S-Acetyl-L-glutathione

Basic Information

• Chemical Name: S-Acetyl-L-glutathione
• CAS Number: 3054-47-5
• Molecular Formula: \(\text{C}_{12}\text{H}_{19}\text{N}_{3}\text{O}_{7}\text{S}\)
• Molecular Weight: 349.36 g/mol
• Classification: Modified form of glutathione (GSH), a naturally occurring tripeptide composed of glutamate, cysteine, and glycine.

Description

Physical Properties

• Appearance: White crystalline powder.
• Solubility:
  • Poorly soluble in water (1 mg/mL in PBS at pH 7.2) 9.
  • Soluble in polar solvents (e.g., ethanol, DMSO).
• Stability:
  • pH Sensitivity: Stable at neutral pH (6.5–8.5) but hydrolyzes in acidic conditions.
  • Thermal Stability: Resistant to degradation in the digestive tract, enabling oral bioavailability 13.
  • Storage: Requires refrigeration (2–8°C) under inert gas (nitrogen or argon) 9.

Chemical Structure

Key Data

• Purity:
  • Pharmaceutical Grade: ≥99% (HPLC) 14.
  • Research Grade: ≥98% (HPLC) 3.
• Boiling Point: 770.2 ± 60.0°C (predicted) 9.
• Density: 1.436 ± 0.06 g/cm³ (predicted) 9.
• pKa: 2.21 ± 0.10 (predicted) 9.
• Loss on Drying: ≤0.5% (USP 35) 5.

Functions

Antioxidant Activity

• Free Radical Scavenging: Neutralizes reactive oxygen species (ROS) and prevents oxidative damage to DNA, proteins, and lipids 2.
• Redox Balance: Reactivates oxidized antioxidants (e.g., vitamin C, vitamin E) and maintains cellular redox homeostasis 13.

Detoxification

• Phase II Metabolism: Enhances glutathione-S-transferase activity to conjugate toxins (e.g., heavy metals, drugs) for excretion 2.

Cellular Protection

• Mitochondrial Health: Preserves mitochondrial function by reducing oxidative stress and improving energy production 15.
• DNA Repair: Supports DNA damage repair mechanisms 12.

Immune Support

• Enhances Immune Cell Function: Boosts lymphocyte activity and cytokine production 13.

Dual Role in Cancer Cells

• Apoptosis Induction: Selectively depletes glutathione in lymphoma cells (e.g., Daudi, Raji), triggering programmed cell death 7.
• Chemotherapy Protection: Safeguards healthy cells from oxidative damage during chemotherapy 9.

Applications

Cosmetics & Skincare

• Anti-Aging: Stimulates collagen synthesis and reduces UV-induced photoaging (e.g., Eslite’s SAG + SOD formulations) 12.
• Skin Whitening: Inhibits melanin production by blocking tyrosinase activity 5.

Nutraceuticals & Supplements

• Oral Supplements: Replenishes glutathione levels in aging individuals or those with deficiency (e.g., Jarrow Formulas’ vegan capsules) 16.
• Liver Support: Attenuates liver injury in conditions like hepatitis or alcoholism 12.

Pharmaceuticals

• HIV/AIDS Treatment: Restores glutathione levels in HIV-infected patients and inhibits viral replication 7.
• Neurodegenerative Diseases: Investigated for Alzheimer’s and Parkinson’s due to neuroprotective effects