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CDS021567

Sigma-Aldrich

5,6-Dihydroxyindole

Synonyme(s) :

Dopamine lutine, Indolylquinol

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About This Item

Formule empirique (notation de Hill):
C8H7NO2
Numéro CAS:
3131-52-0
Poids moléculaire :
149.15
Numéro MDL:
MFCD00798933
Code UNSPSC :
12352200
ID de substance PubChem :
329794831

Description

AldrichCPR

Forme

solid

Chaîne SMILES 

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

Clé InChI

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.

Autres remarques

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.

Pictogrammes

CorrosionExclamation markEnvironment
GHS05,GHS07,GHS09

Mention d'avertissement

Danger

Mentions de danger

H302,H318,H411

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

Désolés, nous n'avons pas de COA pour ce produit disponible en ligne pour le moment.

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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
5, 6-Dihydroxyindole chemistry: unexplored opportunities beyond eumelanin
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