Ombuin

Last updated
Ombuin
Ombuin.svg
Names
Preferred IUPAC name
3,5-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names
4′,7-Dimethylquercetin
7,4′-Di-O-methylquercetin
4′,7-Dimethoxy-3,3′,5-trihydroxyflavone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3 X mark.svgN
    Key: BWORNNDZQGOKBY-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3
    Key: BWORNNDZQGOKBY-UHFFFAOYAW
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)O)O
Properties
C17H14O7
Molar mass 330.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ombuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.

Ombuin can be found in species of the genus Erythroxylum . It can also be synthesized. [1] Ombuin 3-sulfate can be isolated from Flaveria chlorifolia . [2]

Glycosides

Ombuin-3-rutinoside can be isolated from Phytolacca dioica , the ombu tree. [3] Ombuin-3-O-rhamnosylglucoside can be found in Erythroxylum rufum . [4]
Other glycosides (ombuosides) :

Related Research Articles

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Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

<span class="mw-page-title-main">Quercetin</span> Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Quercitrin</span> Chemical compound

Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.

<span class="mw-page-title-main">Sodium dichromate</span> Inorganic compound

Sodium dichromate is the inorganic compound with the formula Na2Cr2O7. However, the salt is usually handled as its dihydrate Na2Cr2O7·2H2O. Virtually all chromium ore is processed via conversion to sodium dichromate and virtually all compounds and materials based on chromium are prepared from this salt. In terms of reactivity and appearance, sodium dichromate and potassium dichromate are very similar. The sodium salt is, however, around twenty times more soluble in water than the potassium salt (49 g/L at 0 °C) and its equivalent weight is also lower, which is often desirable.

<i>Psidium guajava</i> Species of flowering plant

Psidium guajava, the common guava, yellow guava, lemon guava, or apple guava is an evergreen shrub or small tree native to the Caribbean, Central America and South America. It is easily pollinated by insects; when cultivated, it is pollinated mainly by the common honey bee, Apis mellifera.

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

<span class="mw-page-title-main">Anthoxanthin</span>

Anthoxanthins are a type of flavonoid pigments in plants. Anthoxanthins are water-soluble pigments which range in color from white or colorless to a creamy to yellow, often on petals of flowers. These pigments are generally whiter in an acid medium and yellowed in an alkaline medium. They are very susceptible to color changes with minerals and metal ions, similar to anthocyanins.

<span class="mw-page-title-main">Tricin</span> Chemical compound

Tricin is a chemical compound. It is an O-methylated flavone, a type of flavonoid. It can be found in rice bran and sugarcane.

<span class="mw-page-title-main">Taxifolin</span> Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.

<span class="mw-page-title-main">Afzelechin</span> Chemical compound

Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata. It exists as at least 2 major epimers.

The molecular formula C23H24O12 (exact mass: 492.12677623) may refer to:

<span class="mw-page-title-main">Ayanin</span> Chemical compound

Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylated derivative of quercetin.

<span class="mw-page-title-main">Miquelianin</span> Chemical compound

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

Quercetin 3-<i>O</i>-sulfate Chemical compound

Quercetin 3-sulfate is a plasma human metabolite of quercetin. It is the sulfate conjugate of quercetin.

Flaveria chlorifolia, the clasping yellowtops, is a North American plant species of Flaveria within the family Asteraceae. It is native to the southwestern United States and northern Mexico.

<i>Neodiprion sertifer</i> Species of sawfly

Neodiprion sertifer, the European pine sawfly or red pine sawfly, is a sawfly species in the genus Neodiprion. Although native to Europe, it was accidentally introduced to North America in 1925.

Erythroxylum rufum, the rufous false coca, is a flowering plant species in the genus Erythroxylum.

References

  1. Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin. Koppaka V. Rao, Jacob A. Owoyale, Journal of Heterocyclic Chemistry, Volume 13 Issue 6, Pages 1293 - 1295 [ dead link ]
  2. Ombuin 3-sulphate from Flaveria chloraefolia. Denis Barron and Ragai K. Ibrahim, Phytochemistry, Volume 27, Issue 7, 1988, pages 2362-2363, doi : 10.1016/0031-9422(88)80166-3
  3. Über die Synthese von Quercetin-3-glykosiden, II. Synthese des Ombuosids und eine rationelle Synthese von Rutin. Ludwig Hörhammer, Hildebert Wagner, Hans-Günther Arndt, Gustav Hitzler, Lorand Farkas, Chemische Berichte, Volume 101 Issue 4, Pp 1183-1185, 1968 (German)
  4. Flavonoids of Erythroxylum rufum and Erythroxylum ulei. Bruce A. Bohm, David W. Phillips and Fred R. Gander, J. Nat. Prod., 1981, volume 44, issue 6, pages 676–679, doi : 10.1021/np50018a009