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Neohesperidin dihydrochalcone

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Neohesperidin dihydrochalcone[1]

Names

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-methyl-2-

tetrahydropyranyl]oxy]-2-tetrahydropyranyl]oxy]-2,6-

dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one

Identifiers

CAS Number 20702-77-6

ChEBI CHEBI:83535

ChemSpider 28072

ECHA InfoCard 100.039.965

Jmol 3D model Interactive image

PubChem 30231

InChI[show]

SMILES[show]
Properties

Chemical formula 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).

verify (what is ?)

Infobox references

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


is an artificial sweetenerderived from citrus.
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, a compound roughly
1500-1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than
sugar weight-for-weight. 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 European Union approved NHDC's use as a sweetener in 1994. It has not been approved as a
sweetener in the United States. It is sometimes said that NHDC is considered a Generally
Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association, which
is a trade group with no legal standing. NHDC has never appeared on the FDA's GRAS listing.
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.
The product is well known for having a strong synergistic effect when used in conjunction with
other artificial sweeteners such asaspartame, 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.
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 yogurtand ice cream, but is also
widely favoured for use in otherwise naturally bitter products. 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. Other products NHDC can be
found in may include a wide variety of alcoholic beverages (and non-
alcoholic), savoury foods, toothpaste, mouthwash and condiments such
as ketchup and mayonnaise.
NHDC in pure form is found as a white substance not unlike powdered sugar. 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.
Research has shown that at strengths of around and above 20 ppm, NHDC can produce side effects
such as nausea and migraine. This is not widely documented, however is unquestionably known
within the food science communities that have worked with the product, and many recommend
wearing a surgical mask when handling pure NHDC.

Thaumatin
From Wikipedia, the free encyclopedia

Thaumatin family
Ribbon[1][2] diagram of thaumatin I. From PDB:1RQW.

Identifiers

Symbol Thaumatin

Pfam PF00314

InterPro IPR001938

SMART SM00205

PROSITE PDOC00286

SCOP 1thu

SUPERFAMILY 1thu

OPM superfamily 189

OPM protein 1aun

CDD cd09215

[show]Available protein structures:


Thaumatin I

Identifiers

Symbol THM1_THADA

PDB 1RQW More structures

UniProt P02883

Thaumatin II

Identifiers

Symbol THM2_THADA

UniProt P02884

Thaumatin is a low-calorie sweetener and flavour modifier. The protein is often used primarily for its
flavour-modifying properties and not exclusively as a sweetener.[3]
The thaumatins were first found as a mixture of proteins isolated from
the katemfe fruit (Thaumatococcus daniellii Bennett) of westAfrica. Some proteins in the thaumatin
family of sweeteners are roughly 2000 times more potent than sugar. Although very sweet,
thaumatin's taste is markedly different from sugar's. The sweetness of thaumatin builds very slowly.
Perception lasts a long time, leaving a liquorice-like aftertaste at high usage levels. Thaumatin is
highly water-soluble, stable to heating, and stable under acidic conditions.

Biological role[edit]
Thaumatin production is induced in katemfe in response to an attack upon the plant
by viroid pathogens. Several members of the thaumatin protein family display significant in
vitro inhibition of hyphal growth and sporulation by various fungi. The thaumatin protein is
considered a prototype for a pathogen-response protein domain. This thaumatin domain has been
found in species as diverse as rice and Caenorhabditis elegans. Thaumatins are pathogenesis-
related (PR) proteins, which are induced by various agents ranging from ethylene to pathogens, and
are structurally diverse and ubiquitous in plants:[4] They include thaumatin, osmotin, tobacco major
and minor PR proteins, alpha-amylase/trypsin inhibitor, and P21 and PWIR2 soybean and wheat leaf
proteins. The proteins are involved in systematically acquired resistance and stress response in
plants, although their precise role is unknown.[4] Thaumatin is an intensely sweet-tasting protein (on a
molar basis about 100,000 times as sweet as sucrose[5]) found in the West African
shrub Thaumatococcus daniellii: it is induced by attack by viroids, which are single-stranded
unencapsulated RNA molecules that do not code for protein. The thaumatin protein I consists of a
single polypeptide chain of 207 residues.
Like other PR proteins, thaumatin is predicted to have a mainly beta structure, with a high content of
beta-turns and little helix.[4]Tobacco cells exposed to gradually increased salt concentrations develop
a greatly increased tolerance to salt, due to the expression of osmotin,[6] a member of the PR protein
family. Wheat plants attacked by barley powdery mildew express a PR protein (PWIR2), which
results in resistance against that infection.[7] The similarity between this PR protein and other PR
proteins to the maize alpha-amylase/trypsin inhibitor has suggested PR proteins may act as some
form of inhibitor.[7]
The thaumatin-like proteins isolated from kiwi fruit or apple appear to have their allergenic properties
minimally reduced by gastroduodenal digestive processes, but not by heating.[8][9]

Production[edit]

Thaumatin crystal (~1mm long) grown by liquidliquid diffusion under microgravity conditions in outer space.
Arrow marks nucleation point.[10]

Within West Africa, the katemfe fruit has been locally cultivated and used to flavor foods and
beverages for some time. The fruit's seeds are encased in a membranous sac, or aril, that is the
source of thaumatin. In the 1970s, Tate and Lyle began extracting thaumatin from the fruit. In 1990,
researchers at Unilever reported the isolation and sequencing of the two principal proteins found in
thaumatin, which they dubbedthaumatin I and thaumatin II. These researchers were also able to
express thaumatin in genetically engineered bacteria.
Thaumatin has been approved as a sweetener in the European Union (E957), Israel, and Japan. In
the United States, it is generally recognized as safe as a flavoring agent (FEMA GRAS 3732) but not
as a sweetener.

Crystallization of thaumatin[edit]
Since thaumatin crystallizes rapidly and easily in the presence of tartrate ions, thaumatin-tartrate
mixtures are frequently used as model systems to study protein crystallization. Interestingly, the
solubility of thaumatin, its crystal habit, and mechanism of crystal formation are dependent upon
the chirality of precipitant used. When crystallized with L- tartrate, thaumatin forms bipyramidal
crystals and displays a solubility that increases with temperature; with D- and meso-tartrate, it forms
stubby and prismatic crystals and displays a solubility that decreases with temperature.[11]This
suggests control of precipitant chirality may be an important factor in protein crystallization in
general.

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