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59-92-7 - 3,4-Dihydroxy-L-phenylalanine, 98+% - L-DOPA - 3-Hydroxy-L-tyrosine - A11311 - Alfa Aesar

A11311 3,4-Dihydroxy-L-phenylalanine, 98+%

CAS Number
59-92-7
Synonyms
L-DOPA
3-Hydroxy-L-tyrosine

Size Price ($) Quantity Availability
5g 31.93
25g 106.09
100g 353.29
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3,4-Dihydroxy-L-phenylalanine, 98+%

MDL
MFCD00002598
EINECS
200-445-2

Chemical Properties

Formula
C9H11NO4
Formula Weight
197.19
Melting point
ca 295° dec.
Solubility
Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol.

Applications

3,4-dihydroxy-L-phenylalanine (DOPA) is used as a cell adhesion molecule in serum-free cultures of anchorage-dependent mammalian cells. It is also used as an anticholinergic drug and used in the treatment of Parkinson's disease. It acts as an intermediate in the biosynthesis of other catecholamines (norepinephrine, epinephrine) and melanin. It acts as a precursor of dopamine product of tyrosine hydroxylase.

Notes

Incompatible with strong oxidizing agents.

Literature References

Fichman, G.; Adler-Abramovich, L.; Manohar, S.; Mironi-Harpaz, I.; Guterman, T.; Seliktar, D.; Messersmith, P. B.; Gazit, E. Seamless Metallic Coating and Surface Adhesion of Self-Assembled Bioinspired Nanostructures Based on Di-(3,4-dihydroxy-l-phenylalanine) Peptide Motif. ACS Nano. 2014, 8 (7), 7220-7228.

Huang, Y.; Han, Q.; Zhang, Q.; Guo, L.; Guo, D.; Yingzi Fu, Y. A fast chiral sensing to DOPA enantiomers via poly-lysine films matrixes. Electrochim. Acta. 2013, 113, 564-569.

Yue, Q.; Wang, M.; Sun, Z.; Wang, C.; Wang, C.; Deng, Y.; Zhao, D. A versatile ethanol-mediated polymerization of dopamine for efficient surface modification and the construction of functional core-shell nanostructures. J. Mater. Chem. B 2013, 1 (44), 6085-6093.

Xiong, S.; Wang, Y.; Zhu, J.; Yu, J.; Hu, Z. Mussel-Adhesive-Inspired Fabrication of Multifunctional Silver Nanoparticle Assemblies. Langmuir 2015, 31 (19), 5504-5512.

Matin, M. A.; Chitumalla, R. K.; Lim, M.; Gao, X.; Jang, J. Density Functional Theory Study on the Cross-Linking of Mussel Adhesive Proteins. J. Phys. Chem. B 2015, 119 (17), 5496-5504.

GHS Hazard and Precautionary Statements

Hazard Statements: H302

Harmful if swallowed.

Precautionary Statements: P264-P270-P301+P312-P330-P501a

Wash thoroughly after handling. Do not eat, drink or smoke when using this product. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5464
Beilstein
2215169
Harmonized Tariff Code
2922.50
TSCA
Yes
RTECS
AY5600000

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