EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

naringin dihydrochalcone
3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranoside

Supplier Sponsors

Name:3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranoside
CAS Number: 18916-17-1Picture of molecule3D/inchi
FDA UNII: 7233QDO0QW
MDL:MFCD08436145
XlogP3-AA:-0.30 (est)
Molecular Weight:582.55678000
Formula:C27 H34 O14
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
MP: decomposes at 169-171°C.
Category:sweeteners, flavor enhancers
 
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
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2208 naringin dihydrochalcone
DG SANTE Food Flavourings:16.110 naringin dihydrochalcone
FEMA Number:4495 naringin dihydrochalcone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):18916-17-1 ; NARINGIN DIHYDROCHALCONE
 
Physical Properties:
Appearance:white solid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 169.00 to 171.00 °C. @ 760.00 mm Hg
Boiling Point: 916.00 to 917.00 °C. @ 760.00 mm Hg (est)
Flash Point: 577.00 °F. TCC ( 302.70 °C. ) (est)
logP (o/w): 3.383 (est)
Soluble in:
 alcohol
 water, 381.4 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Naringin dihydrochalcone 98%
AuNutra® Industries
Naringin Dihydrochalcone
BOC Sciences
For experimental / research use only.
Naringin Dihydrochalcone
Frutarom
NARINGIN DIHYDROCHALCONE
KOSHER
CBD Offering
Jiangyin Healthway
Naringin Dihydrochalcone
New functional food ingredients
M&U International
NAT. NARINGIN DIHYDROCHALCONE
O'Laughlin Industries
NARINGIN DIHYDROCHALCONE
Penta International
NARINGIN DIHYDROCHALCONE
Santa Cruz Biotechnology
For experimental / research use only.
Naringin Dihydrochalcone
Sigma-Aldrich: Aldrich
For experimental / research use only.
Naringin Dihydrochalcone
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
sweeteners, flavor enhancers
Recommendation for naringin dihydrochalcone usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 120.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 41000 (μg/person/day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
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: 24. Update in publication number(s): 26
Click here to view publication 24
 average usual ppmaverage maximum ppm
baked goods: 5.0000020.00000
beverages(nonalcoholic): 50.0000060.00000
beverages(alcoholic): 50.0000060.00000
breakfast cereal: 150.00000200.00000
cheese: --
chewing gum: 200.00000200.00000
condiments / relishes: 5.0000020.00000
confectionery froastings: 5.0000020.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 50.0000060.00000
fruit ices: 50.0000060.00000
gelatins / puddings: 50.0000060.00000
granulated sugar: --
gravies: 5.0000020.00000
hard candy: 50.0000060.00000
imitation dairy: 50.0000060.00000
instant coffee / tea: --
jams / jellies: 50.0000060.00000
meat products: 50.00000350.00000
milk products: 50.0000060.00000
nut products: --
other grains: --
poultry: 50.00000350.00000
processed fruits: 50.0000060.00000
processed vegetables: 50.0000060.00000
reconstituted vegetables: --
seasonings / flavors: 20.0000030.00000
snack foods: 20.0000030.00000
soft candy: 50.0000060.00000
soups: 20.0000030.00000
sugar substitutes: --
sweet sauces: 50.0000060.00000
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 50.0000060.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): 50.0000060.00000
Processed fruit (04.1): 50.0000060.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): 50.0000060.00000
Confectionery (05.0): 50.0000060.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 150.00000200.00000
Bakery wares (07.0): --
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 50.0000060.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 50.0000060.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 50.0000060.00000
Ready-to-eat savouries (15.0): 50.0000060.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): --
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 32 (FGE.32): Flavonoids (Flavanones and dihydrochalcones) from chemical groups 25 and 30
View page or View pdf

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 :42608892
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranoside
Chemidplus:0018916171
 
References:
 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranoside
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):42608892
Pubchem (sid):125343810
 
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
HMDB (The Human Metabolome Database):Search
FDA Listing of Food Additive Status:View
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
1-[4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
3,5-dihydroxy-4-(phydroxyhydrocinnamoyl)phenyl 2-o-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-glucopyranoside
3,5-dihydroxy-4-(phydroxyhydrocinnamoyl)phenyl 2-ortho-(6-deoxy-alpha-laevo-mannopyranosyl)-, beta-dextro-glucopyranoside
3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranoside
 narinegin dihydrochalcone
1-propanone, 1-[4-[[2-O-(6-deoxy-a-L-mannopyranosyl)-β-L-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
4’-(2-o-alpha-L-rhamno-beta-D-glucopyranoside)phloretin
4’-(2-ortho-alpha-L-rhamno-beta-D-glucopyranoside)phloretin
4’-(2-ortho-alpha-laevo-rhamno-beta-D-glucopyranoside)phloretin
 

Articles:

PubMed:Identification and cloning of an NADPH-dependent hydroxycinnamoyl-CoA double bond reductase involved in dihydrochalcone formation in Malus×domestica Borkh.
PubMed:Comprehensive phenolic profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS reveals novel xanthone and benzophenone constituents.
PubMed:Polyphenols profile and antioxidant activity of skin and pulp of a rare apple from Marche region (Italy).
PubMed:Anti-osteoporotic and antioxidant activities of chemical constituents of the aerial parts of Ducrosia ismaelis.
PubMed:Phloretin promotes osteoclast apoptosis in murine macrophages and inhibits estrogen deficiency-induced osteoporosis in mice.
PubMed:Analysis of different European hazelnut (Corylus avellana L.) cultivars: authentication, phenotypic features, and phenolic profiles.
PubMed:The occurrence, fate and biological activities of C-glycosyl flavonoids in the human diet.
PubMed:Immunomodulation of phloretin by impairing dendritic cell activation and function.
PubMed:Xanthine oxidase inhibitory activity and hypouricemic effect of aspalathin from unfermented rooibos.
PubMed:Determination of artificial sweeteners in sewage sludge samples using pressurised liquid extraction and liquid chromatography-tandem mass spectrometry.
PubMed:Examination of the phenolic profile and antioxidant activity of the leaves of the Australian native plant Smilax glyciphylla.
PubMed:Bioactive compounds present in the Mediterranean sofrito.
PubMed:[Simultaneous determination of twelve sweeteners and nine preservatives in foods by solid-phase extraction and LC-MS/MS].
PubMed:Indirect homologous competitive enzyme-linked immunosorbent assay for the detection of a class of glycosylated dihydrochalcones.
PubMed:A targeted metabolomics approach to understand differences in flavonoid biosynthesis in red and yellow raspberries.
PubMed:Bioavailability of dietary (poly)phenols: a study with ileostomists to discriminate between absorption in small and large intestine.
PubMed:Phenotypic changes associated with RNA interference silencing of chalcone synthase in apple (Malus × domestica).
PubMed:Chemical markers of shiikuwasha juice adulterated with calamondin juice.
PubMed:Novel antiosteoclastogenic activity of phloretin antagonizing RANKL-induced osteoclast differentiation of murine macrophages.
PubMed:Quantitation of flavanols, proanthocyanidins, isoflavones, flavanones, dihydrochalcones, stilbenes, benzoic acid derivatives using ultraviolet absorbance after identification by liquid chromatography-mass spectrometry.
PubMed:Chemistry of color formation during rooibos fermentation.
PubMed:Kinetic optimisation of the reversed phase liquid chromatographic separation of rooibos tea (Aspalathus linearis) phenolics on conventional high performance liquid chromatographic instrumentation.
PubMed:Screening of the polyphenol content of tomato-based products through accurate-mass spectrometry (HPLC-ESI-QTOF).
PubMed:Flavonoids in tropical citrus species.
PubMed:Genetic variability in apple fruit polyphenol composition in Malus × domestica and Malus sieversii germplasm grown in New Zealand.
PubMed:Anti-inflammatory effects and chemical study of a flavonoid-enriched fraction from adlay bran.
PubMed:Roasting affects phenolic composition and antioxidative activity of hazelnuts (Corylus avellana L.).
PubMed:Determination of nine high-intensity sweeteners in various foods by high-performance liquid chromatography with mass spectrometric detection.
PubMed:Influence of apple polyphenols on inflammatory gene expression.
PubMed:Phloretin induces apoptosis in H-Ras MCF10A human breast tumor cells through the activation of p53 via JNK and p38 mitogen-activated protein kinase signaling.
PubMed:The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans.
PubMed:Oxidation of the dihydrochalcone aspalathin leads to dimerization.
PubMed:Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas.
PubMed:Dietary phloridzin reduces blood glucose levels and reverses Sglt1 expression in the small intestine in streptozotocin-induced diabetic mice.
PubMed:Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study.
PubMed:Absorption, metabolism, and excretion of cider dihydrochalcones in healthy humans and subjects with an ileostomy.
PubMed:Aspalathin, a flavonoid in Aspalathus linearis (rooibos), is absorbed by pig intestine as a C-glycoside.
PubMed:Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple.
PubMed:Characterization of phenolic compounds in rooibos tea.
PubMed:The flavonoids of tomatoes.
PubMed:Simultaneous determination of nine intense sweeteners in foodstuffs by high performance liquid chromatography and evaporative light scattering detection--development and single-laboratory validation.
PubMed:Modulation of key elements of the Wnt pathway by apple polyphenols.
PubMed:Phenolic profile of Asturian (Spain) natural cider.
PubMed:Antioxidant and pro-oxidant activities of aqueous extracts and crude polyphenolic fractions of rooibos (Aspalathus linearis).
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:Polyphenol profiles of apple juices.
PubMed:Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
PubMed:Embryotoxicity and teratogenicity study with neohesperidin dihydrochalcone in rats.
PubMed:Antimicrobial activities of eucalyptus leaf extracts and flavonoids from Eucalyptus maculata.
PubMed:Polyphenolic profiles in eight apple cultivars using high-performance liquid chromatography (HPLC).
PubMed:Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and alpha 2-adrenergic receptors in Xenopus laevis melanophores.
PubMed:Dihydrochalcones: evaluation as novel radical scavenging antioxidants.
PubMed:Detection of phloridzin in strawberries (Fragaria x ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy.
PubMed:Quantitative characterization of flavonoid compounds in Rooibos tea (Aspalathus linearis) by LC-UV/DAD.
PubMed:Flavonoids in human urine as biomarkers for intake of fruits and vegetables.
PubMed:Sweetener preference of C57BL/6ByJ and 129P3/J mice.
PubMed:[Determination of neohesperidin dihydrochalcone in foods].
PubMed:Improved water solubility of neohesperidin dihydrochalcone in sweetener blends.
PubMed:PROP (6-n-Propylthiouracil) tasting and sensory responses to caffeine,sucrose, neohesperidin dihydrochalcone and chocolate.
PubMed:Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase.
PubMed:Double functionality of sweeteners: a case of study.
PubMed:Phloretin-induced apoptosis in B16 melanoma 4A5 cells and HL60 human leukemia cells.
PubMed:Phloretin-induced apoptosis in B16 melanoma 4A5 cells by inhibition of glucose transmembrane transport.
PubMed:[Flavonoid intake of adults in a Bavarian subgroup of the national food consumption survey].
PubMed:Validated high-performance liquid chromatographic method for quantitation of neohesperidine dihydrochalcone in foodstuffs.
PubMed:Preparation and taste of certain glycosides of flavanones and of dihydrochalcones.
PubMed:Subchronic (13-week) oral toxicity of neohesperidin dihydrochalcone in rats.
PubMed:Liquid chromatographic determination of naringin and neohesperidin as a detector of grapefruit juice in orange juice.
PubMed:Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
PubMed:Dihydrochalcone sweeteners. Synthesis and sensory evaluation of sulfonate derivatives.
PubMed:Liquid chromatography of neohesperidin dihydrochalcone.
 
Notes:
None found
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