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D9378

Sigma-Aldrich

3,4-Dihydroxy-D-phenylalanine

≥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
Beilstein/REAXYS Number:
2417637
EC Number:
227-343-0
MDL number:
MFCD00063061
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24894286
NACRES:
NA.32

product name

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

assay

≥95%

form

powder

mp

276-278 °C (lit.)

solubility

1 M HCl: soluble
ethanol: insoluble

storage temp.

−20°C

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-/m1/s1

InChI key

WTDRDQBEARUVNC-ZCFIWIBFSA-N

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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.
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
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
Isao Nishimori et al.
Bioorganic & medicinal chemistry, 15(15), 5351-5357 (2007-05-15)
The secretory isozyme of human carbonic anhydrase (hCA, EC 4.2.1.1), hCA VI, has been cloned, expressed, and purified in a bacterial expression system. The kinetic parameters for the CO(2) hydration reaction proved hCA VI to possess a k(cat) of 3.4
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