naringenin chalcone

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

CAS: 73692-50-9 C15 H12 O5 MW: 272.25664000

Identification

Namenaringenin chalcone
IUPAC(E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
CAS Number73692-50-9
FDA UNIISearch
Molecular FormulaC15 H12 O5
Molecular Weight272.25664000
Nikkaji NumberJ258.627D

Regulatory

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
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for naringenin chalcone usage levels up tonot for fragrance use.
Recommendation for naringenin chalcone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

tomato fruit cuticles

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)- iso salipurpol tetrahydroxychalcone 2',4,4',6'- tetrahydroxychalcone 2',4',6',4- tetrahydroxychalcone 2'4'6'4- tetrahydroxychalcone 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.