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93829

Sigma-Aldrich

L-Tyrosine

≥99.0% (NT), suitable for ligand binding assays, BioUltra

Synonym(s):

(S)-2-Amino-3-(4-hydroxyphenyl)propionic acid, 3-(4-Hydroxyphenyl)-L-alanine

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About This Item

Linear Formula:
4-(HO)C6H4CH2CH(NH2)CO2H
CAS Number:
60-18-4
Molecular Weight:
181.19
Beilstein:
392441
EC Number:
200-460-4
MDL number:
MFCD00002606
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57653577
NACRES:
NA.26

product name

L-Tyrosine, BioUltra, ≥99.0% (NT)

product line

BioUltra

Assay

≥99.0% (NT)

form

powder or crystals

optical activity

[α]20/D −11.5±1.0°, c = 4% in 1 M HCl

technique(s)

ligand binding assay: suitable

impurities

insoluble matter, passes filter test
≤0.5% foreign amino acids

ign. residue

≤0.1%

loss

≤0.2% loss on drying, 20 °C (HV)

color

white

mp

>300 °C (dec.) (lit.)

solubility

1 M HCl: 25 mg/mL, clear, colorless (hot)

anion traces

chloride (Cl-): ≤400 mg/kg
sulfate (SO42-): ≤300 mg/kg

cation traces

Al: ≤5 mg/kg
As: ≤0.1 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
NH4+: ≤200 mg/kg
Na: ≤200 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

absorption

cut-off at 310 nm in 1 M HCl at 0.5 M

SMILES string

N[C@@H](Cc1ccc(O)cc1)C(O)=O

InChI

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

InChI key

OUYCCCASQSFEME-QMMMGPOBSA-N

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Application

L-Tyrosine was used in tyrosine hydroxylase (TH) enzyme activity assay. It was also used as a substrate for tyrosinase enzyme in the growth media of Vibrio cholerae strains to stimulate melanin formation. It may be used as a precursor in the synthesis of (-)-MY 336a. MY 336a, a β-adrenergic receptor antagonist, was initially isolated from the culture broth of Streptomyces gabonae KY2234 (ATCC 15282). It may be used in the synthesis of 3-bromo-L-tyrosine and 3,5-dibromo-L-tyrosine.

Other Notes

Amino acid precursor of dopamine and other catecholamines
Growth requirements of various microorganisms

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Andisheh Eslamboli et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 25(4), 769-777 (2005-01-28)
The therapeutic potential of glial cell line-derived neurotrophic factor (GDNF) for Parkinson's disease is likely to depend on sustained delivery of the appropriate amount to the target areas. Recombinant adeno-associated viral vectors (rAAVs) expressing GDNF may be a suitable delivery
V E Coyne et al.
Applied and environmental microbiology, 58(9), 2861-2865 (1992-09-01)
Vibrio cholerae synthesized the pigment melanin in response to specific physiological conditions that were stressful to the bacterium. Pigmentation was induced when V. cholerae was subjected to hyperosmotic stress in conjunction with elevated growth temperatures (above 30 degrees C). The
CRC Handbook of Microbiology, 4, 1-1 (1974)
Robert S Phillips et al.
Amino acids, 44(2), 529-532 (2012-07-28)
L-Tyrosine is converted to 3-bromo-L-tyrosine in good yield by reaction with 1.2 equiv. of DMSO in HBr/AcOH, while reaction with 2.2 equiv. of DMSO under comparable conditions results in formation of 3,5-dibromo-L-tyrosine in good yield. This is the simplest, safest
Total Synthesis of (-)-MY 336a from L-Tyrosine.
Liao XW, et al.
Journal of Heterocyclic Chemistry, 47(1), 50-53 (2010)
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