Home Indole and Oxindoles 3131-52-0
3131-52-0,MFCD00798933
Catalog No.:AA007HOE

3131-52-0 | 5,6-Dihydroxyindole

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1g
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$62.00   $43.00
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5g
95%
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  • Technical Information
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Technical Information
Catalog Number:
AA007HOE
Chemical Name:
5,6-Dihydroxyindole
CAS Number:
3131-52-0
Molecular Formula:
C8H7NO2
Molecular Weight:
149.1467
MDL Number:
MFCD00798933
SMILES:
Oc1cc2[nH]ccc2cc1O
Properties
Computed Properties
 
Complexity:
151  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
3  
XLogP3:
1.3  

Literature

Title: Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization.

Journal: Biomacromolecules 20120813

Title: Age-dependent changes in eumelanin composition in hairs of various ethnic origins.

Journal: International journal of cosmetic science 20120201

Title: The relative importance of innate immune priming in Wolbachia-mediated dengue interference.

Journal: PLoS pathogens 20120201

Title: Immunomodulatory Effect of Rhaphidophora korthalsii on Natural Killer Cell Cytotoxicity.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Exploring the frontiers of synthetic eumelanin polymers by high-resolution matrix-assisted laser/desorption ionization mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20120101

Title: The action of D-dopachrome tautomerase as an adipokine in adipocyte lipid metabolism.

Journal: PloS one 20120101

Title: Multiple tyrosine metabolites are GPR35 agonists.

Journal: Scientific reports 20120101

Title: Melanin-based coatings as lead-binding agents.

Journal: Bioinorganic chemistry and applications 20120101

Title: UV-absorption spectra of melanosomes containing varying 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid content.

Journal: The journal of physical chemistry. B 20111103

Title: New pathways of betanidin and betanin enzymatic oxidation.

Journal: Journal of agricultural and food chemistry 20110914

Title: Antiviral, anti-parasitic, and cytotoxic effects of 5,6-dihydroxyindole (DHI), a reactive compound generated by phenoloxidase during insect immune response.

Journal: Insect biochemistry and molecular biology 20110901

Title: π-Electron manipulation of the 5,6-dihydroxyindole/quinone system by 3-alkynylation: mild acid-mediated entry to (cross)-conjugated scaffolds and paradigms for medium-tunable chromophores.

Journal: The Journal of organic chemistry 20110603

Title: The neurotransmitter serotonin interrupts α-synuclein amyloid maturation.

Journal: Biochimica et biophysica acta 20110501

Title: Alpha-synuclein is a cellular ferrireductase.

Journal: PloS one 20110101

Title: Inhibitory effect of phthalic Acid on tyrosinase: the mixed-type inhibition and docking simulations.

Journal: Enzyme research 20110101

Title: Complex interactions of Tyrp1 in the eye.

Journal: Molecular vision 20110101

Title: First synthetic entry to the trimer stage of 5,6-dihydroxyindole polymerization: ortho-alkynylaniline-based access to the missing 2,7':2',7''-triindole.

Journal: Organic & biomolecular chemistry 20101007

Title: Cyclic structural motifs in 5,6-dihydroxyindole polymerization uncovered: biomimetic modular buildup of a unique five-membered macrocycle.

Journal: Organic letters 20100716

Title: Prostaglandin-E2 is produced by adult human epidermal melanocytes in response to UVB in a melanogenesis-independent manner.

Journal: Pigment cell & melanoma research 20100601

Title: Regulation of DHICA-mediated antioxidation by dopachrome tautomerase: implication for skin photoprotection against UVA radiation.

Journal: Free radical biology & medicine 20100501

Title: Direct measurement of the ultraviolet absorption coefficient of single retinal melanosomes.

Journal: Photochemistry and photobiology 20100101

Title: Modulation of alpha-synuclein aggregation by dopamine analogs.

Journal: PloS one 20100101

Title: 5,6-Dihydroxyindole oxidation in phosphate buffer/polyvinyl alcohol: a new model system for studies of visible chromophore development in synthetic eumelanin polymers.

Journal: Photochemistry and photobiology 20100101

Title: Genetic variations in human glutathione transferase enzymes: significance for pharmacology and toxicology.

Journal: Human genomics and proteomics : HGP 20100101

Title: The hunt for natural skin whitening agents.

Journal: International journal of molecular sciences 20091201

Title: Disentangling eumelanin 'black chromophore': visible absorption changes as signatures of oxidation state- and aggregation-dependent dynamic interactions in a model water-soluble 5,6-dihydroxyindole polymer.

Journal: Journal of the American Chemical Society 20091028

Title: Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds.

Journal: The Journal of organic chemistry 20090918

Title: Ultrafast excited state dynamics of 5,6-dihydroxyindole, a key eumelanin building block: nonradiative decay mechanism.

Journal: The journal of physical chemistry. B 20090917

Title: Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration.

Journal: International journal of molecular sciences 20090901

Title: An updated review of tyrosinase inhibitors.

Journal: International journal of molecular sciences 20090601

Title: Lack of visible chromophore development in the pulse radiolysis oxidation of 5,6-dihydroxyindole-2-carboxylic acid oligomers: DFT investigation and implications for eumelanin absorption properties.

Journal: The Journal of organic chemistry 20090515

Title: Dopamine and the dopamine oxidation product 5,6-dihydroxylindole promote distinct on-pathway and off-pathway aggregation of alpha-synuclein in a pH-dependent manner.

Journal: Journal of molecular biology 20090403

Title: Study of total antioxidant status and glutathione peroxidase activity in Tunisian vitiligo patients.

Journal: Indian journal of dermatology 20090101

Title: Adsorption of Pb(II) and Cd(II) by Squid Ommastrephes bartrami Melanin.

Journal: Bioinorganic chemistry and applications 20090101

Title: Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations.

Journal: The journal of physical chemistry. A 20081106

Title: Solvochromic effects in model eumelanin compounds.

Journal: Photochemistry and photobiology 20080101

Title: Ultra-low temperature oxidation of 5,6-dihydroxyindole: a novel approach to study synthetic melanogenesis.

Journal: Photochemistry and photobiology 20080101

Title: Chemistry of mixed melanogenesis--pivotal roles of dopaquinone.

Journal: Photochemistry and photobiology 20080101

Title: Structural effects on the electronic absorption properties of 5,6-dihydroxyindole oligomers: the potential of an integrated experimental and DFT approach to model eumelanin optical properties.

Journal: Photochemistry and photobiology 20080101

Title: Melanin precursor 5,6-dihydroxyindol: protective effects and cytotoxicity on retinal cells in vitro and in vivo.

Journal: Toxicologic pathology 20071201

Title: 5,6-dihydroxyindole tetramers with 'anomalous' interunit bonding patterns by oxidative coupling of 5,5',6,6'-tetrahydroxy-2,7'-biindolyl: emerging complexities on the way toward an improved model of eumelanin buildup.

Journal: The Journal of organic chemistry 20071123

Title: Parasite suppression of the oxidations of eumelanin precursors in Drosophila melanogaster.

Journal: Archives of insect biochemistry and physiology 20071001

Title: Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation.

Journal: Chemical research in toxicology 20071001

Title: Broad-spectrum antimicrobial activity of the reactive compounds generated in vitro by Manduca sexta phenoloxidase.

Journal: Insect biochemistry and molecular biology 20070901

Title: Kinetic and structural analysis of the early oxidation products of dopamine: analysis of the interactions with alpha-synuclein.

Journal: The Journal of biological chemistry 20070525

Title: Photophysics of eumelanin: ab initio studies on the electronic spectroscopy and photochemistry of 5,6-dihydroxyindole.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20070402

Title: The first 5,6-dihydroxyindole tetramer by oxidation of 5,5',6,6'-tetrahydroxy- 2,4'-biindolyl and an unexpected issue of positional reactivity en route to eumelanin-related polymers.

Journal: Organic letters 20070329

Title: Ionizing radiation changes the electronic properties of melanin and enhances the growth of melanized fungi.

Journal: PloS one 20070101

Title: Oculocutaneous albinism.

Journal: Orphanet journal of rare diseases 20070101

Title: Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation.

Journal: Journal of the American Chemical Society 20061206

Title: Dopaquinone redox exchange with dihydroxyindole and dihydroxyindole carboxylic acid.

Journal: Pigment cell research 20061001

Title: Fe(III)-coordination properties of neuromelanin components: 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid.

Journal: Inorganic chemistry 20060501

Title: Drosophila tan encodes a novel hydrolase required in pigmentation and vision.

Journal: PLoS genetics 20051101

Title: An oxygen transporter hemocyanin can act on the late pathway of melanin synthesis.

Journal: Pigment cell research 20050601

Title: [UV-Vis spectroscopic study of aluminum-manganese cooperative effect on the melanin formation from DOPA oxidation].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20050101

Title: [UV-vis spectroscopic study of the effect of Cu(II) ions on dopachrome].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20040701

Title: Aluminum facilitation of the iron-mediated oxidation of DOPA to melanin.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20040401

Title: Involvement of photooxidation of melanogenic precursors in prolonged pigmentation induced by ultraviolet A.

Journal: The Journal of investigative dermatology 20040201

Title: Aluminum ions accelerated the oxidative stress of copper-mediated melanin formation.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20031101

Title: Melanogenesis in the ink gland of Sepia officinalis.

Journal: Pigment cell research 20031001

Title: Skin-lightening products revisited.

Journal: International journal of cosmetic science 20030801

Title: Effect of aluminum (III) on the conversion of dopachrome in the melanin synthesis pathway.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20030601

Title: The IFPCS presidential lecture: a chemist's view of melanogenesis.

Journal: Pigment cell research 20030601

Title: Melanin as a target for melanoma chemotherapy: pro-oxidant effect of oxygen and metals on melanoma viability.

Journal: Pigment cell research 20030601

Title: Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes.

Journal: Journal of analytical toxicology 20030401

Title: Identification of Drosophila melanogaster yellow-f and yellow-f2 proteins as dopachrome-conversion enzymes.

Journal: The Biochemical journal 20021115

Title: Redox behavior of melanins: direct electrochemistry of dihydroxyindole-melanin and its Cu and Zn adducts.

Journal: Journal of inorganic biochemistry 20020410

Title: Cloning and characterization of a dopachrome conversion enzyme from the yellow fever mosquito, Aedes aegypti.

Journal: Insect biochemistry and molecular biology 20011001

Title: Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: the dominant role of DHI.

Journal: Pigment cell research 20011001

Title: Relationship of melanin degradation products to actual melanin content: application to human hair.

Journal: Analytical biochemistry 20010301

Title: Melanogenesis by tyrosinase action on 3,4-dihydroxyphenylalanine (DOPA) in the presence of polyethylene glycol: a matrix-assisted laser desorption/ionization mass spectrometric investigation.

Journal: Rapid communications in mass spectrometry : RCM 20010101

Title: Zhao P, et al. Antiviral, anti-parasitic, and cytotoxic effects of 5,6-dihydroxyindole (DHI), a reactive compound generated by phenoloxidase during insect immune response. Insect Biochem Mol Biol. 2011 Sep;41(9):645-52.

Title: Heiduschka P, et al. Melanin precursor 5,6-dihydroxyindol: protective effects and cytotoxicity on retinal cells in vitroand in vivo. Toxicol Pathol. 2007 Dec;35(7):1030-8.

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Tags:3131-52-0 Molecular Formula|3131-52-0 MDL|3131-52-0 SMILES|3131-52-0 5,6-Dihydroxyindole