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5,6-DIHYDROXYINDOLE

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5,6-DIHYDROXYINDOLE Basic information
Product Name:5,6-DIHYDROXYINDOLE
Synonyms:INDOLE-5,6-DIOL;DOPAMINE LUTINE;5,6-DIHYDROXYINDOLE;DIHYDROXYINDOLE;5,6-Dihydroxy-1H-indole;1H-indole-5,6-diol;5,6-DIYDROXYINDOLE;5.6-Dihydroxy Indol
CAS:3131-52-0
MF:C8H7NO2
MW:149.15
EINECS:412-130-9
Product Categories:Heterocycles;Impeticbead;3131-52-0;1
Mol File:3131-52-0.mol
5,6-DIHYDROXYINDOLE Structure
5,6-DIHYDROXYINDOLE Chemical Properties
Melting point 140 °C (decomp)
Boiling point 411.2±25.0 °C(Predicted)
density 1.510±0.06 g/cm3(Predicted)
RTECS NL7858000
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
form Solid
pka9.81±0.40(Predicted)
color Off-white to light brown
Cosmetics Ingredients FunctionsHAIR DYEING
InChIInChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
InChIKeySGNZYJXNUURYCH-UHFFFAOYSA-N
SMILESN1C2=C(C=C(O)C(O)=C2)C=C1
LogP0.370 (est)
Safety Information
Hazard Codes Xn,N
Risk Statements 22-41-51/53
Safety Statements 22-26-36/37/39-61
WGK Germany WGK 3
HS Code 2933998090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 2
Eye Dam. 1
MSDS Information
5,6-DIHYDROXYINDOLE Usage And Synthesis
Description5,6-Dihydroxyindole is a melanin precursor. It is one of the toxic compounds in the melanin biosynthetic pathway. 5,6-Dihydroxyindole is an indole derivative that contains two hydroxyl groups attached to the 5th and 6th positions of the indole ring. It is an intermediate in the biosynthesis of melanin, a pigment responsible for the coloration of hair, skin, and eyes in humans and other organisms.
Chemical Properties5,6-Dihydroxyindole is the second isomer of dihydroxyindole. Pure 5,6-dihydroxyindole is soluble in hot water, insoluble in petroleum ether, and stable in the crystalline state, but oxidizes rapidly to melanin-like substances in slightly alkaline solutions.
Uses5,6-Dihydroxyindole is an intermediate in melanogenesis, the production of melanin which is found in our skin, eyes, hair, and inner ear.
DefinitionChEBI: 5,6-dihydroxyindole is a dihydroxyindole. It has a role as a mouse metabolite.
Synthesis Reference(s)Synthetic Communications, 15, p. 321, 1985 DOI: 10.1080/00397918508063806
Synthesis
(2S)-5,6-dioxo-2,4-dihydro-1H-indole-2-carboxylic acid

89762-39-0

5,6-DIHYDROXYINDOLE

3131-52-0

General procedure for the synthesis of 5,6-dihydroxyindole from the compound (CAS: 89762-39-0): sodium chloride was added to the melanin precursor solution (mainly composed of dopachrome) obtained in step 5, adjusting the final concentration to 2.5%. The reaction mixture was allowed to stand at room temperature for 45 min, which significantly accelerated the conversion of dopa pigment to 5,6-dihydroxyindole as compared to the precursor solution without the addition of sodium chloride. If sodium ascorbate solution was added to the reaction system instead of sodium chloride, the yield of 5,6-dihydroxyindole was significantly increased (up to 90% of 5,6-dihydroxyindole in the melanin precursor solution).

IC 50Human Endogenous Metabolite
References[1] Patent: EP1820491, 2007, A1. Location in patent: Page/Page column 12
Tag:5,6-DIHYDROXYINDOLE(3131-52-0) Related Product Information
N,N-dimethyldopamine Methanone, [4-(2-aminoethyl)phenyl]phenyl- 5,6-METHYLENEDIOXY-2-PHENYLINDOLE 5,6-DIHYDROXYINDOLE Solypertine oxypertine 5,6-DIMETHOXY-2-PHENYLINDOLE ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID 5-Benzyloxy-6-methoxyindole Alpertine 5,6-Dimethoxyindole 6-HYDROXYMELATONIN METHYL-6,7-DIMETHOXY-4-ETHYL-BETA-CARBOLINE-3-CARBOXYLATE 5,6-DIACETOXYINDOLE 5,6-DIBENZYLOXYINDOLE 5-hydroxy-6-methoxyindole 6-BENZYLOXY-5-METHOXYINDOLE-2-CARBOXYLIC ACID

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