studies |
| GHK-Cu | Copper-Chelated Signal Tripeptide | Upregulates collagen I/III, SOD1, and tissue remodeling gene expression networks | Focuses on extracellular matrix (ECM) remodeling, gene expression resetting, and superoxide dismutase activation |
Yes, Modern Aminos is a highly trusted vendor for high-purity research chemicals and reference compounds. Every batch of S-Acetyl-L-Glutathione undergoes strict third-party analytical testing (including HPLC and Mass Spectrometry) to verify minimum 98%+ chemical purity, correct thioester acetyl bond geometry, exact molecular weight (349.36 g/mol), and complete absence of heavy metals or synthetic impurities.
S-Acetyl-L-Glutathione is a chemically modified version of reduced Glutathione GSH with an acetyl group bound to the active sulfur atom. This modification increases lipophilicity, allowing the compound to diffuse across cellular and mitochondrial membranes without degradation by extracellular enzymes.
Once SAG passes through the plasma membrane into the cytoplasm, intracellular esterase enzymes hydrolyze the S-acetyl bond. This releases free, active reduced Glutathione GSH directly inside the cell to support antioxidant defense systems.
Standard reduced GSH has low cellular membrane permeability and is rapidly broken down in extracellular fluid by γ-glutamyltranspeptidase (γ-GT). SAG resists γ-GT breakdown and enters cells intact, resulting in superior intracellular GSH elevation.
Mitochondria are major sites of reactive oxygen species (ROS) generation. SAG diffuses into the mitochondrial matrix, where esterases release GSH to maintain mitochondrial Glutathione Peroxidase (GPx}) activity, preventing oxidative lipid peroxidation and membrane damage.
NAC is a precursor amino acid derivative that supplies cysteine for rate-limiting de novo glutathione synthesis. SAG is a pre-formed acetylated tripeptide that delivers active Glutathione directly into cells without depending on upstream synthetic enzymes.
Modern Aminos uses High-Performance Liquid Chromatography (HPLC) to confirm purity profiles exceeding 98% and Mass Spectrometry (MS) to verify exact molecular mass (349.36 g/mol) and structural integrity prior to batch release.
Dry S-Acetyl-L-Glutathione reference material should be stored tightly sealed in a cool, dry environment (15°C to 25°C) or frozen (-20°C) for long-term preservation. Protect from direct heat, light exposure, and atmospheric moisture to maintain solid-state chemical stability.
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