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D9503

Sigma-Aldrich

3,4-Dihydroxy-DL-phenylalanine

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Synonym(s):
3-(3,4-Dihydroxyphenyl)-DL-alanine, DL-3-Hydroxytyrosine, DL-DOPA
Linear Formula:
(HO)2C6H3CH2CH(NH2)COOH
CAS Number:
63-84-3
Molecular Weight:
197.19
Beilstein/REAXYS Number:
3204800
EC Number:
200-566-0
MDL number:
MFCD00063060
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24894298
NACRES:
NA.32

form

powder

Quality Level

100

mp

270-272 °C (lit.)
290 °C (dec.) (lit.)

SMILES string

NC(Cc1ccc(O)c(O)c1)C(O)=O

InChI

1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)

InChI key

WTDRDQBEARUVNC-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)
mouse ... DRD1(13488) , DRD2(13489) , DRD3(13490) , DRD4(13491) , DRD5(13492)
rat ... DRD1(24316) , DRD2(24318) , DRD3(29238) , DRD4(25432) , DRD5(25195)

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Biochem/physiol Actions

3,4-dihydroxyphenylalanine is an immediate precursor of dopamine, which is a product of tyrosine hydroxylase.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Steven L Saville et al.
Nanoscale, 5(5), 2152-2163 (2013-02-08)
It has been recently reported that for some suspensions of magnetic nanoparticles the transverse proton relaxation rate, R(2), is dependent on the time that the sample is exposed to an applied magnetic field. This time dependence has been linked to
Handbook of Developmental Cognitive Neuroscience (2001)
Dopamine formation, from its immediate precursor 3, 4-dihydroxyphenylalanine, along the rat digestive tract
Vieira-Coelho MA and Soares-da-Silva P
Fundamental & Clinical Pharmacology, 7(5), 235-243 (1993)
Luis García-Fernández et al.
Advanced materials (Deerfield Beach, Fla.), 25(4), 529-533 (2012-11-10)
Inspired by the amino acid 2-chloro-4,5-dihydroxyphenylalanine (Cl-DOPA), present in the composition of the proteinaceous glue of the sandcastle worm Phragmatopoma californica, a simple strategy is presented to confer antifouling properties to polymer surfaces using (but not releasing) a bioinspired biocide.
Wei Wei et al.
Journal of the American Chemical Society, 135(1), 377-383 (2012-12-12)
Dopa (3,4-dihydroxyphenylalanine) is recognized as a key chemical signature of mussel adhesion and has been adopted into diverse synthetic polymer systems. Dopa's notorious susceptibility to oxidation, however, poses significant challenges to the practical translation of mussel adhesion. Using a surface
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