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MedKoo Cat#: 597085 | Name: S-Ethyl glutathione

Description:

WARNING: This product is for research use only, not for human or veterinary use.

S-Ethyl glutathione is an inhibitor of the enzyme Glyoxalase 1.

Chemical Structure

S-Ethyl glutathione
S-Ethyl glutathione
CAS#24425-52-3

Theoretical Analysis

MedKoo Cat#: 597085

Name: S-Ethyl glutathione

CAS#: 24425-52-3

Chemical Formula: C12H21N3O6S

Exact Mass: 335.1151

Molecular Weight: 335.37

Elemental Analysis: C, 42.98; H, 6.31; N, 12.53; O, 28.62; S, 9.56

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Synonym
S-Ethyl glutathione; L-gamma-Glutamyl-S-ethyl-L-cysteinylglycine; Glutathione monoethyl ester; Glutathione ethyl ester;
IUPAC/Chemical Name
N5-((R)-1-((carboxymethyl)amino)-3-(ethylthio)-1-oxopropan-2-yl)-L-glutamine
InChi Key
HMFDVPSBWOHOAP-YUMQZZPRSA-N
InChi Code
InChI=1S/C12H21N3O6S/c1-2-22-6-8(11(19)14-5-10(17)18)15-9(16)4-3-7(13)12(20)21/h7-8H,2-6,13H2,1H3,(H,14,19)(H,15,16)(H,17,18)(H,20,21)/t7-,8-/m0/s1
SMILES Code
O=C(O)CNC([C@H](CSCC)NC(CC[C@@H](C(O)=O)N)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 335.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jahan I, Munemasa S, Nakamura T, Nakamura Y, Murata Y. Negative regulation of chitosan-induced stomatal closure by glutathione in Arabidopsis thaliana. Biosci Biotechnol Biochem. 2024 Jul 22;88(8):918-922. doi: 10.1093/bbb/zbae065. PMID: 38777629. 2: Sarentonglaga B, Ashibe S, Kato T, Atchalalt K, Fukumori R, Nagao Y. The effects of glutathione ethyl ester in in vitro maturation on the developmental ability of oocytes derived from cattle with liver abnormalities. Theriogenology. 2021 Aug;170:85-90. doi: 10.1016/j.theriogenology.2021.05.003. Epub 2021 May 6. PMID: 34000521. 3: Jenkins MW, Khalid F, Baby SM, May WJ, Young AP, Bates JN, Cheng F, Seckler JM, Lewis SJ. Glutathione ethyl ester reverses the deleterious effects of fentanyl on ventilation and arterial blood-gas chemistry while prolonging fentanyl-induced analgesia. Sci Rep. 2021 Mar 26;11(1):6985. doi: 10.1038/s41598-021-86458-x. PMID: 33772077; PMCID: PMC7997982. 4: Magata F, Ideta A, Matsuda F, Urakawa M, Oono Y. Glutathione ethyl ester improved the age-induced decline in the developmental competence of bovine oocytes. Theriogenology. 2021 Jun;167:37-43. doi: 10.1016/j.theriogenology.2021.03.004. Epub 2021 Mar 10. PMID: 33744770. 5: García-Martínez T, Vendrell-Flotats M, Martínez-Rodero I, Ordóñez-León EA, Álvarez-Rodríguez M, López-Béjar M, Yeste M, Mogas T. Glutathione Ethyl Ester Protects In Vitro-Maturing Bovine Oocytes against Oxidative Stress Induced by Subsequent Vitrification/Warming. Int J Mol Sci. 2020 Oct 13;21(20):7547. doi: 10.3390/ijms21207547. PMID: 33066129; PMCID: PMC7588878. 6: Knittel LL, Zhao H, Nguyen A, Miranda A, Schuck P, Sousa AA. Ultrasmall Gold Nanoparticles Coated with Zwitterionic Glutathione Monoethyl Ester: A Model Platform for the Incorporation of Functional Peptides. J Phys Chem B. 2020 May 14;124(19):3892-3902. doi: 10.1021/acs.jpcb.0c01444. Epub 2020 Apr 30. PMID: 32352799; PMCID: PMC8435207. 7: Poluektov YM, Petrushanko IY, Undrovinas NA, Lakunina VA, Khapchaev AY, Kapelko VI, Abramov AA, Lakomkin VL, Novikov MS, Shirinsky VP, Mitkevich VA, Makarov AA. Glutathione-related substances maintain cardiomyocyte contractile function in hypoxic conditions. Sci Rep. 2019 Mar 19;9(1):4872. doi: 10.1038/s41598-019-41266-2. PMID: 30890744; PMCID: PMC6425009. 8: Giustarini D, Galvagni F, Dalle Donne I, Milzani A, Severi FM, Santucci A, Rossi R. N-acetylcysteine ethyl ester as GSH enhancer in human primary endothelial cells: A comparative study with other drugs. Free Radic Biol Med. 2018 Oct;126:202-209. doi: 10.1016/j.freeradbiomed.2018.08.013. Epub 2018 Aug 14. PMID: 30114478. 9: Li Z, Gu R, Lu X, Zhao S, Feng Y, Sun Y. Preincubation with glutathione ethyl ester improves the developmental competence of vitrified mouse oocytes. J Assist Reprod Genet. 2018 Jul;35(7):1169-1178. doi: 10.1007/s10815-018-1215-4. Epub 2018 Jun 6. PMID: 29876682; PMCID: PMC6063837. 10: Kahl A, Stepanova A, Konrad C, Anderson C, Manfredi G, Zhou P, Iadecola C, Galkin A. Critical Role of Flavin and Glutathione in Complex I-Mediated Bioenergetic Failure in Brain Ischemia/Reperfusion Injury. Stroke. 2018 May;49(5):1223-1231. doi: 10.1161/STROKEAHA.117.019687. Epub 2018 Apr 11. PMID: 29643256; PMCID: PMC5916474. 11: Chen T, Turner BJ, Beart PM, Sheehan-Hennessy L, Elekwachi C, Muyderman H. Glutathione monoethyl ester prevents TDP-43 pathology in motor neuronal NSC-34 cells. Neurochem Int. 2018 Jan;112:278-287. doi: 10.1016/j.neuint.2017.08.009. Epub 2017 Aug 14. PMID: 28818672. 12: Jia Y, Wang HD, Wang Q, Ding H, Wu HM, Pan H. GSH depletion and consequent AKT inhibition contribute to the Nrf2 knockdown-induced decrease in proliferation in glioblastoma U251 cells. Oncol Rep. 2017 Apr;37(4):2252-2260. doi: 10.3892/or.2017.5467. Epub 2017 Feb 20. PMID: 28260004. 13: Trapphoff T, Heiligentag M, Simon J, Staubach N, Seidel T, Otte K, Fröhlich T, Arnold GJ, Eichenlaub-Ritter U. Improved cryotolerance and developmental potential of in vitro and in vivo matured mouse oocytes by supplementing with a glutathione donor prior to vitrification. Mol Hum Reprod. 2016 Dec;22(12):867-881. doi: 10.1093/molehr/gaw059. Epub 2016 Sep 7. PMID: 27604460. 14: Aminizadeh N, Tiraihi T, Mesbah-Namin SA, Taheri T. Stimulation of cell proliferation by glutathione monoethyl ester in aged bone marrow stromal cells is associated with the assistance of TERT gene expression and telomerase activity. In Vitro Cell Dev Biol Anim. 2016 Aug;52(7):772-81. doi: 10.1007/s11626-016-0021-5. Epub 2016 Jun 1. PMID: 27251157. 15: Habener A, Chowdhury A, Echtermeyer F, Lichtinghagen R, Theilmeier G, Herzog C. MitoNEET Protects HL-1 Cardiomyocytes from Oxidative Stress Mediated Apoptosis in an In Vitro Model of Hypoxia and Reoxygenation. PLoS One. 2016 May 31;11(5):e0156054. doi: 10.1371/journal.pone.0156054. PMID: 27243905; PMCID: PMC4887087. 16: Chung BY, Choi SR, Moon IJ, Park CW, Kim YH, Chang SE. The Glutathione Derivative, GSH Monoethyl Ester, May Effectively Whiten Skin but GSH Does Not. Int J Mol Sci. 2016 Apr 27;17(5):629. doi: 10.3390/ijms17050629. PMID: 27128906; PMCID: PMC4881455. 17: Jahan MS, Nozulaidi M, Khairi M, Mat N. Light-harvesting complexes in photosystem II regulate glutathione-induced sensitivity of Arabidopsis guard cells to abscisic acid. J Plant Physiol. 2016 May 20;195:1-8. doi: 10.1016/j.jplph.2016.03.002. Epub 2016 Mar 8. PMID: 26970687. 18: Martínez I, García-Carpizo V, Guijarro T, García-Gomez A, Navarro D, Aranda A, Zambrano A. Induction of DNA double-strand breaks and cellular senescence by human respiratory syncytial virus. Virulence. 2016 May 18;7(4):427-42. doi: 10.1080/21505594.2016.1144001. Epub 2016 Jan 25. PMID: 26809688; PMCID: PMC4871660. 19: Han H, Jin Q, Wang Y, Chen Y, Ji J. The rational design of a gemcitabine prodrug with AIE-based intracellular light-up characteristics for selective suppression of pancreatic cancer cells. Chem Commun (Camb). 2015 Dec 21;51(98):17435-8. doi: 10.1039/c5cc06654a. Epub 2015 Oct 15. PMID: 26468509. 20: Yi D, Hou Y, Wang L, Long M, Hu S, Mei H, Yan L, Hu CA, Wu G. N-acetylcysteine stimulates protein synthesis in enterocytes independently of glutathione synthesis. Amino Acids. 2016 Feb;48(2):523-33. doi: 10.1007/s00726-015-2105-z. Epub 2015 Oct 3. PMID: 26433892.