PHR1359

Supelco

Glutathione

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):
L-Glutathione reduced, γ-L-Glutamyl-L-cysteinyl-glycine, GSH
Linear Formula:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
CAS Number:
Molecular Weight:
307.32
Beilstein/REAXYS Number:
1729812
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24

Quality Level

grade

certified reference material
pharmaceutical secondary standard

form

neat

CofA

current certificate can be downloaded

application(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

192-195 °C (dec.) (lit.)

Featured Industry

Pharmaceutical (small molecule)

format

neat

pharmacopeia traceability

traceable to PhEur Y0000517
traceable to USP 1294820

SMILES string

N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O

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

InChI key

RWSXRVCMGQZWBV-WDSKDSINSA-N

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Amino Acid Sequence

γ-Glu-Cys-Gly

General description

Glutathione (GSH) is the most important nonprotein thiol widely distributed in animal tissues, plants, and microorganisms. GSH is also a key determinant of redox signaling and protection against oxidative stress.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.

Biochem/physiol Actions

Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA7940 in the slot below. This is an example certificate only and may not be the lot that you receive.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 2

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Glutathione: an overview of biosynthesis and modulation
Anderson ME
Chemico-Biological Interactions, 111, 1-14 (1998)
The glutathione status of cells
International Review of Cytology, 54, 109-160 (1978)
Dalia Gritenaite et al.
Genes & development, 28(14), 1604-1619 (2014-07-18)
A key function of the cellular DNA damage response is to facilitate the bypass of replication fork-stalling DNA lesions. Template switch reactions allow such a bypass and involve the formation of DNA joint molecules (JMs) between sister chromatids. These JMs...
Karen Shahbabian et al.
Nucleic acids research, 42(13), 8692-8704 (2014-07-12)
Messenger RNA (mRNA) localization is coupled to the translational repression of transcripts during their transport. It is still unknown if this coupling depends on physical interactions between translational control and mRNA localization machineries, and how these interactions are established at...
Mikito Owa et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(26), 9461-9466 (2014-07-01)
Outer arm dynein (OAD) in cilia and flagella is bound to the outer doublet microtubules every 24 nm. Periodic binding of OADs at specific sites is important for efficient cilia/flagella beating; however, the molecular mechanism that specifies OAD arrangement remains...

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