The solubility for this product is tested in water at a concentration of 50 mg/ml. This product has not been tested for in vitro applications.
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:
Molecular Weight:
335.38
UNSPSC Code:
12161504
PubChem Substance ID:
NACRES:
NA.26
MDL number:
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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
1 of 4
This Item | |||
|---|---|---|---|
| form powder | form solid | form solid | form powder |
| assay ≥90% (TLC) | assay >98% (titration) | assay ≥95% (HPLC) | assay ≥98% (HPLC) |
| storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. −20°C |
| color white to off-white | color white | color white | color white to off-white |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
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)
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Glutathione ethyl ester supplementation during pancreatic islet isolation improves viability and transplant outcomes in a murine marginal islet mass model
do Amaral ASR, et al.
Testing, 8(2), e55288-e55288 (2013)
The glutathione derivative, GSH monoethyl ester, may effectively whiten skin but GSH does not
Chung B, et al.
International Journal of Molecular Sciences, 17(5), 629-629 (2016)
Cytotoxic effects induced by oxidative stress in cultured mammalian cells and protection provided by Hsp27 expression
Arrigo A, et al.
Methods, 35(2), 126-138 (2005)
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)
Modulation of endothelial GSH concentrations: effect of exogenous GSH and GSH monoethyl ester.
Tsan MF
Journal of Applied Physiology, 66(3), 1029-1034 (1989)
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How do you dilute GSH MEE powder ? With DMSO ? Water ? (for in vitro use)
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If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdfHelpful?
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How is shipping temperature determined? And how is it related to the product storage temperature?
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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