| Identification | More | [Name]
3-Nitro-L-tyrosine | [CAS]
621-44-3 | [Synonyms]
3-NITRO-4-HYDROXY-PHENYLALANINE
3-NITRO-L-TYROSINE
3-NITRO-TYROSINE
H-3-NITRO-L-TYROSINE
H-3-NITRO-TYR-OH
H-4-HYDROXY-3-NITRO-PHE-OH
H-M-NITRO-TYR-OH
H-TYR(3-NO2)-OH
H-TYR(M-NO2)-OH
M-NITRO-L-TYROSINE
NITROTYROSINE
Tyr(3'-NO2)
3-NITRO-TYROSINEH-TYR(3-NO2)-OH
3-Nitro-L-tyrosine 99%
(2R)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
L-Tyrosine, 3-nitro- | [EINECS(EC#)]
210-688-6 | [Molecular Formula]
C9H10N2O5 | [MDL Number]
MFCD00007123 | [Molecular Weight]
226.19 | [MOL File]
621-44-3.mol |
| Chemical Properties | Back Directory | [Appearance]
ochre-yellow to yellow-green powder | [Melting point ]
233-235 °C (dec.) (lit.) | [alpha ]
4 º (c=1, 1N HCl) | [Boiling point ]
367.79°C (rough estimate) | [density ]
1.4160 (rough estimate) | [refractive index ]
1.5373 (estimate) | [storage temp. ]
-15°C | [solubility ]
Aqueous Acid (Slightly), Water | [form ]
crystalline
| [pka]
2.17±0.20(Predicted) | [color ]
yellow to green
| [Water Solubility ]
insoluble | [BRN ]
2813157 | [InChI]
InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1 | [InChIKey]
FBTSQILOGYXGMD-LURJTMIESA-N | [SMILES]
C(O)(=O)[C@H](CC1=CC=C(O)C([N+]([O-])=O)=C1)N | [CAS DataBase Reference]
621-44-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29225090 |
| Hazard Information | Back Directory | [Description]
Nitrotyrosine is formed by peroxynitrite-mediated nitration of protein tyrosine residues. Its presence on proteins can be used as a marker for peroxynitrite formation in vivo.1,2,3,4 Both free and protein-bound nitrotyrosine are commonly found in mammalian tissues and are increased in pathological conditions.2,5,6 The basal levels of free nitrotyrosine in human plasma is approximately 3 nM as determined by gas chromatography/mass spectrometry.7,8 | [Chemical Properties]
ochre-yellow to yellow-green powder | [Uses]
3-Nitro-L-tyrosine is used as an indicator of the formation of peroxynitrite by NO-dependent oxidative damage. | [Uses]
A marker for peroxynitrite. Oxidant and cytotoxic agent. | [Definition]
ChEBI: 3-nitro-L-tyrosine is a 3-nitrotyrosine comprising L-tyrosine having a nitro group at the 3-position on the phenyl ring. It is a L-tyrosine derivative, a non-proteinogenic L-alpha-amino acid and a 3-nitrotyrosine. It is an enantiomer of a 3-nitro-D-tyrosine. | [Biochem/physiol Actions]
Oxidant and cytotoxic agent. | [References]
[1] J S BECKMAN W H K. Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly.[J]. American Journal of Physiology, 1996, 271 5 Pt 1: C1424-37. DOI: 10.1152/ajpcell.1996.271.5.c1424
[2] J S BECKMANN. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry.[J]. Biological chemistry Hoppe-Seyler, 1994, 375 2: 81-88. DOI: 10.1515/bchm3.1994.375.2.81
[3] K ABE. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis.[J]. Neurological Research, 1997, 19 2: 124-128. DOI: 10.1080/01616412.1997.11740784
[4] ROBERT J. FERRANTE PHD. Leslie A S PhD, MD. Increased 3-nitrotyrosine and oxidative damage in mice with a human copper/zinc superoxide dismutase mutation[J]. Annals of Neurology, 2004, 42 3: 326-334. DOI: 10.1002/ana.410420309
[5] I Y HADDAD. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury.[J]. Journal of Clinical Investigation, 1994, 94 6: 2407-2413. DOI: 10.1172/jci117607
[6] M. OHYA. Plasma Nitrotyrosine Concentration Relates to Prognosis in Human Septic Shock[J]. SHOCK, 2002, 18 1: 116-118. DOI: 10.1097/00024382-200208000-00004
[7] DIMITRIOS TSIKAS. Accurate quantification of basal plasma levels of 3-nitrotyrosine and 3-nitrotyrosinoalbumin by gas chromatography–tandem mass spectrometry[J]. Journal of Chromatography B, 2003, 784 1: Pages 77-90. DOI: 10.1016/s1570-0232(02)00751-1
[8] EDZARD SCHWEDHELM. Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State[J]. Analytical biochemistry, 1999, 276 2: Pages 195-203. DOI: 10.1006/abio.1999.4361
[9] JIAN LIU Steven G L. High-fat, low-carbohydrate diet alters myocardial oxidative stress and impairs recovery of cardiac function after ischemia and reperfusion in obese rats[J]. Nutrition Research, 2013, 33 4: Pages 311-321. DOI: 10.1016/j.nutres.2013.02.005 |
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