 | |
| 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 |
| E number | E959(glazing agents, ...) |
| UNII | |
| |
| |
| Properties | |
| C28H36O15 | |
| Molar mass | 612.58 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Neohesperidin dihydrochalcone, sometimes abbreviated toneohesperidin DC or simplyNHDC, is anartificial sweetener derived fromcitrus.
It is particularly effective in masking the bitter tastes of other compounds found in citrus, includinglimonin andnaringin. Industrially, it is produced by extracting neohesperidin from thebitter orange, and then hydrogenating this to make NHDC.
NHDC was discovered during the 1960s as part of aUnited 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 withpotassium hydroxide or another strong base, and thencatalyticallyhydrogenated, it becomes NHDC.
NHDC in pure form is found as a white substance not unlikepowdered sugar. It has an intense sweet taste because it stimulates the sweet receptorTAS1R2+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 thepH of the product.
Like other highly sweetglycosides, such asglycyrrhizin and those found instevia, NHDC's sweet taste has a slower onset than sugar's and lingers in the mouth for some time.
Unlikeaspartame, 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 otherartificial sweeteners such asaspartame,saccharin,acesulfame potassium, andcyclamate, as well as sugar alcohols such asxylitol. 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 theEuropean Union as sweetener (E-959) since 1994, as well as flavouring (FL-16.061). It is also listed as agenerally recognized as safe (GRAS) flavour enhancer by theFlavor and Extract Manufacturers Association.[3]
In November 2020,[4] theFDA issued a no objection letter to the GRAS status of Neohesperidin dihydrochalcone (NHDC). TheFDA 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 inEuropean Pharmacopoeia andUnited States Pharmacopeia, for being used asexcipient 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 theEuropean Food Safety Agency in 2022. Theacceptable daily intake was set at 20 mg/kg of body weight.[8]
In food it is used as aflavour enhancer in concentrations of around 4–5parts per million (ppm) and as anartificial sweetener at around 15–20 ppm.
Pharmaceutical companies are fond of the product as a means of reducing the bitterness ofpharmacologicaldrugs intablet form, and it has been used forlivestock feed as a means of reducing feeding time. It is also widely favoured for use in otherwise naturallybitter products.
As aflavour enhancer, NHDC is used in a wide range of products and is indicated by theE number E 959. It is noted particularly for enhancingsensory effects (known in the industry as 'mouth feel'). An example of this is 'creaminess' indairy foods such asyogurt andice cream.
Other products NHDC can be found in may include a wide variety of beverages,alcoholic and non-alcoholic,savoury foods,toothpaste,mouthwash andcondiments such asketchup andmayonnaise. NHDC is also used asexcipient in drug products to mask the bitter taste of someactive pharmaceutical ingredients.
Media related toNeohesperidin dihydrochalcone at Wikimedia Commons
