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Glutathione

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Name

Glutathione

EINECS 200-725-4
CAS No. 70-18-8 Density 1.441 g/cm3
PSA 197.62000 LogP -0.72400
Solubility Soluble in water Melting Point 192-195 °C (dec.)(lit.)
Formula C10H17N3O6S Boiling Point 754.492 °C at 760 mmHg
Molecular Weight 307.327 Flash Point 410.102 °C
Transport Information N/A Appearance White cryst. powder
Safety 24/25-36/37/39-27-26 Risk Codes 68-36/37/38
Molecular Structure Molecular Structure of 70-18-8 (Glutathione) Hazard Symbols IrritantXi
Synonyms

Glutathione(8CI);Glycine, N-(N-L-g-glutamyl-L-cysteinyl)-;Copren;Glutathion;Glutathione-SH;Glutide;Glutinal;Isethion;L-Glutathione;N-(N-L-g-Glutamyl-L-cysteinyl)glycine;Tathione;g-Glutamylcysteinylglycine;g-L-Glutamyl-L-cysteinylglycine;Glycine, L-g-glutamyl-L-cysteinyl-;GSH;L-Glutathione Reduced;

Article Data 139

Glutathione Synthetic route

(3-((S)-5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)propanoyl)-L-cysteinylglycine

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 7h;76%
131574-47-5

Boc-Glutathione-OBzl

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With methyl-phenyl-thioether; hydrogen fluoride; 3-methyl-phenol at 0℃; for 1h;62.9%
N-t-butoxycarbonyl-α-t-butyl-L-γ-glutamyl-S-ferrocenylmethyl-L-cysteinylglycine t-butyl ester

N-t-butoxycarbonyl-α-t-butyl-L-γ-glutamyl-S-ferrocenylmethyl-L-cysteinylglycine t-butyl ester

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With thiophenol; trifluoroacetic acid for 3h;52%

methylmercury-L-glutathionate

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione

A

70-18-8

GLUTATHIONE

mercury sulfide

C

593-74-8

dimethylmercury

D

2033-53-6

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

Conditions
ConditionsYield
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%

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione

C17H21HgN3O8S

A

70-18-8

GLUTATHIONE

mercury sulfide

C

bis(4-carboxyphenyl)mercury(II)

D

2033-53-6

1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

Conditions
ConditionsYield
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%
27025-41-8

Oxidized glutathione

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
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;
15401-16-8

N-[S-benzyl-N-(N-benzyloxycarbonyl-L-γ-glutamyl)-L-cysteinyl]-glycine

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With ammonia; sodium
52-90-4

L-Cysteine

56-86-0

L-glutamic acid

56-40-6

glycine

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With liver-substance
636-58-8

N-L-γ-glutamyl-L-cysteine

56-40-6

glycine

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
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;
56-40-6

glycine

70-18-8

GLUTATHIONE

Conditions
ConditionsYield
in Leber und Leber-Paeparaten;

Glutathione Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Glutathione Specification

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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