Glutathione
[CAS# 70-18-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: Glutathione
• Synonyms: 5-L-Glutamyl-L-cysteinylglycine; gamma-L-Glutamyl-L-cysteinylglycine; GSH
• Molecular Formula: C₁₀H₁₇N₃O₆S
• Molecular Weight: 307.32
• Protein Sequence: XCG
• CAS Registry Number: 70-18-8
• EC Number: 200-725-4
• SMILES: C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N

Properties

• Solubility: 1.927e+005 mg/L (25 °C water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.572, Calc.^*
• Melting point: 327.84 °C
• Boiling Point: 754.5±60.0 °C (760 mmHg), Calc.^*, 643.06 °C
• Flash Point: 410.1±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H315-H318-H335-H341
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P354+P338-P317-P318-P319-P321-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

Glutathione, often referred to as the “master antioxidant,” was discovered in 1888 by French chemist Dr. J. de Rey-Pailhade. It is a tripeptide composed of three amino acids: cysteine, glutamic acid, and glycine.

Glutathione plays a vital role in cellular defense mechanisms, detoxification processes, and immune function. Glutathione is a potent antioxidant that protects cells from oxidative damage caused by free radicals and reactive oxygen species (ROS). It scavenges free radicals, neutralizes oxidative stress, and regenerates other antioxidants, such as vitamins C and E, which help maintain cellular integrity and reduce the risk of chronic diseases associated with oxidative stress, including cardiovascular disease, cancer, and Neurodegenerative diseases. Glutathione plays a central role in the detoxification process by binding to and neutralizing harmful toxins, heavy metals and environmental pollutants, promoting their elimination from the body. It acts as a cofactor for glutathione S-transferase (GST), which catalyzes the binding of toxins to glutathione, making them more soluble in water and easier to be excreted through urine and bile. Glutathione plays a key role in immune function and regulation by enhancing the activity of immune cells such as lymphocytes, macrophages, and natural killer (NK) cells. It helps modulate immune responses, modulate inflammation, and protect against microbial infections and pathogens. Glutathione is popular for its potential skin whitening benefits, especially in the treatment of hyperpigmentation disorders such as melasma, age spots, and uneven skin tone. Glutathione is commonly administered orally, topically, or intravenously in dermatology clinics and in cosmetic formulations as a skin lightening agent. The role of glutathione in cancer prevention and treatment is multifaceted. It exerts anticancer effects by inhibiting tumor cell proliferation, inducing apoptosis (programmed cell death), and enhancing the efficacy of traditional cancer therapies such as chemotherapy and radiation therapy. Glutathione levels decline with age, leading to age-related decline in cell function, oxidative stress, and increased susceptibility to chronic disease. Supplementing glutathione or its precursors may help counteract age-related oxidative damage, promote cell repair and regeneration, and support healthy aging and longevity.

References

1949. Glykolvergiftung und Alloxandiabetes. Pathologische Anatomie der Glykolvergiftung und des Alloxandiabetes.
DOI: 10.1007/978-3-642-45814-9_3

2023. Glutathione-Related Enzymes and Proteins: A Review. Molecules, 28(3).
DOI: 10.3390/molecules28031447

2023. The Protective Role of Glutathione on Zinc-Induced Neuron Death after Brain Injuries. International Journal of Molecular Sciences, 24(3).
DOI: 10.3390/ijms24032950