D9503

3,4-Dihydroxy-DL-phenylalanine

Name: 3,4-Dihydroxy-<SC>DL-</SC>phenylalanine
Brand: SIGMA

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

NACRES:

NA.32

PubChem Substance ID:

24894298

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

200-566-0

MDL number:

MFCD00063060

Beilstein/REAXYS Number:

3204800

Key Documents

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form

powder

Quality Level

100

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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Show Differences

1 of 4

This Item	H8653	T6062	C0982
Sigma-Aldrich D9503 3,4-Dihydroxy-DL-phenylalanine	Sigma-Aldrich H8653 (±)-7-Hydroxy-2-(di-n-propylamino)tetralin hydrobromide	T6062 Trifluoperazine hydrochloride	C0982 Chlorpromazine hydrochloride
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form -	form powder	form solid
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)	Gene Information human ... DRD3(1814)	Gene Information human ... DRD2(1813), DRD3(1814), DRD4(1815), HTR2A(3356), HTR2C(3358)	Gene Information human ... DRD2(1813), DRD3(1814), DRD4(1815), HTR2A(3356)
mp 270-272 °C (lit.)	mp -	mp 243 °C (dec.) (lit.)	mp 194-196 °C

Biochem/physiol Actions

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

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Handbook of Developmental Cognitive Neuroscience (2001)

Dopamine formation, from its immediate precursor 3, 4-dihydroxyphenylalanine, along the rat digestive tract

Vieira-Coelho MA and Soares-da-Silva P

Fundamental & Clinical Pharmacology, 7(5), 235-243 (1993)

Hydrophobic enhancement of Dopa-mediated adhesion in a mussel foot protein.

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

Mussel-inspired green synthesis of silver nanoparticles on graphene oxide nanosheets for enhanced catalytic applications.

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

Significance of the amide functionality on DOPA-based monolayers on gold.

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.

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Global Trade Item Number

SKU	GTIN
D9503-1G	04061826738467
D9503-5G	04061833590782
D9503-25G	04061833590775

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