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Merck
CN

H2380

6-Hydroxy-DL-DOPA

≥98% (HPLC), powder, APE1 inhibitor

Synonym(s):

2,4,5-Trihydroxy-DL-phenylalanine, 2,5-Dihydroxy-DL-tyrosine

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About This Item

Empirical Formula (Hill Notation):
C9H11NO5
CAS Number:
21373-30-8
Molecular Weight:
213.19
NACRES:
NA.32
PubChem Substance ID:
24278464
UNSPSC Code:
12352200
MDL number:
MFCD00004272
Beilstein/REAXYS Number:
2860065

Key Documents

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Product Name

6-Hydroxy-DL-DOPA, ≥98% (HPLC), powder

InChI

1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)

SMILES string

NC(Cc1cc(O)c(O)cc1O)C(O)=O

InChI key

YLKRUSPZOTYMAT-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

H2O: 3 mg/mL, 1 M HCl: 50 mg/mL (Solutions should be freshly prepared and protected from exposure to light.)

storage temp.

−20°C

Quality Level

200

Related Categories

General description

Dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidant. Solutions should be freshly prepared and protected from exposure to light.

Biochem/physiol Actions

Precursor of the catecholaminergic neurotoxin, 6-hydroxydopamine; converted to 6-hydroxydopamine by L-aromatic amino acid decarboxylase.
6-Hydroxy-DL-DOPA is an inhibitor of APE1 (apurinic/apyrimidinic endonuclease) repair-function activity. APE1 is a nuclease crucial for DNA base excision repair pathway. 6-Hydroxy-DL-DOPA also blocks RAD52 (DNA repair protein) single-stranded DNA binding domain.
Precursor 6-hydroxydopamine.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Disclaimer

Hygroscopic; photosensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3947
BCCM0465
BCCM5089
BCCL2530
BCCK4047

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Gurushankar Chandramouly et al.
Chemistry & biology, 22(11), 1491-1504 (2015-11-10)
Suppression of RAD52 causes synthetic lethality in BRCA-deficient cells. Yet pharmacological inhibition of RAD52, which binds single-strand DNA (ssDNA) and lacks enzymatic activity, has not been demonstrated. Here, we identify the small molecule 6-hydroxy-DL-dopa (6-OH-dopa) as a major allosteric inhibitor
Mass spectrometric studies of the primary sequence and structure of bovine liver and serum amine oxidase.
G W Adams et al.
Methods in enzymology, 258, 90-114 (1995-01-01)
F Karoum et al.
Journal of neurochemistry, 61(4), 1369-1375 (1993-10-01)
Formation of 6-hydroxydopamine (6-OHDA) from dopamine has been hypothesized to mediate neurodegeneration induced by some psychostimulants. Although the emergence of a 6-OHDA-like substance was reported in the striatum of methamphetamine-treated rats, this substance has not been identified by a direct
E K Y Chung et al.
Neuro-Signals, 15(5), 238-248 (2007-04-17)
Overactivity of the glutamatergic system is suggested to be closely related to the onset and pathogenesis of Parkinson's disease. Vesicular glutamate transporters (VGLUT1, T2 and T3) are a group of glutamate transporters in neurons that are responsible for transporting glutamate
Annalisa Pinna et al.
Synapse (New York, N.Y.), 61(8), 606-614 (2007-05-04)
Evidence obtained in rodent and primate models of Parkinson's disease (PD) and preliminary clinical trials, indicates that adenosine A(2A) receptor antagonists might represent a promising nondopaminergic therapeutic tool for the treatment of PD. Those studies demonstrated the ability of adenosine
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