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CDS021567

Sigma-Aldrich

5,6-Dihydroxyindole

Sinónimos:

Dopamine lutine, Indolylquinol

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About This Item

Fórmula empírica (notación de Hill):
C8H7NO2
Número de CAS:
3131-52-0
Peso molecular:
149.15
MDL number:
MFCD00798933
UNSPSC Code:
12352200
PubChem Substance ID:
329794831

description

AldrichCPR

form

solid

SMILES string

OC1=CC(C=CN2)=C2C=C1O

InChI

1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H

InChI key

SGNZYJXNUURYCH-UHFFFAOYSA-N

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Application

5,6-Dihydroxyindole can be used as a building block to synthesize:
  • Eumelanin biopolymers via copolymerization reaction with 2-carboxy-5,6-dihydroxyindoles.
  • 4-[bis(1H-5,6-diacetoxyindol-2-yl)methyl]-1,2-diacetoxybenzene by reacting with 3,4-dihydroxybenzaldehyde.
  • Fluoride anion sensing acetylated trimer molecule via acid-catalyzed polymerization followed by acetylation reaction.

Other Notes

Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY, (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE, OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY, WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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5, 6-Dihydroxyindole chemistry: unexplored opportunities beyond eumelanin
d?Ischia M, et al.
European Journal of Organic Chemistry, 2011(28), 5501-5516 (2011)
A novel fluoride-sensing scaffold by a peculiar acid-promoted trimerization of 5, 6-dihydroxyindole
Panzella L, et al.
Tetrahedron, 65(10), 2032-2036 (2009)
T G Costa et al.
Bioinorganic chemistry and applications, 2012, 712840-712840 (2012-12-20)
In this work, we measured the metal-binding sites of natural and synthetic dihydroxyindole (DHI) melanins and their respective interactions with Fe(III) ions. Besides the two acid groups detected for the DHI system: catechol (Cat) and quinone-imine (QI), acetate groups were
Yongwoo Jang et al.
Experimental & molecular medicine, 53(1), 19-29 (2021-01-23)
Until recently, Nurr1 (NR4A2) was known as an orphan nuclear receptor without a canonical ligand-binding domain, featuring instead a narrow and tight cavity for small molecular ligands to bind. In-depth characterization of its ligand-binding pocket revealed that it is highly
John M Bruning et al.
Cell chemical biology, 26(5), 674-685 (2019-03-12)
Nurr1, a nuclear receptor essential for the development, maintenance, and survival of midbrain dopaminergic neurons, is a potential therapeutic target for Parkinson's disease, a neurological disorder characterized by the degeneration of these same neurons. Efforts to identify Nurr1 agonists have

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