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SML3708

Sigma-Aldrich

L-Meta-tyrosine

≥98% (HPLC)

Synonym(s):

(S)-2-Amino-3-(3-hydroxyphenyl)propanoic acid, 3-Hydroxy-L-phenylalanine, L-3-Hydroxyphenylalanine, L-m-Tyrosine, m-Tyr, meta-Tyrosine

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About This Item

Empirical Formula (Hill Notation):
C9H11NO3
CAS Number:
587-33-7
Molecular Weight:
181.19
MDL number:
MFCD00063059
UNSPSC Code:
12352209
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

2 mg/mL, clear (0.1N HCl)

storage temp.

-10 to -25°C

SMILES string

[N+H3][C@@H](Cc1cc(ccc1)O)C(=O)[O-]

InChI

1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1

InChI key

JZKXXXDKRQWDET-QMMMGPOBSA-N

Biochem/physiol Actions

L-Meta-tyrosine is metabolite of L-Phenylalanine generated within the living organism by hydroxyl free radical. It is a marker of oxidative stress. Circulating L-Meta-tyrosine cold be incorporated into protein through the binding to the tRNAPhe. In plants L-Meta-tyrosine (m-Tyr) is also synthesized enzymatically and has been shown to act as a natural herbicide. It inhibits the growth of plants. L-Meta-tyrosine is a potent and selective competitive inhibitor of Enterobacteriaceae (Citrobacter, Proteus, Erwinia) tyrosine phenol-lyase that exhibits a renoprotective effect in diabetic mice. L-Meta-tyrosine decreases plasma phenyl sulfate and indoxyl sulfate levels and reduces albuminuria in diabetic mice models. Also, L-Meta-tyrosine inhibits bacterial tryptophan indole-lyase. It does not alter composition of microbiota in renal failure mice model.
Metabolite of L-Phenylalanine generated within the living organism by hydroxyl free radical; potent and selective competitive inhibitor of Enterobacteriaceae tyrosine phenol-lyase

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000403649
0000403649
0000380467
0000380465
0000380467

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Marcin Tyminski et al.
Plants (Basel, Switzerland), 10(12) (2021-12-29)
L-Tyrosine (Tyr) is one of the twenty proteinogenic amino acids and also acts as a precursor for secondary metabolites. Tyr is prone to modifications, especially under conditions of cellular redox imbalance. The oxidation of Tyr precursor phenylalanine leads to the
Koichi Kikuchi et al.
Nature communications, 10(1), 1835-1835 (2019-04-25)
Diabetic kidney disease is a major cause of renal failure that urgently necessitates a breakthrough in disease management. Here we show using untargeted metabolomics that levels of phenyl sulfate, a gut microbiota-derived metabolite, increase with the progression of diabetes in
Judit Mohás-Cseh et al.
Biomedicines, 10(5) (2022-05-29)
A link between oxidative stress and insulin resistance has been suggested. Hydroxyl free radicals are known to be able to convert phenylalanine (Phe) into the non-physiological tyrosine isoforms ortho- and meta-tyrosine (o-Tyr, m-Tyr). The aim of our study was to

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