Glutathione
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| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05822 |
| CAS | 70-18-8 |
| Molecular Weight | 307.32 |
| Molecular Formula | C10H17N3O6S |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-05822 | 100 g | $285 | In stock |
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Glutathione (GSH) is an endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione may decrease the concentrations of inflammatory cytokines (IL-6, IL-18), and neutrophils in lung tissue, increase the level of serum Ca2+, and be useful for the treatment of ANP. Glutathione can be used not only as medicine but also as a base material for functional foods. It is widely used in functional foods for delaying aging, enhancing immunity, and anti-tumor. Glutathione is the main ingredient in ''whitening needle'' injections, and it is also the main ingredient in many beauty products on the market.
Specification
| Synonyms | L-γ-Glutamyl-L-cysteinyl-glycine; Agifutol S; Bakezyme RX; Copren; Deltathione; GSH; Glutathion; Glutathione-SH; Glutide; Glutinal; Isethion; L-Glutathione; Neuthion; Reduced glutathione; Tathion; Tathione; Triptide; N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine |
| Sequence | H-gGlu-Cys-Gly-OH |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid |
| Canonical SMILES | C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N |
| 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 |
| InChI Key | RWSXRVCMGQZWBV-WDSKDSINSA-N |
Properties
| Appearance | White to Off-white Solid |
| Application | Ingredient of health care products. |
| Boiling Point | 754.5±60.0°C (Predicted) |
| Melting Point | 192-195°C |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Aqueous Base (Slightly), DMSO (Slightly), Water (Slightly) |
| LogP | -6.4 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. GSH is known as a cofactor in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. |
| Toxicity | ORL-MUS LD50 5000 mg/kg, IPR-MUS LD50 4020 mg/kg, SCU-MUS LD50 5000 mg/kg, IVN-RBT LD50 > 2000 mg/kg, IMS-MUS LD50 4000 mg/kg. |
Reference Reading
1.Glutathione plays an essential role in nitric oxide-mediated iron-deficiency signaling and iron-deficiency tolerance in Arabidopsis.
Shanmugam V;Wang YW;Tsednee M;Karunakaran K;Yeh KC Plant J. 2015 Nov;84(3):464-77. doi: 10.1111/tpj.13011.
Iron (Fe) deficiency is a common agricultural problem that affects both the productivity and nutritional quality of plants. Thus, identifying the key factors involved in the tolerance of Fe deficiency is important. In the present study, the zir1 mutant, which is glutathione deficient, was found to be more sensitive to Fe deficiency than the wild type, and grew poorly in alkaline soil. Other glutathione-deficient mutants also showed various degrees of sensitivity to Fe-limited conditions. Interestingly, we found that the glutathione level was increased under Fe deficiency in the wild type. By contrast, blocking glutathione biosynthesis led to increased physiological sensitivity to Fe deficiency. On the other hand, overexpressing glutathione enhanced the tolerance to Fe deficiency. Under Fe-limited conditions, glutathione-deficient mutants, zir1, pad2 and cad2 accumulated lower levels of Fe than the wild type. The key genes involved in Fe uptake, including IRT1, FRO2 and FIT, are expressed at low levels in zir1; however, a split-root experiment suggested that the systemic signals that govern the expression of Fe uptake-related genes are still active in zir1. Furthermore, we found that zir1 had a lower accumulation of nitric oxide (NO) and NO reservoir S-nitrosoglutathione (GSNO).
2.Protective effect of aspartate and glutamate on cardiac mitochondrial function during myocardial infarction in experimental rats.
Sivakumar R;Anandh Babu PV;Shyamaladevi CS Chem Biol Interact. 2008 Nov 25;176(2-3):227-33. doi: 10.1016/j.cbi.2008.08.008. Epub 2008 Aug 22.
The present study investigates the effect of aspartate and glutamate on mitochondrial function during myocardial infarction (MI) in wistar rats. Male albino wistar rats were pretreated with aspartate [100 mg(kgbody weight)(-1) day(-1)] or glutamate [100 mg(kg body weight)(-1) day(-1)] intraperitoneally for a period of 7 days. Following amino acid treatment, MI was induced in rats by subcutaneous injection of isoproterenol [200 mg(kg body weight)(-1) day(-1)] for 2 days at an interval of 24 h. Isoproterenol (ISO) induction resulting in significant (P<0.05) increase in the levels of cardiac mitochondrial lipid peroxidation with a decrease in reduced glutathione level. The activities of glutathione peroxidase and glutathione reductase were significantly (P<0.05) decreased by ISO. ISO-induction also caused significant (P<0.05) decrease in the activities of mitochondrial tricarboxylic acid cycle enzymes (malate dehydrogenase, isocitrate dehydrogenase, succinate dehydrogenase, alpha-ketoglutarate dehydrogenase) and respiratory chain enzymes (NADH dehydrogenase and cytochrome-c-oxidase). ISO significantly (P<0.05) reduced the cytochrome contents, ATP production, ADP/O ratio and oxidation of succinate in state 3/state 4 whereas significantly (P<0.
3.Buthionine sulfoximine diverts the melanogenesis pathway toward the production of more soluble and degradable pigments.
Galván I;Wakamatsu K;Alonso-Alvarez C;Solano F Bioorg Med Chem Lett. 2014 May 1;24(9):2150-4. doi: 10.1016/j.bmcl.2014.03.031. Epub 2014 Mar 21.
Buthionine sulfoximine (BSO) is a specific inhibitor of γ-glutamylcysteine synthetase, thus blocking the synthesis of glutathione (GSH). It is known that this makes that BSO affects melanin synthesis because of the role of thiols in melanogenesis. However, BSO may also react with the intermediate oxidation products of melanogenesis, a possibility that has not been investigated from the initial steps of the pathway. We created in vitro conditions simulating eumelanogenesis (oxidation of L-DOPA in the absence of GSH) and pheomelanogenesis (oxidation of L-DOPA in the presence of GSH) under presence or absence of BSO. BSO made that eumelanogenesis results in pigments more soluble and less resistant to degradation by hydrogen peroxide than pigments obtained without BSO. A similar but less marked effect was observed for pheomelanogenesis only at subsaturating concentrations of GSH. These results suggest that BSO diverts the melanogenesis pathway toward the production of more soluble and degradable pigments.
Spectrum
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)
Experimental Conditions
Instrument Type: GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
Ionization Mode: Positive
Chromatography Type: GC
Base Peak: 156
Retention Index: 1696.6
Retention Time: 789.613
Column Type: DB-17MS
Derivative Type: x TMS
Ionization Mode: Positive
Chromatography Type: GC
Base Peak: 156
Retention Index: 1696.6
Retention Time: 789.613
Column Type: DB-17MS
Derivative Type: x TMS
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C10H17N3O6S
Molecular Weight (Monoisotopic Mass): 307.0838 Da
Molecular Weight (Avergae Mass): 307.323 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C10H17N3O6S
Molecular Weight (Monoisotopic Mass): 307.0838 Da
Molecular Weight (Avergae Mass): 307.323 Da
LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)
Experimental Conditions
Sample Concentration: 1.0 mM
Sample Mass: 1.0 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Quattro_QQQ
Collision Energy Level: low
Collision Energy Voltage: 10
Ionization Mode: Positive
Sample Mass: 1.0 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Quattro_QQQ
Collision Energy Level: low
Collision Energy Voltage: 10
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H17N3O6S
Molecular Weight (Monoisotopic Mass): 307.0838 Da
Molecular Weight (Avergae Mass): 307.323 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H17N3O6S
Molecular Weight (Monoisotopic Mass): 307.0838 Da
Molecular Weight (Avergae Mass): 307.323 Da
1H NMR Spectrum
Experimental Conditions
Sample Concentration: 49.0 mM
Solvent: Water
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Varian
Nucleus: 1H
Frequency: 500 MHz
Sample pH: 4.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: DSS
Solvent: Water
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Varian
Nucleus: 1H
Frequency: 500 MHz
Sample pH: 4.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: DSS
[1H,13C] 2D NMR Spectrum
Experimental Conditions
Sample Concentration: 50.0 mM
Solvent: Water
Sample Mass: 15.4 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: DSS
Solvent: Water
Sample Mass: 15.4 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: DSS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
