All Photos(5)

D9628

Sigma-Aldrich

3,4-Dihydroxy-L-phenylalanine

≥98% (TLC)

Synonym(s):
L-DOPA, L-3-Hydroxytyrosine, Levodopa, 3-(3,4-Dihydroxyphenyl)-L-alanine
Linear Formula:
(HO)2C6H3CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
197.19
Beilstein:
2215169
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

powder

color

white to off-white

mp

276-278 °C (lit.)

application(s)

peptide synthesis

storage temp.

room temp

SMILES string

N[C@@H](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)/t6-/m0/s1

InChI key

WTDRDQBEARUVNC-LURJTMIESA-N

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Application

3,4-Dihydroxy-L-phenylalanine or L-DOPA has been used to stain melanocytes. It has also been used to study its effects on a Drosophila model of Parkinson′s disease.

Packaging

5, 25, 100, 500 g in poly bottle

Biochem/physiol Actions

3,4-Dihydroxy-L-phenylalanine or L-DOPA is a natural isomer of the immediate precursor of dopamine that crosses the blood-brain barrier. It is used for the treatment of Parkinson′s disease and is a product of tyrosine hydroxylase.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Effects of small-molecule amyloid modulators on a Drosophila model of Parkinson?s disease
Malgorzata Pokrzywa
PLoS ONE (2017)
Primary culture of human face skin melanocytes for the study of hyperpigmentation
Cytotechnology, 66(6) (2014)
Alan J. Sinclair, John E. Morley, Bruno Vellas
Pathy's Principles and Practice of Geriatric Medicine (2012)
Sebastiaan P van Kessel et al.
Nature communications, 10(1), 310-310 (2019-01-20)
Human gut microbiota senses its environment and responds by releasing metabolites, some of which are key regulators of human health and disease. In this study, we characterize gut-associated bacteria in their ability to decarboxylate levodopa to dopamine via tyrosine decarboxylases.
Nicolas Morin et al.
Experimental neurology, 256, 105-116 (2013-01-31)
The treatment of motor symptoms of Parkinson disease (PD) with the dopamine (DA) precursor, l-3,4-dihydroxyphenylalanine (l-DOPA) introduced 50years ago still remains a very effective medication. However, involuntary movements termed l-DOPA-induced dyskinesias (LID) appear in the vast majority of PD patients

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