neohesperidin

Also known as (S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

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 Flavor and Extract Manufacturers Association.

Chemical data

Formula: C28H34O15
Molecular weight: 610.6 g/mol
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]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
SMILES: 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
InChIKey: ARGKVCXINMKCAZ-UZRWAPQLSA-N
XLogP: -0.5
Polar surface area: 234 Å²
H-bond donors: 8
H-bond acceptors: 15
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 610.18977

Show 6 more facts

canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)CO)O)O)O)O)O
found in taxon: Citrus japonica
chemical formula: C₂₈H₃₄O₁₅
isomeric SMILES: 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
Commons category: Neohesperidin
has characteristic: bitterness

Sources (2)

via Wikidata · CC0

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Encyclopedic overview

2 sections

Contents

References
External links

{{chembox | ImageFile= Neohesperidin.svg | ImageSize=220px | IUPACName = (2S)-3′,5-Dihydroxy-4′-methoxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavan-4-one | SystematicName = (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 | OtherNames = Hesperetin 7-O-neohesperidoside |Section1= |Section2= |Section3= }}

Excerpted from Wikipedia’s “neohesperidin” article, available under the CC BY-SA 4.0 licence.