Retusin (flavonol)

Last updated
Retusin
Retusin.svg
Names
IUPAC name
5-Hydroxy-3,3′,4′,7-tetramethoxyflavone
Systematic IUPAC name
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one
Other names
Quercetin tetramethylether
Quercetin-3,7,3',4'-tetramethyl ether
Tetramethylquercetin
Retusine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.013.629 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-991-4
PubChem CID
UNII
  • InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3 X mark.svgN
    Key: HHGPYJLEJGNWJA-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
    Key: HHGPYJLEJGNWJA-UHFFFAOYAJ
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC
Properties
C19H18O7
Molar mass 358.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Retusin is an O-methylated flavonol, a type of flavonoid. It can be found in Origanum vulgare [1] and in Ariocarpus retusus . [2]

Related Research Articles

<span class="mw-page-title-main">Marjoram</span> Perennial herb

Marjoram is a cold-sensitive perennial herb or undershrub with sweet pine and citrus flavours. In some Middle Eastern countries, marjoram is synonymous with oregano, and there the names sweet marjoram and knotted marjoram are used to distinguish it from other plants of the genus Origanum. It is also called pot marjoram, although this name is also used for other cultivated species of Origanum.

<span class="mw-page-title-main">Oregano</span> Species of flowering plant

Oregano is a species of flowering plant in the mint family Lamiaceae. It was native to the Mediterranean region, but widely naturalised elsewhere in the temperate Northern Hemisphere.

<span class="mw-page-title-main">Thymol</span> Chemical compound found in plants including thyme

Thymol, C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris, ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.

<span class="mw-page-title-main">Za'atar</span> Levantine herb or herb blend

Za'atar is a Levantine culinary herb or family of herbs. It is also the name of a spice mixture that includes the herb along with toasted sesame seeds, dried sumac, often salt, and other spices. As a family of related Levantine herbs, it contains plants from the genera Origanum (oregano), Calamintha, Thymus, and Satureja (savory) plants. The name za'atar alone most properly applies to Origanum syriacum, considered in biblical scholarship to be the ezov of the Hebrew Bible, often translated as hyssop but distinct from modern Hyssopus officinalis.

<i>Origanum dictamnus</i> Species of flowering plant

Origanum dictamnus, the dittany of Crete, Cretan dittany or hop marjoram, is a tender perennial plant that grows 20–30 cm high. It is known in Greek as δίκταμο or in the Cretan dialect as έρωντας. It is a therapeutic and aromatic plant that grows wild only on the mountainsides and gorges of the Greek island of Crete. It is widely used for food flavouring and medicinal purposes, in addition to featuring as an ornamental plant in gardens. This small, lanate shrub is easily recognised by the distinctive soft, woolly covering of white-grey hair on its stems and round green leaves, giving it a velvety texture. Its tiny rose-pink flowers are surrounded by brighter purple-pink bracts in summer and autumn. The dittany is classified as vulnerable on the IUCN Red List of Threatened Plant Species 1997.

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

Origanum is a genus of herbaceous perennial flowering plants and subshrubs in the family Lamiaceae. They are native to Europe, North Africa, and much of temperate Asia, where they are found in open or mountainous habitats. A few species also naturalized in scattered locations in North America and other regions.

<i>Ariocarpus</i> Genus of cacti

Ariocarpus is a small genus of succulent, subtropical plants of the family Cactaceae.

Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.

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

Caryophyllene, more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

<i>Ariocarpus fissuratus</i> Species of cactus

Ariocarpus fissuratus is a species of cactus found in small numbers in northern Mexico and Texas in the United States. Common names include living rock cactus, false peyote, chautle, dry whiskey and star cactus.

<span class="mw-page-title-main">Rosmarinic acid</span> Chemical compound found in a variety of plants

Rosmarinic acid, named after rosemary, is a polyphenol constituent of many culinary herbs, including rosemary, perilla, sage, mint, and basil.

<i>Ariocarpus agavoides</i> Species of cactus

Ariocarpus agavoides is a species of cactus. It is endemic to Mexico. It grows in dry shrubland in rocky calcareous substrates. Some taxonomists place it in a separate genus as Neogomezia agavoides. The locals use the slime from the roots of the plants as glue to repair pottery. The sweet-tasting warts are eaten and often added to salads

<i>Ariocarpus kotschoubeyanus</i> Species of cactus

Ariocarpus kotschoubeyanus is a species of plant in the family Cactaceae.

<i>Ariocarpus scaphirostris</i> Species of cactus

Ariocarpus scaphirostris is a species of plant in the family Cactaceae. The Ariocarpus scaphirostris was originally called Ariocarpus scapharostrus in the 1930.

<i>Ariocarpus retusus</i> Species of cactus

Ariocarpus retusus is a species of cactus, from the genus Ariocarpus, found mainly in Mexico. It is one of the largest and fastest-growing species in this genus known for a slow rate of growth. Despite its slow growth, often taking ten years to reach flowering age, the retusus is a desirable cactus for cultivation, having attractive flowers and an unusual form for a cactus. It is also one of the most easily cultivated species in the genus.

<span class="mw-page-title-main">Retusin (isoflavone)</span> Chemical compound

Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata, in Dalbergia retusa and in Millettia nitida. It can also be found in Maackia amurensis cell cultures.

<i>Dalbergia retusa</i> Species of legume

Dalbergia retusa is a plant species in the genus Dalbergia found in Pacific regions of Central America, ranging from Panama to southwestern Mexico. It produces the cocobolo wood. It is a fair-sized tree, reported to reach 20–25 m in height. This is probably the species contributing most of the wood in the trade. Because of the wood's great beauty and high value, the trees yielding this wood have been heavily exploited and are now rare outside national parks, reserves, and plantations.

Many cacti are known to be psychoactive, containing phenethylamine alkaloids such as mescaline. However, the two main ritualistic (folkloric) genera are Echinopsis, of which the most psychoactive species occur in the San Pedro cactus group, and Lophophora, with peyote being the most psychoactive species. Several other species pertaining to other genera are also psychoactive, though not always used with a ritualistic intent.

<i>Origanum onites</i> Species of plant

Origanum onites, the Cretan oregano, Greek oregano, pot marjoram or Ellinikí rίgani in Greek, is a plant species in the genus Origanum found in Sicily, Greece and Turkey. It has similar flavors as common oregano.It has antimicrobial activities.

Bicyclogermacrene synthase is an enzyme with systematic name (2E,6E))-farnesyl-diphosphate diphosphate-lyase (bicyclogermacrene-forming). This enzyme catalyses the following chemical reaction

References

  1. Skoula, Melpomene; Grayer, Renée J.; Kite, Geoffrey C.; Veitch, Nigel C. (2008). "Exudate flavones and flavanones in Origanum species and their interspecific variation". Biochemical Systematics and Ecology. 36 (8): 646–654. Bibcode:2008BioSE..36..646S. doi:10.1016/j.bse.2008.05.003.
  2. Retusin (Ariocarpus) on kanaya.naist.jp