Glutathione
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Glutathione
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CAS No:
70-18-8
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Formula:
C10H17N3O6S
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Chemical Name:
Glutathione
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Synonyms:
Glycine,L-γ-glutamyl-L-cysteinyl-;Glutathione;Glycine,N-(N-L-γ-glutamyl-L-cysteinyl)-;L-γ-Glutamyl-L-cysteinylglycine;γ-L-Glutamyl-L-cysteinylglycine;Glutathione-SH;GSH;L-Glutathione;Reduced glutathione;Triptide;Glutide;Tathion;Tathione;Copren;Deltathione;Glutathion;Glutinal;Isethion;Neuthion;Agifutol S;γ-Glutamylcysteinylglycine;N-(N-L-γ-Glutamyl-L-cysteinyl)glycine;Bakezyme RX;ReadiSorb;Atomolan;High Thione Extract YH 15;N5-((R)-1-((Carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine;TAD 600;1109226-07-4;1655518-50-5
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CAS No:
Description
L-Glutathione reduced (GSH; γ-L-Glutamyl-L-cysteinyl-glycine) is an endogenous antioxidant and is capable of scavenging oxygen-derived free radicals.
Solid
Glutathione is a tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine. It has a role as a skin lightening agent, a human metabolite, an Escherichia coli metabolite, a mouse metabolite, an antioxidant and a cofactor. It is a tripeptide, a thiol and a L-cysteine derivative. It is a conjugate acid of a glutathionate(1-).|A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides.|Glutathione is a tripeptide comprised of three amino acids (cysteine, glutamic acid, and glycine) present in most mammalian tissue. Glutathione acts as an antioxidant, a free radical scavenger and a detoxifying agent. Glutathione is also important as a cofactor for the enzyme glutathione peroxidase, in the uptake of amino acids, and in the synthesis of leukotrienes. As a substrate for glutathione S-transferase, this agent reacts with a number of harmful chemical species, such as halides, epoxides and free radicals, to form harmless inactive products. In erythrocytes, these reactions prevent oxidative damage through the reduction of methemoglobin and peroxides. Glutathione is also involved in the formation and maintenance of disulfide bonds in proteins and in the transport of amino acids across cell membranes.
Glutathione Basic Attributes
307.32300
307.32
200-725-4
GAN16C9B8O
758199
DTXSID6023101
C523
V - Various
2930909090
Characteristics
197.62000
-4.5
Solid
1.441 g/cm3
195 °C
410.1ºC
410.1±32.9 °C
1.571
H2O: 292.5 mg/mL
2-8ºC
167.4 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|168.23 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|164.24 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|165 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|167.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|167 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|162.1 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|164.8 Ų [M+Na-2H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|165.7 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|164.8 Ų [M-2H+Na]-
Safety Information
NONH for all modes of transport
2
R68
S24/25
MC0556000
Xi
Stable. Incompatible with strong oxidizing agents.
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501
H302
|Danger|H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 56 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
ORL-MUS LD50 5000 mg/kg, IPR-MUS LD50 4020 mg/kg, SCU-MUS LD50 5000 mg/kg, IVN-RBT LD50 > 2000 mg/kg, IMS-MUS LD50 4000 mg/kg
Drug Information
For nutritional supplementation, also for treating dietary shortage or imbalance
Research suggests that glutathione is not orally bioactive, and that very little of oral glutathione tablets or capsules is actually absorbed by the body.
Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It also plays a role in the hepatic biotransformation and detoxification process; it acts as a hydrophilic molecule that is added to other lipophilic toxins or wastes prior to entering biliary excretion. It participates in the detoxification of methylglyoxal, a toxic by-product of metabolism, mediated by glyoxalase enzymes. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. GSH is a cofactor of conjugation and reduction reactions that are catalyzed by glutathione S-transferase enzymes expressed in the cytosol, microsomes, and mitochondria. However, it is capable of participating in non-enzymatic conjugation with some chemicals, as it is hypothesized to do to a significant extent with n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450 reactive metabolite formed by toxic overdose of acetaminophen. Glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein sulfhydryl groups which would otherwise be toxically adducted. The preferred medical treatment to an overdose of this nature, whose efficacy has been consistently supported in literature, is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and allow a usable GSH pool.
gamma L Glu L Cys Gly
Glutathione Use and Manufacturing
Glutathione may decrease the concentrations of inflammatory cytokines (IL-6, IL-18), neutrophils in lung tissue and increase the level of serum Ca2+ and be useful for the treatment of ANP. Glutathione production is regulated via distinct pathways in stressed and non-stressed cortical neurons
Glycine, L-.gamma.-glutamyl-L-cysteinyl-: ACTIVE
Human drugs -> Rare disease (orphan)|Cosmetics -> Reducing
Computed Properties
Molecular Weight:307.33
XLogP3:-4.5
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:307.08380644
Monoisotopic Mass:307.08380644
Topological Polar Surface Area:160
Heavy Atom Count:20
Complexity:389
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Tripeptide compounds containing sulfhydryl (SH) groups have important physiological activities in the human body, such as activating the redox system, activating SH enzymes, and detoxifying. They participate in the tricarboxylic acid cycle and sugar metabolism in the body, promote the production of high energy in the body, and act as a coenzyme. They are the cofactor of glyceraldehyde phosphate dehydrogenase, and the coenzyme of glyoxalase and triose phosphate dehydrogenase. They can activate SH enzymes in the body, promote the metabolism of carbohydrates, fats, and proteins, and regulate the metabolic process of cell membranes. They participate in the combination of various exogenous and endogenous toxic substances to produce attenuated substances.
Registered Holders
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ANMOL CHEMICALS PRIVATE LTD
Active
United States
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Beijing Yimingyuan Pharmaceutical Technology Co., Ltd.
Active
China
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Yunnan JIDA BIOTECH Limited
Active
China
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