D9378

3,4-Dihydroxy-D-phenylalanine

Name: 3,4-Dihydroxy-<SC>D-</SC>phenylalanine
Brand: SIGMA
Price: 279 USD

≥95% (TLC), powder, DOPA enantiomer

Synonym(s):

3-(3,4-Dihydroxyphenyl)-D-alanine, D-3-Hydroxytyrosine, D-DOPA

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₁NO₄

CAS Number:

5796-17-8

Molecular Weight:

197.19

NACRES:

NA.32

PubChem Substance ID:

24894286

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

227-343-0

MDL number:

MFCD00063061

Beilstein/REAXYS Number:

2417637

Assay:

≥95%

Form:

powder

Quality level:

100

Key Documents

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Product Name

3,4-Dihydroxy-D-phenylalanine, powder, ≥95%

InChI key

WTDRDQBEARUVNC-ZCFIWIBFSA-N

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-/m1/s1

SMILES string

N[C@H](Cc1ccc(O)c(O)c1)C(O)=O

assay

≥95%

form

powder

mp

276-278 °C (lit.)

solubility

1 M HCl: soluble, ethanol: insoluble

storage temp.

−20°C

Quality Level

100

Related Categories

Bioactive Small Molecules

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1 of 4

This Item	D9628	A0912	47435
Sigma-Aldrich D9378 3,4-Dihydroxy-D-phenylalanine	Sigma-Aldrich D9628 3,4-Dihydroxy-L-phenylalanine	Sigma-Aldrich A0912 D-Ala-D-Ala	Sigma-Aldrich 47435 Fmoc-β-(3-pyridyl)-D-Ala-OH
form powder	form powder	form powder	form -
assay ≥95%	assay ≥98% (TLC)	assay ≥99%	assay ≥98.0% (HPLC)
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 100
storage temp. −20°C	storage temp. room temp	storage temp. −20°C	storage temp. 2-8°C
solubility 1 M HCl: soluble, ethanol: insoluble	solubility -	solubility -	solubility -
mp 276-278 °C (lit.)	mp 276-278 °C (lit.)	mp -	mp -

Application

3,4-Dihydroxy-D-phenylalanine has been used as a standard in high-performance liquid chromatography (HPLC) analysis of L-DOPA extracted from both germinated and raw seed flours of velvet bean.

Biochem/physiol Actions

3,4-Dihydroxy-D-phenylalanine (D-DOPA) is a DOPA enantiomer. It exhibits antimicrobial activity. D-DOPA serves as a precursor for dopamine.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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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Human D-amino acid oxidase: an update and review.

Tomoya Kawazoe et al.

Chemical record (New York, N.Y.), 7(5), 305-315 (2007-10-10)

The flavoprotein D-amino acid oxidase (DAO) degrades the gliotransmitter D-Ser, a potent activator of N-methyl-D-aspartate-type glutamate receptors. A body of evidence suggests that DAO, together with its activator, G72 protein, may play a key role in the pathophysiology of schizophrenia.

Recent advances in microchip enantioseparation and analysis.

Nan Lu et al.

Electrophoresis (2020-09-20)

This review summarizes recent developments (over the past decade) in the field of microfluidics-based solutions for enantiomeric separation and detection. The progress in various formats of microchip electrodriven separations, such as MCE, microchip electrochromatography, and multidimensional separation techniques, is discussed.

A novel electrochemical approach for prolonged measurement of absolute levels of extracellular dopamine in brain slices.

Mark H Burrell et al.

ACS chemical neuroscience, 6(11), 1802-1812 (2015-09-01)

Tonic dopamine (DA) levels influence the activity of dopaminergic neurons and the dynamics of fast dopaminergic transmission. Although carbon fiber microelectrodes and fast-scan cyclic voltammetry (FSCV) have been extensively used to quantify stimulus-induced release and uptake of DA in vivo

Impairment of neuronal mitochondrial function by L-DOPA in the absence of oxygen-dependent auto-oxidation and oxidative cell damage.

Philipp Hörmann et al.

Cell death discovery, 7(1), 151-151 (2021-07-07)

L-3,4-Dihydroxyphenylalanin (L-DOPA or levodopa) is currently the most used drug to treat symptoms of Parkinson's disease (PD). After crossing the blood-brain barrier, it is enzymatically converted to dopamine by neuronal cells and restores depleted endogenous neurotransmitter levels. L-DOPA is prone

Carbonic anhydrase activators. Activation of the membrane-associated isoform XV with amino acids and amines.

Alessio Innocenti et al.

Bioorganic & medicinal chemistry letters, 19(13), 3430-3433 (2009-05-26)

An activation study of the membrane-associated carbonic anhydrase (CA, EC 4.2.1.1) isoform XV with a series of natural and non-natural amino acids and aromatic/heterocyclic amines is reported. Murine CA XV was strongly activated by some amino acids (d-Phe, l-/d-DOPA, d-Trp

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3,4-Dihydroxy-D-phenylalanine