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naringenin 7-beta-rutinoside

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CAS Number: 14259-46-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:238-138-0
XlogP3-AA:-1.10 (est)
Molecular Weight:580.54084000
Formula:C27 H32 O14
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavoring agents
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
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
FEMA Number:2769 naringen
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Regulation:
Subpart A--General Provisions
Sec. 182.20 Essential oils, oleoresins (solvent-free), and natural extractives (including distillates).
Physical Properties:
Appearance:white to beige crystals (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 175.00 °C. @ 760.00 mm Hg
Boiling Point: 924.00 to 925.00 °C. @ 760.00 mm Hg
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): -0.522 (est)
Soluble in:
 water, 2369 mg/L @ 25 °C (est)
 ph from 5 - 11
 up to 23.3% naoh
 up to 24.5% nacl
 up to 6.8% nahco3
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. bland
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
AuNutra® Industries
BOC Sciences
For experimental / research use only.
Narirutin >98%
Citrus and Allied Essences
Naringen recrystallized (natural)
Market Report
For experimental / research use only.
Naringen from Plants ≥98%
Odor: characteristic
Use: Anti-allergic, anti-inflammatory, antiproliferative and anti-oxidant properties. The flavonoid narirutin could reduce airway inflammation in ovalbumin (OVA)-sensitized / challenged NC / Nga mice, a model of allergic eosinophilic airway inflammation.
For experimental / research use only.
Narirutin (HPLC) ≥99%
naringen natural
George Uhe Company
H. Interdonati, Inc.
Naringin extract (Citrus paradisi Macf.)
Featured Products
Penta International
Penta International
Penta International
Reincke & Fichtner
Reincke & Fichtner
Naringin natural
Naringenin, natural (US), 98%
Certified Food Grade Products
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
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:
flavoring agents
Recommendation for naringen usage levels up to:
 not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -71.00000
beverages(alcoholic): -0.20000
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -5.70000
fruit ices: -5.70000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
Safety References:
EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :85704
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):85704
Pubchem (sid):135043891
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
FDA Substances Added to Food (formerly EAFUS):View
KEGG (GenomeNet):C09793
HMDB (The Human Metabolome Database):HMDB33740
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 cynara scolymus
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 lemon leaf
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 lemon pericarp
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 mandarin fruit juice
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 mandarin pericarp
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 orange fruit juice
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 orange pericarp
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 petitgrain lemon oil
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 naringen natural
 naringen recrystallized (natural)
 naringen tech grade
 naringenin 7-beta-rutinoside
 naringenin 7-rutinoside
 naringin extract (citrus paradisi macf.)


Google Patents:Flavor-improving method
PubMed:Quality evaluation and pattern recognition analyses of marker compounds from five medicinal drugs of Rutaceae family by HPLC/PDA.
PubMed:Leaf polyphenol profile and SSR-based fingerprinting of new segregant Cynara cardunculus genotypes.
PubMed:Huanglongbing modifies quality components and flavonoid content of 'Valencia' oranges.
PubMed:In vitro bioaccessibility of carotenoids, flavonoids, and vitamin C from differently processed oranges and orange juices [Citrus sinensis (L.) Osbeck].
PubMed:Pharmacokinetics of flavanone glycosides after ingestion of single doses of fresh-squeezed orange juice versus commercially processed orange juice in healthy humans.
PubMed:Evaluation of antioxidant-associated efficacy of flavonoid extracts from a traditional Chinese medicine Hua Ju Hong (peels of Citrus grandis (L.) Osbeck).
PubMed:[Determination of twelve active compounds in Qili Qiangxin capsules by UPLC-MS].
PubMed:Systematic Analysis of Main Constituents in Rat Biological Samples after Oral Administration of the Methanol Extract of Fructus Aurantii by HPLC-ESI-MS/MS.
PubMed:Simultaneous determination of 10 active components in baizhu shaoyao san and its single herbs by high-performance liquid chromatography coupled with diode array detection.
PubMed:Auraptene in the Peels of Citrus kawachiensis (Kawachi Bankan) Ameliorates Lipopolysaccharide-Induced Inflammation in the Mouse Brain.
PubMed:Quality evaluation of Houttuynia cordata Thunb. by high performance liquid chromatography with photodiode-array detection (HPLC-DAD).
PubMed:Sonochemical effects on 14 flavonoids common in citrus: relation to stability.
PubMed:Protective Effect against Hydroxyl-induced DNA Damage and Antioxidant Activity of Citri reticulatae Pericarpium.
PubMed:[Simultaneous determination of six ingredients in Huoxiang Zhengqi oral liquid by UPLC].
PubMed:Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts.
PubMed:Influence of process parameters on the extraction of flavanones from mandarin peel.
PubMed:Simplified miniaturized ultrasound-assisted matrix solid phase dispersion extraction and high performance liquid chromatographic determination of seven flavonoids in citrus fruit juice and human fluid samples: hesperetin and naringenin as biomarkers.
PubMed:Analysis of major constituents in Fructus aurantii-Magnolia bark decoction by UPLC-PDA.
PubMed:Down-regulation of tyrosinase, TRP-1, TRP-2 and MITF expressions by citrus press-cakes in murine B16 F10 melanoma.
PubMed:Fragmentation characterization and differentiation of isomeric diglycosyl flavonoids using ultra-high-performance liquid chromatography electrospray ionization quadrupole time-of-flight tandem mass spectrometry in negative ion mode.
PubMed:Polymethoxylated, C- and O-glycosyl flavonoids in tangelo (Citrus reticulata×Citrus paradisi) juice and their influence on antioxidant properties.
PubMed:Rapid Quantitation of Furanocoumarins and Flavonoids in Grapefruit Juice using Ultra-Performance Liquid Chromatography.
PubMed:Enzymatic modification enhances the protective activity of citrus flavonoids against alcohol-induced liver disease.
PubMed:Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice.
PubMed:Gustatory sensing mechanism coding for multiple oviposition stimulants in the swallowtail butterfly, Papilio xuthus.
PubMed:Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.
PubMed:A new prenylated naphthoquinoid from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze.
PubMed:Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.
PubMed:Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds.
PubMed:Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits.
PubMed:Simultaneous UPLC analysis of three major flavonoids in granule decoctions of Fructus aurantii-type formulae.
PubMed:Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation.
PubMed:Protective effects of fermented Citrus unshiu peel extract against ultraviolet-A-induced photoageing in human dermal fibrobolasts.
PubMed:Changes on phenolic and carotenoid composition of high intensity pulsed electric field and thermally treated fruit juice-soymilk beverages during refrigerated storage.
PubMed:Citrus flavanone naringenin enhances melanogenesis through the activation of Wnt/β-catenin signalling in mouse melanoma cells.
PubMed:Administration of chinpi, a component of the herbal medicine ninjin-youei-to, reverses age-induced demyelination.
PubMed:α-L-rhamnosidase of Aspergillus terreus immobilized on ferromagnetic supports.
PubMed:Proline betaine and its biotransformation products in fasting urine samples are potential biomarkers of habitual citrus fruit consumption.
PubMed:Influence of rootstock and cultivar on bioactive compounds in citrus peels.
PubMed:Optimization of flavanones extraction by modulating differential solvent densities and centrifuge temperatures.
PubMed:Role of the cultivar in choosing Clementine fruits with a high level of health-promoting compounds.
PubMed:[Flavonoids--bioactive compounds in fruits juice].
PubMed:Analysis of bioactive compounds in seven citrus cultivars.
PubMed:Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.
PubMed:Effect of added citrus fibre and spice essential oils on quality characteristics and shelf-life of mortadella.
PubMed:Flavonoid composition and antioxidant activity of juices from Chinotto ( Citrus x myrtifolia Raf.) fruits at different ripening stages.
PubMed:Bioactive phenolics and antioxidant propensity of flavedo extracts of Mauritian citrus fruits: potential prophylactic ingredients for functional foods application.
PubMed:Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from alpha-rhamnosidase-treated orange juice in human subjects.
PubMed:Cloning and characterization of a functional flavanone-3ß-hydroxylase gene from Medicago truncatula.
PubMed:Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract.
PubMed:Application of an efficient strategy based on MAE, HPLC-DAD-MS/MS and HSCCC for the rapid extraction, identification, separation and purification of flavonoids from Fructus Aurantii Immaturus.
PubMed:Phenolic contribution of South African herbal teas to a healthy diet.
PubMed:Hydrolysis of flavanone glycosides and degradation of the corresponding aglycones from dried immature Citrus fruit by human fecal flora in vitro.
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:Phenolic compounds and antioxidant activity of extracts from ultrasonic treatment of Satsuma Mandarin (Citrus unshiu Marc.) peels.
PubMed:Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities.
PubMed:Flavanone 3beta-hydroxylases from rice: key enzymes for favonol and anthocyanin biosynthesis.
PubMed:Flavonoid glycosides and limonoids from Citrus molasses.
PubMed:Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.
PubMed:Influence of postharvest hot water treatment on nutritional and functional properties of kumquat (Fortunella japonica Lour. Swingle Cv. Ovale) fruit.
PubMed:Origin identification on the commercial samples of Aurantii Fructus.
PubMed:Narirutin inhibits airway inflammation in an allergic mouse model.
PubMed:Flavanone plasma pharmacokinetics from blood orange juice in human subjects.
PubMed:Determination of diastereomerization barrier of some flavanones by high-performance liquid chromatography methods.
PubMed:Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers.
PubMed:Influence of cation adduction on the separation characteristics of flavonoid diglycoside isomers using dual gate-ion mobility-quadrupole ion trap mass spectrometry.
PubMed:Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract.
PubMed:An HPLC/MS method for identifying major constituents in the hypocholesterolemic extracts of Chinese medicine formula 'Xue-Fu-Zhu-Yu decoction'.
PubMed:[Historical and pharmalogical study of Citrus hassaku.].
PubMed:Antihypertensive effect of sweetie fruit in patients with stage I hypertension.
PubMed:[History and therapeutic evaluation of Citrus hassaku HORT. Tanaka].
PubMed:Analysis of flavanone-7-O-glycosides in citrus juices by short-end capillary electrochromatography.
PubMed:Isolation and purification of closely related citrus limonoid glucosides by flash chromatography.
PubMed:HPLC separation of hesperidin and the C-2 epimer in commercial hesperidin samples and herbal medicines.
PubMed:Bioactive compounds of grapefruit (Citrus paradisi Cv. Rio Red) respond differently to postharvest irradiation, storage, and freeze drying.
PubMed:Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS.
PubMed:Phenolic metabolites from honeybush tea (Cyclopia subternata).
PubMed:Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry.
PubMed:High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara.
PubMed:Study of the extraction procedure by experimental design and validation of a LC method for determination of flavonoids in Citrus bergamia juice.
PubMed:Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation.
PubMed:Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis.
PubMed:Influence of solvents on the antioxidant property of flavonoids.
PubMed:Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice.
PubMed:Analysis of antioxidative phenolic compounds in artichoke (Cynara scolymus L.).
PubMed:Effect of processing techniques at industrial scale on orange juice antioxidant and beneficial health compounds.
PubMed:Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.
PubMed:Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice.
PubMed:Flavanone glycosides from Citrus junos and their anti-influenza virus activity.
PubMed:Flavonoids in pigmented orange juice and second-pressure extracts.
PubMed:Dissolution profiles of principal ingredients in Kampo medicinal powders by high-performance liquid chromatography.
PubMed:Ligand structure-dependent differences in activation of estrogen receptor alpha in human HepG2 liver and U2 osteogenic cancer cell lines.
PubMed:Variance of common flavonoids by brand of grapefruit juice.
PubMed:Validation of a liquid chromatography ionspray mass spectrometry method for the analysis of flavanones, flavones and flavonols.
PubMed:Analytical monitoring of citrus juices by using capillary electrophoresis.
PubMed:Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography.
PubMed:Hesperidin as an inhibitor of lipases from porcine pancreas and Pseudomonas.
PubMed:Effect of ethylene on naringin, narirutin and nootkatone accumulation in grapefruit.
PubMed:[Studies on the preparation and evaluation of Kijitsu, the immature citrus fruits. IV. Biological activities of immature fruits of different citrus species].
PubMed:Inhibition of growth and xylogenesis and promotion of vacuolation in prunus callus by the flavanone prunin.
Obt. from Camellia sinensis (tea)
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