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CDS021567

Sigma-Aldrich

5,6-Dihydroxyindole

Synonym(s):

Dopamine lutine, Indolylquinol

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100 MG
CN¥2,882.72

CN¥2,882.72

Estimated to ship onMay 08, 2025Details

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100 MG
CN¥2,882.72

About This Item

Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
3131-52-0
Molecular Weight:
149.15
MDL number:
MFCD00798933
UNSPSC Code:
12352200
PubChem Substance ID:
329794831

CN¥2,882.72

Estimated to ship onMay 08, 2025Details

Request a Bulk Order

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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Show Differences

1 of 4

This Item
CDS005198918709H31859
5,6-Dihydroxyindole

CDS021567

5,6-Dihydroxyindole

7-hydroxyindole AldrichCPR

CDS005198

7-hydroxyindole

5,6-Dihydroxyindole

918709

5,6-Dihydroxyindole

5-Hydroxyindole 97%

H31859

5-Hydroxyindole

description

AldrichCPR

description

-

description

-

description

-

Application

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

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.

Signal Word

Danger

Hazard Statements

H302,H318,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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