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neohesperidin dihydrochalcone
neohesperidin DC

Supplier Sponsors

Name:1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
CAS Number: 20702-77-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:243-978-6
FDA UNII: 3X476D83QV
Nikkaji Web:J2.757J
MDL:MFCD00017711
XlogP3-AA:-0.30 (est)
Molecular Weight:612.58292000
Formula:C28 H36 O15
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
Register name to be changed to Neohesperidin dihydrochalcone. Other trivial names: Hesperetin dihydrochalcone 4'-Oneohesperidoside and hesperetin 4'-O-(2-O-alpha- L-rhamnosyl)-beta-Dglucoside.
Category:cosmetic and flavor 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
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
GRN 902 Neohesperidin dihydrochalcone View - notice PDF
DG SANTE Food Flavourings:16.061 neohesperidin dihydrochalcone
DG SANTE Food Additives:neohesperidin dihydrochalcone
FEMA Number:3811 neohesperidin dihydrochalcone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):20702-77-6 ; NEOHESPERIDIN DIHYDROCHALCONE
 
Physical Properties:
Appearance:white to pale yellow powder (est)
Assay: 96.00 to 100.00 sum of isomers
Food Chemicals Codex Listed: No
Melting Point: 156.00 to 158.00 °C. @ 760.00 mm Hg
Boiling Point: 927.13 °C. @ 760.00 mm Hg (est)
Flash Point:> 200.00 °F. TCC ( > 93.33 °C. )
logP (o/w): 0.205 (est)
Soluble in:
 water, 342.1 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Type: odorless
Odor Strength:none
Odor Description:at 100.00 %. bland odor
Luebke, William tgsc, (1999)
Odor sample from: CA Aromatics Company Inc.
Odor Description:No apparent odor
Mosciano, Gerard P&F 20, No. 1, 31, (1995)
Flavor Type: sweet
licorice sweet
Taste Description: at 10.00 ppm. Licorice-like with a lingering sweetness
Mosciano, Gerard P&F 20, No. 1, 31, (1995)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data2
CosIng:cosmetic data
Cosmetic Uses: flavoring agents
fragrance
perfuming agents
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Neohesperidin dihydrochalcone 98%
Aromiens International
Neohesperidin Dihydrochlalcone
AuNutra® Industries
neoDesperidin Dihydrochalcone
Beijing Lys Chemicals
neoHesperidin Dihydrochalcone
BOC Sciences
For experimental / research use only.
neoHesperidin Dihydrochalcone
Citrus and Allied Essences
neoHesperidin DC
Market Report
ECSA Chemicals
NEOHESPERIDIN DIHYDROCHALCONE
ECSA TRADE THE MOST UPDATED FINANCIAL PUBLICATION ON THE WORLD OF CHEMISTRY
ExtraSynthese
For experimental / research use only.
neoHesperidin Dihydrochalcone (HPLC) ≥90%
Firmenich
NEOHESPERIDINE DIHYDROCHALCONE Kosher
for flavor
Flavor: Sweet
NATACTONE® can be widely applied in fruit flavors where lactones are used. It gives great effect to yellow fruit flavors such as mango pineapple and peach. Its coumarinic and minty twist is perfect for tea and mint flavors
Frutarom
NEOHESPERIDIN DIHYDROCHALCONE
KOSHER
CBD Offering
George Uhe Company
neoHesperidine DC (Flavor Enhancer)
Glentham Life Sciences
Neohesperidin dihydrochalcone
IFF
NEOHESPERIDIN DIHYDROCHALCONE
KOSHER
Indis NV
For experimental / research use only.
Neohesperidine Dihydrochalcone
Jiangyin Healthway
Neohesperidin dihydrochalcone
New functional food ingredients
Layn Natural ingredients
Neohesperidin Dihydrochalcone
M&U International
neoHesperidin Dihydrochalcone, Kosher
O'Laughlin Industries
NEOHESPERIDIN DIHYDROCHALCONE NATURAL
O'Laughlin Industries
SWEETOLONE (NHDC)
Parchem
neohesperidin dihydrochalcone
Penta International
NEOHESPERIDIN DIHYDROCHALCONE EP GRADE
Penta International
NEOHESPERIDIN DIHYDROCHALCONE
Santa Cruz Biotechnology
For experimental / research use only.
neoHesperidin Dihydrochalcone ≥95%
Sigma-Aldrich
Neohesperidin dihydrochalcone, ≥96%, FG
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
neoHesperidin Dihydrochalcone >98.0%(T)
Tianjin Danjun International
Neohesperidin dihydrochalcone
United International
Neosperidin dihydrochalcone
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
 
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-rat LD50 [sex: M,F] > 5000 mg/kg
(Nutrilite, 1980)

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic and flavor agents
Recommendation for neohesperidin dihydrochalcone usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 12.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1400 (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: 17. Update in publication number(s): 18, 20, 23, 25, 28
Click here to view publication 17
 average usual ppmaverage maximum ppm
baked goods: 5.000007.00000
beverages(nonalcoholic): 5.0000015.00000
beverages(alcoholic): 5.0000015.00000
breakfast cereal: 8.0000020.00000
cheese: 3.000004.00000
chewing gum: 200.00000300.00000
condiments / relishes: 2.000003.00000
confectionery froastings: 3.000003.00000
egg products: 2.000003.00000
fats / oils: 4.000004.00000
fish products: 2.000003.00000
frozen dairy: 2.000008.00000
fruit ices: 2.000003.00000
gelatins / puddings: 3.000008.00000
granulated sugar: --
gravies: 3.000004.00000
hard candy: 5.0000015.00000
imitation dairy: 3.0000010.00000
instant coffee / tea: 3.000006.00000
jams / jellies: 2.000003.00000
meat products: 2.000003.00000
milk products: 3.0000010.00000
nut products: 3.000004.00000
other grains: 3.000004.00000
poultry: 2.000003.00000
processed fruits: 2.000003.00000
processed vegetables: 2.000003.00000
reconstituted vegetables: 2.000003.00000
seasonings / flavors: 3.000004.00000
snack foods: 3.000003.00000
soft candy: 4.0000010.00000
soups: 5.000007.00000
sugar substitutes: --
sweet sauces: 2.000003.00000
 
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): 2.000003.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 4.000004.00000
Edible ices, including sherbet and sorbet (03.0): 1.000002.00000
Processed fruit (04.1): 2.000003.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 2.000004.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 3.000003.00000
Bakery wares (07.0): 4.000004.00000
Meat and meat products, including poultry and game (08.0): 2.000003.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.000003.00000
Eggs and egg products (10.0): 2.000003.00000
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.000003.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.000003.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 2.000003.00000
Ready-to-eat savouries (15.0): 2.000005.00000
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

Scientific Opinion on the safety and efficacy of neohesperidine dihydrochalcone when used as a sensory additive for piglets, pigs for fattening, calves for rearing and fattening, lambs for rearing and fattening, dairy sheep, ewes for reproduction, salmonids and dogs
View page or View pdf

Scientific Opinion on the safety of neohesperidine dihydrochalcone as a sensory additive for fish
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :30231
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
Chemidplus:0020702776
EPA/NOAA CAMEO:hazardous materials
RTECS:LZ5785000 for cas# 20702-77-6
 
References:
 1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):30231
Pubchem (sid):134994277
 
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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB30542
FooDB:FDB002416
Export Tariff Code:2938.90.0000
FDA Listing of Food Additive Status:View
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
FLlicorice
FLsweet
 
Occurrence (nature, food, other):note
 not found in nature
 orange pericarp
Search Trop Picture
 
Synonyms:
1-(4-((2-O-(6-deoxy-alpha-1-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-(4-((2-O-(6-deoxy-alpha-1-mannopyranosyl)-beta-dextro-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl) propan-1-one
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
neohesperidin DC
 

Articles:

PubMed:Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro.
PubMed:Dietary supplementation with lactose or artificial sweetener enhances swine gut Lactobacillus population abundance.
PubMed:Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats.
PubMed:4-methoxychalcone enhances cisplatin-induced oxidative stress and cytotoxicity by inhibiting the Nrf2/ARE-mediated defense mechanism in A549 lung cancer cells.
PubMed:Occurrence of seven artificial sweeteners in the aquatic environment and precipitation of Tianjin, China.
PubMed:[Simultaneous determination of twelve sweeteners and nine preservatives in foods by solid-phase extraction and LC-MS/MS].
PubMed:Evaluation of taste-masking effects of pharmaceutical sweeteners with an electronic tongue system.
PubMed:2-Hydroxychalcone and xanthohumol inhibit invasion of triple negative breast cancer cells.
PubMed:Neohesperidin dihydrochalcone: presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector.
PubMed:The content of high-intensity sweeteners in different categories of foods available on the Polish market.
PubMed:Characterization and quantification of major constituents of Xue Fu Zhu Yu by UPLC-DAD-MS/MS.
PubMed:Dihydrochalcone glycosides from Oxytropis myriophylla.
PubMed:Determination of nine high-intensity sweeteners in various foods by high-performance liquid chromatography with mass spectrometric detection.
PubMed:Retention behaviour of some high-intensity sweeteners on different SPE sorbents.
PubMed:Expression of Na+/glucose co-transporter 1 (SGLT1) is enhanced by supplementation of the diet of weaning piglets with artificial sweeteners.
PubMed:Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).
PubMed:The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor.
PubMed:Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death.
PubMed:Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China.
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:Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
PubMed:Cloning and expression of a phloretin hydrolase gene from Eubacterium ramulus and characterization of the recombinant enzyme.
PubMed:Crystal architecture and conformational properties of the inclusion complex, neohesperidin dihydrochalcone-cyclomaltoheptaose (beta-cyclodextrin), by X-ray diffraction.
PubMed:Oral zinc sulfate solutions inhibit sweet taste perception.
PubMed:Embryotoxicity and teratogenicity study with neohesperidin dihydrochalcone in rats.
PubMed:Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and alpha 2-adrenergic receptors in Xenopus laevis melanophores.
PubMed:Sense of taste in a new world monkey, the common marmoset: recordings from the chorda tympani and glossopharyngeal nerves.
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:Neohesperidin dihydrochalcone is not a taste enhancer in aqueous sucrose solutions.
PubMed:Synergism among ternary mixtures of fourteen sweeteners.
PubMed:Effect of temperature, pH, and ions on sweet taste.
PubMed:Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase.
PubMed:An estimation of the detection and quantitation limits of neohesperidine DC by high-performance liquid chromatography.
PubMed:Double functionality of sweeteners: a case of study.
PubMed:Selective inhibition of sweetness by the sodium salt of +/-2-(4-methoxyphenoxy)propanoic acid.
PubMed:In vitro scavenger and antioxidant properties of hesperidin and neohesperidin dihydrochalcone.
PubMed:Lowering effect of phenolic glycosides on the rise in postprandial glucose in mice.
PubMed:Validated high-performance liquid chromatographic method for quantitation of neohesperidine dihydrochalcone in foodstuffs.
PubMed:Structure-taste correlations in sweet dihydrochalcone, sweet dihydroisocoumarin, and bitter flavone compounds.
PubMed:Bitterness of sweeteners as a function of concentration.
PubMed:Investigation of synergism in binary mixtures of sweeteners.
PubMed:Adaptation of sweeteners in water and in tannic acid solutions.
PubMed:Subchronic (13-week) oral toxicity of neohesperidin dihydrochalcone in rats.
PubMed:High-potency sweeteners and dental health.
PubMed:Sweet tastants stimulate adenylate cyclase coupled to GTP-binding protein in rat tongue membranes.
PubMed:Liquid chromatographic determination of naringin and neohesperidin as a detector of grapefruit juice in orange juice.
PubMed:Caffeine intensifies taste of certain sweeteners: role of adenosine receptor.
PubMed:Gustatory reaction time to various sweeteners in human adults.
PubMed:In vivo exposure to plant flavonols. Influence on frequencies of micronuclei in mouse erythrocytes and sister-chromatid exchange in rabbit lymphocytes.
PubMed:Taste responses to neohesperidin dihydrochalcone in rats and baboon monkeys.
PubMed:Genetic toxicological of some plant flavonoids by the micronucleus test.
PubMed:Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
PubMed:Sweeteners--an overview. Part. 1.
PubMed:An exponential model for adaptation in taste.
PubMed:Qualitative differences among sweeteners.
PubMed:Saccharin and other sweeteners: mutagenic properties.
PubMed:Nonnutritive sweeteners: taste-structure relationships for some new simple dihydrochalcones.
PubMed:Liquid chromatography of neohesperidin dihydrochalcone.
 
Notes:
Intensely sweet, 612 times more sweet than sucrose. ADI 5 mg/kg (1987). Permitted in EU at low concs. (=10 ppm) for certain applications, e.g. low-alcohol beer. Generally recognised as safe (GRAS) in the USA. Practical use limited by slow development of taste sensation and peculiar aftertaste Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.; The European Union approved NHDC's use as a sweetener in 1994. It has not been approved as a sweetener in the United States. It is sometimes said that NHDC is considered a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association, which is a trade group with no legal standing. NHDC has never appeared on the FDA's GRAS listing.
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