saponarin

Also known as 7-O-(β-D-glucosyl)isovitexin, 7-O-(beta-D-glucosyl)isovitexin

Saponarin is a flavone glucoside. It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower. This coloration has been shown to be an example of copigmentation, a result of the presence of malvin (an anthocyanin) and saponarin in the ratio 1:9. Under the alkaline conditions (pH 7.9) found in the sap of the epidermal cells, this combination produced a blue-green pigmentation; the pH of the colorless inner floral tissue was found to be lower, at pH 5.6. Experiments showed that saponarin produced a strong yellow colo

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Vinony's link graph records 66 inbound references to saponarin, and connects out to pH, digital object identifier and chemical formula.

It sits within the topics C-glycoside natural phenols, Chembox image size set and Flavone glucosides.

Vinony links it to 5 Wikipedia language editions.

Chemical data

Formula: C27H30O15
Molecular weight: 594.5 g/mol
IUPAC name: 5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
InChIKey: HGUVPEBGCAVWID-KETMJRJWSA-N
XLogP: -1.6
Polar surface area: 256 Å²
H-bond donors: 10
H-bond acceptors: 15
Formal charge: 0

via PubChem

Wikidata facts

Mass: 594.15847026

Show 4 more facts

found in taxon: Ziziphus spina-christi
isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
chemical formula: C₂₇H₃₀O₁₅
canonical SMILES: O=C1C=C(OC=2C=C(OC3OC(CO)C(O)C(O)C3O)C(=C(O)C12)C4OC(CO)C(O)C(O)C4O)C=5C=CC(O)=CC5

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Encyclopedic overview

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Contents

References

{{Chembox | ImageFile = Saponarin.svg | ImageSize = 250px | ImageAlt = Chemical structure of saponarin | IUPACName = 5-Hydroxy-6-(β-D-glucopyranosyl)-7-(β-D-glucopyranosyloxy)flavone | SystematicName = 5-Hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | OtherNames = Isovitexin-7-O-glucosideSaponaretin-7-O-glucoside |Section1= |Section2= |Section3= }} Saponarin is a flavone glucoside. It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower. This coloration has been shown to be an example of copigmentation, a result of the presence of malvin (an anthocyanin) and saponarin in the ratio 1:9. Under the alkaline conditions (pH 7.9) found in the sap of the epidermal cells, this combination produced a blue-green pigmentation; the pH of the colorless inner floral tissue was found to be lower, at pH 5.6. Experiments showed that saponarin produced a strong yellow colouring in slightly alkaline conditions, resulting in the greenish tone of the flower. It is also found in passion flowers (Passiflora sp.).

== References ==

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