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Home > Indoles and Oxindole > 3131-52-0
3131-52-0 | 5,6-Dihydroxyindole
CAS No: 3131-52-0 Catalog No: AG007HR6 MDL No:MFCD00798933
Product Description
Catalog Number:
AG007HR6
Chemical Name:
5,6-Dihydroxyindole
CAS Number:
3131-52-0
Molecular Formula:
C8H7NO2
Molecular Weight:
149.1467
MDL Number:
MFCD00798933
IUPAC Name:
1H-indole-5,6-diol
InChI:
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
SMILES:
Oc1cc2[nH]ccc2cc1O
EC Number:
412-130-9
UNII:
Z3OC8499KG
Properties
Complexity:
151
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
149.048g/mol
Formal Charge:
0
Heavy Atom Count:
11
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
149.149g/mol
Monoisotopic Mass:
149.048g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
56.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.3
Literature
| Title | Journal |
|---|---|
| Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization. | Biomacromolecules 20120813 |
| Age-dependent changes in eumelanin composition in hairs of various ethnic origins. | International journal of cosmetic science 20120201 |
| The relative importance of innate immune priming in Wolbachia-mediated dengue interference. | PLoS pathogens 20120201 |
| Immunomodulatory Effect of Rhaphidophora korthalsii on Natural Killer Cell Cytotoxicity. | Evidence-based complementary and alternative medicine : eCAM 20120101 |
| Exploring the frontiers of synthetic eumelanin polymers by high-resolution matrix-assisted laser/desorption ionization mass spectrometry. | Journal of mass spectrometry : JMS 20120101 |
| The action of D-dopachrome tautomerase as an adipokine in adipocyte lipid metabolism. | PloS one 20120101 |
| Multiple tyrosine metabolites are GPR35 agonists. | Scientific reports 20120101 |
| Melanin-based coatings as lead-binding agents. | Bioinorganic chemistry and applications 20120101 |
| UV-absorption spectra of melanosomes containing varying 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid content. | The journal of physical chemistry. B 20111103 |
| New pathways of betanidin and betanin enzymatic oxidation. | Journal of agricultural and food chemistry 20110914 |
| Antiviral, anti-parasitic, and cytotoxic effects of 5,6-dihydroxyindole (DHI), a reactive compound generated by phenoloxidase during insect immune response. | Insect biochemistry and molecular biology 20110901 |
| 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. | The Journal of organic chemistry 20110603 |
| The neurotransmitter serotonin interrupts α-synuclein amyloid maturation. | Biochimica et biophysica acta 20110501 |
| Alpha-synuclein is a cellular ferrireductase. | PloS one 20110101 |
| Inhibitory effect of phthalic Acid on tyrosinase: the mixed-type inhibition and docking simulations. | Enzyme research 20110101 |
| Complex interactions of Tyrp1 in the eye. | Molecular vision 20110101 |
| First synthetic entry to the trimer stage of 5,6-dihydroxyindole polymerization: ortho-alkynylaniline-based access to the missing 2,7':2',7''-triindole. | Organic & biomolecular chemistry 20101007 |
| Cyclic structural motifs in 5,6-dihydroxyindole polymerization uncovered: biomimetic modular buildup of a unique five-membered macrocycle. | Organic letters 20100716 |
| Prostaglandin-E2 is produced by adult human epidermal melanocytes in response to UVB in a melanogenesis-independent manner. | Pigment cell & melanoma research 20100601 |
| Regulation of DHICA-mediated antioxidation by dopachrome tautomerase: implication for skin photoprotection against UVA radiation. | Free radical biology & medicine 20100501 |
| Direct measurement of the ultraviolet absorption coefficient of single retinal melanosomes. | Photochemistry and photobiology 20100101 |
| Modulation of alpha-synuclein aggregation by dopamine analogs. | PloS one 20100101 |
| 5,6-Dihydroxyindole oxidation in phosphate buffer/polyvinyl alcohol: a new model system for studies of visible chromophore development in synthetic eumelanin polymers. | Photochemistry and photobiology 20100101 |
| Genetic variations in human glutathione transferase enzymes: significance for pharmacology and toxicology. | Human genomics and proteomics : HGP 20100101 |
| The hunt for natural skin whitening agents. | International journal of molecular sciences 20091201 |
| 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 of the American Chemical Society 20091028 |
| 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. | The Journal of organic chemistry 20090918 |
| Ultrafast excited state dynamics of 5,6-dihydroxyindole, a key eumelanin building block: nonradiative decay mechanism. | The journal of physical chemistry. B 20090917 |
| Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration. | International journal of molecular sciences 20090901 |
| An updated review of tyrosinase inhibitors. | International journal of molecular sciences 20090601 |
| 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. | The Journal of organic chemistry 20090515 |
| 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 of molecular biology 20090403 |
| Study of total antioxidant status and glutathione peroxidase activity in Tunisian vitiligo patients. | Indian journal of dermatology 20090101 |
| Adsorption of Pb(II) and Cd(II) by Squid Ommastrephes bartrami Melanin. | Bioinorganic chemistry and applications 20090101 |
| Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations. | The journal of physical chemistry. A 20081106 |
| Solvochromic effects in model eumelanin compounds. | Photochemistry and photobiology 20080101 |
| Ultra-low temperature oxidation of 5,6-dihydroxyindole: a novel approach to study synthetic melanogenesis. | Photochemistry and photobiology 20080101 |
| Chemistry of mixed melanogenesis--pivotal roles of dopaquinone. | Photochemistry and photobiology 20080101 |
| 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. | Photochemistry and photobiology 20080101 |
| Melanin precursor 5,6-dihydroxyindol: protective effects and cytotoxicity on retinal cells in vitro and in vivo. | Toxicologic pathology 20071201 |
| 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. | The Journal of organic chemistry 20071123 |
| Parasite suppression of the oxidations of eumelanin precursors in Drosophila melanogaster. | Archives of insect biochemistry and physiology 20071001 |
| Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. | Chemical research in toxicology 20071001 |
| Broad-spectrum antimicrobial activity of the reactive compounds generated in vitro by Manduca sexta phenoloxidase. | Insect biochemistry and molecular biology 20070901 |
| Kinetic and structural analysis of the early oxidation products of dopamine: analysis of the interactions with alpha-synuclein. | The Journal of biological chemistry 20070525 |
| Photophysics of eumelanin: ab initio studies on the electronic spectroscopy and photochemistry of 5,6-dihydroxyindole. | Chemphyschem : a European journal of chemical physics and physical chemistry 20070402 |
| 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. | Organic letters 20070329 |
| Ionizing radiation changes the electronic properties of melanin and enhances the growth of melanized fungi. | PloS one 20070101 |
| Oculocutaneous albinism. | Orphanet journal of rare diseases 20070101 |
| Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. | Journal of the American Chemical Society 20061206 |
| Dopaquinone redox exchange with dihydroxyindole and dihydroxyindole carboxylic acid. | Pigment cell research 20061001 |
| Fe(III)-coordination properties of neuromelanin components: 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid. | Inorganic chemistry 20060501 |
| Drosophila tan encodes a novel hydrolase required in pigmentation and vision. | PLoS genetics 20051101 |
| An oxygen transporter hemocyanin can act on the late pathway of melanin synthesis. | Pigment cell research 20050601 |
| [UV-Vis spectroscopic study of aluminum-manganese cooperative effect on the melanin formation from DOPA oxidation]. | Guang pu xue yu guang pu fen xi = Guang pu 20050101 |
| [UV-vis spectroscopic study of the effect of Cu(II) ions on dopachrome]. | Guang pu xue yu guang pu fen xi = Guang pu 20040701 |
| Aluminum facilitation of the iron-mediated oxidation of DOPA to melanin. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20040401 |
| Involvement of photooxidation of melanogenic precursors in prolonged pigmentation induced by ultraviolet A. | The Journal of investigative dermatology 20040201 |
| Aluminum ions accelerated the oxidative stress of copper-mediated melanin formation. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20031101 |
| Melanogenesis in the ink gland of Sepia officinalis. | Pigment cell research 20031001 |
| Skin-lightening products revisited. | International journal of cosmetic science 20030801 |
| Effect of aluminum (III) on the conversion of dopachrome in the melanin synthesis pathway. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20030601 |
| The IFPCS presidential lecture: a chemist's view of melanogenesis. | Pigment cell research 20030601 |
| Melanin as a target for melanoma chemotherapy: pro-oxidant effect of oxygen and metals on melanoma viability. | Pigment cell research 20030601 |
| Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes. | Journal of analytical toxicology 20030401 |
| Identification of Drosophila melanogaster yellow-f and yellow-f2 proteins as dopachrome-conversion enzymes. | The Biochemical journal 20021115 |
| Redox behavior of melanins: direct electrochemistry of dihydroxyindole-melanin and its Cu and Zn adducts. | Journal of inorganic biochemistry 20020410 |
| Cloning and characterization of a dopachrome conversion enzyme from the yellow fever mosquito, Aedes aegypti. | Insect biochemistry and molecular biology 20011001 |
| Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: the dominant role of DHI. | Pigment cell research 20011001 |
| Relationship of melanin degradation products to actual melanin content: application to human hair. | Analytical biochemistry 20010301 |
| Melanogenesis by tyrosinase action on 3,4-dihydroxyphenylalanine (DOPA) in the presence of polyethylene glycol: a matrix-assisted laser desorption/ionization mass spectrometric investigation. | Rapid communications in mass spectrometry : RCM 20010101 |
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