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G4251

Sigma-Aldrich

L-Glutathione reduced

≥98.0%

Synonym(s):

Glutathione-SH, γ-L-Glutamyl-L-cysteinyl-glycine, GSH

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10 MG
$25.40
300 MG
$31.70
1 G
$33.03
5 G
$71.60
10 G
$110.00
25 G
$198.00
50 G
$356.00
100 G
$664.00
250 G
$1,390.00
500 G
$2,520.00

$25.40

Available to ship onMay 12, 2025Details

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10 MG
$25.40
300 MG
$31.70
1 G
$33.03
5 G
$71.60
10 G
$110.00
25 G
$198.00
50 G
$356.00
100 G
$664.00
250 G
$1,390.00
500 G
$2,520.00

About This Item

Linear Formula:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
CAS Number:
70-18-8
Molecular Weight:
307.32
Beilstein/REAXYS Number:
1729812
EC Number:
200-725-4
MDL number:
MFCD00065939
UNSPSC Code:
12352209
PubChem Substance ID:
24895164
NACRES:
NA.26

$25.40

Available to ship onMay 12, 2025Details

Request a Bulk Order

Product Name

L-Glutathione reduced, ≥98.0%

Quality Level

300

assay

≥98.0%

form

powder

color

white

mp

192-195 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear, colorless

application(s)

detection

functional group

amine
carboxylic acid
thiol

storage temp.

2-8°C

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 a ubiquitous molecule found in many cells and tissues. The three amino acids present in GSH are glycine, cysteine, and glutamic acid.[1]

Application

L-Glutathione (GSH) reduced has been used in the elution buffer to elute GST (glutathione S-transferase)-fused proteins using glutathione-agarose beads.[2][3] It has been used to prepare a standard curve for GSH analyses.[4]
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.

Biochem/physiol Actions

Glutathione (GSH) forms conjugates with various metabolites and xenobiotics. It acts as an important co-factor for various enzymes. GSH is involved in many metabolic and signaling pathways. Glutathione functions as a thiol buffer for cellular proteins like thioredoxins and metallothioneins. GSH is also involved in the regeneration of antioxidants like tocopherols and ascorbate.[1]
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.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000447206
0000447189
0000447205
0000447205
0000447189

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Nitric oxide as an independent regulatory factor in regenerating rat liver.
Tuncyurek P, et al.
Acta Chirurgica Belgica, 106, 581-581 (2006)
Surface Plasmon Resonance (SPR) Analysis of Binding Interactions of Inner-Ear Proteins.
Drescher DG, et al.
Methods in Molecular Biology, 1427, 165-165 (2016)
Co-purification and direct interaction of Ras with caveolin, an integral membrane protein of caveolae microdomains. Detergent-free purification of caveolae microdomains.
Song KS, et al.
The Journal of Biological Chemistry, 271, 9690-9690 (1996)
Cu 2 O/NiO x/graphene oxide modified glassy carbon electrode for the enhanced electrochemical oxidation of reduced glutathione and nonenzyme glucose sensor.
Yuan B et al.
Electrochimica Acta, 104, 78-78 (2013)
Hee Woong Yang et al.
FEBS letters, 593(15), 2060-2068 (2019-06-11)
Ribosomal protein S3 (rpS3) has endonuclease activity for DNA repair. In particular, rpS3 cleaves the phosphodiester bonds of damaged DNA. In this study, we show that the repair domain of rpS3 spans amino acids 144-189. We fused rpS3 with the
View All Related Papers

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Questions

1–8 of 8 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. 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/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. 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

      Helpful?

  3. Can an aqueous solution of L-Glutathione be autoclaved?

    1 answer

    1. L-Glutathione Reduced aqueous solutions should not be autoclaved as the high temperature and pressure during autoclaving can degrade the compound. It is recommended to filter-sterilize the solution using a sterile filter with a pore size of 0.2 micrometers.

      Helpful?

  4. Is glutathione (reduced) safe to store at room temperature in the powder format? I mistakenly stored it at room temperature for ~ 1 month.

    1 answer

    1. This product is stored at 2-8°C but is stable for short periods at room temperature. The items ship at ambient temperature and are stable for up to 2 weeks without refrigeration. The stability of the material beyond 2 weeks has not been evaluated. The end user would have to determine the suitability for specific applications experimentally.

      Helpful?

  5. After reconstitution, what temperature should the L-glutathione reduced be stored at?

    1 answer

    1. The stability of the product in solution has not been determined. However, it is recommended to prepare solutions fresh for best results.

      Helpful?

  6. What is the solution stability of Product G4251, L-Glutathione reduced?

    1 answer

    1. Aqueous solutions readily oxidize in air to oxidized glutathione, GSSG.  Half-lives of reduced glutathione in solution at various pHs and temperatures have been reported.  The half-life of reduced glutathione is increased in the presence of a chelating agent.  For supporting references, please consult the product information sheet (under Documents, above).

      Helpful?

  7. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  8. How do I solubilize Product G4251, L-Glutathione reduced?

    1 answer

    1. Reduced glutathione is freely soluble in water, dilute alcohol, liquid ammonia, and DMF.

      Helpful?

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