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4790-08-3,MFCD02181103
Catalog No.:AA00DD8O

4790-08-3 | 5,6-Dihydroxy-1h-indole-2-carboxylic acid

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25mg
95%
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$81.00   $57.00
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100mg
95%
in stock  
$101.00   $71.00
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250mg
95%
in stock  
$152.00   $107.00
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1g
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$183.00   $128.00
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5g
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$809.00   $567.00
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10g
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$1,407.00   $985.00
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25g
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$2,804.00   $1,963.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DD8O
Chemical Name:
5,6-Dihydroxy-1h-indole-2-carboxylic acid
CAS Number:
4790-08-3
Molecular Formula:
C9H7NO4
Molecular Weight:
193.1562
MDL Number:
MFCD02181103
SMILES:
Oc1cc2[nH]c(cc2cc1O)C(=O)O
Properties
Computed Properties
 
Complexity:
245  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
1  
XLogP3:
1.2  

Literature

Title: The eumelanin intermediate 5,6-dihydroxyindole-2-carboxylic acid is a messenger in the cross-talk among epidermal cells.

Journal: The Journal of investigative dermatology 20120401

Title: Topical hypopigmenting agents for pigmentary disorders and their mechanisms of action.

Journal: Annals of dermatology 20120201

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: New insights into the evolution of metazoan tyrosinase gene family.

Journal: PloS one 20120101

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

Journal: Bioinorganic chemistry and applications 20120101

Title: A complex genomic rearrangement involving the endothelin 3 locus causes dermal hyperpigmentation in the chicken.

Journal: PLoS genetics 20111201

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: Inactivation of Pmel alters melanosome shape but has only a subtle effect on visible pigmentation.

Journal: PLoS genetics 20110901

Title: Mutations in or near the transmembrane domain alter PMEL amyloid formation from functional to pathogenic.

Journal: PLoS genetics 20110901

Title: Maintenance of immune hyporesponsiveness to melanosomal proteins by DHICA-mediated antioxidation: Possible implications for autoimmune vitiligo.

Journal: Free radical biology & medicine 20110501

Title: Is DHICA the key to dopachrome tautomerase and melanocyte functions?

Journal: Pigment cell & melanoma research 20110201

Title: Original article title: 'Comparison of therapeutic efficacy of topical corticosteroid and oral zinc sulfate-topical corticosteroid combination in the treatment of vitiligo patients: a clinical trial'.

Journal: BMC dermatology 20110101

Title: Ethnic and mouse strain differences in central corneal thickness and association with pigmentation phenotype.

Journal: PloS one 20110101

Title: Complex interactions of Tyrp1 in the eye.

Journal: Molecular vision 20110101

Title: Hypothesis: zinc can be effective in treatment of vitiligo.

Journal: Indian journal of dermatology 20110101

Title: UV-dissipation mechanisms in the eumelanin building block DHICA.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20100802

Title: Elevated oxidative membrane damage associated with genetic modifiers of Lyst-mutant phenotypes.

Journal: PLoS genetics 20100701

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: Spectrum of candidate gene mutations associated with Indian familial oculocutaneous and ocular albinism.

Journal: Molecular vision 20100101

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

Journal: Human genomics and proteomics : HGP 20100101

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: Structural, electrical, electronic and optical properties of melanin films.

Journal: The European physical journal. E, Soft matter 20090301

Title: Physico-chemical evaluation of rationally designed melanins as novel nature-inspired radioprotectors.

Journal: PloS one 20090101

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

Journal: Indian journal of dermatology 20090101

Title: Role of solvent, pH, and molecular size in excited-state deactivation of key eumelanin building blocks: implications for melanin pigment photostability.

Journal: Journal of the American Chemical Society 20081217

Title: Effect of dimerization on vibrational spectra of eumelanin precursors.

Journal: Photochemistry and photobiology 20080101

Title: Solvochromic effects in model eumelanin compounds.

Journal: Photochemistry and photobiology 20080101

Title: Synthesis and polymerization studies of organic-soluble eumelanins.

Journal: Photochemistry and photobiology 20080101

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

Journal: Photochemistry and photobiology 20080101

Title: Computational systems analysis of dopamine metabolism.

Journal: PloS one 20080101

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

Journal: Archives of insect biochemistry and physiology 20071001

Title: Changes of melanosome morphology associated with the differentiation of epidermal melanocytes in slaty mice.

Journal: Anatomical record (Hoboken, N.J. : 2007) 20070801

Title: Transition dipole strength of eumelanin.

Journal: Physical review. E, Statistical, nonlinear, and soft matter physics 20070801

Title: Convergent proton-transfer photocycles violate mirror-image symmetry in a key melanin monomer.

Journal: Journal of the American Chemical Society 20070530

Title: Evaluation of efficacy and safety of rucinol serum in patients with melasma: a randomized controlled trial.

Journal: The British journal of dermatology 20070501

Title: Evolution of pigment synthesis pathways by gene and genome duplication in fish.

Journal: BMC evolutionary biology 20070101

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

Journal: PloS one 20070101

Title: Pathway aberrations of murine melanoma cells observed in Paired-End diTag transcriptomes.

Journal: BMC cancer 20070101

Title: Multiple splice variants within the bovine silver homologue (SILV) gene affecting coat color in cattle indicate a function additional to fibril formation in melanophores.

Journal: BMC genomics 20070101

Title: Oculocutaneous albinism.

Journal: Orphanet journal of rare diseases 20070101

Title: Hyperbranched molecular structures with potential antiviral activity: derivatives of 5,6-dihydroxyindole-2-carboxylic Acid.

Journal: Molecules (Basel, Switzerland) 20061218

Title: Synthesis, discovery and mechanism of 2,6-dimethoxy-N-(4-methoxyphenyl)benzamide as potent depigmenting agent in the skin.

Journal: Biochemical and biophysical research communications 20061013

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

Journal: Pigment cell research 20061001

Title: Characterization of the pigment produced by the planarian, Dugesia ryukyuensis.

Journal: Pigment cell research 20060601

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

Journal: Inorganic chemistry 20060501

Title: Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance.

Journal: Biophysical journal 20060201

Title: Functional amyloid formation within mammalian tissue.

Journal: PLoS biology 20060101

Title: Genetic context determines susceptibility to intraocular pressure elevation in a mouse pigmentary glaucoma.

Journal: BMC biology 20060101

Title: Quantitative fluorescence excitation spectra of synthetic eumelanin.

Journal: The journal of physical chemistry. B 20051103

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

Journal: Pigment cell research 20050601

Title: Metal-ion interactions and the structural organization of Sepia eumelanin.

Journal: Pigment cell research 20050201

Title: Comparisons of the structural and chemical properties of melanosomes isolated from retinal pigment epithelium, iris and choroid of newborn and mature bovine eyes.

Journal: Photochemistry and photobiology 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: Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors.

Journal: Antiviral chemistry & chemotherapy 20040301

Title: Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin.

Journal: Biochemical pharmacology 20040215

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

Journal: The Journal of investigative dermatology 20040201

Title: Changes in the proliferation and differentiation of neonatal mouse pink-eyed dilution melanocytes in the presence of excess tyrosine.

Journal: Pigment cell research 20031201

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

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

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

Journal: Journal of analytical toxicology 20030401

Title: Stimulation of the proliferation and differentiation of mouse pink-eyed dilution epidermal melanocytes by excess tyrosine in serum-free primary culture.

Journal: Journal of cellular physiology 20020501

Title: Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects.

Journal: Pigment cell research 20020201

Title: Tyrp1 and oculocutaneous albinism type 3.

Journal: Pigment cell research 20011201

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: The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase.

Journal: The Biochemical journal 20010215

Title: Interaction of major coat color gene functions in mice as studied by chemical analysis of eumelanin and pheomelanin.

Journal: Pigment cell research 20010201

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

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Tags:4790-08-3 Molecular Formula|4790-08-3 MDL|4790-08-3 SMILES|4790-08-3 5,6-Dihydroxy-1h-indole-2-carboxylic acid