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A member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage.
E 959 is found in sweet orange.
E 959 off-white crystals or powder.
CAS: 20702-77-6
MF: C28H36O15
MW: 612.58
EINECS: 243-978-6
Insoluble in water.
E 959, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.
E 959 is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin.
Industrially, E 959 is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC.
Food additive E 959, Neohesperidine dihydrocalcon DC is a semi-synthetic sweetener with high sweetening power.
E 959 is a derivative of natural flavones from the inner layer of the citrus peel, for example narginine (the bitter principle in grapefruit peel), neohesperidine from Seville oranges, and prunine.
E 959, is an artificial sweetener derived from citrus.
E 959 is well known for having a strong synergistic effect when used in conjunction with other artificial sweeteners.
E 959 was discovered during the 1960s as part of a United States Department of Agriculture research program to find methods for minimizing the taste of bitter flavorants in citrus juices.
E 959 is one such bitter compound.
When treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, E 959 becomes NHDC.
E 959 is approved in the European Union as sweetener (E-959) since 1994, as well as flavouring (FL-16.061).
E 959 is also listed as a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association.
In November 2020, the FDA issued a no objection letter to the Generally Recognized as Safe status of E 959.
FDA concluded that E 959 is GRAS (based on scientific procedures) for its intended use.
E 959 is intended to be used as a sweetener in various food categories at maximum levels of 10-1000 ppm.
E 959 is also included both in European Pharmacopoeia and United States Pharmacopoeia, for being used as excipient in drug products.
The safety of E 959 has been extensively tested.
Safety studies have indicated that E 959 is neither toxic, mutagenic nor carcinogenic.
Like other flavonoids, E 959 is easily metabolized by intestinal microbiota to innocuous products.
The safety of E 959 has been thoroughly tested again by the European Food Safety Agency in 2022.
The acceptable daily intake was set at 20 mg/kg of body weight.
E 959 in pure form is found as a white substance not unlike powdered sugar.
E 959 has an intense sweet taste because it stimulates the sweet receptor TAS1R2+TAS1R3 in humans, although this is species-dependent, as the equivalent receptor in rats does not respond to the molecule.
E 959 is roughly 1500-1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than sugar.
E 959's potency is naturally affected by such factors as the application in which it is used, and the pH of the product.
Like other highly sweet glycosides, such as glycyrrhizin and those found in stevia, E 959's sweet taste has a slower onset than sugar's and lingers in the mouth for some time.
Unlike aspartame, E 959 is stable to elevated temperatures and to acidic or basic conditions, and so can be used in applications that require a long shelf life.
E 959 itself can stay foodsafe for up to five years when stored in optimal conditions.
E 959 is well known for having a strong synergistic effect when used in conjunction with other artificial sweeteners such as aspartame, saccharin, acesulfame potassium, and cyclamate, as well as sugar alcohols such as xylitol.
E 959 usage boosts the effects of these sweeteners at lower concentrations than would otherwise be required; smaller amounts of other sweeteners are needed.
This provides a cost benefit.
E 959 is accepted for use in food products either as a sweetener or flavor modifier in a number of areas including Europe, USA, Australia, New Zealand, and several countries in Africa and Asia.
E 959 is also used in a number of oral pharmaceutical formulations.
Animal toxicity studies suggest that E 959 is a nontoxic, nonteratogenic, and noncarcinogenic material at the levels used in foods and pharmaceuticals.
In Europe, an acceptable daily intake of 0–5 mg/kg body-weight has been established.
E 959 is stable for over three years when stored at room temperature.
Accelerated stability studies on aqueous solutions stored at 30–60°C and pH 1–7 for 140 days indicate that E 959 solutions are likely to be stable for 12 months at room temperature and pH 2–6.
Solutions formulated with some or all of the water replaced by solvents with a lower dielectric constant are reported to have longer shelf-lives.
The bulk material should be stored in a cool, dry, place protected from light.
Uses
In food E 959 is used as a flavour enhancer in concentrations of around 4-5 parts per million (ppm) and as an artificial sweetener at around 15-20 ppm.
E 959, is a flavonoid sweetening agent with potent antioxidant activity.
E 959 is antioxidant agent. artificial sweetener.
Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit.
E 959 is used as sweetening agent, especially in chewing gum and dentifrices.
Sweetening agent, especially in chewing gum and dentifrices.
Masking
Pharmaceutical companies are fond of E 959 as a means of reducing the bitterness of pharmacological drugs in tablet form, and it has been used for livestock feed as a means of reducing feeding time.
E 959 is also widely favoured for use in otherwise naturally bitter products.
Enhancer
As a flavour enhancer, E 959 is used in a wide range of products and is indicated by the E number E 959.
E 959 is noted particularly for enhancing sensory effects (known in the industry as 'mouth feel').
An example of this is 'creaminess' in dairy foods such as yogurt and ice cream.
Other uses
Other products E 959 can be found in may include a wide variety of beverages, alcoholic and non-alcoholic, savoury foods, toothpaste, mouthwash and condiments such as ketchup and mayonnaise.
E 959 is also used as excipient in drug products to mask the bitter taste of some active pharmaceutical ingredients.
Why is E 959 useful and necessary to use E959?
The E 959 additive has a special characteristic because, in addition to its use as a sweetener in food formulations, E 959 can also act as a flavour enhancer as well as a masking agent, which makes it different from other alternative sweeteners used in the industry.
– Due to E 959's pleasant and intense sweet taste the additive is accepted in different applications and sectors, always satisfying the end consumer.
– As a flavour enhancer, the E 959 works by enhancing the flavours of fruit and cocoa derivatives.
– As a masking agent, E 959 reduces unwanted flavours in various food formulations, such as acidity, bitterness, etc.
– E 959 can be used in low concentrations and is one of the natural sweeteners with a higher sweetening intensity.
– The pleasant mouthfeel of E 959 lingers longer than other sweeteners, making the intake more enjoyable for the end consumer.
– E 959 improves mouthfeel and texture, providing creaminess to various foods.
– Both the caloric intake of E 959 and its glycemic index are zero.
This advantage allows E 959 to be used in more products than other sweeteners, including products for the population suffering from pathologies associated with obesity or metabolic syndrome.
– E 959's high stability at different temperatures allows Neohesperidin DC to be used in different sectors and at different stages of the production process.
– E 959's versatility as a sweetener, enhancer or flavour masker using effective amounts on the order of ppm, less than other known sweeteners would require, makes Neohesperidin DC an economical food ingredient.
E 959 has the ability to achieve its desired effects using small amounts of it and also has synergistic effects with other more expensive sweeteners.
This allows a smaller amount of the more expensive regular sweetener and a smaller amount of E 959 to achieve a similar taste effect for which a larger amount of the regular individual sweetener would be required.
Pharmaceutical Applications
E 959 is a synthetic intense sweetening agent approximately 1500–1800 times sweeter than sucrose and 20 times sweeter than saccharin.
Structurally E 959 is an analogue of neohesperidin, a flavanone that occurs naturally in Seville oranges (Citrus aurantium). E 959 is used in pharmaceutical and food applications as a sweetening agent and flavor enhancer.
The sweetness profile is characterized by a lingering sweet/menthol-like aftertaste.
The typical level used in foods is 1–5 ppm although much higher levels may be used in certain applications such as chewing gum.
Synergistic effects occur with other intense and bulk sweeteners such as acesulfame K, aspartame, polyols, and saccharin.
In pharmaceutical applications, E 959 is useful in masking the unpleasant bitter taste of a number of drugs such as antacids, antibiotics, and vitamins.
In antacid preparations, levels of 10–30 ppm result in improved palatability.
E 959 Chemical Properties
Melting point: 156-158 °C(lit.)
Boiling point: 927.1±65.0 °C(Predicted)
Density: 1.61±0.1 g/cm3(Predicted)
Vapor pressure: 0Pa at 20℃
FEMA: 3811 | NEOHESPERIDIN DIHYDROCHALCONE
Storage temp.: Sealed in dry,Store in freezer, under -20°C
Solubility: Practically insoluble in water, freely soluble in dimethyl sulfoxide, soluble in methanol, practically insoluble in methylene chloride.
pka: 6.85±0.40(Predicted)
Form: crystalline
Color: light yellow
Water Solubility: Insoluble
Merck: 14,6452
Stability: Hygroscopic
InChIKey: ITVGXXMINPYUHD-CUVHLRMHSA-N
LogP: 0.67 at 20℃
CAS DataBase Reference: 20702-77-6(CAS DataBase Reference)
EPA Substance Registry System:E 959 (20702-77-6)
Production Methods
E 959 is synthesized commercially from either of the bitter-flavanones neohesperidin or naringin by catalytic hydrogenation under alkaline conditions in a process first described in the 1960s, in which neohesperidin is purified by recrystallization from water solutions.
E 959 is obtained by the alkaline hydrogenation of neohesperidin.
Reactivity Profile
E 959 is a ether-alcohol derivative.
The ether being relatively unreactive.
Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents.
They react with oxoacids and carboxylic acids to form esters plus water.
Oxidizing agents convert alcohols to aldehydes or ketones.
Alcohols exhibit both weak acid and weak base behavior.
They may initiate the polymerization of isocyanates and epoxides.
Synonyms
neohesperidin dihydrochalcone
20702-77-6
Nhdc
Neohesperidin dc
Neohesperidin dhc
Neohesperidine dihydrochalcone
Neohesperidine
NCI-C60764
Neohesperidin-dihydrochalcone
Neosperidin dihydrochalcone
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 dihydrochalone
CHEBI:83535
3X476D83QV
1-(4-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-Propanone, 1-[4-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-
Citrosa
neohesperidine DC
1-(4-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-Propanone, 1-(4-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-
CCRIS 4848
EINECS 243-978-6
UNII-3X476D83QV
Neohesperidin Dihydrochalcone (Nhdc)
Neosperidin-dihydrochalcone
DSSTox_CID_5706
NeohesperidinDihydrochalcone
DSSTox_RID_77887
DSSTox_GSID_25706
1-(4-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-
1-Propanone, 1-(4-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-me
3,5-Dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl) 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
SCHEMBL909958
CHEMBL1159645
DTXSID3025706
FEMA NO. 3811
ITVGXXMINPYUHD-CUVHLRMHSA-
HMS3884H13
HY-N0154
ZINC4175639
Tox21_200303
s2331
1-(4-((2-O-[6-Deoxy-&alpha
AKOS015895239
CCG-270237
CS-6419
NCGC00091109-01
NCGC00091109-02
NCGC00091109-04
NCGC00257857-01
1-(4-((2-O-[6-Deoxy-alpha-L-mannopyranosyl]-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone
3,5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
AC-34860
AS-15190
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-, .beta.-D-
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl-2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
NEOHESPERIDIN DIHYDROCHALCONE [MI]
Neohesperidin dihydrochalcone, >=96%, FG
NEOHESPERIDIN DIHYDROCHALONE [FHFI]
CAS-20702-77-6
NEOHESPERIDIN DIHYDROCHALCONE [INCI]
NEOHESPERIDINE DIHYDROCHALCONE [FCC]
N0675
NEOHESPERIDIN DIHYDROCHALCONE [USP-RS]
Neohesperidin dihydrochalcone, >=95% (HPLC)
NEOHESPERIDINE DIHYDROCHALCONE [USP-RS]
Neohesperidin dihydrochalcone, analytical standard
702N776
A81482
Q424595
SR-01000883756
NEOHESPERIDIN-DIHYDROCHALCONE [EP MONOGRAPH]
Q-201457
SR-01000883756-1
BRD-K61032563-001-02-9
HESPERETIN DIHYDROCHALCONE-4'-.BETA.-NEOHESPERIDOSIDE
Neohesperidin dihydrochalcone, European Pharmacopoeia (EP) Reference Standard
Neohesperidin dihydrochalcone, United States Pharmacopeia (USP) Reference Standard
1-(4-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-DIHYDROCHALCONE 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-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-[4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-2-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]oxy-tetrahydropyran-3-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one
1-PROPANONE, 1-(4-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,6-DIHYDROXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-
GLUCOPYRANOSIDE, 3,5-DIHYDROXY-4-(3-HYDROXY-4-METHOXYHYDROCINNAMOYL)PHENYL 2-O-.ALPHA.-L-RHAMNOPYRANOSYL-
