Basic information
- Standard SMILES
NC(CCC(=O)NC(CS)C(=O)NCC(=O)O)C(=O)O- InChIKey
RWSXRVCMGQZWBV-UHFFFAOYSA-N- Molecular formula
- C10H17N3O6S
- Average molar mass
- 307.33 g/mol
- Monoisotopic mass
- 307.08380626
Overview
L-Glutathione (reduced) is an oligopeptide.
Names & identifiers
- Preferred name
- 2-Azaniumyl-5-((1-(Carboxymethylamino)-1-Oxo-3-Sulfanylpropan-2-Yl)Amino)-5-Oxopentanoate
- IUPAC
- 2-amino-5-[[1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
- English name
- Glutathione
- Molecular formula
- C10H17N3O6S
- Molecular weight
- 307.32
Names & synonyms
Show more names
Database identifiers
- CAS
70-18-8- PubChem CID
- 745
- DTXSID
DTXSID70859082- ChEMBL
CHEMBL100476- ChEBI
CHEBI:177535- Nikkaji
- J1.025.254G
Properties
Computed structural properties
- XLogP
- -4.5
- Topological polar surface area
- 160 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 9
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 389
Physicochemical properties
- Melting point
- 192 · 192-195 °C (dec.) (lit.)
- alpha
- -16.5 · -16.5 º (c=2, H2O)
- Boiling point
- 754.5 · 754.5±60.0 °C(Predicted)
- Density
- 1.4482 · 1.4482 (rough estimate)
- bulk density
- 160 kg/m3 · 160kg/m3
- refractive index
- -17 ° · -17 ° (C=2, H2O)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- powder
- pka
- 1 · pK1 2.12; pK2 3.53; pK3 8.66; pK4 9.12(at 25℃)
- color
- White
- PH
- 3 · 3 (10g/l, H2O, 20°C)
- Odor
- Odorless
- optical activity
- -21.327 · -21.327 (H2O)
- Water Solubility
- soluble
- Merck
- 14 · 14,4475
- BRN
- 1729812 · 1729812
- Sequence
- H-γ-Glu-Cys-Gly-OH
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Cosmetics Ingredients Functions
- REDUCING
- InChI
- 1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
- InChIKey
- RWSXRVCMGQZWBV-WDSKDSINSA-N
- SMILES
- N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
- LogP
- -1.645 · -1.645 (est)
- CAS DataBase Reference
- 70 · 70-18-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- glutathione
- FDA UNII
- 16 C9B8O · GAN16C9B8O
- NCI Drug Dictionary
- glutathione
- ATC code
- 3 AB32 · V03AB32
- EPA Substance Registry System
- Glutathione (70-18-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 68 · 68-36/37/38
- Safety Statements
- 24 · 24/25-36/37/39-27-26
- WGK Germany
- 2 · 2
- RTECS
- 556000 · MC0556000
- F
- 9 · 9-23
- TSCA
- TSCA listed
- HS Code
- 29309070 · 29309070
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety data
- F
- 9-23
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- MC0556000
- hs_code
- 29309070
- risk_code
- 68-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36/37/39-27-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Uses1.Reduced glutathione is a kind of small molecular peptide, a large number of peptides in living organisms, especially in liver cells, protect the liver cell membrane, promote the role of liver enzyme activity, and with a number of toxic chemicals in combination with play the role of detoxification.To the drug poisoning, alcoholism and other causes of liver injury, disease such as cirrhosis of the liver have good curative effect. 2.With antioxidant, scavenging free radicals, detoxification, enhance immunity, anti-aging, anti-cancer, anti radiation damage, and other functions. 3. Used as biochemical reagents,detoxification drugs, it is mainly used for the poisoning of heavy metals, acrylonitrile, fluoride, carbon monoxide and organic solvents.
DescriptionGlutathione (GSH) is a tripeptide (γ-glutamylcysteinylglycine) widely distributed in both plants and animals. GSH serves as a nucleophilic co-substrate to glutathione transferases in the detoxification of xenobiotics and is an essential electron donor to glutathione peroxidases in the reduction of hydroperoxides. GSH is also involved in amino acid transport and maintenance of protein sulfhydryl reduction status. The concentration of GSH ranges from a few micromolar in plasma to several millimolar in tissues such as liver.
Usesglutathione is a peptide composed of cysteine, glycine, and glutamate. It is believed to enhance the skin’s cellular metabolism and oxygen utilization. It has been found to protect the fibroblast against free radical-induced oxidation and act as a powerful antioxidant. Studies indicate that it can inactivate the tyrosinase enzyme and quench free radicals that contribute to tyrosinase and melanin formation, thereby serving as a skin-lightening or de- pigmenting agent. glutathione is a component of plant and animal tissue, naturally occurring in the body and essential for the proper functioning of the immune system.
UsesL-Glutathione is used in the treatment of lung diseases for patients who are HIV positive. It protects the cancerous cells by conferring resistance to chemotherapeutic drugs. It is involved in many aspects of metabolism including transport of g-glutanyl amino acids and reductive cleavage of disulfide bonds. As an antioxidant, it prevents damage to important cellular components that arise due to reactive oxygen species like free radicals and peroxide. It is also used to decrease the concentrations of inflammatory cytokines (IL-6, IL-18) as well as involved in increasing the level of serum Ca2+ ions. It is also used in white wine production.
General DescriptionGlutathione (GSH) is the most important nonprotein thiol widely distributed in animal tissues, plants, and microorganisms. GSH is also a key determinant of redox signaling and protection against oxidative stress.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.
Related reactions
Linked notes
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