GLUTATHIONE
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 7h; | 76% |
Boc-Glutathione-OBzl
GLUTATHIONE
Conditions | Yield |
---|---|
With methyl-phenyl-thioether; hydrogen fluoride; 3-methyl-phenol at 0℃; for 1h; | 62.9% |
GLUTATHIONE
Conditions | Yield |
---|---|
With thiophenol; trifluoroacetic acid for 3h; | 52% |
A
GLUTATHIONE
C
dimethylmercury
D
1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one
Conditions | Yield |
---|---|
Stage #1: methylmercury-L-glutathionate; 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione In water; acetonitrile at 37℃; for 1h; Stage #2: With sodium hydrogencarbonate In water; acetonitrile at 37℃; for 5h; | A n/a B 11 mg C n/a D 40% |
Conditions | Yield |
---|---|
Stage #1: 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione; C17H21HgN3O8S In water; acetonitrile at 37℃; for 2h; Stage #2: With sodium hydrogencarbonate In water; acetonitrile at 37℃; | A n/a B 12 mg C n/a D 32% |
Oxidized glutathione
GLUTATHIONE
Conditions | Yield |
---|---|
durch elektrolytische Reduktion in saurer Loesung an Quecksilber-Kathoden; | |
With 4,4'-bipyridinium-1,1'-dipropionate modified glutathione reductase; hydrogen; platinum In water under 760 Torr; Product distribution; Mechanism; Ambient temperature; | |
With N-Ethylmaleimide; potassium borohydride; ethylenediaminetetraacetic acid at 60℃; for 0.166667h; Product distribution; different disulfides; investigation of reaction conditions; |
N-[S-benzyl-N-(N-benzyloxycarbonyl-L-γ-glutamyl)-L-cysteinyl]-glycine
GLUTATHIONE
Conditions | Yield |
---|---|
With ammonia; sodium |
Conditions | Yield |
---|---|
With liver-substance |
Conditions | Yield |
---|---|
in Gegenwart von Enzym-Praeparaten aus tierischen Geweben oder aus Mikroorganismen; | |
With dipotassium hydrogenphosphate; glutathione synthetase; edetate disodium; ATP; sodium hydroxide; magnesium chloride In water for 20h; pH=7.5; Enzymatic reaction; | 63.5 %Chromat. |
With phosphoenolpyruvic acid; adenosine 5'-triphosphate disodium salt hydrate; β-nicotinamideadenine dinucleotide, reduced disodium salt hydrate; glutathione synthetase mutant wild type; type II rabbit muscle lactate dehydrogenase; type II rabbit muscle pyruvate kinase In aq. buffer at 37℃; for 2h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; |
Conditions | Yield |
---|---|
in Leber und Leber-Paeparaten; |
(2S)-2-amino-5-((2R)-1-(carboxymethylamino)-3-(1-hydroxy-2-oxopropylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid
A
GLUTATHIONE
B
2-oxopropanal
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; | |
With hyman erythrocyte glyoxalase I In phosphate buffer at 25℃; pH=7.0; Enzyme kinetics; Further Variations:; Catalysts; Hydrolysis; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
A
DL-glyceraldehyde 3-phosphate
B
GLUTATHIONE
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With Phorbol 12-myristate 13-acetate; glyoxalase II effect of TPA on enzyme activity; |
Oxidized glutathione
L-Cysteine
A
GLUTATHIONE
B
N5-((R)-3-(((R)-2-amino-2-carboxyethyl)disulfanyl)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; | |
With sodium chloride In water-d2 at 25℃; Rate constant; Equilibrium constant; various pD values; |
Oxidized glutathione
L-homocysteine
A
GLUTATHIONE
B
(S)-2-Amino-4-[(R)-2-((S)-3-amino-3-carboxy-propyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; various pD values; |
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; various pD values; |
L-Cysteine
N5-((R)-3-(((R)-2-amino-2-carboxyethyl)disulfanyl)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine
A
L-cystine
B
GLUTATHIONE
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; |
L-homocysteine
(S)-2-Amino-4-[(R)-2-((S)-3-amino-3-carboxy-propyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
A
L-homocystine
B
GLUTATHIONE
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; various pD values; |
3,3-dimethyl-D-cysteine
A
D-Penicillamin-disulfid
B
GLUTATHIONE
C
(S)-2-Amino-3-[(R)-2-((R)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethyldisulfanyl]-3-methyl-butyric acid
Conditions | Yield |
---|---|
Equilibrium constant; Rate constant; pH 7.4; |
2-amino-2-methylpropanethiol
A
GLUTATHIONE
B
2-(2-Amino-2-methyl-propyldisulfanyl)-1,1-dimethyl-ethylamine
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; various pD values; |
GLUTATHIONE
Oxidized glutathione
Conditions | Yield |
---|---|
With bis(4-methoxyphenyl)telluride; rose bengal In water; isopropyl alcohol at 0℃; for 1h; Irradiation; | 100% |
With Cumene hydroperoxide; tert-butyl (S)-(tetrahydrotellurophen-3-yl)carbamate In dichloromethane; water at 25℃; Flow reactor; | 100% |
With imino urea In methanol for 1.83333h; Ambient temperature; | 99% |
GLUTATHIONE
Conditions | Yield |
---|---|
With sodium hydroxide; arsenic(III) trioxide In water for 2h; | 100% |
GLUTATHIONE
Conditions | Yield |
---|---|
With arsenic(III) trioxide In water for 96h; | 100% |
With arsenic(III) trioxide In water for 96h; N2 atmosphere; | 86% |
GLUTATHIONE
N-acetyl-S-(2-phenylpropan-3-ol)-L-cysteine
Conditions | Yield |
---|---|
100% |
GLUTATHIONE
Conditions | Yield |
---|---|
In methanol; dichloromethane; water at 20℃; for 3h; | 100% |
GLUTATHIONE
Conditions | Yield |
---|---|
In methanol; dichloromethane; water at 20℃; for 3h; | 100% |
GLUTATHIONE
Conditions | Yield |
---|---|
In methanol; dichloromethane; water at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With PcpC-C14S glutathione transferase; ascorbic acid at 30 - 65℃; for 0.333333h; pH=6.5; aq. phosphate buffer; Enzymatic reaction; | 100% |
GLUTATHIONE
diethyl [1-methyl-1-([4-(iodoacetamido)benzylidene]azinoyl)ethyl]phosphonate
C26H40N5O11PS
Conditions | Yield |
---|---|
at 25℃; pH=7.4; aq. phosphate buffer; Darkness; | 100% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water; N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
GLUTATHIONE
N-(3-{5-fluoro-2-[4-(2-methoxy-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-phenyl)-acrylamide
Conditions | Yield |
---|---|
With triethylamine In methanol; dichloromethane at 0 - 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
With 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride In water for 3h; UV-irradiation; | 100% |
GLUTATHIONE
4-(5-phenyl-3-(selenocyanatomethyl)-1H-pyrazol-1-yl)benzenesulfonamide
Conditions | Yield |
---|---|
In tetrahydrofuran; water Alkaline conditions; | 100% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 1h; pH=8.2; | 100% |
In aq. buffer at 37℃; for 0.5h; Darkness; |
Conditions | Yield |
---|---|
In methanol for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
for 24h; pH=8; | 100% |
GLUTATHIONE
3,5-bis(2-hydroxybenzylidene)tetrahydro-4H-pyran-4-one
Conditions | Yield |
---|---|
In water; acetonitrile for 2h; Reflux; | 100% |
GLUTATHIONE
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In aq. acetate buffer for 4h; pH=4; Irradiation; | 100% |
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; Inert atmosphere; | 100% |
GLUTATHIONE
Conditions | Yield |
---|---|
In water; acetonitrile at 20℃; | 100% |
Conditions | Yield |
---|---|
at 37℃; for 0.166667h; pH=7.4; aq. phosphate buffer; | 99.3% |
GLUTATHIONE
2-desoxy-2-C-methylene-D-threo-pentono-1,4-lactone
2-Amino-4-[1-(carboxymethyl-carbamoyl)-2-((4R,5R)-4-hydroxy-5-hydroxymethyl-2-oxo-tetrahydro-furan-3-ylmethylsulfanyl)-ethylcarbamoyl]-butyric acid
Conditions | Yield |
---|---|
In water at 25℃; for 1h; | 99% |
GLUTATHIONE
Norophthalamic acid
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triethyl phosphite In aq. phosphate buffer; acetonitrile at 20℃; for 2h; pH=7; Catalytic behavior; Solvent; Reagent/catalyst; pH-value; Irradiation; | 99% |
With triethyl borane; triethyl phosphite 1.) CH3CN, H2O, RT, 2 min, 2.) CH3CN, H2O, RT, irradiation, 8 h; Multistep reaction; | |
With tris(2,2'-bipyridyl)ruthenium dichloride; trisodium tris(3-sulfophenyl)phosphine; 2-methylpropan-2-thiol In aq. phosphate buffer at 20℃; for 5h; pH=7.4; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation; | 87 %Spectr. |
UV-irradiation; | |
With di-tert-butyl peroxide; trisodium tris(3-sulfophenyl)phosphine In aq. phosphate buffer at 20℃; for 6h; pH=7; UV-irradiation; |
Conditions | Yield |
---|---|
In water at 20℃; for 1h; Addition; | 99% |
With phosphate buffer; ethylenediaminetetraacetic acid In water at 25℃; Kinetics; Addition; Michael addition; | |
In ethanol; water at 37℃; for 2h; pH=8; aq. phosphate buffer; |
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In water for 2h; Concentration; Irradiation; | 99% |
GLUTATHIONE
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=8.2; stereoselective reaction; | 99% |
GLUTATHIONE
S-Nitrosoglutathione
Conditions | Yield |
---|---|
With diethylenetriaminopentaacetic acid; L-phenylalanine; 1-nitrosopyrrolidine-2-thiocarboxamide at 37℃; pH=1.5; Reagent/catalyst; Darkness; | 98% |
With hydrogenchloride; diethylenetriaminopentaacetic acid; 3-nitroso-1,3-thiazolidine-4-thiocarboxamide In aq. phosphate buffer; acetonitrile at 37℃; pH=1.5; Kinetics; Reagent/catalyst; Darkness; | 95% |
With hydrogenchloride; sodium nitrite In water at 5℃; for 0.666667h; Inert atmosphere; | 77% |
GLUTATHIONE
(1H-benzo[d][1,2,3]triazol-1-yl)(naphthalen-2-yl)methanone
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In methanol; water at 20℃; | 98% |
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
Glutathione (CAS NO.70-18-8), its Synonyms are Glycine, N-(N-L-gamma-Glutamyl-L-cysteinyl)glycine ; Copren ; Deltathione ; Glutide ; Glutinal ; Glutathione ; gamma-L-Glutamylcysteinylglycine ; Glycine, L-gamma-glutamyl-L-cysteinyl- . It is white powder. Glutathione (GSH) is a tripeptide with a gamma peptide linkage between the amine group of cysteine (which is attached by normal peptide linkage to a glycine) and the carboxyl group of the glutamate side-chain. It is an antioxidant, preventing damage to important cellular components caused by reactive oxygen species such as free radicals and peroxides.
Physical properties about Glutathione are: (1)ACD/LogP: -1.645; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -5.12; (4)ACD/LogD (pH 7.4): -5.15; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00 ; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 9; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 11; (12)Index of Refraction: 1.572; (13)Molar Refractivity: 70.105 cm3; (14)Molar Volume: 213.204 cm3; (15)Polarizability: 27.792 10-24cm3; (16)Surface Tension: 69.3659973144531 dyne/cm; (17)Density: 1.441 g/cm3; (18)Flash Point: 410.102 °C; (19)Enthalpy of Vaporization: 119.618 kJ/mol; (20)Boiling Point: 754.492 °C at 760 mmHg
Uses of Glutathione: Glutathione (CAS NO.70-18-8) is a biological and chemical reagents, detoxification drugs which is mainly used for poisoning such as heavy metals, acrylonitrile, fluoride, carbon monoxide and organic solvents. Glutathione can also 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.
When you are using this chemical, please be cautious about it as the following:
1.Avoid contact with skin and eyes;
2.Wear suitable protective clothing, gloves and eye/face protection;
3.Take off immediately all contaminated clothing;
4.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure:
(1)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;
(2)InChIKey=RWSXRVCMGQZWBV-WDSKDSINSA-N;
(3)SmilesN[C@@H](CCC(=O)N[C@H](C(=O)NCC(=O)O)CS)C(=O)O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intramuscular | 4gm/kg (4000mg/kg) | "Modern Pharmaceuticals of Japan, III," Tokyo, Japan Pharmaceutical, Medical and Dental Suppl Exporters' Assoc., 1968Vol. -, Pg. 97, 1968. | |
mouse | LD50 | intraperitoneal | 4020mg/kg (4020mg/kg) | "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1972Vol. -, Pg. 93, 1972. | |
mouse | LD50 | intravenous | 2238mg/kg (2238mg/kg) | Japanese Journal of Antibiotics. Vol. 38, Pg. 137, 1985. | |
mouse | LD50 | oral | 5gm/kg (5000mg/kg) | "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1972Vol. -, Pg. 93, 1972. | |
mouse | LD50 | subcutaneous | 5gm/kg (5000mg/kg) | "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1972Vol. -, Pg. 93, 1972. | |
rabbit | LD50 | intravenous | > 2gm/kg (2000mg/kg) | Biochemical Journal. Vol. 41, Pg. 325, 1947. |
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