Glutathione: Chemical Properties
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Chemical Properties
| Molecular Formula | C₁₀H₁₇N₃O₆S |
| Molecular Weight | 307.32 g/mol |
| CAS Number | 70-18-8 |
| PubChem CID | 124886 |
| Sequence (3-Letter) | γ-Glu-Cys-Gly |
| Sequence (1-Letter) | γ-E-C-G |
| IUPAC Name | (2S)-2-Amino-5-({(2R)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanylpropan-2-yl}amino)-5-oxopentanoic acid |
| Structure | Tripeptide with gamma-peptide linkage between γ-carboxyl of glutamate and α-amino of cysteine; contains free thiol (sulfhydryl) group; forms intermolecular disulfide bond (GSSG) upon oxidation |
| Origin | Endogenous tripeptide synthesized in virtually all mammalian cells from L-glutamate, L-cysteine, and glycine via a two-step ATP-dependent enzymatic process (GCL and GS) |
| Classification | Endogenous Tripeptide Antioxidant / Redox Modulator / Research Compound |
| Half-Life | Plasma half-life < 3 minutes (IV administration); intracellular turnover regulated by γ-glutamyl cycle |
| Bioavailability | Low oral bioavailability due to intestinal hydrolysis by γ-glutamyl transpeptidase (GGT); enhanced by liposomal or sublingual delivery |
Identifiers
| Purity Standard | ≥98% by HPLC |
| Synonyms | GSH, L-Glutathione, Reduced Glutathione, γ-L-glutamyl-L-cysteinylglycine, Isethion, Tathione, Glutatiol |
| InChI Key | RWSXRVCMGQZWBV-WDSKDSINSA-N |
| SMILES | N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O |
| InChI | 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 |
References
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- Arjinpathana N, Asawanonda P. Glutathione as an oral whitening agent: a randomized, double-blind, placebo-controlled study. Journal of Dermatological Treatment, 23(2), 97-102, 2012.
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