(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 127585
• Molecular Formular: C20H32N6O12S2
• Molecular Mass: 612.63108
• Monoisotopic Mass: 612.15196249
• SMILES: C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
• InChIKey: YPZRWBKMTBYPTK-BJDJZHNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: glutathione disulfide
• Synonyms: L-Glutathione oxidized; Glutathiol; (-)-Glutathione, oxidized; Glutathione disulfide; GSSG; L-Glutathione oxidized; N,N'-[Dithiobis[1-[(carboxymethyl)carbamoyl]ethylene]]diglutamine; Glutathione Disulphide; Glutathione Oxidized; Glutathione-S-S-glutathione; Glutathione-SSG; Glutathone Disulfide; Oxidized L-Glutathione; Oxidized Glutathione; Oxiglutatione; L-谷胱甘肽（氧化型）; (-)-谷胱甘肽（氧化型）; 氧化谷胱甘肽; L-谷胱甘肽（氧化型）

Database IDs

• CAS Number: 27025-41-8
• EC Number: 248-170-7
• MDL Number: MFCD00063106
• Beilstein Number: 1718700
• PubChem SID: 24895265; 24895174; 24849044; 24873118; 24873116; 24895168; 162221904
• PubChem CID: 65359
• CHEMBL: 1372
• Chemspider ID: 58835
• Wikipedia Title: Glutathione_disulfide

CALCULATED PROPERTIES

• Acid pKa: 1.438368
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -13.715199
• LogD (pH = 7.4): -16.599508
• Log P: -10.109055
• Molar Refractivity: 136.6544 cm^3
• Polarizability: 54.28691 Å^3
• Polar Surface Area: 317.64 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble10 mg/mL, clear, colorless; Water
• Apperance: lyophilized powder; powder; White Solid
• Melting Point: 178 °C (dec.)(lit.); 180-182°C
• Optical Rotation: [α]20/D -100±4°, c = 2% in H2O; [α]20/D -100±7°, c = 2% in H2O; [α]20/D -92.0 to -106.0°, c = 2% in H2O

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~98%; ≥95% (HPLC); ≥98%; ≥98% (HPLC); ≥99.0% (sum of enantiomers, HPLC)
• Ignition Residue: ≤0.5%
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; ≤6% ethanol; ≤6% water; ≤6% water (Karl Fischer); Ethanol, free
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.001%; Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Mg: ≤0.0005%; Mg: ≤10 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.005%; Na: ≤500 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Purified By: crystallization
• Quality Level: PREMIUM
• Linear Formula: [HO2CCH(NH2)CH2CH2CONHCH(CONHCH2CO2H)CH2S-]2
• Empirical Formula (Hill Notation): C20H32N6O12S2

DETAILS

Sigma Aldrich - G4376

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]

Sigma Aldrich - 49740

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]
Other Notes
Review1

Sigma Aldrich - G4501

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]

Sigma Aldrich - G9027

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]

Sigma Aldrich - 49741

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]

Sigma Aldrich - G6654

Amino Acid Sequence
Glu-Cys-Gly, Glu-Cys-Gly [Disulfide bridge: 2a-2b]

Sigma Aldrich - 150568

Packaging
5 g in glass bottle
500 mg in glass bottle
Application
Hydrogen acceptor in the enzymic determination of NADP and NADPH.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 150568.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G597970

A biomarker for fatty liver disease.

REFERENCES

• Tsou, P.-S., et al.: J. Pharmacol. Exp. Ther., 329, 649 (2009)
• Yu, Y-C., et al.: J. Neurosci. Res., 87, 1884 (2009)