apiin

Also known as 7-((2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone, apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside], 5,7,4'-trihydroxyflavone 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside], 7-O-(beta-D-Apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4'-trihydroxyflavone

Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley and celery, and in banana leaf. The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed. The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.

Chemical data

Formula: C26H28O14
Molecular weight: 564.5 g/mol
IUPAC name: 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 564.147906

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chemical formula: C₂₆H₂₈O₁₄
canonical SMILES: C1C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)(CO)O
isomeric SMILES: C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)(CO)O

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{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457811880 | Name = Apiin | Reference= | ImageFile = Apiin.svg | ImageSize = 270px | ImageName = Apigenin | IUPACName = 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β-D-erythrofuranosyl-(1→2)-β-D-glucopyranosyloxy]flavone | SystematicName = 7-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | OtherNames = ApiosideApigenin-7-apioglucosideApigenin-7-O-apioglucoside |Section1= |Section2= | Section7= }}