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Glutathione is a substance made from the amino acids glycine, cysteine, and glutamic acid. Glutathione is produced by the liver and involved in many body processes.
Glutathione is involved in tissue building and repair, making chemicals and proteins needed in the body, and in immune system function.
CAS: 70-18-8
MF: C10H17N3O6S
MW: 307.32
EINECS: 200-725-4
Synonyms
glutatiol;glutatione;glutide;glutinal;isethion;l-glutatione;N(N-L-.gamma.-Glutamyl-L-cysteinyl)glycine;n-(n-l-gamma-glutamyl-l-cysteinyl)-glycin;glutathione;70-18-8;L-Glutathione;L-Glutathione reduced;Glutathion;Isethion;Tathion;Glutathione-SH;Glutinal;Tathione;reduced glutathione;Deltathione;Neuthion;Copren;Glutide;Triptide;Ledac;Glutatione;Glutatiol;GSH;Panaron;Glutathione SH;L-Glutatione;Glutathione (reduced);glutathione reduced;Agifutol S;L-Glutathione, reduced;L-gamma-glutamyl-L-cysteinylglycine;gamma-L-Glutamyl-L-cysteinylglycine;Glutathione [JAN];5-L-Glutamyl-L-cysteinylglycine;Glutham;gamma-L-glutamyl-L-cysteinyl-glycine;Reduced l-glutathione;CCRIS 2094;gamma-L-Glutamylcysteinylglycine;glutathione red;Aec glutathione;Glycine, L-gamma-glutamyl-Lcysteinyl-;red. glutathione;Bakezyme RX;UNII-GAN16C9B8O;(S)-2-Amino-5-(((R)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-5-oxopentanoic acid;EINECS 200-725-4;GAN16C9B8O;gamma-Glutamylcysteinylglycine;NSC 400639;L-Glutathione reduce;(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid;DTXSID6023101;CHEBI:16856;N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine;N-(N-L-gamma-Glutamyl-L-cysteinyl)glycine;glycine, N-(N-L-gamma-glutamyl-L-cysteinyl)-;Glutathione(Reduced type);L-glutamyl-L-cysteinylglycine;L-Glutathione (reduced form);(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid;DTXCID903101;BenzenaMine, 2-[(4-Methoxyphenyl)Methoxy]-;106272-20-2;95687-20-0;GLUTATHIONE (II);GLUTATHIONE [II];MFCD00065939;GLUTATHIONE (MART.);GLUTATHIONE [MART.];GLUTATHIONE (USP-RS);GLUTATHIONE [USP-RS];[Glu(-Cys)]n-Gly;GLUTATHIONE (EP MONOGRAPH);GLUTATHIONE [EP MONOGRAPH];C10H17N3O6S;NSC400639;N5-((R)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine;CAS-70-18-8;(S)-2-Amino-5-((R)-1-(carboxymethylamino)-3-mercapto-1-oxopropan-2-ylamino)-5-oxopentanoicacid;Glutathione, Reduced;Glutathione; l-gamma-Glutamyl-l-cysteinylglycine;SR-05000002567;Glutathione [BAN:JAN];L-gamma-glutamyl-L-cysteinyl-glycine;L-Glutathione reduced form;phytochelatins;ReadiSorb;1lbk;NSC-400639;NCGC00094976-01;gamma-Glu-Cys-Gly;Tathion (TN);Glutathione (JP18);Spectrum_000419;1oe7;1oe8;1r4w;C(N-.gamma.Glu-)G;GLUTATHIONE, L-;Glycine, L-.gamma.-glutamyl-L-cysteinyl-;GLUTATHIONE [MI];Reduced Glutathione,(S);Spectrum2_001500;Spectrum3_000946;Spectrum4_001056;Spectrum5_000940;?-Glutamylcysteinylglycine;Glutathione, Reduced Form;bmse000185;bmse000952;bmse000956;GLUTATHIONE [VANDF];Cys(N-.gamma.Glu-)-Gly;SCHEMBL9167;CHEMBL1543;GLUTATHIONE [WHO-DD];KBioGR_001352;KBioSS_000899;MLS001333069;DivK1c_000075;SPECTRUM1502248;SPBio_001519;gamma-glutamyl-cysteinyl-glycine;GTPL6737;?-L-Glutamyl-L-cysteinylglycine;L-?-glutamyl-L-cysteinylglycine;L-Glutathione reduced, 97.0%;CHEBI:60836;HMS500D17;KBio1_000075;KBio2_000899;KBio2_003467;KBio2_006035;KBio3_00201;(gamma-Glutamylcysteine)n-glycine;L-g-glutamyl-L-cysteinyl-glycine;NINDS_000075;HMS1921N22;Pharmakon1600-01502248;HARUTO HANGOVER DEFENCEPATCH;HY-D0187;L-Glutathione reduced, >=98.0%;Tox21_111371;BDBM50422268;CCG-38876;NSC758199;s4606;AKOS015999135;Tox21_111371_1;CS-7948;DB00143;NSC-758199;SDCCGMLS-0066687.P001;.gamma.-L-Glutamyl-L-cysteinyl-glycine;IDI1_000075;N-(N-L-?-Glutamyl-L-cysteinyl)glycine;Pharm Biol 11: 539 (1968);SMP1_000247;NCGC00264046-02;DS-14675;GSH;gamma-L-Glutamyl-L-cysteinyl-glycine;SMR000857220;SBI-0051743.P002;L-Glutathione reduced, BioXtra, >=98.0%;G0074;Glycine, N-(N-L-gamma-glutamyl-L-cysteinyl);N-(N-L-.gamma.-Glutamyl-L-cysteinyl)glycine;C00051;C02471;D00014;EN300-311690;G-3980;P19615
;AB00443568_03;Glutathione 100 microg/mL in Acetonitrile:Water;Q116907;SR-05000002567-1;SR-05000002567-2;BRD-K69346723-001-04-8;L-Glutathione reduced, Vetec(TM) reagent grade, >=98%;Z2183947556;Glutathione, European Pharmacopoeia (EP) Reference Standard;Glutathione, United States Pharmacopeia (USP) Reference Standard;Glutathione, Pharmaceutical Secondary Standard; Certified Reference Material;L-Glutathione reduced, cell culture tested, BioReagent, >=98.0%, powder
(2S)-2-AMINO-4-{[(1R)-1-[(CARBOXYMETHYL)CARBAMOYL]-2-SULFANYLETHYL]CARBAMOYLBUTANOIC ACID
glutathione; l-glutathione reduced; 5-l-glutamyl-l-cysteinylglycine; gamma-l-glutamyl-l-cysteinylglycine; gsh
Glutathione is an organic compound with the chemical formula HOCOCH(NH2)CH2CH2CONHCH(CH2SH)CONHCH2COOH.
Glutathione is a tripeptide cysteine-glycine-glutamic acid which exists in cells in the reduced form (this product) or oxidised form.
Reduced Glutathione is an antioxidant protecting cell components from endogenous and exogeneous reactive oxygen and nitrogen species.
Reduced glutathione has also been intensely used in the affinity purification of proteins with glutathione S-transferase (GST) tag.
In the protein purification process, glutathione is used for the elution of GST-fused recombinant proteins from a glutathione-immobilised resins.
In the elution buffers, reduced glutathione is typically used in the 10 â 40 mM concentration range.
Glutathione is a tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.
Glutathione has a role as a skin lightening agent, a human metabolite, an Escherichia coli metabolite, a mouse metabolite, a geroprotector, an antioxidant and a cofactor.
Glutathione is a tripeptide, a thiol and a L-cysteine derivative.
Glutathione is a conjugate acid of a glutathionate(1-).
Glutathione is an antioxidant in plants, animals, fungi, and some bacteria and archaea.
Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, peroxides, lipid peroxides, and heavy metals.
Glutathione is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and cysteine.
The carboxyl group of the cysteine residue is attached by normal peptide linkage to glycine.
People take glutathione for aging, alcohol use disorder, liver disease, heart disease, and many other conditions, but there is no good scientific evidence to support these uses.
Glutathione is composed of glutamic acid, cysteine and glycine by peptide bonds condensation of three peptide compounds,which is the most important antioxidant stress of low molecular mercaptan in mammalian cells.
In 1921 and determined the chemical structure in 1930 , the famous American nutrition health experts said Dr Al sensitive del glutathione is three times the efficiency of the anti-aging amino acid, also known as the antioxidant master of nature, the appearance is colorless transparent thin granular crystal, Glutathione is soluble in water, dilute alcohol, liquid ammonia, dimethyl formamide,and it’s insoluble in ethanol, ether, acetone.
Glutathione's solid character is stable, its aqueous solution is easy oxidized in the air for oxidized glutathione, widely exists in baker's yeast, wheat germ, animal liver, chicken blood, pig blood, tomato, pineapple, cucumber, of which is highest in the wheat germ and liver, content as high as 100~1000 mg/100 g.
With antioxidant, scavenging free radicals, detoxification, enhance immunity, anti-aging, anti-cancer, anti radiation damage, and other functions.
Glutathione also helps white blood cells to kill bacteria and prevent the oxidation of the vitamins C and E, to prevent stroke and cataract formation.
In addition, Glutathione can bind the carcinogen, than excrete them through the urine in vitro.
The liver is the most important detoxification organs, which contains rich in glutathione (GSH) on the liver function such as synthesis, detoxification, estrogen inactivated protection.
Glutathione is the first anti-oxidant that the human body is to counteract the damage of free radicals, and the free radical is a contributing factor to the aging and disease.
When the liver is damage, such as suffering from all kinds of liver disease, the body will consume large amounts of GSH to help repair the injured liver and detoxification, that cause the body's glutathione are greatly reduced.
Thus, glutathione peptide drugs are suitable for viral hepatitis (hepatitis a and hepatitis b, etc.), alcoholic liver disease,drug-induced liver disease, fatty liver disease ,Glutathione’s a good medicine to protect liver.
Glutathione is a tripeptide (γ-glutamylcysteinylglycine) widely distributed in both plants and animals.
Glutathione 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.
Glutathione is also involved in amino acid transport and maintenance of protein sulfhydryl reduction status.
The concentration of Glutathione ranges from a few micromolar in plasma to several millimolar in tissues such as liver.
A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.
Glutathione is the most important nonprotein thiol widely distributed in animal tissues, plants, and microorganisms.
Glutathione 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.
Biochemical function
Glutathione exists in reduced (GSH) and oxidized (GSSG) states.
The ratio of reduced glutathione to oxidized glutathione within cells is a measure of cellular oxidative stress where increased GSSG-to-GSH ratio is indicative of greater oxidative stress.
In the reduced state, the thiol group of cysteinyl residue is a source of one reducing equivalent.
Glutathione is thereby generated.
The oxidized state is converted to the reduced state by NADPH.
This conversion is catalyzed by glutathione reductase:
NADPH + GSSG + H2O → 2 GSH + NADP+ + OH−
Glutathione Chemical Properties
Melting point: 192-195 °C (dec.) (lit.)
Alpha: -16.5 º (c=2, H2O)
Boiling point: 754.5±60.0 °C(Predicted)
Density: 1.4482 (rough estimate)
Refractive index: -17 ° (C=2, H2O)
Storage temp.: 2-8°C
Solubility: H2O: 50 mg/mL
Form: powder
pka: pK1 2.12; pK2 3.53; pK3 8.66; pK4 9.12(at 25℃)
Color: White
PH: 3 (10g/l, H2O, 20°C)
Odor: Odorless
Optical activity: -21.327 (H2O)
Water Solubility: soluble
Merck: 14,4475
BRN: 1729812
Sequence: H-γ-Glu-Cys-Gly-OH
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey: RWSXRVCMGQZWBV-WDSKDSINSA-N
LogP: -1.645 (est)
CAS DataBase Reference: 70-18-8(CAS DataBase Reference)
EPA Substance Registry System: Glutathione (70-18-8)
Food additives
1. join the flour products, can play a role of reduction.
Not only make the time of making bread reduced to half of the original or a third, labor conditions greatly improved, and a food nutrition reinforcement and other functions.
2. Glutathione added to the yogurt and infant foods, the equivalent of vitamin C, can have the effect of stabilizing agent.
3.to the fish cake, Glutathionecan prevent the color deepened.
4.added to foods such as meat and cheese, with strong flavor of effect.
Uses
1.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, Glutathione is mainly used for the poisoning of heavy metals, acrylonitrile, fluoride, carbon monoxide and organic solvents.
Glutathione is a peptide composed of cysteine, glycine, and glutamate.
Glutathione is believed to enhance the skin’s cellular metabolism and oxygen utilization.
Glutathione has been found to protect the fibroblast against free radical-induced oxidation and act as a powerful antioxidant.
Studies indicate that Glutathione 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.
Glutathione is used in the treatment of lung diseases for patients who are HIV positive.
Glutathione protects the cancerous cells by conferring resistance to chemotherapeutic drugs.
Glutathione is involved in many aspects of metabolism including transport of g-glutanyl amino acids and reductive cleavage of disulfide bonds.
As an antioxidant, Glutathione prevents damage to important cellular components that arise due to reactive oxygen species like free radicals and peroxide.
Glutathione 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.
Glutathione is also used in white wine production.
Manufacturing Process
The tripeptide thiol Glutathione found in virtually all cells functions in metabolism, transport and cellular protection.
Glutathione may be obtained from an yeast or synthetically.
A yeast containing 600 parts of yeast solids is heated just to the boiling point of water.
The yeast solids are removed by centrifuging or filtration.
Sulphuric acid is added to the filtrate to give 0.5 N strength as sulphuric acid 6 parts of ascorbic acid are added.
Then 2 parts of cuprous oxide are added with stirring.
The reaction mixture is then centrifuged and washed until the precipitate is free from sulphates.
The precipitate is suspended in 100 parts of water and hydrogen sulfide is bubbled through the water until all of the copper is precipitated as copper sulphide.
The filtrate is evaporated and the glutathione is purified by recrystallization from 50% ethanol.
All parts are by weight.
The preparation of glutathion by methods of peptide synthesis is expansive and gives 20-30% yield of Glutathione.
For the first time synthetic glutathion was prepared by M. Bergmann et al.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst.
Glutathione-S-transferase catalyzes the formation of Glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center.
Glutathione also forms disulfide bonds with cysteine residues in proteins.
Via these mechanisms, Glutathione can have the paradoxical effect of reducing the efficacy of anti-cancer agents.
