Naringin dihydrochalcone

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Naringin dihydrochalcone
Naringin dihydrochalcone.svg
Names
IUPAC name
1-[4-[(3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2, 6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Systematic IUPAC name
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-L-glucopyranoside
Other names
Naringin DC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.127.977
PubChem CID
UNII
Properties
C27H34O14
Molar mass 582.555 g·mol−1
AppearanceWhite powder
Melting point 169 to 170 °C (336 to 338 °F; 442 to 443 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Naringin dihydrochalcone, sometimes abbreviated to naringin DC, is an artificial sweetener derived from naringin, a bitter compound found in citrus. [1]

Naringin dihydrochalcone is a phloretin glycoside discovered at the same time as neohesperidin dihydrochalcone 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.

When naringin is treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes a dihydrochalcone that is roughly 300–1800 times sweeter than sugar at threshold concentrations. [2]

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Citrus cavaleriei or Citrus ichangensis, the Ichang papeda, is a slow-growing species of papeda that has characteristic lemon-scented foliage and flowers.

Neohesperidin dihydrochalcone chemical compound

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

Bitter orange species of plant, Bitter orange

Bitter orange, Seville orange, sour 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 between the Pomelo, Citrus maxima, and the Mandarin orange, Citrus reticulata.

Jaffa orange Variety of orange fruit

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Bergamot orange nothospecies of plant, Bergamot orange

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Naringenin chemical compound

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.

Naringin chemical compound

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's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans naringin is metabolized to the aglycone naringenin by naringinase present in the gut.

Grapefruit–drug interactions

Some fruit juices and fruits can interact with numerous drugs, in many cases causing adverse effects. The effect was first discovered accidentally, when a test of drug interactions with alcohol used grapefruit juice to hide the taste of the ethanol.

Zest (ingredient) Scraped skin of citrus fruit

Zest is a food ingredient that is prepared by scraping or cutting from the rind of unwaxed citrus fruits such as lemon, orange, citron, and lime. Zest is used to add flavor to foods.

Orange (fruit) Citrus fruit

The orange is the fruit of various citrus species in the family Rutaceae ; it primarily refers to Citrus × sinensis, which is also called sweet orange, to distinguish it from the related Citrus × aurantium, referred to as bitter orange. The sweet orange reproduces asexually ; varieties of sweet orange arise through mutations.

Naringinase is a debittering enzyme that is used in the commercial production of citrus juices. It breaks down the compound naringin that gives citrus juices its bitter taste. It is a multienzyme complex which possesses alpha-L-rhamnosidase and beta glucosidase active centers. The E.C. No.(EC 3.2.1.40) of the naringinase and rhamnosidase are the same. First rhamnosidase breaks naringin into prunin and rhamnose. Lastly glucosidase breaks prunin into glucose and naringenin, a flavorless flavanone also found in various citrus.

Phloretin chemical compound

Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot.

Dihydrochalcone chemical compound

Dihydrochalcone (DHC) is a chemical compound related to chalcone.

Chōzaburō Tanaka or often Romanized as Tyôzaburô Tanaka was a Japanese botanist and mycologist. He established one of the two major taxonomic classification systems for citrus and related genera currently in use, and is now considered to be a taxonomic "splitter". He is the author of 180 botanical names in the citrus family Rutaceae, including for example Citrus × latifolia and Citrus tangerina (tangerine). Many of the species Tanaka described are still recognized, but his overall scheme is not supported by modern genetic research.

Narirutin chemical compound

Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose.

Neohesperidin chemical compound

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 Flavour and Extract Manufacturers' Association.

Prunin chemical compound

Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin.

References

  1. Ikan, R. (1991). "1-Flavonoides. E. Synthesis of Naringin Dihydrochalcone — A Sweetening Agent". Natural Products: A Laboratory Guide (2nd ed.). Academic Press. pp. 17–18. ISBN   0-12-370551-7.
  2. Tomasik, P., ed. (2003). Chemical and Functional Properties of Food Saccharides . Boca Raton: CRC Press. p.  389. ISBN   978-0-84-931486-5.