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neohesperidin dihydrochalcone

Chemical Structure

General Material Information

Preferred name neohesperidin dihydrochalcone
Trivial Name Neohesperidin dihydrochalcone
Short Description neohesperidin DC
Formula C28 H36 O15
CAS Number 20702-77-6
FEMA Number 3811
Flavis Number 16.061
ECHA Number 243-978-6
FDA UNII 3X476D83QV
Nikkaji Number J2.757J
MDL MFCD00017711
xLogP3-AA -0.30 (est)
Bio Activity Summary External link
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 20702-77-6 ; NEOHESPERIDIN DIHYDROCHALCONE
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
  • neo hesperidin DC
  • 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
  • 1-Propanone, 1-[4-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-
  • Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-, β-D-
  • Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-α-L-rhamnopyranosyl-
  • 1-[4-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone
  • Neohesperidin DHC
  • Neohesperidine dihydrochalcone
  • NHDC
  • Neohesperidin DC
  • Citrosa

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Literature & 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
Publications by PubMed
Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro.
Dietary supplementation with lactose or artificial sweetener enhances swine gut Lactobacillus population abundance.
Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats.
4-methoxychalcone enhances cisplatin-induced oxidative stress and cytotoxicity by inhibiting the Nrf2/ARE-mediated defense mechanism in A549 lung cancer cells.
Occurrence of seven artificial sweeteners in the aquatic environment and precipitation of Tianjin, China.
[Simultaneous determination of twelve sweeteners and nine preservatives in foods by solid-phase extraction and LC-MS/MS].
Evaluation of taste-masking effects of pharmaceutical sweeteners with an electronic tongue system.
2-Hydroxychalcone and xanthohumol inhibit invasion of triple negative breast cancer cells.
Neohesperidin dihydrochalcone: presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector.
The content of high-intensity sweeteners in different categories of foods available on the Polish market.
Characterization and quantification of major constituents of Xue Fu Zhu Yu by UPLC-DAD-MS/MS.
Dihydrochalcone glycosides from Oxytropis myriophylla.
Determination of nine high-intensity sweeteners in various foods by high-performance liquid chromatography with mass spectrometric detection.
Retention behaviour of some high-intensity sweeteners on different SPE sorbents.
Expression of Na+/glucose co-transporter 1 (SGLT1) is enhanced by supplementation of the diet of weaning piglets with artificial sweeteners.
Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).
The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor.
Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death.
Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China.
Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC.
Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
Cloning and expression of a phloretin hydrolase gene from Eubacterium ramulus and characterization of the recombinant enzyme.
Crystal architecture and conformational properties of the inclusion complex, neohesperidin dihydrochalcone-cyclomaltoheptaose (beta-cyclodextrin), by X-ray diffraction.
Oral zinc sulfate solutions inhibit sweet taste perception.
Embryotoxicity and teratogenicity study with neohesperidin dihydrochalcone in rats.
Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and alpha 2-adrenergic receptors in Xenopus laevis melanophores.
Sense of taste in a new world monkey, the common marmoset: recordings from the chorda tympani and glossopharyngeal nerves.
Sweetener preference of C57BL/6ByJ and 129P3/J mice.
[Determination of neohesperidin dihydrochalcone in foods].
Improved water solubility of neohesperidin dihydrochalcone in sweetener blends.
PROP (6-n-Propylthiouracil) tasting and sensory responses to caffeine,sucrose, neohesperidin dihydrochalcone and chocolate.
Neohesperidin dihydrochalcone is not a taste enhancer in aqueous sucrose solutions.
Synergism among ternary mixtures of fourteen sweeteners.
Effect of temperature, pH, and ions on sweet taste.
Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase.
An estimation of the detection and quantitation limits of neohesperidine DC by high-performance liquid chromatography.
Double functionality of sweeteners: a case of study.
Selective inhibition of sweetness by the sodium salt of +/-2-(4-methoxyphenoxy)propanoic acid.
In vitro scavenger and antioxidant properties of hesperidin and neohesperidin dihydrochalcone.
Lowering effect of phenolic glycosides on the rise in postprandial glucose in mice.
Validated high-performance liquid chromatographic method for quantitation of neohesperidine dihydrochalcone in foodstuffs.
Structure-taste correlations in sweet dihydrochalcone, sweet dihydroisocoumarin, and bitter flavone compounds.
Bitterness of sweeteners as a function of concentration.
Investigation of synergism in binary mixtures of sweeteners.
Adaptation of sweeteners in water and in tannic acid solutions.
Subchronic (13-week) oral toxicity of neohesperidin dihydrochalcone in rats.
High-potency sweeteners and dental health.
Sweet tastants stimulate adenylate cyclase coupled to GTP-binding protein in rat tongue membranes.
Liquid chromatographic determination of naringin and neohesperidin as a detector of grapefruit juice in orange juice.
Caffeine intensifies taste of certain sweeteners: role of adenosine receptor.
Gustatory reaction time to various sweeteners in human adults.
In vivo exposure to plant flavonols. Influence on frequencies of micronuclei in mouse erythrocytes and sister-chromatid exchange in rabbit lymphocytes.
Taste responses to neohesperidin dihydrochalcone in rats and baboon monkeys.
Genetic toxicological of some plant flavonoids by the micronucleus test.
Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
Sweeteners--an overview. Part. 1.
An exponential model for adaptation in taste.
Qualitative differences among sweeteners.
Saccharin and other sweeteners: mutagenic properties.
Nonnutritive sweeteners: taste-structure relationships for some new simple dihydrochalcones.
Liquid chromatography of neohesperidin dihydrochalcone.

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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 612.58294677734
Melting Point 156 to 158°C @ 760 mm Hg
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 0.205 est
Solubility
water, 342.1 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Odorless
Odor strength none
Luebke, William tgsc, (1999) At 100.00 %. bland odor
Mosciano, Gerard P&F 20, No. 1, 31, (1995) No apparent odor
Flavor Type: Sweet
licorice, sweet
Mosciano, Gerard P&F 20, No. 1, 31, (1995) At 10.00 ppm. Licorice-like with a lingering sweetness

Occurrences

Potential Uses

Applications
Flavoring purposes Licorice, Sweet
Cosmetic purposes Flavoring agents, Fragrance, Perfuming agents

Safety Information

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