Neohesperidin dihydrochalcone

Last updated
Neohesperidin dihydrochalcone [1]
Neohesperidin dihydrochalcone.png
Names
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 OOjs UI icon edit-ltr-progressive.svg
E number E959 (glazing agents, ...)
PubChem CID
UNII
  • InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1 X mark.svgN
    Key: ITVGXXMINPYUHD-CUVHLRMHSA-N X mark.svgN
  • InChI=1/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
    Key: ITVGXXMINPYUHD-CUVHLRMHBZ
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC)O)O)CO)O)O)O)O)O
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.

Contents

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.

Discovery

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. 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.

Approval and safety

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]

Uses

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.

Masking

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.

Enhancer

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 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.

Related Research Articles

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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.

<span class="mw-page-title-main">Flavoring</span> Food additive used to change its aroma or taste

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<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

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.

<span class="mw-page-title-main">Sucralose</span> Non-nutritive sweetener

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<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

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<span class="mw-page-title-main">Cyclamate</span> Chemical compound

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<span class="mw-page-title-main">Saccharin</span> Chemical compound

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.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

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
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

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<span class="mw-page-title-main">Diet Pepsi</span> Sugar-free, artificially sweetened soda

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<span class="mw-page-title-main">Sweetness</span> Basic taste

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References

  1. Merck Index , 11th Edition, 6367.
  2. 1 2 Winnig, Marcel; Bufe, Bernd; Kratochwil, Nicole A.; Slack, Jay P.; Meyerhof, Wolfgang (2007-10-12). "The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor". BMC Structural Biology. 7 (1): 66. doi: 10.1186/1472-6807-7-66 . ISSN   1472-6807. PMC   2099433 . PMID   17935609.
  3. Cohen, S.M.; et al. (July 2018). "GRAS 28 Flavoring Substances" (PDF). FEMA. Retrieved 2018-08-08.
  4. "GRAS Notices". www.cfsanappsexternal.fda.gov. Retrieved 2021-01-08.
  5. Fennema's Food Chemistry , 4th Edition, 722.
  6. Food Additive User's Handbook , J. Smith, 1st Edition, 70.
  7. EFSA Flavouring Group Evaluation 32 Scientific Opinion , EFSA Journal 2010; 8(9):1065
  8. EFSA Panel on Food Additives and Flavourings (FAF); Younes, Maged; Aquilina, Gabriele; Castle, Laurence; Degen, Gisela; Engel, Karl-Heinz; Fowler, Paul J; Frutos Fernandez, Maria José; Fürst, Peter; Gundert-Remy, Ursula; Gürtler, Rainer; Husøy, Trine; Manco, Melania; Mennes, Wim; Moldeus, Peter (November 2022). "Re-evaluation of neohesperidine dihydrochalcone (E 959) as a food additive". EFSA Journal. 20 (11): e07595. doi:10.2903/j.efsa.2022.7595. PMC   9669802 . PMID   36406883.