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| Identifiers | |
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3D model (JSmol) | |
PubChem CID |
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| Properties | |
| C14H14O5 | |
| Molar mass | 262.261 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Vaginol is a chemical compound of the furanocoumarin class. Its glucoside is apterin. [1]
It has been prepared by the following reaction sequence:
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.
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
Angelica archangelica, commonly known as garden angelica, wild celery, and Norwegian angelica, is a biennial plant from the family Apiaceae, a subspecies of which is cultivated for its sweetly scented edible stems and roots. Like several other species in Apiaceae, its appearance is similar to several poisonous species, and should not be consumed unless it has been identified with absolute certainty. Synonyms include Archangelica officinalis Hoffm. and Angelica officinalis Moench.
Hydrangea macrophylla is a species of flowering plant in the family Hydrangeaceae, native to Japan. It is a deciduous shrub growing to 2 m (7 ft) tall by 2.5 m (8 ft) broad with large heads of pink or blue flowers in summer and autumn. Common names include bigleaf hydrangea, French hydrangea, lacecap hydrangea, mophead hydrangea, penny mac and hortensia. It is widely cultivated in many parts of the world in many climates. It is not to be confused with H. aspera 'Macrophylla'.
Ipomoea purpurea, the common morning-glory, tall morning-glory, or purple morning glory, is a species in the genus Ipomoea, native to Mexico and Central America.
Coniferyl alcohol is a colourless crystalline organic compound. One of the monolignols, it is a phytochemical synthesized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol.
Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.
Apterin is a furanocoumarin and the glucoside of vaginol. It has been isolated from the root of plants in the family Apiaceae such as members of the genus Angelica, including the garden angelica and Zizia aptera.
Phellodendron amurense is a species of tree in the family Rutaceae, commonly called the Amur cork tree. It is a major source of huáng bò, one of the 50 fundamental herbs used in traditional Chinese medicine. The Ainu people used this plant, called shikerebe-ni, as a painkiller. It is known as hwangbyeok in Korean and (キハダ) kihada in Japanese.
Phytotoxins are substances that are poisonous or toxic to the growth of plants. Phytotoxic substances may result from human activity, as with herbicides, or they may be produced by plants, by microorganisms, or by naturally occurring chemical reactions.
Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species Stevia phlebophylla and in the plant Rubus chingii (Rosaceae).
The furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. Most of the plant species found to contain furanocoumarins belong to a handful of plant families. The families Apiaceae and Rutaceae include the largest numbers of plant species that contain furanocoumarins. The families Moraceae and Fabaceae include a few, widely distributed plant species that contain furanocoumarins.
Aesculetin is a derivative of coumarin. It is a natural lactone that derives from the intramolecular cyclization of a cinnamic acid derivative.
Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.
Dandelion 'coffee' is a tisane made from the root of the dandelion plant. The roasted dandelion root pieces and the beverage have some resemblance to coffee in appearance and taste, and it is thus commonly considered a coffee substitute. Dandelion root is used for both medicinal and culinary purposes and is thought to be a detoxifying herb.
Coumaroyl-coenzyme A is a chemical compound found in plants. The compound is the thioester of coenzyme-A and coumaric acid.
Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as Bituminaria bituminosa. It has a skin permeability coefficient (LogKp) of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in this database. The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarine.
Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside can be found in the cork from Quercus suber.
Syringin is a natural chemical compound first isolated from the bark of lilac by Meillet in 1841. It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus. It is also found in dandelion coffee. Syringin may potentially have antidiabetic effects.
Isopimpinellin is a natural product synthesized by numerous plant species, especially species in the carrot family Apiaceae. The compound can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. Several studies have looked into the effects of isopimpinellin and other furanocoumarins as anticarcinogens. These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors. Evidence has also been reported that links these compounds to the inhibition of breast cancers.
Coumarin glycosides contain coumarin or a derivative as aglycone, e.g., apterin is a coumarin glycoside. It is a furanocoumarin, the glucoside of vaginol. It has been isolated from the root of plants in the Apiaceae (Angelica spp. Zizia aptera ...
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