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D9503

Sigma-Aldrich

3,4-Dihydroxy-DL-phenylalanine

Synonym(s):

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

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About This Item

Linear Formula:
(HO)2C6H3CH2CH(NH2)COOH
CAS Number:
63-84-3
Molecular Weight:
197.19
Beilstein:
3204800
EC Number:
200-566-0
MDL number:
MFCD00063060
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24894298
NACRES:
NA.32

form

powder

mp

270-272 °C (lit.)
290 °C (dec.) (lit.)

SMILES string

NC(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)

InChI key

WTDRDQBEARUVNC-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)
mouse ... DRD1(13488) , DRD2(13489) , DRD3(13490) , DRD4(13491) , DRD5(13492)
rat ... DRD1(24316) , DRD2(24318) , DRD3(29238) , DRD4(25432) , DRD5(25195)

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Biochem/physiol Actions

3,4-dihydroxyphenylalanine is an immediate precursor of dopamine, which is a product of tyrosine hydroxylase.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

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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Karlo J Lizarraga et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 30-36 (2013-10-30)
Brain metastases are frequently treated with radiation. It is critical to distinguish recurrent or progressive brain metastases (RPBM) from late or delayed radiation injury (LDRI). The purpose of this study was to examine the diagnostic accuracy as well as the
Wei Wei et al.
Journal of the American Chemical Society, 135(1), 377-383 (2012-12-12)
Dopa (3,4-dihydroxyphenylalanine) is recognized as a key chemical signature of mussel adhesion and has been adopted into diverse synthetic polymer systems. Dopa's notorious susceptibility to oxidation, however, poses significant challenges to the practical translation of mussel adhesion. Using a surface
Eun Kyung Jeon et al.
Chemical communications (Cambridge, England), 49(33), 3392-3394 (2013-02-26)
We report a facile green approach to the synthesis of silver nanoparticles (Ag NPs) on the surface of graphene oxide nanosheets functionalized with mussel-inspired dopamine (GO-Dopa) without additional reductants or stabilizers at room temperature. The resulting hybrid Ag/GO-Dopa exhibits good
Dina Rībena et al.
Langmuir : the ACS journal of surfaces and colloids, 28(49), 16900-16908 (2012-11-20)
The adhesive proteins secreted by marine mussels contain an unusual amino acid, 3,4-dihydroxyphenylalanine (DOPA), that is responsible for the cohesive and adhesive strength of this natural glue and gives mussels the ability to attach themselves to rocks, metals, and plastics.
Lionel C Libert et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 54(7), 1154-1161 (2013-05-10)
6-(18)F-fluoro-L-dopa ((18)F-FDOPA) has proven to be a useful radiopharmaceutical for the evaluation of presynaptic dopaminergic function using PET. In comparison to electrophilic synthesis, the no-carrier-added (NCA) nucleophilic method has several advantages. These include much higher available activity and specific activity.
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