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CDS021567

Sigma-Aldrich

5,6-Dihydroxyindole

Synonyma:

Dopamine lutine, Indolylquinol

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About This Item

Empirický vzorec (Hillův zápis):
C8H7NO2
Číslo CAS:
3131-52-0
Molekulová hmotnost:
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

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Osvědčení o analýze (COA)

Lot/Batch Number

Je nám líto, ale pro tento produkt momentálně nemáme COA k dispozici online.

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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
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)
5, 6-Dihydroxyindole chemistry: unexplored opportunities beyond eumelanin
d?Ischia M, et al.
European Journal of Organic Chemistry, 2011(28), 5501-5516 (2011)
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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