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D9628

Sigma-Aldrich

3,4-Dihydroxy-L-phenylalanine

≥98% (TLC)

Synonym(s):
3-(3,4-Dihydroxyphenyl)-L-alanine, L-3-Hydroxytyrosine, L-DOPA, Levodopa
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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1 of 4

This Item
72816L0400000PHR1271
Levodopa European Pharmacopoeia (EP) Reference Standard

L0400000

Levodopa

Levodopa Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1271

Levodopa

form

powder

form

-

form

-

form

-

color

white to off-white

color

-

color

-

color

-

mp

276-278 °C (lit.)

mp

276-278 °C (lit.)

mp

276-278 °C (lit.)

mp

276-278 °C (lit.)

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

application(s)

peptide synthesis

application(s)

food and beverages

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

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.

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Molly J Crockett et al.
Current biology : CB, 25(14), 1852-1859 (2015-07-07)
An aversion to harming others is a core component of human morality and is disturbed in antisocial behavior. Deficient harm aversion may underlie instrumental and reactive aggression, which both feature in psychopathy. Past work has highlighted monoaminergic influences on aggression
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.

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