CDS021567
5,6-Dihydroxyindole
Synonym(s):
Dopamine lutine, Indolylquinol
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About This Item
Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
Molecular Weight:
149.15
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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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.
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
Precautionary Statements
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)
5, 6-Dihydroxyindole chemistry: unexplored opportunities beyond eumelanin
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