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CAS Number: 20702-77-6
European Community (EC) Number: 243-978-6
Chemical formula: C28H36O15
Molar mass: 612.58 g/mol
IUPAC 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
Description:
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.
Neohesperidin dihydrochalcone is a synthetic glycoside chalcone, is added to various foods and beverages as a low caloric artificial sweetener.
Neohesperidin dihydrochalcone is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin.
Industrially, Neohesperidin dihydrochalcone is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC.
Neohesperidin dihydrochalcone appears as off-white crystals or powder.
Neohesperidin dihydrochalcone is Insoluble in water.
Neohesperidin dihydrochalcone is Off-white, odourless, crystalline powder.
Neohesperidin dihydrochalcone is approximately between 1 000 and 1 800 times as sweet as sucrose
Neohesperidin dihydrochalcone is an artificial sweetener.
Neohesperidin dihydrochalcone is a Flavonoid sweetening agent with potent antioxidant activity.
Neohesperidin dihydrochalcone can be prepared by the hydrogenation of neohesperidin, a bitter flavonone found in citrus fruits.
Neohesperidin dihydrochalcone, also named Neohesperidin DC, is an intensive sweetener produced from neohesperidin.
Neohesperidin DC is considered an intense and non-nutritive sweetener, with a pleasant taste and with the ability to improve the quality and sweetness profile in different food formulations.
Neohesperidin DC is a flavonoid present naturally in citrus, mainly in the bitter Seville orange (Citrus aurantium).
Neohesperidin is found mainly in the peels of citrus fruits, but they are also found in:
-Citrus pulps
-Citrus purees
-Citrus juice
Bordas extract Neohesperidin from all of them: pulps, purees and juices.
Bordas Neohesperidin DC is always manufactured making an exhaustive selection of the highest quality raw materials.
Neohesperidin dihydrochalcone shows remarkable radical scavenging activity against stable radical and reactive oxygen species (ROS) in concentration dependent manner.
Especially, neohesperidin dihydrochalcone is the most potent inhibitor of H2O2 and HOCl. Neohesperidin dihydrochalcone shows HOCl scavenging activity of 93.5% and H2O2 scavenging property of 73.5%.
Neohesperidin dihydrochalcone shows extensive inhibitory effect especially on non-radical ROS H2O2 and HOCl with IC50 values of 205.1, 25.5 μM.
Neohesperidin dihydrochalcone is found to be an activator of porcine pancreatic alpha-amylase (PPA) with an IC50 of 389 μM.
Neohesperidin dihydrochalcone administration results in significant reduction in activities of two useful markers of liver damage, AST and ALT.
The relative levels of NF-κB, IL-6, IL-1β and TNF-α protein in the liver of PQ-treated mice are inhibited by neohesperidin dihydrochalcone.
The embryotoxicity/teratogenicity of neohesperidin dihydrochalcone is examined in Wistar Crl:(WI)WU BR rats.
No adverse effects are observed at neohesperidin dihydrochalcone levels of up to 5% of the diet, the highest dose level tested, at which the rats consumed about 3.3 g/kg body weight/day.
Discovery of Neohesperidin dihydrochalcone:
NHDC 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.
Neohesperidin is one such bitter compound.
When treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes NHDC.
Profile
NHDC in pure form is found as a white substance not unlike powdered sugar.
NHDC has an intense sweet taste because Neohesperidin dihydrochalcone 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.
Neohesperidin dihydrochalcone is roughly 1500-1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than sugar.
Its 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, NHDC's sweet taste has a slower onset than sugar's and lingers in the mouth for some time.
Unlike aspartame, NHDC is stable to elevated temperatures and to acidic or basic conditions, and so can be used in applications that require a long shelf life.
NHDC itself can stay foodsafe for up to five years when stored in optimal conditions.
Neohesperidin dihydrochalcone 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.
NHDC 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.
Approval and safety of Neohesperidin dihydrochalcone:
NHDC is approved in the European Union as sweetener (E-959) since 1994, as well as flavouring (FL-16.061).
Neohesperidin dihydrochalcone 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 Neohesperidin dihydrochalcone (NHDC).
FDA concluded that NHDC is GRAS (based on scientific procedures) for its intended use.
NHDC is intended to be used as a sweetener in various food categories at maximum levels of 10-1000 ppm.
NHDC is also included both in European Pharmacopoeia and United States Pharmacopoeia, for being used as excipient in drug products.
The safety of NHDC has been extensively tested.
Safety studies have indicated that NHDC is neither toxic, mutagenic nor carcinogenic.
Like other flavonoids, NHDC is easily metabolized by intestinal microbiota to innocuous products.
Uses of Neohesperidin dihydrochalcone:
In food it 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.
Neohesperidin dihydrochalcone has been used in a study to assess levels of nine high-intensity sweeteners in various foods. It can be used as a therapeutic agent on reactive oxygen species-related inflammatory disease.
Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit.
Neohesperidin dihydrochalcone is used as sweetening agent, especially in chewing gum and dentifrices.
Masking
Pharmaceutical companies are fond of the product as a means of reducing the bitterness of pharmacological drugs in tablet form, and Neohesperidin dihydrochalcone has been used for livestock feed as a means of reducing feeding time.
Neohesperidin dihydrochalcone is also widely favoured for use in otherwise naturally bitter products.
Enhancer
As a flavour enhancer, NHDC is used in a wide range of products and is indicated by the E number E 959.
Neohesperidin dihydrochalcone 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 NHDC 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. NHDC is also used as excipient in drug products to mask the bitter taste of some active pharmaceutical ingredients.
PRODUCERS AND MANUFACTURERS OF NEOHESPERIDIN:
Bordas company manufactures Neohesperidin DC as we have great experience with the treatment and processing of fruits, in particular citrus fruits.
The citrus fruits are Bordas raw materials for the synthesis of many of our products, both in the field of fruit derivatives:
• Candied
• Cells
• Concentrates
• Dehydrates
• Juices
• Peels
• Pulps
• Purees
• Slices
and in the extraction and manufacturing of functional ingredients:
• Diosmin
• Hesperidin
• Naringin
• Citrus Bioflavonoides Complex (CBC)
• Neohesperidin DC
All these raw materials come mainly from Bordas owned farms of bitter orange in Seville, which allows us to have a total control of the quality and traceability of each product.
CERTIFIED PRODUCT QUALITY:
Years of experience guarantee the quality of the products and processes of production in Bordas. NEOHESPERIDIN DC manufacturing, as well as all our finished products, meets international quality standards.
Through a correct selection of each raw material and an optimization of the production process, in which our R&D department works constantly, Bordas manufacture safe high quality tailor-made products.
PROPERTIES AND CHARACTERISTICS OF NEOHESPERIDIN DC:
Worldwide approved food additive: Neohesperidin DC is approved as a food additive in Europe (E-959 code), being regulated according to the food categories where it is used.
In addition, its use is also approved and regulated in the United States and Japan.
High sweetening power: Neohesperidin DC has a sweetness intensity around 1800 times compared to sucrose at threshold levels
Taste Enhancer: In addition to its sweetening power, Neohesperidin DC can also act as a product flavour enhancer.
Masking agent: Neohesperidin DC is also known as a less pleasant taste masking agent.
This property differentiates it from the rest of the alternative sweeteners used in the industry.
Pleasant to taste: The organoleptic profile of NEOHESPERIDIN DC is characterized by an intense sweet taste.
Using high concentrations, NEOHESPERIDIN DC presents an aftertaste with notes similar to liquorice.
Persistence: As an intensive sweetener, NEOHESPERIDIN DC has a very characteristic intensity-time profile.
Due to this, NEOHESPERIDIN DC produces a longer and more persistent sweetness sensation.
Synergistic effects: Neohesperidin DC has remarkable synergistic effects used together with other sweeteners currently used in the food industry.
These synergistic effects have been widely corroborated in different studies.
Final product unaltered: Many studies have proven that Neohesperidin DC, even improving the taste and flavour organoleptic properties, does not alter other organoleptic characteristics such as the smell of the product.
Stability: Neohesperidin DC is stable under normal processing and storage conditions of foods with a solubility at room temperature of 0.4 g / L, although this increases exponentially with the temperature reaching values up to 650 g / L at 80 ° C.
However, this is far to be an inconvenience for its use, due to that just ppm quantity of it is required to achieve perceptible effects.
Healthy: Neohesperidin DC is a sweetener that does not provide calories and has a zero glycemic index.
NEOHESPERIDIN DC ADVANTAGES AND BENEFITS RESPECT TO OTHER SWEETENERS:
Versatility: NEOHESPERIDIN DC has a particular feature since, in addition to NEOHESPERIDIN DC’s use as a sweetener in food formulations NEOHESPERIDIN DC can also act as a flavour enhancer as well as a masking agent, which makes NEOHESPERIDIN DC different from the rest of alternative sweeteners used in the industry.
Pleasant taste: Its pleasant and intense sweet taste makes Neohesperidin widely accepted in different applications and sectors, always pleasing the final consumer.
Flavour enhancer: As a flavour enhancer, NEOHESPERIDIN DC works by increasing fruit and cocoa derivatives flavours.
Masking agent: As a masking agent, NEOHESPERIDIN DC reduces undesirable flavours in different food formulations such as acidity, bitterness, etc.
Low concentrations: Neohesperidin DC is one of the sweeteners of natural origin with higher sweetness intensity.
Better consumer experience: The persistence of the pleasant taste in mouth of Neohesperidin DC is longer than the rest of sweeteners, making the intake more enjoyable for the final consumer.
Pleasant to the palate: Neohesperidin DC improves the sensation and texture in mouth, providing creaminess to different food formulations.
Healthy: Both, the caloric intake of Neohesperidin DC and its glycemic index, are zero.
This advantage allows the use of Neohesperidin DC in more products than other sweeteners, including products addressed to population that suffer pathologies associated with obesity or metabolic syndrome.
Stability: NEOHESPERIDIN DC’s high stability at different temperatures allows the NEOHESPERIDIN DC to be used in different sectors and in different stages of the production process.
Economic: NEOHESPERIDIN DC’s versatility as a sweetener, enhancer or flavour masker using effective quantities of the order of ppm, less than other known sweeteners would require, makes NEOHESPERIDIN DC an economic food ingredient.
Costs savings: Neohesperidin DC has the capacity of achieving its desired effects using low quantities of it, and has also synergistic effects with other more expensive sweeteners.
That allows to reach, with a smaller amount of the usual more expensive sweetener and a small amount of NEOHESPERIDIN DC, a similar taste effect for which it would be required higher amount of the usual individual sweetener.
NEOHESPERIDIN DC APPLICATIONS
Neohesperidin DC is recognised as a multitask, economic and stable solution to different challenges in many sectors.
Due to its versatility as a food additive, Neohesperidin DC can be used in different food industries and with different desired effects:
1. As sweetener and taste enhancer, Neohesperidin is widely used in:
• Desserts, ice cream and dairy products.
• Confectionery.
• Beverage, soft drinks and juice industries.
• Candies.
2. NEOHESPERIDIN DC’s flavour enhancing power is highly appreciated in the following industries:
• Sauces and soups.
• Animal feed and health industries.
3. In the pharmaceutical industry, Neohesperidin DC is used primarily as a masking agent.
4. Personal care products such as mouth rinses, toothpastes use NEOHESPERIDIN DC flavonoid thanks to its sweetening effect.
Roles Classification of Neohesperidin DC:
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Sweetening agent: Substance that sweeten food, beverages, medications, etc.
Xenobiotic: A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism.
Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Chemical and Physical Properties of NHDC:
Molecular Weight: 612.6 g/mol
XLogP3-AA: -0.3
Hydrogen Bond Donor Count: 9
Hydrogen Bond Acceptor Count: 15
Rotatable Bond Count: 10
Exact Mass: 612.20542044 g/mol
Monoisotopic Mass: 612.20542044 g/mol
Topological Polar Surface Area: 245 Ų
Heavy Atom Count: 43
Formal Charge: 0
Complexity: 882
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Melting Point: 313 to 313 °F
storage conditions:
Powder: temperature: -20°C time: 3 years
Temperature: 4°C time: 2 years
In solvent: temperature: -80°C time: 6 months
Temperature: -20°C time:1 month
Appearance: white to pale yellow powder (est)
Physical State : Solid
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)
Odor Type: odorless
Odor Strength:none
Odor Description:at 100.00 %. bland odor
Odor sample from: CA Aromatics Company Inc.
Odor Description:No apparent odor
Flavor Type: sweet
licorice sweet
Taste Description: at 10.00 ppm.
Licorice-like with a lingering sweetness
Shipping: Room temperature in continental US; may vary elsewhere.
Solvent & Solubility:
1.Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% saline
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
2.Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in saline)
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
3.Add each solvent one by one: 10% DMSO 90% corn oil
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
SAFETY INFORMATION:
FIRST AID MEASURES
Description of First Aid Measures
If Neohesperidin dihydrochalcone is Inhaled:
If inhaled, move person to fresh air.
If not breathing, give artificial respiration and consult a physician.
In Case of Skin Contact:
Wash affected area with soap and water.
Consult a physician if any exposure symptoms are observed.
In Case of Eye Contact:
Immediately rinse eyes with plenty of water for at least 15 minutes.
Consult a physician.
If Neohesperidin dihydrochalcone is Swallowed:
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Do NOT induce vomiting unless advised to do so by a physician or Poison Control Center.
Seek medical attention.
Most Important Symptoms and Effects, Both Acute and Delayed:
The most important known symptoms and effects are described in the labeling
FIREFIGHTING MEASURES
Extinguishing Media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special Hazards Arising from the Substance or Mixture:
Carbon oxides
Advice for Firefighters:
Wear self contained breathing apparatus for fire fighting if necessary.
ACCIDENTAL RELEASE MEASURES:
Personal precautions:
Wear respiratory protection.
Avoid dust formation.
Avoid breathing vapours, mist or gas.
Ensure adequate ventilation.
Evacuatepersonnel to safe areas.
Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Method and materials for containment and cleaning up
Pick up and arrange disposal without creating dust.
Sweep up and shovel.
Keep in suitable, closed containers for disposal.
HANDLING AND STORAGE:
Precautions for safe handling
Avoid contact with skin and eyes.
Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage:
Keep container tightly closed in a dry and well-ventilated place.
Keep in a dry place.
Specific End Uses:
For scientific research and development only.
Not for use in humans or animals.
EXPOSURE CONTROLS/PERSONAL PROTECTION:
Control Parameters:
Contains no components with established occupational exposure limits.
Appropriate Engineering Controls:
A laboratory fumehood or other appropriate form of local exhaust ventilation should be used to avoid exposure.
Personal Protective Equipment:
All recommendations below are advisory in nature and a risk assessment should be performed by the employer/end user prior to use of Neohesperidin dihydrochalcone.
The type of protective equipment must be selected based on the amount and concentration of the dangerous material being used in the workplace.
Exposure Controls:
Storage conditions: -20˚C Freezer
Eye/Face Protection:
Safety goggles or face shield.
All equipment should have been tested and approved under appropriate standards, such as NIOSH
(US), CSA (Canada), or EN 166 (EU).
Skin Protection:
Gloves should be used when handling this material.
Gloves are to be inspected prior to use.
Contaminated gloves are to be removed using proper glove removal technique so that the outer surface of the glove does not contact bare skin.
Dispose of contaminated gloves after use in compliance with good laboratory practices and local requirements.
Gloves used for incidental exposures (splash protection) should be designated as “chemical resistant” by EU standard EN 374 with the resistance codes corresponding to the anticipated use of the material.
Unrated gloves are not recommended.
Suggested gloves: AnsellPro Sol-Vex nitrile gloves style 37-175, 15 mil thickness.
Penetration time has not been determined.
Gloves used for prolonged direct exposure (immersion) should be designated “chemical resistant” as per EN 734 with the resistance codes corresponding to the anticipated use of the material.
Suggested gloves: AnsellPro Viton/Butyl gloves style 38-612, 4/8 mil thickness.
Penetration time has not been determined.
These recommendations may not apply if the material is mixed with any other chemical, or dissolved into a solution.
A risk assessment must be performed to ensure the gloves will still offer acceptable protection.
Body Protection:
Fire resistant (Nomex) lab coat or coveralls.
Respiratory Protection:
Recommended respirators are NIOSH-approved N100 or CEN-approved FFP3 particulate respirators. These are to be only used as a backup to local exhaust ventilation or other engineering controls.
If the respirator is the only means of protection, a full-face supplied air respirator must be used.
SYNONYMS OF Neohesperidin Dihydrochalcone
MeSH Entry Terms:
neohesperidin dihydrochalcone
neohesperidine DC
neohesperidine dihydrochalcone
Depositor-Supplied Synonyms:
neohesperidin dihydrochalcone
20702-77-6
Nhdc
Neohesperidin dc
Neohesperidin dhc
Neohesperidine dihydrochalcone
Neohesperidine
Neosperidin dihydrochalcone
NCI-C60764
UNII-3X476D83QV
neohesperidin dihydrochalone
Neohesperidin-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
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)-
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
Neohesperidin Dihydrochalcone (Nhdc)
C28H36O15
Neosperidin-dihydrochalcone
DSSTox_CID_5706
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
ITVGXXMINPYUHD-CUVHLRMHSA-
HMS3884H13
HY-N0154
ZINC4175639
Tox21_200303
MFCD00017711
s2331
1-(4-((2-O-[6-Deoxy-&alpha
AKOS015895239
CCG-270237
CS-6419
NCGC00091109-01
NCGC00091109-02
NCGC00091109-04
NCGC00257857-01
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-
O413
Neohesperidin dihydrochalcone, >=96%, FG
CAS-20702-77-6
N0675
Neohesperidin dihydrochalcone, >=95% (HPLC)
Neohesperidin dihydrochalcone, analytical standard
702N776
A814825
Q424595
SR-01000883756
Q-201457
SR-01000883756-1
BRD-K61032563-001-02-9
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-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone
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
NEOHESPERIDIN DIHYDROCHALCONE (NHDC)
CAS Number: 20702-77-6
European Community (EC) Number: 243-978-6
Chemical formula: C28H36O15
Molar mass: 612.58 g/mol
IUPAC 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
Description:
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.
Neohesperidin dihydrochalcone is a synthetic glycoside chalcone, is added to various foods and beverages as a low caloric artificial sweetener.
Neohesperidin dihydrochalcone is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin.
Industrially, Neohesperidin dihydrochalcone is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC.
Neohesperidin dihydrochalcone appears as off-white crystals or powder.
Neohesperidin dihydrochalcone is Insoluble in water.
Neohesperidin dihydrochalcone is Off-white, odourless, crystalline powder.
Neohesperidin dihydrochalcone is approximately between 1 000 and 1 800 times as sweet as sucrose
Neohesperidin dihydrochalcone is an artificial sweetener.
Neohesperidin dihydrochalcone is a Flavonoid sweetening agent with potent antioxidant activity.
Neohesperidin dihydrochalcone can be prepared by the hydrogenation of neohesperidin, a bitter flavonone found in citrus fruits.
Neohesperidin dihydrochalcone, also named Neohesperidin DC, is an intensive sweetener produced from neohesperidin.
Neohesperidin DC is considered an intense and non-nutritive sweetener, with a pleasant taste and with the ability to improve the quality and sweetness profile in different food formulations.
Neohesperidin DC is a flavonoid present naturally in citrus, mainly in the bitter Seville orange (Citrus aurantium).
Neohesperidin is found mainly in the peels of citrus fruits, but they are also found in:
-Citrus pulps
-Citrus purees
-Citrus juice
Bordas extract Neohesperidin from all of them: pulps, purees and juices.
Bordas Neohesperidin DC is always manufactured making an exhaustive selection of the highest quality raw materials.
Neohesperidin dihydrochalcone shows remarkable radical scavenging activity against stable radical and reactive oxygen species (ROS) in concentration dependent manner.
Especially, neohesperidin dihydrochalcone is the most potent inhibitor of H2O2 and HOCl. Neohesperidin dihydrochalcone shows HOCl scavenging activity of 93.5% and H2O2 scavenging property of 73.5%.
Neohesperidin dihydrochalcone shows extensive inhibitory effect especially on non-radical ROS H2O2 and HOCl with IC50 values of 205.1, 25.5 μM.
Neohesperidin dihydrochalcone is found to be an activator of porcine pancreatic alpha-amylase (PPA) with an IC50 of 389 μM.
Neohesperidin dihydrochalcone administration results in significant reduction in activities of two useful markers of liver damage, AST and ALT.
The relative levels of NF-κB, IL-6, IL-1β and TNF-α protein in the liver of PQ-treated mice are inhibited by neohesperidin dihydrochalcone.
The embryotoxicity/teratogenicity of neohesperidin dihydrochalcone is examined in Wistar Crl:(WI)WU BR rats.
No adverse effects are observed at neohesperidin dihydrochalcone levels of up to 5% of the diet, the highest dose level tested, at which the rats consumed about 3.3 g/kg body weight/day.
Discovery of Neohesperidin dihydrochalcone:
NHDC 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.
Neohesperidin is one such bitter compound.
When treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes NHDC.
Profile
NHDC in pure form is found as a white substance not unlike powdered sugar.
NHDC has an intense sweet taste because Neohesperidin dihydrochalcone 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.
Neohesperidin dihydrochalcone is roughly 1500-1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than sugar.
Its 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, NHDC's sweet taste has a slower onset than sugar's and lingers in the mouth for some time.
Unlike aspartame, NHDC is stable to elevated temperatures and to acidic or basic conditions, and so can be used in applications that require a long shelf life.
NHDC itself can stay foodsafe for up to five years when stored in optimal conditions.
Neohesperidin dihydrochalcone 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.
NHDC 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.
Approval and safety of Neohesperidin dihydrochalcone:
NHDC is approved in the European Union as sweetener (E-959) since 1994, as well as flavouring (FL-16.061).
Neohesperidin dihydrochalcone 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 Neohesperidin dihydrochalcone (NHDC).
FDA concluded that NHDC is GRAS (based on scientific procedures) for its intended use.
NHDC is intended to be used as a sweetener in various food categories at maximum levels of 10-1000 ppm.
NHDC is also included both in European Pharmacopoeia and United States Pharmacopoeia, for being used as excipient in drug products.
The safety of NHDC has been extensively tested.
Safety studies have indicated that NHDC is neither toxic, mutagenic nor carcinogenic.
Like other flavonoids, NHDC is easily metabolized by intestinal microbiota to innocuous products.
Uses of Neohesperidin dihydrochalcone:
In food it 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.
Neohesperidin dihydrochalcone has been used in a study to assess levels of nine high-intensity sweeteners in various foods. It can be used as a therapeutic agent on reactive oxygen species-related inflammatory disease.
Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit.
Neohesperidin dihydrochalcone is used as sweetening agent, especially in chewing gum and dentifrices.
Masking
Pharmaceutical companies are fond of the product as a means of reducing the bitterness of pharmacological drugs in tablet form, and Neohesperidin dihydrochalcone has been used for livestock feed as a means of reducing feeding time.
Neohesperidin dihydrochalcone is also widely favoured for use in otherwise naturally bitter products.
Enhancer
As a flavour enhancer, NHDC is used in a wide range of products and is indicated by the E number E 959.
Neohesperidin dihydrochalcone 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 NHDC 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. NHDC is also used as excipient in drug products to mask the bitter taste of some active pharmaceutical ingredients.
PRODUCERS AND MANUFACTURERS OF NEOHESPERIDIN:
Bordas company manufactures Neohesperidin DC as we have great experience with the treatment and processing of fruits, in particular citrus fruits.
The citrus fruits are Bordas raw materials for the synthesis of many of our products, both in the field of fruit derivatives:
• Candied
• Cells
• Concentrates
• Dehydrates
• Juices
• Peels
• Pulps
• Purees
• Slices
and in the extraction and manufacturing of functional ingredients:
• Diosmin
• Hesperidin
• Naringin
• Citrus Bioflavonoides Complex (CBC)
• Neohesperidin DC
All these raw materials come mainly from Bordas owned farms of bitter orange in Seville, which allows us to have a total control of the quality and traceability of each product.
CERTIFIED PRODUCT QUALITY:
Years of experience guarantee the quality of the products and processes of production in Bordas. NEOHESPERIDIN DC manufacturing, as well as all our finished products, meets international quality standards.
Through a correct selection of each raw material and an optimization of the production process, in which our R&D department works constantly, Bordas manufacture safe high quality tailor-made products.
PROPERTIES AND CHARACTERISTICS OF NEOHESPERIDIN DC:
Worldwide approved food additive: Neohesperidin DC is approved as a food additive in Europe (E-959 code), being regulated according to the food categories where it is used.
In addition, its use is also approved and regulated in the United States and Japan.
High sweetening power: Neohesperidin DC has a sweetness intensity around 1800 times compared to sucrose at threshold levels
Taste Enhancer: In addition to its sweetening power, Neohesperidin DC can also act as a product flavour enhancer.
Masking agent: Neohesperidin DC is also known as a less pleasant taste masking agent.
This property differentiates it from the rest of the alternative sweeteners used in the industry.
Pleasant to taste: The organoleptic profile of NEOHESPERIDIN DC is characterized by an intense sweet taste.
Using high concentrations, NEOHESPERIDIN DC presents an aftertaste with notes similar to liquorice.
Persistence: As an intensive sweetener, NEOHESPERIDIN DC has a very characteristic intensity-time profile.
Due to this, NEOHESPERIDIN DC produces a longer and more persistent sweetness sensation.
Synergistic effects: Neohesperidin DC has remarkable synergistic effects used together with other sweeteners currently used in the food industry.
These synergistic effects have been widely corroborated in different studies.
Final product unaltered: Many studies have proven that Neohesperidin DC, even improving the taste and flavour organoleptic properties, does not alter other organoleptic characteristics such as the smell of the product.
Stability: Neohesperidin DC is stable under normal processing and storage conditions of foods with a solubility at room temperature of 0.4 g / L, although this increases exponentially with the temperature reaching values up to 650 g / L at 80 ° C.
However, this is far to be an inconvenience for its use, due to that just ppm quantity of it is required to achieve perceptible effects.
Healthy: Neohesperidin DC is a sweetener that does not provide calories and has a zero glycemic index.
NEOHESPERIDIN DC ADVANTAGES AND BENEFITS RESPECT TO OTHER SWEETENERS:
Versatility: NEOHESPERIDIN DC has a particular feature since, in addition to NEOHESPERIDIN DC’s use as a sweetener in food formulations NEOHESPERIDIN DC can also act as a flavour enhancer as well as a masking agent, which makes NEOHESPERIDIN DC different from the rest of alternative sweeteners used in the industry.
Pleasant taste: Its pleasant and intense sweet taste makes Neohesperidin widely accepted in different applications and sectors, always pleasing the final consumer.
Flavour enhancer: As a flavour enhancer, NEOHESPERIDIN DC works by increasing fruit and cocoa derivatives flavours.
Masking agent: As a masking agent, NEOHESPERIDIN DC reduces undesirable flavours in different food formulations such as acidity, bitterness, etc.
Low concentrations: Neohesperidin DC is one of the sweeteners of natural origin with higher sweetness intensity.
Better consumer experience: The persistence of the pleasant taste in mouth of Neohesperidin DC is longer than the rest of sweeteners, making the intake more enjoyable for the final consumer.
Pleasant to the palate: Neohesperidin DC improves the sensation and texture in mouth, providing creaminess to different food formulations.
Healthy: Both, the caloric intake of Neohesperidin DC and its glycemic index, are zero.
This advantage allows the use of Neohesperidin DC in more products than other sweeteners, including products addressed to population that suffer pathologies associated with obesity or metabolic syndrome.
Stability: NEOHESPERIDIN DC’s high stability at different temperatures allows the NEOHESPERIDIN DC to be used in different sectors and in different stages of the production process.
Economic: NEOHESPERIDIN DC’s versatility as a sweetener, enhancer or flavour masker using effective quantities of the order of ppm, less than other known sweeteners would require, makes NEOHESPERIDIN DC an economic food ingredient.
Costs savings: Neohesperidin DC has the capacity of achieving its desired effects using low quantities of it, and has also synergistic effects with other more expensive sweeteners.
That allows to reach, with a smaller amount of the usual more expensive sweetener and a small amount of NEOHESPERIDIN DC, a similar taste effect for which it would be required higher amount of the usual individual sweetener.
NEOHESPERIDIN DC APPLICATIONS
Neohesperidin DC is recognised as a multitask, economic and stable solution to different challenges in many sectors.
Due to its versatility as a food additive, Neohesperidin DC can be used in different food industries and with different desired effects:
1. As sweetener and taste enhancer, Neohesperidin is widely used in:
• Desserts, ice cream and dairy products.
• Confectionery.
• Beverage, soft drinks and juice industries.
• Candies.
2. NEOHESPERIDIN DC’s flavour enhancing power is highly appreciated in the following industries:
• Sauces and soups.
• Animal feed and health industries.
3. In the pharmaceutical industry, Neohesperidin DC is used primarily as a masking agent.
4. Personal care products such as mouth rinses, toothpastes use NEOHESPERIDIN DC flavonoid thanks to its sweetening effect.
Roles Classification of Neohesperidin DC:
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Sweetening agent: Substance that sweeten food, beverages, medications, etc.
Xenobiotic: A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism.
Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Chemical and Physical Properties of NHDC:
Molecular Weight: 612.6 g/mol
XLogP3-AA: -0.3
Hydrogen Bond Donor Count: 9
Hydrogen Bond Acceptor Count: 15
Rotatable Bond Count: 10
Exact Mass: 612.20542044 g/mol
Monoisotopic Mass: 612.20542044 g/mol
Topological Polar Surface Area: 245 Ų
Heavy Atom Count: 43
Formal Charge: 0
Complexity: 882
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Melting Point: 313 to 313 °F
storage conditions:
Powder: temperature: -20°C time: 3 years
Temperature: 4°C time: 2 years
In solvent: temperature: -80°C time: 6 months
Temperature: -20°C time:1 month
Appearance: white to pale yellow powder (est)
Physical State : Solid
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)
Odor Type: odorless
Odor Strength:none
Odor Description:at 100.00 %. bland odor
Odor sample from: CA Aromatics Company Inc.
Odor Description:No apparent odor
Flavor Type: sweet
licorice sweet
Taste Description: at 10.00 ppm.
Licorice-like with a lingering sweetness
Shipping: Room temperature in continental US; may vary elsewhere.
Solvent & Solubility:
1.Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% saline
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
2.Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in saline)
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
3.Add each solvent one by one: 10% DMSO 90% corn oil
Solubility: ≥ 2.5 mg/mL (4.08 mM); Clear solution
SAFETY INFORMATION:
FIRST AID MEASURES
Description of First Aid Measures
If Neohesperidin dihydrochalcone is Inhaled:
If inhaled, move person to fresh air.
If not breathing, give artificial respiration and consult a physician.
In Case of Skin Contact:
Wash affected area with soap and water.
Consult a physician if any exposure symptoms are observed.
In Case of Eye Contact:
Immediately rinse eyes with plenty of water for at least 15 minutes.
Consult a physician.
If Neohesperidin dihydrochalcone is Swallowed:
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Do NOT induce vomiting unless advised to do so by a physician or Poison Control Center.
Seek medical attention.
Most Important Symptoms and Effects, Both Acute and Delayed:
The most important known symptoms and effects are described in the labeling
FIREFIGHTING MEASURES
Extinguishing Media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special Hazards Arising from the Substance or Mixture:
Carbon oxides
Advice for Firefighters:
Wear self contained breathing apparatus for fire fighting if necessary.
ACCIDENTAL RELEASE MEASURES:
Personal precautions:
Wear respiratory protection.
Avoid dust formation.
Avoid breathing vapours, mist or gas.
Ensure adequate ventilation.
Evacuatepersonnel to safe areas.
Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Method and materials for containment and cleaning up
Pick up and arrange disposal without creating dust.
Sweep up and shovel.
Keep in suitable, closed containers for disposal.
HANDLING AND STORAGE:
Precautions for safe handling
Avoid contact with skin and eyes.
Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage:
Keep container tightly closed in a dry and well-ventilated place.
Keep in a dry place.
Specific End Uses:
For scientific research and development only.
Not for use in humans or animals.
EXPOSURE CONTROLS/PERSONAL PROTECTION:
Control Parameters:
Contains no components with established occupational exposure limits.
Appropriate Engineering Controls:
A laboratory fumehood or other appropriate form of local exhaust ventilation should be used to avoid exposure.
Personal Protective Equipment:
All recommendations below are advisory in nature and a risk assessment should be performed by the employer/end user prior to use of Neohesperidin dihydrochalcone.
The type of protective equipment must be selected based on the amount and concentration of the dangerous material being used in the workplace.
Exposure Controls:
Storage conditions: -20˚C Freezer
Eye/Face Protection:
Safety goggles or face shield.
All equipment should have been tested and approved under appropriate standards, such as NIOSH
(US), CSA (Canada), or EN 166 (EU).
Skin Protection:
Gloves should be used when handling this material.
Gloves are to be inspected prior to use.
Contaminated gloves are to be removed using proper glove removal technique so that the outer surface of the glove does not contact bare skin.
Dispose of contaminated gloves after use in compliance with good laboratory practices and local requirements.
Gloves used for incidental exposures (splash protection) should be designated as “chemical resistant” by EU standard EN 374 with the resistance codes corresponding to the anticipated use of the material.
Unrated gloves are not recommended.
Suggested gloves: AnsellPro Sol-Vex nitrile gloves style 37-175, 15 mil thickness.
Penetration time has not been determined.
Gloves used for prolonged direct exposure (immersion) should be designated “chemical resistant” as per EN 734 with the resistance codes corresponding to the anticipated use of the material.
Suggested gloves: AnsellPro Viton/Butyl gloves style 38-612, 4/8 mil thickness.
Penetration time has not been determined.
These recommendations may not apply if the material is mixed with any other chemical, or dissolved into a solution.
A risk assessment must be performed to ensure the gloves will still offer acceptable protection.
Body Protection:
Fire resistant (Nomex) lab coat or coveralls.
Respiratory Protection:
Recommended respirators are NIOSH-approved N100 or CEN-approved FFP3 particulate respirators. These are to be only used as a backup to local exhaust ventilation or other engineering controls.
If the respirator is the only means of protection, a full-face supplied air respirator must be used.
SYNONYMS OF Neohesperidin Dihydrochalcone
MeSH Entry Terms:
neohesperidin dihydrochalcone
neohesperidine DC
neohesperidine dihydrochalcone
Depositor-Supplied Synonyms:
neohesperidin dihydrochalcone
20702-77-6
Nhdc
Neohesperidin dc
Neohesperidin dhc
Neohesperidine dihydrochalcone
Neohesperidine
Neosperidin dihydrochalcone
NCI-C60764
UNII-3X476D83QV
neohesperidin dihydrochalone
Neohesperidin-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
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)-
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
Neohesperidin Dihydrochalcone (Nhdc)
C28H36O15
Neosperidin-dihydrochalcone
DSSTox_CID_5706
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
ITVGXXMINPYUHD-CUVHLRMHSA-
HMS3884H13
HY-N0154
ZINC4175639
Tox21_200303
MFCD00017711
s2331
1-(4-((2-O-[6-Deoxy-&alpha
AKOS015895239
CCG-270237
CS-6419
NCGC00091109-01
NCGC00091109-02
NCGC00091109-04
NCGC00257857-01
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-
O413
Neohesperidin dihydrochalcone, >=96%, FG
CAS-20702-77-6
N0675
Neohesperidin dihydrochalcone, >=95% (HPLC)
Neohesperidin dihydrochalcone, analytical standard
702N776
A814825
Q424595
SR-01000883756
Q-201457
SR-01000883756-1
BRD-K61032563-001-02-9
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-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone
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
