Names | |
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IUPAC name 1-{2,6-Dihydroxy-4-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]phenyl}-3-(3-hydroxy-4-methoxyphenyl)propan-1-one | |
Systematic IUPAC name (12S,13R,14R,15R,16S,32S,33R,34S,35S,36R)-13,14,15,34,35,53,55,93-Octahydroxy-36-(hydroxymethyl)-94-methoxy-16-methyl-2,4-dioxa-1(2),3(3,2)-bis(oxana)-5(1,4),9(1)-dibenzenanonaphan-6-one | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.039.965 |
E number | E959 (glazing agents, ...) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C28H36O15 | |
Molar mass | 612.58 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.
It is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin. Industrially, it is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC.
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.
NHDC in pure form is found as a white substance not unlike powdered sugar. It has an intense sweet taste because it stimulates the sweet receptor TAS1R2+TAS1R3 in humans, [2] although this is species-dependent, as the equivalent receptor in rats does not respond to the molecule. [2]
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 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.
The product 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.
NHDC is approved in the European Union as sweetener (E-959) since 1994, as well as flavouring (FL-16.061). It is also listed as a generally recognized as safe (GRAS) flavour enhancer by the Flavor and Extract Manufacturers Association. [3]
In November 2020, [4] the FDA issued a no objection letter to the GRAS status of Neohesperidin dihydrochalcone (NHDC). The FDA concluded that NHDC is GRAS (based on scientific procedures) for its intended use 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 Pharmacopeia, for being used as excipient in drug products.
The safety of NHDC has been extensively tested. [5] Safety studies have indicated that NHDC is neither toxic, mutagenic nor carcinogenic. [6] Like other flavonoids, NHDC is easily metabolized by intestinal microbiota to innocuous products. [7]
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. [8]
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.
Pharmaceutical companies are fond of the product 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. It is also widely favoured for use in otherwise naturally bitter products.
As a flavour enhancer, 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 and ice cream.
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.
Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.
A flavoring, also known as flavor 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 gustatory and olfactory systems. Along with additives, other components like sugars determine the taste of food.
Stevia is a sweet sugar substitute that is about 50 to 300 times sweeter than sugar. It is extracted from the leaves of Stevia rebaudiana, a plant native to areas of Paraguay and Brazil. The active compounds in stevia are steviol glycosides. Stevia is heat-stable, pH-stable, and not fermentable. Humans cannot metabolize the glycosides in stevia, and it therefore has zero calories. Its taste has a slower onset and longer duration than that of sugar, and at high concentrations some of its extracts may have an aftertaste described as licorice-like or bitter. Stevia is used in sugar and calorie-reduced food and beverage products as an alternative for variants with sugar.
Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds very little food energy. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose, 3 times as sweet as both aspartame and acesulfame potassium, and 2 times as sweet as sodium saccharin.
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 be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.
Cyclamate is an artificial sweetener. It is 30–50 times sweeter than sucrose, making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; the mixture of 10 parts cyclamate to 1 part saccharin is common and masks the off-tastes of both sweeteners. It is less expensive than most sweeteners, including sucralose, and is stable under heating. Safety concerns led to it being banned in a few countries, though the European Union considers it safe.
Saccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a sultam that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products, such as drinks, candies, baked goods, tobacco products, excipients, and for masking the bitter taste of some medicines. It appears as white crystals and is odorless.
Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. Acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4H
4KNO
4S and a molecular weight of 201.24 g/mol.
Diet sodas are soft drinks which contain little or no sugar or calories. First introduced onto the market in 1949, diet sodas are typically marketed for those with diabetes or who wish to reduce their sugar or caloric intake.
Neotame, also known by the brand name Newtame, is a non-caloric artificial sweetener and aspartame analog by NutraSweet. By mass, it is 7,000 to 13,000 times sweeter than sucrose. It has no notable off-flavors when compared to sucrose. It enhances original food flavors. It can be used alone, but is often mixed with other sweeteners to increase their individual sweetness and decrease their off-flavors. It is chemically somewhat more stable than aspartame. Its use can be cost effective in comparison to other sweeteners as smaller amounts of neotame are needed.
Diet Pepsi, currently stylised in all caps as PEPSI DIET, is a diet carbonated cola soft drink produced by PepsiCo, introduced in 1964 as a variant of Pepsi with no sugar. First test marketed in 1963 under the name Patio Diet Cola, it was re-branded as Diet Pepsi the following year, becoming the first diet cola to be distributed on a national scale in the United States. In the 1960s and 1970s, its competition consisted of the Coca-Cola Company's subsequently discontinued Tab. The United States represents the largest single market for Diet Pepsi.
Lactisole is the sodium salt and commonly supplied form of 2-(4-methoxyphenoxy)propionic acid, a natural carboxylic acid found in roasted coffee beans. Like gymnemic acid, it has the property of masking sweet flavors and is used for this purpose in the food industry.
Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, and sugar alcohols. Some are sweet at very low concentrations, allowing their use as non-caloric sugar substitutes. Such non-sugar sweeteners include saccharin, aspartame, sucralose and stevia. Other compounds, such as miraculin, may alter perception of sweetness itself.
Siraitia grosvenorii, also known as monk fruit, monkfruit, luó hàn guǒ, or Swingle fruit, is a herbaceous perennial vine of the gourd family, Cucurbitaceae. It is native to southern China. The plant is cultivated for its fruit extract containing mogrosides. Mogroside extract has been used as a low-calorie sweetener for drinks and in traditional Chinese medicine. One mogroside, mogroside V, creates a sweetness sensation 250 times stronger than sucrose.
D-Psicose (C6H12O6), also known as D-allulose or simply allulose, is an epimer of fructose that is used by some commercial food and beverage manufacturers as a low-calorie sweetener. Allulose occurs naturally in small quantities in a variety of foods. It was first identified in the 1940s, although the enzymes needed to produce it on an industrial scale were not discovered until the 1990s.
The artificial sweetener aspartame has been the subject of several controversies since its initial approval by the U.S. Food and Drug Administration (FDA) in 1974. The FDA approval of aspartame was highly contested, beginning with suspicions of its involvement in brain cancer, alleging that the quality of the initial research supporting its safety was inadequate and flawed, and that conflicts of interest marred the 1981 approval of aspartame, previously evaluated by two FDA panels that concluded to keep the approval on hold before further investigation. In 1987, the U.S. Government Accountability Office concluded that the food additive approval process had been followed properly for aspartame. The irregularities fueled a conspiracy theory, which the "Nancy Markle" email hoax circulated, along with claims—counter to the weight of medical evidence—that numerous health conditions are caused by the consumption of aspartame in normal doses.
T1R2 - Taste receptor type 1 member 2 is a protein that in humans is encoded by the TAS1R2 gene.
Naringin dihydrochalcone, sometimes abbreviated to naringin DC, is an artificial sweetener derived from naringin, a bitter compound found in citrus.
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 has an intense sweet taste, and is listed as a generally recognized as safe flavour enhancer by the Flavor and Extract Manufacturers Association.
Advantame is a non-caloric artificial sweetener and aspartame analog by Ajinomoto. By mass, it is about 20,000 times sweeter than sucrose and about 110 times sweeter than aspartame. It has no notable off-flavors when compared to sucrose and tastes sweet a bit longer than aspartame and is chemically more stable. It can be blended with many other natural and artificial sweeteners.