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naringenin chalcone
2-propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-

Supplier Sponsors

Name:(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
CAS Number: 73692-50-9Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J258.627D
XlogP3-AA:2.80 (est)
Molecular Weight:272.25664000
Formula:C15 H12 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:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 358.00 to 359.00 °C. @ 760.00 mm Hg (est)
Flash Point: 561.00 °F. TCC ( 293.60 °C. ) (est)
logP (o/w): 2.826 (est)
Soluble in:
 alcohol
 water, 104.4 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Naringenin chalcone 98%
BOC Sciences
For experimental / research use only.
Naringenin Chalcone
 
Safety Information:
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for naringenin chalcone usage levels up to:
 not for fragrance use.
 
Recommendation for naringenin chalcone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280960
National Institute of Allergy and Infectious Diseases:Data
(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
Chemidplus:0073692509
 
References:
 (E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280960
Pubchem (sid):135111386
 
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):C06561
HMDB (The Human Metabolome Database):HMDB29631
FooDB:FDB000801
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 tomato fruit cuticles
Search Picture
 
Synonyms:
 chalconaringenin
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
 naringenin chalcone, (E)-isomer
2-propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
isosalipurpol
 tetrahydroxychalcone
2',4,4',6'-tetrahydroxychalcone
2',4',6',4-tetrahydroxychalcone
2'4'6'4-tetrahydroxychalcone
 

Articles:

PubMed:Identification and Mode of Inheritance of Quantitative Trait Loci for Secondary Metabolite Abundance in Tomato.
PubMed:Electrochemical tomato (Solanum lycopersicum L.) characterisation using contact probe in situ voltammetry.
PubMed:Functional characterization of a chalcone synthase from the liverwort Plagiochasma appendiculatum.
PubMed:Genetic mapping of semi-polar metabolites in pepper fruits (Capsicum sp.): towards unravelling the molecular regulation of flavonoid quantitative trait loci.
PubMed:The flavonoid biosynthetic enzyme chalcone isomerase modulates terpenoid production in glandular trichomes of tomato.
PubMed:Home processing of tomatoes (Solanum lycopersicum): effects on in vitro bioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity.
PubMed:Functional diversification of duplicated chalcone synthase genes in anthocyanin biosynthesis of Gerbera hybrida.
PubMed:Selenium fertilization alters the chemical composition and antioxidant constituents of tomato (Solanum lycopersicon L.).
PubMed:[Flavonoids from Humulus lupulus].
PubMed:Imbalance in expression of hop (Humulus lupulus) chalcone synthase H1 and its regulators during hop stunt viroid pathogenesis.
PubMed:Identification and characterization of a type III polyketide synthase involved in quinolone alkaloid biosynthesis from Aegle marmelos Correa.
PubMed:Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein.
PubMed:Induction of electrophile-responsive element (EpRE)-mediated gene expression by tomato extracts in vitro.
PubMed:Enzymatic Properties and Mutational Studies of Chalcone Synthase from Physcomitrella patens.
PubMed:Combinatorial analysis of lupulin gland transcription factors from R2R3Myb, bHLH and WDR families indicates a complex regulation of chs_H1 genes essential for prenylflavonoid biosynthesis in hop (Humulus Lupulus L.).
PubMed:HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops.
PubMed:[Cloning, expression and charaterization of chalcone synthase from Saussurea medusa].
PubMed:Structural classification and properties of ketoacyl synthases.
PubMed:Properties of chalconaringenin and rutin isolated from cherry tomatoes.
PubMed:Differential expression of anthocyanin biosynthetic genes and anthocyanin accumulation in tartary buckwheat cultivars 'Hokkai t8' and 'Hokkai t10'.
PubMed:The role of chalcones in suppression of NF-κB-mediated inflammation and cancer.
PubMed:Core structure of flavonoids precursor as an antihyperglycemic and antihyperlipidemic agent: an in vivo study in rats.
PubMed:Genetics of flavonoid, carotenoid, and chlorophyll pigments in melon fruit rinds.
PubMed:Naringenin chalcone improves adipocyte functions by enhancing adiponectin production.
PubMed:Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.
PubMed:Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells.
PubMed:LAP3, a novel plant protein required for pollen development, is essential for proper exine formation.
PubMed:Fruit-surface flavonoid accumulation in tomato is controlled by a SlMYB12-regulated transcriptional network.
PubMed:Biochemical and molecular analysis of pink tomatoes: deregulated expression of the gene encoding transcription factor SlMYB12 leads to pink tomato fruit color.
PubMed:TOMATO AGAMOUS-LIKE 1 is a component of the fruit ripening regulatory network.
PubMed:Identification and quantification of metabolites of orally administered naringenin chalcone in rats.
PubMed:A novel type III polyketide synthase encoded by a three-intron gene from Polygonum cuspidatum.
PubMed:Metabolome analysis of biosynthetic mutants reveals a diversity of metabolic changes and allows identification of a large number of new compounds in Arabidopsis.
PubMed:Accumulation of isoflavone genistin in transgenic tomato plants overexpressing a soybean isoflavone synthase gene.
PubMed:Differential gene expression profiles of red and green forms of Perilla frutescens leading to comprehensive identification of anthocyanin biosynthetic genes.
PubMed:Anticarcinogenic compounds in the Uzbek medicinal plant, Helichrysum maracandicum.
PubMed:The flavonoids of tomatoes.
PubMed:Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.).
PubMed:Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages.
PubMed:Constitutive expression of a grapevine stilbene synthase gene in transgenic hop (Humulus lupulus L.) yields resveratrol and its derivatives in substantial quantities.
PubMed:Expression of a functional type-I chalcone isomerase gene is localized to the infected cells of root nodules of Elaeagnus umbellata.
PubMed:An evaluation of the clinical efficacy of tomato extract for perennial allergic rhinitis.
PubMed:Cloning and characterization of chalcone synthase from the moss, Physcomitrella patens.
PubMed:Overexpression of the Saussurea medusa chalcone isomerase gene in S. involucrata hairy root cultures enhances their biosynthesis of apigenin.
PubMed:Content of chalconaringenin and chlorogenic acid in cherry tomatoes is strongly reduced during postharvest ripening.
PubMed:The genotypic variation of the antioxidant potential of different tomato varieties.
PubMed:Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae.
PubMed:Seasonal variations in the level of plant constituents in greenhouse production of cherry tomatoes.
PubMed:A stilbene synthase gene (SbSTS1) is involved in host and nonhost defense responses in sorghum.
PubMed:Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone isomerases.
PubMed:Anti-allergic activity of naringenin chalcone from a tomato skin extract.
PubMed:Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
PubMed:Enzymatic reactions by five chalcone synthase homologs from hop (Humulus lupulus L.).
PubMed:First bacterial chalcone isomerase isolated from Eubacterium ramulus.
PubMed:Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits.
PubMed:Aromatic and pyrone polyketides synthesized by a stilbene synthase from Rheum tataricum.
PubMed:High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1.
PubMed:Increasing antioxidant levels in tomatoes through modification of the flavonoid biosynthetic pathway.
PubMed:Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities.
PubMed:Transformation of acridone synthase to chalcone synthase.
PubMed:Flavonoids and UV photoprotection in Arabidopsis mutants.
PubMed:Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration.
PubMed:Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols.
PubMed:Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes.
PubMed:Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities.
PubMed:Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro.
PubMed:Evidence for catalytic cysteine-histidine dyad in chalcone synthase.
PubMed:Identification of amino acid residues important in the cyclization reactions of chalcone and stilbene synthases.
PubMed:Chalcone and stilbene synthases expressed in eucaryotes exhibit reduced cross-reactivity in vitro.
PubMed:Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells.
PubMed:Cross-reaction of chalcone synthase and stilbene synthase overexpressed in Escherichia coli.
PubMed:Water permeability of isolated cuticular membranes: a structural analysis.
PubMed:Molecular analysis of chalcone and dihydropinosylvin synthase from Scots pine (Pinus sylvestris), and differential regulation of these and related enzyme activities in stressed plants.
PubMed:Stilbene and chalcone synthases: related enzymes with key functions in plant-specific pathways.
PubMed:Time courses for phytochrome-induced enzyme levels in phenylpropanoid metabolism (phenylalanine ammonia-lyase, naringenin-chalcone synthase) compared with time courses for phytochrome-mediated end-product accumulation (anthocyanin, quercetin).
PubMed:Molecular analysis of resveratrol synthase. cDNA, genomic clones and relationship with chalcone synthase.
PubMed:Biochemical, immunological, and immunocytochemical evidence for the association of chalcone synthase with endoplasmic reticulum membranes.
PubMed:Chalcone synthase from cell suspension cultures of Daucus carota L.
PubMed:Chalcone synthesis and hydroxylation of flavonoids in 3'-position with enzyme preparations from flowers of Dianthus caryophyllus L. (carnation).
PubMed:Genetic control of chalcone isomerase activity in flowers of Dianthus caryophyllus.
PubMed:Highly purified "flavanone synthase" from parsley catalyzes the formation of naringenin chalcone.
PubMed:Genetic control of chalcone isomerase activity in anthers of Petunia hybrida.
 
Notes:
Isol. from tomato fruit cuticles
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