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purpurin
9,10-anthracenedione, 1,2,4-trihydroxy- (9CI)

Supplier Sponsors

Name:1,2,4-trihydroxyanthracene-9,10-dione
CAS Number: 81-54-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-359-8
FDA UNII: L1GT81LS6N
Nikkaji Web:J3.859H
Beilstein Number:1887127
MDL:MFCD00001203
XlogP3-AA:2.90 (est)
Molecular Weight:256.21376000
Formula:C14 H8 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:dark red powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 259.00 °C. @ 760.00 mm Hg
Boiling Point: 525.10 °C. @ 760.00 mm Hg (est)
Flash Point: 546.00 °F. TCC ( 285.40 °C. ) (est)
logP (o/w): 4.600 (est)
Soluble in:
 water, 6.4 mg/L @ 25 °C (exp)
 water, 7.184 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Purpurin 98%
BOC Sciences
For experimental / research use only.
Purpurin >98%
Odor: characteristic
Use: Source from herbs of Rubia cordifolia L. Purpurin is a novel specific inhibitor of Adipocyte-derived leucine aminopeptidase and could be developed as a new anti-angiogenic agent. It may represent a potential candidate that deserves further investigations anti-bacterial and anti-inflammatory
Coompo
For experimental / research use only.
Purpurin from Plants ≥98%
Glentham Life Sciences
Purpurin (C.I. 58205)
Santa Cruz Biotechnology
For experimental / research use only.
Purpurin
Sigma-Aldrich
For experimental / research use only.
Purpurin for spectrophotometric det. (of B, Pb)
TCI AMERICA
For experimental / research use only.
Purpurin >95.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD > 500 mg/kg
"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 321, 1952.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for purpurin usage levels up to:
 not for fragrance use.
 
Recommendation for purpurin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6683
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1,2,4-trihydroxyanthracene-9,10-dione
Chemidplus:0000081549
EPA/NOAA CAMEO:hazardous materials
RTECS:CB8200000 for cas# 81-54-9
 
References:
 1,2,4-trihydroxyanthracene-9,10-dione
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:81-54-9
Pubchem (cid):6683
Pubchem (sid):134972814
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10395
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2914.69.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Wikipedia2:View2
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
9,10-anthracenedione, 1,2,4-trihydroxy-
9,10-anthracenedione, 1,2,4-trihydroxy- (9CI)
 anthraquinone, 1,2,4-trihydroxy-
 C.I. natural red 16
 C.I. natural red 8
 purpurine
 smoke brown G
1,2,4-trihydroxy-9,10-anthracenedione
1,2,4-trihydroxy-9,10-anthraquinone
1,2,4-trihydroxyanthra-9,10-quinone
1,2,4-trihydroxyanthracene-9,10-dione
1,2,4-trihydroxyanthraquinone
 verantin
 

Articles:

PubMed:A simple, rapid and low-cost staining method for gel-electrophoresis separated phosphoproteins via the fluorescent purpurin dye.
PubMed:Purpurin inhibits adipocyte-derived leucine aminopeptidase and angiogenesis in a zebrafish model.
PubMed:Synthesis and characterization of novel purpurinimides as photosensitizers for photodynamic therapy.
PubMed:Chemical compounds isolated from Talinum triangulare (Portulacaceae).
PubMed:Antitrypanosomal activity & docking studies of components of Crateva adansonii DC leaves: novel multifunctional scaffolds.
PubMed:Sub-MIC levels of purpurin inhibit membrane ATPase-mediated proton efflux activity in the human fungal pathogen Candida albicans.
PubMed:Microscopic analysis of the localization of two chlorin-based photosensitizers in OSC19 tumors in the mouse oral cavity.
PubMed:Purpurin triggers caspase-independent apoptosis in Candida dubliniensis biofilms.
PubMed:An antioxidant extract of tropical lichen, Parmotrema reticulatum, induces cell cycle arrest and apoptosis in breast carcinoma cell line MCF-7.
PubMed:A molecular mechanism of optic nerve regeneration in fish: the retinoid signaling pathway.
PubMed:Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation.
PubMed:Overlapping substrate and inhibitor specificity of human and murine ABCG2.
PubMed:Effects of lovastatin, clomazone and methyl jasmonate treatment on the accumulation of purpurin and mollugin in cell suspension cultures of Rubia cordifolia.
PubMed:Spectroscopic and in silico evaluation of interaction of DNA with six anthraquinone derivatives.
PubMed:Size-dependent photodynamic activity of gold nanoparticles conjugate of water soluble purpurin-18-N-methyl-d-glucamine.
PubMed:Application of a novel microtitre plate-based assay for the discovery of new inhibitors of DNA gyrase and DNA topoisomerase VI.
PubMed:Advance in photosensitizers and light delivery for photodynamic therapy.
PubMed:[Simultaneous determination of four quinone compounds in carbonized Rubiae Radix et Rhizoma by UPLC].
PubMed:Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes.
PubMed:Purpurin suppresses Candida albicans biofilm formation and hyphal development.
PubMed:[Study on intestinal absorption of mollugin and purpurin in rats].
PubMed:Effect of hydrosoluble chlorine-mediated antimicrobial photodynamic therapy on clinical parameters and cytokine profile in ligature-induced periodontitis in dogs.
PubMed:Identification of the first known inhibitors of O-acetylpeptidoglycan esterase: a potential new antibacterial target.
PubMed:Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation.
PubMed:Free radical scanvenging and antioxidant effects of some anthraquinone derivatives.
PubMed:Preparation of photosensitizer-loaded PLLA nanofibers and its anti-tumor effect for photodynamic therapy in vitro.
PubMed:Photophysical properties of alizarin and purpurin Al(III) complexes in solution and in solid state.
PubMed:HPLC-DAD-MS analysis of dyes identified in textiles from Mount Athos.
PubMed:Purpurin as a specific inhibitor of spermidine-induced autoactivation of the protease plasma hyaluronan-binding protein.
PubMed:Bright light: microspectrofluorimetry for the characterization of lake pigments and dyes in works of art.
PubMed:Anthraquinone distribution in the hypogeal apparatus of Rubia peregrina L. growing wild in Sardinia.
PubMed:Novel antifungal activity of purpurin against Candida species in vitro.
PubMed:A hypoplastic retinal lamination in the purpurin knock down embryo in zebrafish.
PubMed:Blockade of LTB4-induced chemotaxis by bioactive molecules interfering with the BLT2-Galphai interaction.
PubMed:Horseradish peroxidase-catalyzed oxidation of chlorophyll a with hydrogen peroxide: characterization of the products and mechanism of the reaction.
PubMed:The neovessel occlusion efficacy of 15-hydroxypurpurin-7-lactone dimethyl ester induced with photodynamic therapy.
PubMed:In vitro evaluation of Radachlorin sensitizer for photodynamic therapy.
PubMed:Purpurin is a key molecule for cell differentiation during the early development of zebrafish retina.
PubMed:Newly synthesized water soluble cholinium-purpurin photosensitizers and their stabilized gold nanoparticles as promising anticancer agents.
PubMed:Ad-hoc surface-enhanced Raman spectroscopy methodologies for the detection of artist dyestuffs: thin layer chromatography-surface enhanced Raman spectroscopy and in situ on the fiber analysis.
PubMed:Compared to purpurinimides, the pyropheophorbide containing an iodobenzyl group showed enhanced PDT efficacy and tumor imaging (124I-PET) ability.
PubMed:Involvement of retinoic acid signaling in goldfish optic nerve regeneration.
PubMed:Fluorescence investigation of the binding of model PDT drugs to nonionic and zwitterionic surfactants.
PubMed:An insight into the solution equilibria of magnesium(II) with purpurin and spectrophotometric determination of magnesium.
PubMed:Rapid test methods for minor components analysis of hydraulic cement. Spectrophotometric determination of manganese oxide content of Portland cement and cement raw meal.
PubMed:A multivariate study of the performance of an ultrasound-assisted madder dyes extraction and characterization by liquid chromatography-photodiode array detection.
PubMed:Pigment alterations in the brown mussel Perna perna.
PubMed:[New amphiphilic chlorins in the chlorophyll a series].
PubMed:The use of microspectrofluorimetry for the characterization of lake pigments.
PubMed:Analysis of ancient Greco-Roman cosmetic materials using laser desorption ionization and electrospray ionization mass spectrometry.
PubMed:Investigation of common fluorophores for the detection of nitrated explosives by fluorescence quenching.
PubMed:Ultrafast energy transfer dynamics of a bioinspired dyad molecule.
PubMed:Extraction of heavy metal ions from leachate of cement-based stabilized waste using purpurin functionalized resin.
PubMed:Electrocoagulation of quinone pigments.
PubMed:Self-aggregation behavior of synthetic zinc 3-hydroxymethyl-13/15-carbonyl-chlorins as models of main light-harvesting components in photosynthetic green bacteria.
PubMed:Identification and characterization of artists' red dyes and their mixtures by surface-enhanced Raman spectroscopy.
PubMed:Steady state and time-resolved fluorescence investigation of the specific binding of two chlorin derivatives with human serum albumin.
PubMed:Comparative in vitro and in vivo studies on long-wavelength photosensitizers derived from bacteriopurpurinimide and Bacteriochlorin p6: fused imide ring enhances the in vivo PDT efficacy.
PubMed:A spectrometric and chromatographic approach to the study of ageing of madder (Rubia tinctorum L.) dyestuff on wool.
PubMed:Isolation and identification of impurities in chlorin e6.
PubMed:Purpurin expression in the zebrafish retina during early development and after optic nerve lesion in adults.
PubMed:Micellar electrokinetic chromatography method for the determination of several natural red dyestuff and lake pigments used in art work.
PubMed:Purpurinimide carbohydrate conjugates: effect of the position of the carbohydrate moiety in photosensitizing efficacy.
PubMed:Simultaneous identification of natural dyes in the collection of drawings and maps from The Royal Chancellery Archives in Granada (Spain) by CE.
PubMed:Enhancement of phase II enzyme activity by purpurin resulting in the suppression of MeIQx-DNA-adduct formation in mice.
PubMed:Effect of increased hydrophobicity on the binding of two model amphiphilic chlorin drugs for photodynamic therapy with blood plasma and its components.
PubMed:Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography.
PubMed:Spectroscopic determination of proton position in the proton-coupled electron transfer pathways of donor-acceptor supramolecule assemblies.
PubMed:A double-blind, controlled evaluation of the value of sarapin in neural blockade.
PubMed:Sampling and identification of natural dyes in historical maps and drawings by liquid chromatography with diode-array detection.
PubMed:Investigation of red natural dyes used in historical objects by HPLC-DAD-MS.
PubMed:In vivo stability and photodynamic efficacy of fluorinated bacteriopurpurinimides derived from bacteriochlorophyll-a.
PubMed:Difference in the effects of surfactants and albumin on the extent of deaggregation of purpurin 18, a model of hydrophobic photosensitizer.
PubMed:Characterization of porphyrins, chlorins, and bacteriochlorins formed via allomerization of bacteriochlorophyll a. Synthesis of highly stable bacteriopurpurinimides and their metal complexes.
PubMed:[Examination of the anthraquinone composition in root-stock and root samples of Rubia tinctorium L. plants of different origins].
PubMed:[Synthesis of purpure-18-imide and study on its interaction with bovine serum albumins by fluorescence].
PubMed:Pharmacokinetics and phototoxicity of purpurin-18 in human colon carcinoma cells using liposomes as delivery vehicles.
PubMed:Evaluation of photo-mutagenicity and photo-cytotoxicity of food coloring agents.
PubMed:Optimization of microwave-assisted extraction for alizarin and purpurin in Rubiaceae plants and its comparison with conventional extraction methods.
PubMed:Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation.
PubMed:Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars.
PubMed:Using a kinase screen to investigate the constituents of the sponge Stelletta clavosa obtained from diverse habitats.
PubMed:Role of purpurin as a retinol-binding protein in goldfish retina during the early stage of optic nerve regeneration: its priming action on neurite outgrowth.
PubMed:Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity.
PubMed:Selectivity of protein carbonylation in the apoptotic response to oxidative stress associated with photodynamic therapy: a cell biochemical and proteomic investigation.
PubMed:The solid-phase conjugation of purpurin-18 with a synthetic targeting peptide.
PubMed:Identification of anthraquinone coloring matters in natural red dyes by electrospray mass spectrometry coupled to capillary electrophoresis.
PubMed:Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species.
PubMed:Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection.
PubMed:Photophysical and photochemical properties of 1,2,4-trihydroxy-9,10-anthraquinone adsorbed on inorganic oxides.
PubMed:Protection against Trp-P-2 DNA adduct formation in C57bl6 mice by purpurin is accompanied by induction of cytochrome P450.
PubMed:Electrochemical identification of anthraquinone-based dyes in solid microsamples by square wave voltammetry using graphite/polyester composite electrodes.
PubMed:Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection.
PubMed:Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.
PubMed:Peroxidase-mediated transformation of hydroxy-9,10-anthraquinones.
PubMed:[Studies on the synthesis and experimental therapeutic effects of metal chlorin on 60Co-irridiated mice].
PubMed:Structure of acid-stable carmine.
PubMed:Atmospheric pressure chemical ionisation normal phase liquid chromatography mass spectrometry and tandem mass spectrometry of chlorophyll a allomers.
PubMed:Synthesis of beta-galactose-conjugated chlorins derived by enyne metathesis as galectin-specific photosensitizers for photodynamic therapy.
PubMed:Photosensitizer delivery for photodynamic therapy of choroidal neovascularization.
PubMed:Preventive effects of anthraquinone food pigments on the DNA damage induced by carcinogens in Drosophila.
PubMed:Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.
PubMed:Purpurin-18 in combination with light leads to apoptosis or necrosis in HL60 leukemia cells.
PubMed:Purpurinimides as photosensitizers: effect of the presence and position of the substituents in the in vivo photodynamic efficacy.
PubMed:Effect of substituents in directing the formation of benzochlorins and isobacteriochlorins in porphyrin and chlorin systems.
PubMed:Protection against Trp-P-2 mutagenicity by purpurin: mechanism of in vitro antimutagenesis.
PubMed:Photosensitizers related to purpurin-18-N-alkylimides: a comparative in vivo tumoricidal ability of ester versus amide functionalities.
PubMed:High-performance liquid chromatographic determination of some anthraquinone and naphthoquinone dyes occurring in historical textiles.
PubMed:Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment.
PubMed:Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore.
PubMed:Revised Relative and Absolute Stereochemistry of (+)-Purpurin
PubMed:Photodynamic therapy in the management of metastatic cutaneous adenocarcinomas: case reports from phase 1/2 studies using tin ethyl etiopurpurin (SnET2).
PubMed:Inhibition of xanthine oxidase by hydroxylated anthraquinones and related compounds.
PubMed:Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase.
PubMed:Increased photosensitivity in HL60 cells expressing wild-type p53.
PubMed:Photodynamic therapy-mediated oxidative stress can induce expression of heat shock proteins.
PubMed:Aberrant crypts as a biomarker for colon cancer: evaluation of potential chemopreventive agents in the rat.
PubMed:Toxicity and tumorigenicity of purpurin, a natural hydroxanthraquinone in rats: induction of bladder neoplasms.
PubMed:Production of reactive oxygen species by hemocytes from the marine mussel, Mytilus edulis: lysosomal localization and effect of xenobiotics.
PubMed:Inhibitors of cAMP-dependent protein kinase impair long-term memory formation in day-old chicks.
PubMed:The lipocalin protein family: a role in cell regulation.
PubMed:Screening of natural and synthetic drugs against Trypanosoma cruzi. 1. Establishing a structure/activity relationship.
PubMed:Spectroscopic studies of tin ethyl etiopurpurin in homogeneous and heterogeneous systems.
PubMed:Ligand-dependent secretion of rat retinol-binding protein expressed in HeLa cells.
PubMed:A genetically engineered purpurin/retinol-binding protein hybrid that binds to transthyretin.
PubMed:Treatment of the transplantable FANFT induced bladder tumors with the purpurin SnET2 and red light emitted by a pulsed frequency doubled Nd:YAG laser.
PubMed:Retinol-binding protein and transthyretin expressed in HeLa cells form a complex in the endoplasmic reticulum in both the absence and the presence of retinol.
PubMed:Photodynamic therapy: effect on the endothelial cell of the rat aorta.
PubMed:Hydroxyanthraquinones as tumor promoters: enhancement of malignant transformation of C3H mouse fibroblasts and growth stimulation of primary rat hepatocytes.
PubMed:Metallopurpurins and light: effect on transplantable rat bladder tumors and murine skin.
PubMed:Activin is a nerve cell survival molecule.
PubMed:Biochemical differentiation of nascent neurite junctions: unilateral localization of adheron components.
PubMed:New fluorescence reactions in DNA cytochemistry. 2. Microscopic and spectroscopic studies on fluorescent aluminum complexes.
PubMed:Genotoxicity of naturally occurring hydroxyanthraquinones.
PubMed:Aluminium binding to chromatin DNA as revealed by formation of fluorescent complexes with 8-hydroxyquinoline and other ligands.
PubMed:New sensitizers for photodynamic therapy: controlled synthesis of purpurins and their effect on normal tissue.
PubMed:Release of iron from ferritin by semiquinone, anthracycline, bipyridyl, and nitroaromatic radicals.
PubMed:Molecular modeling of protein-glycosaminoglycan interactions.
PubMed:Laser flash photolysis of purpurins: novel potential photosensitizers of interest in photodynamic therapy.
PubMed:Photodynamic sensitizers from chlorophyll: purpurin-18 and chlorin p6.
PubMed:New photosensitizers for photodynamic therapy: combined effect of metallopurpurin derivatives and light on transplantable bladder tumors.
PubMed:Sequence analysis, cellular localization, and expression of a neuroretina adhesion and cell survival molecule.
PubMed:A dose response analysis of purpurin derivatives used as photosensitizers for the photodynamic treatment of transplantable FANFT induced urothelial tumors.
PubMed:Morphological study of the combined effect of purpurin derivatives and light on transplantable rat bladder tumors.
PubMed:Study of the mixed-metal lanthanummagnesium-purpurin complex: spectrophotometric determination of yttrium and lanthanides.
PubMed:A chick neural retina adhesion and survival molecule is a retinol-binding protein.
PubMed:Role of purpurin in neural retina histogenesis.
PubMed:Isolation of an adhesion-mediating protein from chick neural retina adherons.
PubMed:Spectrophotometric determination of trace amounts of iron(III) in oxalates by extraction of the mixed-ligand iron-oxalate-purpurin complex.
PubMed:Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives.
PubMed:Microbial glucosidation of 1,2,4-trihydroxy-9,10-anthraquinone (purpurin).
PubMed:Spectrophotometric determination of trace amounts of iron(III) by extraction of the mixed-ligand iron-fluoride-purpurin complex.
PubMed:Isolectins from Dictyostelium purpureum. Purification and characterization of seven functionally distinct forms.
PubMed:Endogenous cell surface lectin in Dictyostelium: quantitation, elution by sugar, and elicitation by divalent immunoglobulin.
PubMed:Chicken tissue binding sites for a purified chicken lectin.
PubMed:Studies on plant bile pigments, II[1]. Chemical and photochemical oxygenation of a phytochrome Pr chromophore model pigment to purpurins.
PubMed:Mutagenesis by 9,10-anthraquinone derivatives and related compounds in Salmonella typhimurium.
PubMed:Thin layer chromatography of certain preformed metal complex dyes used in biological staining.
PubMed:[A new pathway for biosynthesis of anthraquinones: incorporation of shikimic acid into 1,2-dihydroxyanthraquinone (alizarin) and 1,2,4-trihydroxyanthraquinone (purpurin) in Rubia tinctorum L].
PubMed:THE PURPURIN METHOD OF LOCALIZING CALCIUM.
 
Notes:
a natural pigment from roots of madder root (rubia tinctorum); other purpurin terms are available.
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