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phloroglucinol
1,3,5-trihydroxycyclohexatriene

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Name:benzene-1,3,5-triol
CAS Number: 108-73-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-611-2
FDA UNII: DHD7FFG6YS
Nikkaji Web:J2.866E
Beilstein Number:1341907
MDL:MFCD00002286
XlogP3:0.20 (est)
Molecular Weight:126.11142000
Formula:C6 H6 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 218.00 to 219.00 °C. @ 760.00 mm Hg
Boiling Point: 331.00 to 332.00 °C. @ 760.00 mm Hg (est)
Flash Point: 347.00 °F. TCC ( 174.90 °C. ) (est)
logP (o/w): 0.160
Soluble in:
 water, 1.06E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: hair dyeing agents
 
Suppliers:
EMD Millipore
For experimental / research use only.
Phloroglucinol
sds
Glentham Life Sciences
Phloroglucinol, anhydrous
Penta International
PHLOROGLUCINOL
Sigma-Aldrich: Aldrich
For experimental / research use only.
Phloroglucinol ≥99.0% (HPLC)
sds
TCI AMERICA
For experimental / research use only.
Phloroglucinol Anhydrous >99.0%(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:
oral-rat LD50 4000 mg/kg
Therapie. Vol. 17, Pg. 1349, 1962.

intraperitoneal-rat LD50 3180 mg/kg
Drugs in Japan Vol. 6, Pg. 740, 1982.

oral-mouse LD50 4550 mg/kg
Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 187, 1969.

intraperitoneal-mouse LD50 4050 mg/kg
Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 187, 1969.

intravenous-dog LDLo > 250 mg/kg
Therapie. Vol. 17, Pg. 1349, 1962.

Dermal Toxicity:
subcutaneous-rat LD50 4850 mg/kg
Drugs in Japan Vol. 6, Pg. 740, 1982.

subcutaneous-mouse LD50 991 mg/kg
Zeitschrift fuer die Gesamte Innere Medizin und Ihre Grenzgebiete. Vol. 2, Pg. 333, 1947.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for phloroglucinol usage levels up to:
 not for fragrance use.
 
Recommendation for phloroglucinol 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
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):108-73-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :359
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
benzene-1,3,5-triol
Chemidplus:0000108736
RTECS:SY1050000 for cas# 108-73-6
 
References:
 benzene-1,3,5-triol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:108-73-6
Pubchem (cid):359
Pubchem (sid):134970685
 
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
UM BBD:Search
KEGG (GenomeNet):C02183
HMDB (The Human Metabolome Database):Search
FooDB:FDB013879
Export Tariff Code:2907.29.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 hair dyeing agents
 
Occurrence (nature, food, other):note
 blueberry plant
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 carob bean
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 garlic plant
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 onion
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 onion bulb
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 tarragon plant
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 tea leaf
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Synonyms:
 benzene-1,3,5-triol
1,3,5-benzenetriol
3,5-dihydroxyphenol
5-hydroxyresorcinol
 phloroglucine
5-oxyresorcinol
1,3,5-trihydroxybenzene
sym-trihydroxybenzene
1,3,5-trihydroxycyclohexatriene
 

Articles:

PubMed:First Evidence that Ecklonia cava-Derived Dieckol Attenuates MCF-7 Human Breast Carcinoma Cell Migration.
PubMed:Profiling of the molecular weight and structural isomer abundance of macroalgae-derived phlorotannins.
PubMed:Screening of inhibitors for mushroom tyrosinase using surface plasmon resonance.
PubMed:Phloroglucinol Attenuates Free Radical-induced Oxidative Stress.
PubMed:Changes of major tea polyphenols and production of four new B-ring fission metabolites of catechins from post-fermented Jing-Wei Fu brick tea.
PubMed:A mechanistic study on the toxic effect of copper oxide nanoparticles in soybean (Glycine max L.) root development and lignification of root cells.
PubMed:Phloroglucinol induces apoptosis via apoptotic signaling pathways in HT-29 colon cancer cells.
PubMed:Effects of condensed tannins on anthocyanins and colour of authentic pomegranate (Punica granatum L.) juices.
PubMed:Four species of arboreal folivore show differential tolerance to a secondary metabolite.
PubMed:Phloroglucinol induces apoptosis through the regulation of insulin-like growth factor 1 receptor signaling pathways in human colon cancer HT-29 cells.
PubMed:Measuring protection of aromatic wine thiols from oxidation by competitive reactions vs wine preservatives with ortho-quinones.
PubMed:Development of a new high-performance liquid chromatography method with diode array and electrospray ionization-mass spectrometry detection for the metabolite fingerprinting of bioactive compounds in Humulus lupulus L.
PubMed:2-Alkenal-scavenging ability of m-diphenols.
PubMed:In vitro anti-osteoporosis properties of diverse Korean Drynariae rhizoma phenolic extracts.
PubMed:Preparative isolation and purification of phlorotannins from Ecklonia cava using centrifugal partition chromatography by one-step.
PubMed:Separation and characterization of phlorotannins from brown algae Cystoseira abies-marina by comprehensive two-dimensional liquid chromatography.
PubMed:Essential Structural Requirements and Additive Effects for Flavonoids to Scavenge Methylglyoxal.
PubMed:Protective effect of the edible brown alga Ecklonia stolonifera on doxorubicin-induced hepatotoxicity in primary rat hepatocytes.
PubMed:Evidence for contributions of interactions of constituents to the anti-inflammatory activity of Hypericum perforatum.
PubMed:Phlorotannins isolated from the edible brown alga Ecklonia stolonifera exert anti-adipogenic activity on 3T3-L1 adipocytes by downregulating C/EBPα and PPARγ.
PubMed:Feeding rates of a mammalian browser confirm the predictions of a 'foodscape' model of its habitat.
PubMed:Chemical and in vitro assessment of Alaskan coastal vegetation antioxidant capacity.
PubMed:Characterization of a Yariv precipitated arabinogalactan-protein from fruits of rye (Secale cereale L.).
PubMed:Enhancement of skin radical scavenging activity and stratum corneum lipids after the application of a hyperforin-rich cream.
PubMed:Potential antiradical and alpha-glucosidase inhibitors from Ecklonia maxima (Osbeck) Papenfuss.
PubMed:Anti-inflammatory activity of edible brown alga Eisenia bicyclis and its constituents fucosterol and phlorotannins in LPS-stimulated RAW264.7 macrophages.
PubMed:Enrichment of polyphenol contents and antioxidant activities of Irish brown macroalgae using food-friendly techniques based on polarity and molecular size.
PubMed:Valuable compounds in macroalgae extracts.
PubMed:Protective effect of marine algae phlorotannins against AAPH-induced oxidative stress in zebrafish embryo.
PubMed:Modulation of Nrf2-dependent gene transcription by bilberry anthocyanins in vivo.
PubMed:Neuroprotective effect of edible brown alga Eisenia bicyclis on amyloid beta peptide-induced toxicity in PC12 cells.
PubMed:Relationship between the sensory-determined astringency and the flavanolic composition of red wines.
PubMed:Effect of polymerization on antioxidant and xanthine oxidase inhibitory potential of sea buckthorn (H. rhamnoides) proanthocyanidins.
PubMed:Cytotoxic and antioxidant constituents from Garcinia subelliptica.
PubMed:A method to quantify quinone reaction rates with wine relevant nucleophiles: a key to the understanding of oxidative loss of varietal thiols.
PubMed:Antiplatelet effect of phloroglucinol is related to inhibition of cyclooxygenase, reactive oxygen species, ERK/p38 signaling and thromboxane A2 production.
PubMed:Polyphenolic constituents of Cynomorium songaricum Rupr. and antibacterial effect of polymeric proanthocyanidin on methicillin-resistant Staphylococcus aureus.
PubMed:Phloroglucinol: antioxidant properties and effects on cellular oxidative markers in human HepG2 cell line.
PubMed:Isolation of a new phlorotannin, a potent inhibitor of carbohydrate-hydrolyzing enzymes, from the brown alga Sargassum patens.
PubMed:Vascular barrier protective effects of phlorotannins on HMGB1-mediated proinflammatory responses in vitro and in vivo.
PubMed:Pancreatic lipase inhibitory activity of phlorotannins isolated from Eisenia bicyclis.
PubMed:Purification and characterization of polyphenol oxidase from cauliflower (Brassica oleracea L.).
PubMed:Metabolism of oak leaf ellagitannins and urolithin production in beef cattle.
PubMed:Phloroglucinol Inhibits the in vitro Differentiation Potential of CD34 Positive Cells into Endothelial Progenitor Cells.
PubMed:Can phlorotannins purified extracts constitute a novel pharmacological alternative for microbial infections with associated inflammatory conditions?
PubMed:Procyanidins from wild grape (Vitis amurensis) seeds regulate ARE-mediated enzyme expression via Nrf2 coupled with p38 and PI3K/Akt pathway in HepG2 cells.
PubMed:Evaluation of antioxidant properties of a new compound, pyrogallol-phloroglucinol-6,6'-bieckol isolated from brown algae, Ecklonia cava.
PubMed:Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation endproducts by scavenging reactive carbonyls.
PubMed:Phlorofucofuroeckol A inhibits the LPS-stimulated iNOS and COX-2 expressions in macrophages via inhibition of NF-κB, Akt, and p38 MAPK.
PubMed:Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel.
PubMed:DIMINUTO 1 affects the lignin profile and secondary cell wall formation in Arabidopsis.
PubMed:Isolation of phlorotannins from Eisenia bicyclis and their hepatoprotective effect against oxidative stress induced by tert-butyl hyperoxide.
PubMed:Protein tyrosine phosphatase 1B and α-glucosidase inhibitory Phlorotannins from edible brown algae, Ecklonia stolonifera and Eisenia bicyclis.
PubMed:Phloroglucinol (PG) purified from Ecklonia cava attenuates radiation-induced apoptosis in blood lymphocytes and splenocytes.
PubMed:Anthocyanin-rich blackberry extract suppresses the DNA-damaging properties of topoisomerase I and II poisons in colon carcinoma cells.
PubMed:Influenza virus neuraminidase inhibitory activity of phlorotannins from the edible brown alga Ecklonia cava.
PubMed:Antithrombotic and profibrinolytic activities of phloroglucinol.
PubMed:pH-responsive lyotropic liquid crystals for controlled drug delivery.
PubMed:Role of volatile and non-volatile plant secondary metabolites in host tree selection by Christmas beetles.
PubMed:Characterization of unusual proanthocyanidins in leaves of bayberry ( Myrica rubra Sieb. et Zucc.).
PubMed:Intestinal transit and systemic metabolism of apple polyphenols.
PubMed:Xanthine oxidase inhibitory triterpenoid and phloroglucinol from guttiferaceous plants inhibit growth and induced apoptosis in human NTUB1 cells through a ROS-dependent mechanism.
PubMed:Broad-range antagonistic rhizobacteria Pseudomonas fluorescens and Serratia plymuthica suppress Agrobacterium crown gall tumours on tomato plants.
PubMed:Effect of phloroglucinol on oxidative stress and inflammation.
PubMed:The phenolic acids from bacterial degradation of the mangiferin aglycone are quantified in the feces of pigs after oral ingestion of an extract of Cyclopia genistoides (honeybush tea).
PubMed:A metabolomic approach to identifying chemical mediators of mammal-plant interactions.
PubMed:Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.
PubMed:Development and characterization of an oat TILLING-population and identification of mutations in lignin and beta-glucan biosynthesis genes.
PubMed:A genetically engineered Pseudomonas fluorescens strain possesses the dual activity against phytopathogenic fungi and insects.
PubMed:Structural investigations on arabinogalactan-protein from wheat, isolated with Yariv reagent.
PubMed:Interaction between grape-derived proanthocyanidins and cell wall material. 1. Effect on proanthocyanidin composition and molecular mass.
PubMed:Metabolism of (-)-epigallocatechin gallate by rat intestinal flora.
PubMed:HPLC-MS analysis of proanthocyanidin oligomers and other phenolics in 15 strawberry cultivars.
PubMed:Cellular uptake, stability, visualization by 'Naturstoff reagent A', and multidrug resistance protein 1 gene-regulatory activity of cyanidin in human keratinocytes.
PubMed:Grape skin and seed proanthocyanidins from Monastrell x Syrah grapes.
PubMed:Phloroglucinols inhibit chemical mediators and xanthine oxidase, and protect cisplatin-induced cell death by reducing reactive oxygen species in normal human urothelial and bladder cancer cells.
PubMed:Antimicrobial activity of benzophenones and extracts from the fruits of Garcinia brasiliensis.
PubMed:Inhibitory effects and molecular mechanism of dieckol isolated from marine brown alga on COX-2 and iNOS in microglial cells.
PubMed:Induction of apoptosis by phloroglucinol derivative from Ecklonia Cava in MCF-7 human breast cancer cells.
PubMed:Inhibitory effect of phlorotannins isolated from Ecklonia cava on mushroom tyrosinase activity and melanin formation in mouse B16F10 melanoma cells.
PubMed:Determination of proanthocyanidin A2 content in phenolic polymer isolates by reversed-phase high-performance liquid chromatography.
PubMed:Anti-allergic effects of phlorotannins on histamine release via binding inhibition between IgE and Fc epsilonRI.
PubMed:Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation.
PubMed:Antioxidant effects of phlorotannins isolated from Ishige okamurae in free radical mediated oxidative systems.
PubMed:Bioactive constituent production in St. John's Wort in vitro hairy roots. Regenerated plant lines.
PubMed:Characterizing the metabolic fingerprint and anti-inflammatory activity of Hypericum gentianoides.
PubMed:Determination of formaldehyde in foodstuffs by flow injection spectrophotometry using phloroglucinol as chromogenic agent.
PubMed:Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH).
PubMed:Permeability profile estimation of flavonoids and other phenolic compounds by biopartitioning micellar capillary chromatography.
PubMed:Inhibition of prostaglandin E(2) production by anti-inflammatory hypericum perforatum extracts and constituents in RAW264.7 Mouse Macrophage Cells.
PubMed:Behavioural contributions to the regulated intake of plant secondary metabolites in koalas.
PubMed:Hypericin and hyperforin production in St. John's wort in vitro culture: influence of saccharose, polyethylene glycol, methyl jasmonate, and Agrobacterium tumefaciens.
PubMed:Ethylidene-bridged Flavan-3-ols in red wine and correlation with wine age.
PubMed:Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats.
PubMed:Analysis of ethylidene-bridged flavan-3-ols in wine.
PubMed:Anatomical, histological, and histochemical changes in grape seeds from Vitis vinifera L. cv Cabernet franc during fruit development.
PubMed:Structural identification and distribution of proanthocyanidins in 13 different hops.
PubMed:Comparison of methods for the exhaustive extraction of hypericins, flavonoids, and hyperforin from Hypericum perforatum L.
PubMed:Approach to novel functional foods for stress control 4. Regulation of serotonin transporter by food factors.
PubMed:Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds.
PubMed:Reduction of ethanol intake by chronic treatment with Hypericum perforatum, alone or combined with naltrexone in rats.
PubMed:A cytotoxic triketone-phloroglucinol-bullatenone hybrid from Lophomyrtus bullata.
PubMed:Regulation of gene transcription by botanicals: novel regulatory mechanisms.
PubMed:Tree use by koalas in a chemically complex landscape.
PubMed:Large-scale isolation of flavan-3-ol phloroglucinol adducts by high-speed counter-current chromatography.
PubMed:Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
PubMed:Phloroglucinol from phlorin hydrolysis for testing quality of commercial orange juices and beverages.
PubMed:Beta-D-glucosyl and alpha-D-galactosyl Yariv reagents: syntheses from p-nitrophenyl-D-glycosides by transfer reduction using ammonium formate.
PubMed:Tyrosinase inhibitors isolated from the edible brown alga Ecklonia stolonifera.
PubMed:Antiherbivore chemistry of Eucalyptus-cues and deterrents for marsupial folivores.
PubMed:Antioxidant oligomeric proanthocyanidins from sea buckthorn (Hippophae rhamnoides) Pomace.
PubMed:The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids.
PubMed:Liquid chromatographic determination of St. John's wort components in functional foods.
PubMed:Instability of St. John's wort (Hypericum perforatum L.) and degradation of hyperforin in aqueous solutions and functional beverage.
PubMed:Microbial products trigger amino acid exudation from plant roots.
PubMed:Efficient clonal propagation method for Decalepis hamiltonii, an endangered shrub, under the influence of phloroglucinol.
PubMed:Analysis of the oxidative degradation of proanthocyanidins under basic conditions.
PubMed:Inhibitory phlorotannins from the edible brown alga Ecklonia stolonifera on total reactive oxygen species (ROS) generation.
PubMed:In vitro metabolism of hyperforin in rat liver microsomal systems.
PubMed:Direct method for determining seed and skin proanthocyanidin extraction into red wine.
PubMed:Analysis of proanthocyanidins by high-performance gel permeation chromatography.
PubMed:Differential susceptibility to Eucalyptus secondary compounds explains feeding by the common ringtail (Pseudocheirus peregrinus) and common brushtail possum (Trichosurus vulpecula).
PubMed:Bactericidal activity of phlorotannins from the brown alga Ecklonia kurome.
PubMed:Determination of hyperforin in human plasma using solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
PubMed:Supercritical fluid extraction and high-performance liquid chromatographic determination of phloroglucinols in St. John's Wort (Hypericum perforatum L.).
PubMed:Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.
PubMed:Composition of grape skin proanthocyanidins at different stages of berry development.
PubMed:Comparison of quercetin and a non-orthohydroxy flavonol as antioxidants by competing in vitro oxidation reactions.
PubMed:Phenols in citrus peel byproducts. Concentrations of hydroxycinnamates and polymethoxylated flavones in citrus peel molasses.
PubMed:Effects of a methanolic extract and a hyperforin-enriched CO2 extract of Hypericum perforatum on alcohol intake in rats.
PubMed:Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol.
PubMed:Phlorin screening in various citrus species and varieties.
PubMed:Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (Sainfoin).
PubMed:Convenient synthesis of 2,4-diacetylphloroglucinol, a natural antibiotic involved in the control of take-all disease of wheat.
PubMed:Isolation and characterization of macrocarpals B--G antibacterial compounds from Eucalyptus macrocarpa.
PubMed:Biotransformation of the Pentahydroxy Flavone Quercetin by Rhizobium loti and Bradyrhizobium Strains (Lotus).
PubMed:Chemosensitivity of lobster,Homarus americanus, to secondary plant compounds: Unused receptor capabilities.
PubMed:Catabolism of phloroglucinol by the rumen anaerobe coprococcus.
PubMed:Polyphenols in brown algaeFucus vesiculosus andAscophyllum nodosum: Chemical defenses against the marine herbivorous snail,Littorina littorea.
PubMed:Effect of Phloroglucinol and Resorcinol on the Clingstone Peach Polyphenol Oxidase-catalyzed Oxidation of 4-Methylcatechol.
 
Notes:
1,3,5-benzenetriol. a trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.
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