Neohesperidin

Last updated
Neohesperidin
Neohesperidin.svg
Names
IUPAC name
(2S)-3′,5-Dihydroxy-4′-methoxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavan-4-one
Systematic IUPAC name
(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Hesperetin 7-O-neohesperidoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.032.910 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
    Key: ARGKVCXINMKCAZ-UZRWAPQLSA-N
  • InChI=1/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
    Key: ARGKVCXINMKCAZ-UZRWAPQLBV
  • 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(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)CO)O)O)O)O)O
Properties
C28H34O15
Molar mass 610.565 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Neohesperidin is a flavanone glycoside found in citrus fruits. [1] 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. [2]

UV 280 nm chromatogram after UHPLC separation of commercial orange juice Orange juice UHPLC UV chromatogram.png
UV 280 nm chromatogram after UHPLC separation of commercial orange juice

Related Research Articles

<span class="mw-page-title-main">Gin</span> Distilled alcoholic drink flavoured with juniper

Gin is a distilled alcoholic drink that derives its flavour from juniper berries and other botanical ingredients.

<span class="mw-page-title-main">Kumquat</span> Species of small fruit-bearing tree

Kumquats, or cumquats in Australian English, are a group of small fruit-bearing trees in the flowering plant family Rutaceae. Their taxonomy is disputed. They were previously classified as forming the now-historical genus Fortunella or placed within Citrus, sensu lato. Different classifications have alternatively assigned them to anywhere from a single species, C. japonica, to numerous species representing each cultivar. Recent genomic analysis would define three pure species, Citrus hindsii, C. margarita and C. crassifolia, with C. x japonica being a hybrid of the last two.

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

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

<span class="mw-page-title-main">Earl Grey tea</span> Tea blend flavoured with oil of bergamot

Earl Grey tea is a tea blend which has been flavoured with oil of bergamot. The rind's fragrant oil is added to black tea to give Earl Grey its unique taste. Traditionally, Earl Grey was made from black teas such as Chinese keemun, and therefore intended to be served without milk. Some blend the tea with lapsang souchong tea which lends a smoky character. Other varieties have been introduced as well, such as green or oolong.

<span class="mw-page-title-main">Coriander</span> Annual herb

Coriander, also known as cilantro, is an annual herb in the family Apiaceae. All parts of the plant are edible, but the fresh leaves and the dried seeds are the parts most traditionally used in cooking.

<span class="mw-page-title-main">Polo (confectionery)</span> Mint confectionery

Polo is a brand of breath mint whose defining feature is the hole in the middle. The peppermint flavoured Polo was first manufactured in the United Kingdom in 1948, by employee John Bargewell at the Rowntree's Factory, York, and a range of flavours followed. The name may derive from "polar", referencing the cool, fresh taste of the mint. Polo mints are also sold in other countries such as India and Sri Lanka by Nestlé. Polo mints are usually sold in a 34g pack containing 23 individual mints.

Horilka is a Ukrainian alcoholic beverage.

<span class="mw-page-title-main">Kofola</span>

Kofola is a carbonated soft drink produced by the eponymous Czech company, which is headquartered in Krnov, Czech Republic. It is the principal rival of Coca-Cola and Pepsi in the Czech Republic and Slovakia. The company is one of the leading soft drink producers and distributors in Central and Eastern Europe.

<span class="mw-page-title-main">Bergamot orange</span> Cultivated variety of citrus fruit

Citrus bergamia, the bergamot orange, is a fragrant citrus fruit the size of an orange, with a yellow or green color similar to a lime, depending on ripeness.

<span class="mw-page-title-main">Mandarinquat</span> Hybrid Species of fruit and plant

The mandarinquat, also misleadingly called orangequat, is any cross between a mandarin and a kumquat. Mandarinquats are members of the citrofortunella group.

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

Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin are not found to a significant extent in Citrus spp.

<i>Citrus glauca</i> Species of plant

Citrus glauca, commonly known as the desert lime, is a thorny shrub or small tree native to Queensland, New South Wales, and South Australia. The 1889 book The Useful Native Plants of Australia records common names native kumquat and desert lemon.

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

Neohesperidose is the disaccharide which is present in some flavonoids. It can be found in species of Typha.

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

Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs.

<span class="mw-page-title-main">Bergamot essential oil</span> Cold-pressed essential oil

Bergamot essential oil is a cold-pressed essential oil produced by cells inside the rind of a bergamot orange fruit. It is a common flavoring and top note in perfumes. The scent of bergamot essential oil is similar to a sweet light orange peel oil with a floral note.

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

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

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

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

References

  1. Rouseff, Russell L.; Martin, Shirley F.; Youtsey, Charles O. (1987). "Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus". Journal of Agricultural and Food Chemistry . 35 (6): 1027–1030. doi:10.1021/jf00078a040. ISSN   0021-8561.
  2. Cohen, S.M.; et al. (July 2018). "GRAS 28 Flavoring Substances" (PDF). FEMA. Retrieved 2018-08-08.