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Neohesperidin

From Wikipedia, the free encyclopedia
Neohesperidin
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 Edit this at Wikidata
KEGG
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 Flavor and Extract Manufacturers Association.[2]

UV 280 nm chromatogram after UHPLC separation of commercial orange juice

References

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  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.
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