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Merck

G1404

Glutathione reduced ethyl ester

≥90% (TLC)

Synonym(s):

γ-Glu-Cys-Gly-OEt, GSH-MEE

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About This Item

Empirical Formula (Hill Notation):
C12H21N3O6S
CAS Number:
92614-59-0
Molecular Weight:
335.38
UNSPSC Code:
12161504
PubChem Substance ID:
329799840
NACRES:
NA.26
MDL number:
MFCD00156117

Key Documents

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Product Name

Glutathione reduced ethyl ester, ≥90% (TLC)

SMILES string

CCOC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O

InChI

1S/C12H21N3O6S/c1-2-21-10(17)5-14-11(18)8(6-22)15-9(16)4-3-7(13)12(19)20/h7-8,22H,2-6,13H2,1H3,(H,14,18)(H,15,16)(H,19,20)/t7-,8-/m0/s1

InChI key

JKRODHBGNBKZLE-YUMQZZPRSA-N

assay

≥90% (TLC)

form

powder

color

white to off-white

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Glutathione reduced ethyl ester has been used:
  • to increase intracellular glutathione levels in mouse fibroblast L929 cells
  • as a medium supplement in Spodoptera frugiperda (Sf)9 cells
  • to evaluate its effect on lipid peroxidation after spinal cord injury

Biochem/physiol Actions

Glutathione reduced ethyl ester (GSH-MEE) is a membrane/lipid permeable derivative of GSH that may be used to partially supplement the GSH supply within cells subjected to cysteine and/or GSH depletion. GSH-MEE is hydrolysed by intracellular esterases to release GSH, thereby increases the concentrations of intracellular GSH. It prevents the toxic effects of acetaminophen in animal cells. It protects human lymphoid cells and skin fibroblasts against the damage caused due to radiation.
Glutathione reduced ethyl ester inhibits melanin synthesis by inhibiting tyrosinase activity in Melan-A cells. Its antimelanogenic functionality has potential in treating hyperpigmentation skin disorders. GEE supplementation during islets isolation form pancreas reduces reactive oxygen species production and apoptosis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

G1404-BULK: + G1404-100MG: + G1404-VAR: + G1404-25MG:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
0000448147
0000448147
BCCM6324
BCCL8999
BCCJ0599

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I Rahman et al.
Biochemical pharmacology, 62(6), 787-794 (2001-09-12)
The airway epithelium is injured by oxidants inhaled as atmospheric pollutants or produced during inflammatory responses. We studied the effect of modulating the antioxidant intracellular glutathione, both using thiol compounds and by the adaptive effect of hyperoxia, on oxidant-induced injury
Reticular dysgenesis-associated AK2 protects hematopoietic stem and progenitor cell development from oxidative stress.
Rissone A
The Journal of Experimental Medicine, 212(8), 1185-1202 (2015)
Modulation of endothelial GSH concentrations: effect of exogenous GSH and GSH monoethyl ester.
Tsan MF
Journal of Applied Physiology, 66(3), 1029-1034 (1989)
Epigallocatechin-3-gallate inhibits growth of activated hepatic stellate cells by enhancing the capacity of glutathione synthesis.
Fu Y
Molecular Pharmacology, 73(5), 1465-1473 (2008)
M E Anderson et al.
Analytical biochemistry, 183(1), 16-20 (1989-11-15)
Glutathione monoesters in which the glycine carboxyl group is esterified are effective cellular glutathione delivery agents because they are readily transported into cells and are deesterified intracellularly. In contrast, glutathione itself is not effectively transported into cells. Detailed procedures are
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