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.

In the Vinony graph

Vinony's link graph records 8 inbound references to neohesperidin, and connects out to Citrus, digital object identifier and chemical formula.

It is catalogued under topics including Chembox image size set, ECHA InfoCard ID from Wikidata and Flavanone glycosides.

Vinony links it to 8 Wikipedia language editions.

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

~1 min read

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.