Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an

artificial sweetener A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie () or low-calorie sweetener. Artificial sweeteners may b ...

derived from

citrus ''Citrus'' is a genus of flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, lemons, grapefruits, pomelos, and limes. The genus ''Citrus'' is native to ...

. It is particularly effective in masking the bitter tastes of other compounds found in citrus, including

limonin Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as fu ...

and

naringin Naringin is a flavanone-7-''O''- glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit' ...

. Industrially, it is produced by extracting neohesperidin from the

bitter orange Bitter orange, Seville orange, bigarade orange, or marmalade orange is the citrus tree ''Citrus'' × ''aurantium'' and its fruit. It is native to Southeast Asia and has been spread by humans to many parts of the world. It is probably a cross be ...

, and then hydrogenating this to make NHDC.

Discovery

NHDC was discovered during the 1960s as part of a

United States Department of Agriculture The United States Department of Agriculture (USDA) is the federal executive department responsible for developing and executing federal laws related to farming, forestry, rural economic development, and food. It aims to meet the needs of com ...

research program to find methods for minimizing the taste of bitter flavorants in citrus juices.

Neohesperidin Neohesperidin is a flavanone glycoside found in citrus fruits. It is the 7-O- neohesperidose derivative of hesperetin, which in turn is the 4'-methoxy derivative of eriodictyol. Neohesperidin dihydrochalcone Neohesperidin dihydrochalcone, sometim ...

is one such bitter compound. When treated with

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...

or another strong base, and then catalytically

hydrogenated Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

, it becomes NHDC.

Profile

NHDC in pure form is found as a white substance not unlike

powdered sugar Powdered sugar, also called confectioners' sugar, or icing sugar, is a finely ground sugar produced by milling granulated sugar into a powdered state. It usually contains between 2% and 5% of an anti-caking agent – such as corn starch, p ...

. It has an intense sweet taste because it stimulates the sweet receptor

TAS1R2 Taste receptor type 1 member 2 is a protein that in humans is encoded by the ''TAS1R2'' gene. The sweet taste receptor is predominantly formed as a dimer of T1R2 and T1R3 by which different organisms sense this taste. In songbirds, however, the T1 ...

TAS1R3 Taste receptor type 1 member 3 is a protein that in humans is encoded by the ''TAS1R3'' gene. The ''TAS1R3'' gene encodes the human homolog of mouse Sac taste receptor, a major determinant of differences between sweet-sensitive and -insensitive ...

in humans, although this is species-dependent, as the equivalent receptor in rats does not respond to the molecule. It 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

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycoside ...

s, such as

glycyrrhizin Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of ''Glycyrrhiza glabra'' ( liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmet ...

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. The product is well known for having a strong synergistic effect when used in conjunction with other

s such as aspartame,

saccharin Saccharin (''aka'' saccharine, Sodium sacchari) is an artificial sweetener with effectively no nutritional value. It is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is ...

, acesulfame potassium, and

cyclamate Cyclamate is an artificial sweetener. It is 30–50 times sweeter than sucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; ...

, as well as sugar alcohols such as

xylitol Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classifi ...

. 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

NHDC is approved in the

European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...

as sweetener (E-959) since 1994, as well as flavouring (FL-16.061). It is also listed as a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association. In November 2020, the

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

issued a no objection letter to the Generally Recognized as Safe status of Neohesperidin dihydrochalcone (NHDC).

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 The ''European Pharmacopoeia'' (''Pharmacopoeia Europaea'', ''Ph. Eur.'') is a major regional pharmacopoeia which provides common quality standards throughout the pharmaceutical industry in Europe to control the quality of medicines, and the su ...

and

United States Pharmacopoeia The ''United States Pharmacopeia'' (''USP'') is a pharmacopeia (compendium of drug information) for the United States published annually by the United States Pharmacopeial Convention (usually also called the USP), a nonprofit organization that ...

, for being used as

excipient An excipient is a substance formulated alongside the active ingredient of a medication, included for the purpose of long-term stabilization, bulking up solid formulations that contain potent active ingredients in small amounts (thus often referred ...

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. The safety of NHDC 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.

Uses

In food it is used as a

flavour enhancer A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gust ...

in concentrations of around 4-5

parts per million In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, th ...

(ppm) and as an

at around 15-20 ppm.

Masking

Pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field an ...

companies are fond of the product as a means of reducing the bitterness of

pharmacological Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...

drugs in tablet form, and it has been used for

livestock Livestock are the domesticated animals raised in an agricultural setting to provide labor and produce diversified products for consumption such as meat, eggs, milk, fur, leather, and wool. The term is sometimes used to refer solely to animal ...

feed as a means of reducing feeding time. It is also widely favoured for use in otherwise naturally

bitter Bitter may refer to: Common uses * Resentment, negative emotion or attitude, similar to being jaded, cynical or otherwise negatively affected by experience * Bitter (taste), one of the five basic tastes Books * '' Bitter (novel)'', a 2022 nove ...

products.

Enhancer

As a

, NHDC is used in a wide range of products and is indicated by the E number E 959. It 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 Yogurt (; , from tr, yoğurt, also spelled yoghurt, yogourt or yoghourt) is a food produced by bacterial fermentation of milk. The bacteria used to make yogurt are known as ''yogurt cultures''. Fermentation of sugars in the milk by these bac ...

and

ice cream Ice cream is a sweetened frozen food typically eaten as a snack or dessert. It may be made from milk or cream and is flavoured with a sweetener, either sugar or an alternative, and a spice, such as cocoa or vanilla, or with fruit such as ...

Other uses

Other products NHDC can be found in may include a wide variety of beverages,

alcoholic Alcoholism is, broadly, any drinking of alcohol that results in significant mental or physical health problems. Because there is disagreement on the definition of the word ''alcoholism'', it is not a recognized diagnostic entity. Predomina ...

and non-alcoholic, savoury foods,

toothpaste Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, ...

mouthwash Mouthwash, mouth rinse, oral rinse, or mouth bath is a liquid which is held in the mouth passively or swilled around the mouth by contraction of the perioral muscles and/or movement of the head, and may be gargled, where the head is tilted back ...

and

condiment A condiment is a preparation that is added to food, typically after cooking, to impart a specific flavor, to enhance the flavor, or to complement the dish. A table condiment or table sauce is more specifically a condiment that is served separat ...

s such as

ketchup Ketchup or catsup is a table condiment with a sweet and tangy flavor. The unmodified term ("ketchup") now typically refers to tomato ketchup, although early recipes used egg whites, mushrooms, oysters, grapes, mussels, or walnuts, among o ...

and mayonnaise. NHDC is also used as

in drug products to mask the bitter taste of some

active pharmaceutical ingredients An active ingredient is any ingredient that provides biologically active or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease or to affect the structure or any function of the body of humans or animals. The ...

References

Internal link

* Naringin dihydrochalcone

External links

*
EVESA
{{Dihydrochalcone Sugar substitutes Food additives Dihydrochalcone glycosides E-number additives