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flavanone

natural substances and extractives
2D:
3D:
CAS Number: 487-26-3
ECHA EC Number: 207-654-8
FDA UNII: WX22P730FB
Category: natural substances and extractives
IUPAC Name: flavanone
InChI : InChI=1/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
Std.InChI: InChI=1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
InChIKey : ZONYXWQDUYMKFB-UHFFFAOYAD
Std.InChIKey: ZONYXWQDUYMKFB-UHFFFAOYSA-N
SMILES : O=C2c3c(OC(c1ccccc1)C2)cccc3
MDL: MFCD00006841
Molar Refractivity : 64.60 ± 0.3 cm3 (est)
Parachor : 489.8 ± 6.0 cm3 (est)
Index of Refraction : 1.603 ± 0.02 (est)
Surface Tension : 46.0 ± 3.0 dyne/cm (est)
Density : 1.192 ± 0.06 g/cm3 (est)
Polarizability : 25.61 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 77.00 °C. @ 760.00 mm Hg
Boiling Point: 386.23 °C. @ 760.00 mm Hg (est)
Flash Point: 360.00 °F. TCC ( 181.90 °C. ) (est)
logP (o/w): 3.140
Soluble in:
water, 68.01 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

ExtraSynthese
For experimental / research use only.
Flavanone (HPLC) ≥90%
Penta International
FLAVANONE
Santa Cruz Biotechnology
For experimental / research use only.
Flavanone
Sigma-Aldrich: Aldrich
For experimental / research use only.
Flavanone 98%

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-bird - wild LD50 75 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for flavanone usage levels up to:
not for fragrance use.
Recommendation for flavanone flavor usage levels up to:
not for flavor use.

Safety References:

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):487-26-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10251
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-phenyl-2,3-dihydrochromen-4-one
Chemidplus:0000487263
RTECS:LK6906500 for cas# 487-26-3

References:

2-phenyl-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10251
Pubchem (sid):134973149

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
Golm Metabolome Database:Search
KEGG (GenomeNet):C00766
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.90.4500
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

found in nature

Synonyms:

4H-1-benzopyran-4-one, 2,3-dihydro-2-phenyl-
2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one
2,3-dihydro-2-phenyl-4H-benzopyran-4-one
2 3-dihydroflavone
2,3-dihydroflavone
4-flavanone
flavone, 2,3-dihydro-
2-phenyl-2,3-dihydro-4H-chromen-4-one
2-phenyl-2,3-dihydrochromen-4-one
2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
2-phenyl-4-chromanone
2-phenyl-chroman-4-one
2-phenylchroman-4-one
2-phenylchromanone

Articles:

PubMed:Effect of calcium on strawberry fruit flavonoid pathway gene expression and anthocyanin accumulation.
PubMed:Hesperidin, nobiletin, and tangeretin are collectively responsible for the anti-neuroinflammatory capacity of tangerine peel (Citri reticulatae pericarpium).
PubMed:Active naringin-chitosan films: impact of UV irradiation.
PubMed:Identification of phenolic compositions and the antioxidant capacity of mandarin juices and wines.
PubMed:Blue light irradiation affects anthocyanin content and enzyme activities involved in postharvest strawberry fruit.
PubMed:Metabolite profiling of polyphenols in peels of Citrus limetta Risso by combination of preparative high-speed countercurrent chromatography and LC-ESI-MS/MS.
PubMed:Phenylalanine ammonia-lyase, flavanone 3β-hydroxylase and flavonol synthase enzyme activity by a new in vitro assay method in berry fruits.
PubMed:Volunteer Stratification Is More Relevant than Technological Treatment in Orange Juice Flavanone Bioavailability.
PubMed:New highly in vitro antioxidative 3,8″-linked Biflav(an)ones and Flavanone-C-glycosides from Garcinia buchananii stem bark.
PubMed:Absorption, metabolism, and excretion of fermented orange juice (poly)phenols in rats.
PubMed:Identifying 2 prenylflavanones as potential hepatotoxic compounds in the ethanol extract of Sophora flavescens.
PubMed:Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts.
PubMed:Targeted analysis of polyphenol metabolism during development of hop (Humulus lupulus L.) cones following treatment with prohexadione-calcium.
PubMed:Antioxidant activity and spectroscopic data of isoxanthohomol oxime and related compounds.
PubMed:Fermented orange juice: source of higher carotenoid and flavanone contents.
PubMed:First action methods adopted for flavanols, SMPRs approved for ingredients and heavy metals.
PubMed:NMR metabolomics for identification of adenosine A1 receptor binding compounds from Boesenbergia rotunda rhizomes extract.
PubMed:Genetic engineering of novel bluer-colored chrysanthemums produced by accumulation of delphinidin-based anthocyanins.
PubMed:Effects of naringenin and its phase II metabolites on in vitro human macrophage gene expression.
PubMed:Dietary flavonoid and lignan intake and mortality in a Spanish cohort.
PubMed:Polymethoxylated, C- and O-glycosyl flavonoids in tangelo (Citrus reticulata×Citrus paradisi) juice and their influence on antioxidant properties.
PubMed:Preparative thin-layer chromatographic separation followed by identification of antifungal compound in Cassia laevigata by RP-HPLC and GC-MS.
PubMed:RNA interference silencing of CHS greatly alters the growth pattern of apple (Malus x domestica).
PubMed:Effects of molecular structure of polyphenols on their noncovalent interactions with oat β-glucan.
PubMed:Dynamic residual complexity of the isoliquiritigenin-liquiritigenin interconversion during bioassay.
PubMed:Identification of metabolic profiling of cell culture of licorice compared with its native one.
PubMed:Phenotypic changes associated with RNA interference silencing of chalcone synthase in apple (Malus × domestica).
PubMed:Enzyme-based online monitoring and measurement of antioxidant activity using an optical oxygen sensor coupled to an HPLC system.
PubMed:Assessment of dietary flavonoid intake among 50-year-old inhabitants of Wroclaw in 2008.
PubMed:Metabolism of 7-ethoxycoumarin, safrole, flavanone and hydroxyflavanone by cytochrome P450 2A6 variants.
PubMed:Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins.
PubMed:The risk of lung cancer related to dietary intake of flavonoids.
PubMed:Differential expression of anthocyanin biosynthetic genes and transcription factor PcMYB10 in pears (Pyrus communis L.).
PubMed:Anti-inflammatory effects of naringin in chronic pulmonary neutrophilic inflammation in cigarette smoke-exposed rats.
PubMed:HPLC-PDA-MS and NMR characterization of a hydroalcoholic extract of Citrus aurantium L. var. amara peel with antiedematogenic activity.
PubMed:Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells.
PubMed:Altered leaf colour is associated with increased superoxide-scavenging activity in aureusidin-producing transgenic plants.
PubMed:Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry.
PubMed:The composition of volatile aroma components, flavanones, and polymethoxylated flavones in Shiikuwasha (Citrus depressa Hayata) peels of different cultivation lines.
PubMed:Bioevaluation of human serum albumin-hesperidin bioconjugate: insight into protein vector function and conformation.
PubMed:The naringenin-induced proapoptotic effect in breast cancer cell lines holds out against a high bisphenol a background.
PubMed:Liquiritigenin inhibits tumor growth and vascularization in a mouse model of HeLa cells.
PubMed:Naringenin inhibits extracellular matrix production via extracellular signal-regulated kinase pathways in nasal polyp-derived fibroblasts.
PubMed:Engineering the production of major catechins by Escherichia coli carrying metabolite genes of Camellia sinensis.
PubMed:Accumulation of tilianin and rosmarinic acid and expression of phenylpropanoid biosynthetic genes in Agastache rugosa.
PubMed:Synthesis of naringin 6"-ricinoleate using immobilized lipase.
PubMed:Citrus flavanones: what is their role in cardiovascular protection?
PubMed:Habitual flavonoid intakes are positively associated with bone mineral density in women.
PubMed:Inhibition of quorum sensing (QS) in Yersinia enterocolitica by an orange extract rich in glycosylated flavanones.
PubMed:Inhibitory effect of liquiritigenin on migration via downregulation proMMP-2 and PI3K/Akt signaling pathway in human lung adenocarcinoma A549 cells.
PubMed:Elevated gene expression in chalcone synthase enzyme suggests an increased production of flavonoids in skin and synchronized red cell cultures of North American native grape berries.
PubMed:Dietary flavonoids and risk of stroke in women.
PubMed:Re-examination of chromogenic quantitative assays for determining flavonoid content.
PubMed:Efficient modification of floral traits by heavy-ion beam irradiation on transgenic Torenia.
PubMed:Tandemly arranged chalcone synthase A genes contribute to the spatially regulated expression of siRNA and the natural bicolor floral phenotype in Petunia hybrida.
PubMed:Isolation and structure elucidation of highly antioxidative 3,8″-linked biflavanones and flavanone-C-glycosides from Garcinia buchananii bark.
PubMed:Bioactive polyphenols in leaves, stems, and berries of Saskatoon (Amelanchier alnifolia Nutt.) cultivars.
PubMed:Transport mechanisms of flavanone aglycones across Caco-2 cell monolayers and artificial PAMPA membranes.
PubMed:Binding of citrus flavanones and their glucuronides and chalcones to human serum albumin.
PubMed:Isolation and identification of flavonoids accumulated in proanthocyanidin-free barley.
PubMed:Characterization of two distinct glycosyl hydrolase family 78 alpha-L-rhamnosidases from Pediococcus acidilactici.
PubMed:Cardamonin suppresses nitric oxide production via blocking the IFN-γ/STAT pathway in endotoxin-challenged peritoneal macrophages of ICR mice.
PubMed:Estimated dietary intakes of flavonols, flavanones and flavones in the European Prospective Investigation into Cancer and Nutrition (EPIC) 24 hour dietary recall cohort.
PubMed:Influence of rootstock and cultivar on bioactive compounds in citrus peels.
PubMed:Seasonal variation of defense-related gene expression in leaves from Bois noir affected and recovered grapevines.
PubMed:NMR investigation of a novel excipient, α-glucosylhesperidin, as a suitable solubilizing agent for poorly water-soluble drugs.
PubMed:Physicochemical properties of acidified skim milk gels containing cocoa flavanols.
PubMed:Anthocyanin accumulation and expression of anthocyanin biosynthetic genes in radish (Raphanus sativus).
PubMed:[Flavonoids--bioactive compounds in fruits juice].
PubMed:The citrus flavonoid hesperidin induces p53 and inhibits NF-κB activation in order to trigger apoptosis in NALM-6 cells: involvement of PPARγ-dependent mechanism.
PubMed:High temperature reduces apple fruit colour via modulation of the anthocyanin regulatory complex.
PubMed:Analysis of bioactive compounds in seven citrus cultivars.
PubMed:Flavonoid intake in relation to cognitive function in later life in the Lothian Birth Cohort 1936.
PubMed:Isolation and identification of compounds responsible for antioxidant capacity of Euryale ferox seeds.
PubMed:Effect of flavonoids on basal and insulin-stimulated 2-deoxyglucose uptake in adipocytes.
PubMed:Inactivation of nuclear factor-κB by citrus flavanone hesperidin contributes to apoptosis and chemo-sensitizing effect in Ramos cells.
PubMed:(+)-methyl jasmonate-induced bioformation of myricetin, quercetin and kaempferol in red raspberries.
PubMed:Fruit polyphenols and CVD risk: a review of human intervention studies.
PubMed:Potent modification of inducible CYP1A1 expression by flavonoids.
PubMed:Liquiritigenin induces mitochondria-mediated apoptosis via cytochrome c release and caspases activation in HeLa Cells.
PubMed:Chemical synthesis of citrus flavanone glucuronides.
PubMed:Antimicrobial properties of prunin, a citric flavanone glucoside, and its prunin 6″-O-lauroyl ester.
PubMed:Chemical characterization of orange juice from trees infected with citrus greening (Huanglongbing).
PubMed:Stereoselective conjugation, transport and bioactivity of s- and R-hesperetin enantiomers in vitro.
PubMed:Concentration and solubility of flavanones in orange beverages affect their bioavailability in humans.
PubMed:Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.
PubMed:Identification of bioactive compounds from flowers of black elder (Sambucus nigra L.) that activate the human peroxisome proliferator-activated receptor (PPAR) gamma.
PubMed:Flavonoid composition and antioxidant activity of juices from Chinotto ( Citrus x myrtifolia Raf.) fruits at different ripening stages.
PubMed:The effect of co-administered flavonoids on the metabolism of hesperetin and the disposition of its metabolites in Caco-2 cell monolayers.
PubMed:Bioactive phenolics and antioxidant propensity of flavedo extracts of Mauritian citrus fruits: potential prophylactic ingredients for functional foods application.
PubMed:Differential expression of CHS7 and CHS8 genes in soybean.
PubMed:Lippia origanoides chemotype differentiation based on essential oil GC-MS and principal component analysis.
PubMed:Quercetin and naringenin transport across human intestinal Caco-2 cells.
PubMed:Dietary flavonoid intake and colorectal cancer: a case-control study.
PubMed:A citrus extract containing flavanones represses plasminogen activator inhibitor-1 (PAI-1) expression and regulates multiple inflammatory, tissue repair, and fibrosis genes in human colon fibroblasts.
PubMed:Some phenolic compounds increase the nitric oxide level in endothelial cells in vitro.
PubMed:Efficient synthesis of flavanone glucuronides.
PubMed:Efficacy of the potential chemopreventive agent, hesperetin (citrus flavanone), on 1,2-dimethylhydrazine induced colon carcinogenesis.
PubMed:Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas.
PubMed:The citrus flavanone naringenin inhibits inflammatory signalling in glial cells and protects against neuroinflammatory injury.
PubMed:Measuring flavonoid enzyme activities in tissues of fruit species.
PubMed:Tyrosinase inhibitory polyphenols from roots of Morus lhou.
PubMed:Environmental and seasonal influences on red raspberry anthocyanin antioxidant contents and identification of quantitative traits loci (QTL).
PubMed:Effect of liquiritigenin, a flavanone existed from Radix glycyrrhizae on pro-apoptotic in SMMC-7721 cells.
PubMed:Analysis of flavonoids in propolis and Ginkgo biloba by micellar electrokinetic capillary chromatography.
PubMed:Bioavailability and metabolism of orange juice flavanones in humans: impact of a full-fat yogurt.
PubMed:Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and generation of advanced glycation endproducts.
PubMed:Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion.
PubMed:Inhibitory effects of flavonoids on aldehyde oxidase activity.
PubMed:A chalcone synthase-like gene is highly expressed in the tapetum of both wheat (Triticum aestivum L.) and triticale (xTriticosecale Wittmack).
PubMed:Dietary flavonoid sources in Australian adults.
PubMed:Phenolic compounds and antioxidant activity of extracts from ultrasonic treatment of Satsuma Mandarin (Citrus unshiu Marc.) peels.
PubMed:In vivo pharmacokinetics of hesperidin are affected by treatment with glucosidase-like BglA protein isolated from yeasts.
PubMed:Development of a potential reference material for evaluating antioxidant activity.
PubMed:Flavonoid profiling and biosynthetic gene expression in flesh and peel of two tomato genotypes grown under UV-B-depleted conditions during ripening.
PubMed:Estimating bergamot juice adulteration of lemon juice by high-performance liquid chromatography (HPLC) analysis of flavanone glycosides.
PubMed:LC-DAD-MS (ESI+) analysis and antioxidant capacity of crocus sativus petal extracts.
PubMed:Characterization of phenolic compounds in rooibos tea.
PubMed:Cytotoxic chalcones and antioxidants from the fruits of a Syzygium samarangense (Wax Jambu).
PubMed:Polyphenols and antioxidant properties of almond skins: influence of industrial processing.
PubMed:Differential effects of dietary flavonoids on reactive oxygen and nitrogen species generation and changes in antioxidant enzyme expression induced by proinflammatory cytokines in Chang Liver cells.
PubMed:Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.
PubMed:Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers.
PubMed:Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
PubMed:[Effects of flavonoids with different structures on proliferation of leukemia cell line HL-60].
PubMed:Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.).
PubMed:Activation of pro-survival Akt and ERK1/2 signalling pathways underlie the anti-apoptotic effects of flavanones in cortical neurons.
PubMed:In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa.
PubMed:Permeability profile estimation of flavonoids and other phenolic compounds by biopartitioning micellar capillary chromatography.
PubMed:Isoflavonoids in non-leguminous taxa: a rarity or a rule?
PubMed:Inhibition of the formation of the neurotoxin 5-S-cysteinyl-dopamine by polyphenols.
PubMed:Kinetic model for the antiradical activity of the isolated p-catechol group in flavanone type structures using the free stable radical 2,2-diphenyl-1-picrylhydrazyl as the antiradical probe.
PubMed:Interaction between the aryl hydrocarbon receptor and its antagonists, flavonoids.
PubMed:Antioxidant and cytotoxic activities of naturally occurring phenolic and related compounds: a comparative study.
PubMed:Racemization at C-2 of naringin in sour oranges with increasing maturity determined by chiral high-performance liquid chromatography.
PubMed:Absorption and pharmacokinetics of grapefruit flavanones in beagles.
PubMed:Flavanone plasma pharmacokinetics from blood orange juice in human subjects.
PubMed:Effect of the citrus flavanone naringenin on oxidative stress in rats.
PubMed:Effect of heat treatment on the phenolic compounds and antioxidant capacity of citrus peel extract.
PubMed:Flavonoids and risk of squamous cell esophageal cancer.
PubMed:Transcriptome analysis reveals a critical role of CHS7 and CHS8 genes for isoflavonoid synthesis in soybean seeds.
PubMed:Sequence analysis of a "true" chalcone synthase (chs_H1) oligofamily from hop (Humulus lupulus L.) and PAP1 activation of chs_H1 in heterologous systems.
PubMed:Expression of the chalcone synthase gene from grape and preparation of an anti-CHS antibody.
PubMed:Modulation of peroxynitrite-induced fibroblast injury by hesperetin: a role for intracellular scavenging and modulation of ERK signalling.
PubMed:Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China.
PubMed:Molecular characterization of a stable antisense chalcone synthase phenotype in strawberry (Fragaria x ananassa).
PubMed:Two-phase flavonoid formation in developing strawberry (Fragaria x ananassa) fruit.
PubMed:Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli.
PubMed:Characterization of flavonoids and pectins from bergamot (Citrus bergamia Risso) peel, a major byproduct of essential oil extraction.
PubMed:Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC.
PubMed:Anthocyanins accumulation and related gene expression in red orange fruit induced by low temperature storage.
PubMed:[Historical and pharmalogical study of Citrus hassaku.].
PubMed:Molecular mechanisms of the naringin low uptake by intestinal Caco-2 cells.
PubMed:Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS.
PubMed:[History and therapeutic evaluation of Citrus hassaku HORT. Tanaka].
PubMed:In vitro free radical and ONOO- scavengers from Sophora flavescens.
PubMed:Bioavailability and antioxidant effects of orange juice components in humans.
PubMed:Cloning and molecular analysis of the regulatory factor HlMyb1 in hop (Humulus lupulus L.) and the potential of
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