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IUPAC name 3,4,5-Trihydroxy-2-({(1'R,3R,3aS,4'R,5'S,6S,6aR,23'R,25'S,26'R,35'R,36'R,37'R)-3a,6,11',12',15',16',17',31',32',36',37'-undecahydroxy-2,2',7',20',28',41'-hexaoxo-25'-[(3,4,5-trihydroxybenzoyl)oxy]-3a, 5,6,6a-tetrahydrospiro[furo[3,2-b]furan-3,39'-[3,6,21,24,27,38,42]heptaoxanonacyclo[35.2.2.133,36.01,35.04,23.05,26.08,13.014,19.029,34]dotetraconta[8,10,12,14,16,18,29,31,33]nonaen]-10' -yl}oxy)benzoic acid | |
Other names 1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose | |
Identifiers | |
3D model (JSmol) | |
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PubChem CID | |
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Properties | |
C54H38O37 | |
Molar mass | 1278.86 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus . [1] This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group (dehydrohexahydroxydiphenic acid or DHHDP) which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.
Tannins are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids.
Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.
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.
Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).
Proanthocyanidins are a class of polyphenols found in a variety of plants such as blueberry. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.
Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
Phlobaphenes are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with mineral acids. The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.
A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.
The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.
Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.
Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect.
Punigluconin is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Emblica officinalis. It is a molecule having a hexahydroxydiphenic acid group and two gallic acids attached to a gluconic acid core.
Punicacortein C is an ellagitannin, a phenolic compound. It is found in the bark of Punica granatum (pomegranate). The molecule contains a gallagic acid component.
Punicacortein D is an ellagitannin, a type of phenolic compound. It is found in the bark and heartwood of Punica granatum (pomegranate). The molecule contains a gallagic acid component.
Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.
Nupharin A is an ellagitannin found in Nuphar japonica. It is a molecule with three gallic acid units and one hexahydroxydiphenic acid unit attached to a glucose residue. It is an isomer of punicafolin and tellimagrandin II.
Mallotus japonicus, also known as East Asian mallotus, the food wrapper plant or "Akamegashiwa" in Japanese, is a plant species in the genus Mallotus native to China. It is also found in Japan and Korea. This species was first described in 1865, its name was verified by AAS Systematic Botanists on October 2, 2015.
Mallotusinic acid is a hydrolysable tannin found in the bark of Mallotus japonicus. It is more generally present in Geraniales.
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