Okanin

Last updated
Okanin
Okanin.svg
Names
IUPAC name
(E)-3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Other names
3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
Properties
C15H12O6
Molar mass 288.25 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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Infobox references

Okanin is a chalconoid. It can be found in the plant Bidens pilosa (Picao preto). [1]

Glycosides / Acetylations

Marein is the 4'-O-glucoside of okanin.

Methylated okanin derivatives can be isolated from Bidens torta . Those include okanin 3,4,3′,4′-tetramethyl ether, okanin 3,4,3′-trimethyl ether 4′-glucoside, okanin 4-methyl ether 4′-glucoside and okanin 4-methyl ether 4′-glucoside monoacetate. Okanin 3,4-dimethyl ether 4′-glucoside can also be isolated. [2]

Related Research Articles

A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms — CH3. In formulas, the group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, it can be found on its own in any of three forms: anion, cation or radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These terms are commonly used in chemistry, biochemistry, soil science, and the biological sciences.

<i>Bidens</i> Genus of flowering plants

Bidens is a genus of flowering plants in the aster family, Asteraceae. The common names beggarticks, black jack, burr marigolds, cobbler's pegs, Spanish needles, stickseeds, tickseeds and tickseed sunflowers refer to the fruits of the plants, most of which are bristly and barbed, with two sharp pappi at the end. The generic name refers to the same character; Bidens comes from the Latin bis ("two") and dens ("tooth").

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.

Methoxy group

A methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3. On a benzene ring, the Hammett equation classifies a methoxy substituent at the para position as an electron-donating group, but as an electron-withdrawing group if at the meta position. At the ortho position, steric effects are likely to cause a significant alteration in the Hammett equation prediction which otherwise follows the same trend as that of the para position.

The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.

Dimethyl sulfate

Dimethyl sulfate is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

<i>beta</i>-Sitosterol

β-Sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

<i>Bidens pilosa</i> Species of flowering plant in the daisy family Asteraceae

Bidens pilosa is an annual species of herbaceous flowering plant in the daisy family Asteraceae. Its many common names include black-jack, beggarticks, farmer’s friends and Spanish needle, but most commonly referred to as cobblers pegs. It is native to the Americas but is widely distributed as an introduced species in other regions worldwide including Eurasia, Africa, Australia, South America and the Pacific Islands.

Petunidin

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many redberries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

Tricin

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

Isorhamnetin

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments. Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. Others sources include the spice, herbal medicinal and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate. Nopal is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.

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

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

Ombuin

Ombuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.

5-<i>O</i>-Methylmyricetin

5-O-Methylmyricetin is an O-methylated flavonol, a type of flavonoid. It is the 5-O-methyl derivative of myricetin.

Centaureidin

Centaureidin is an O-methylated flavonol. It can be isolated from Tanacetum microphyllum, Achillea millefolium, Brickellia veronicaefolia, Bidens pilosa and Polymnia fruticosa.

<i>Bidens torta</i>

Bidens torta, the corkscrew beggarticks, is a flowering plant species in the sunflower family.

Fraxetin

Fraxetin is an O-methylated coumarin. It can be found in Fraxinus rhynchophylla and seeds of Datura stramonium. Fraxin is a glucoside of fraxetin.

Methylepitiostanol

Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use. It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan. Similarly to mepitiostane, methylepitiostanol is an orally active variant of epitiostanol. Due to its C17α methyl group, the drug is considered to have a high potential for hepatotoxicity.

References