Flavogallonic acid

Last updated
Flavogallonic acid
Flavogallonic acid.svg
Names
Preferred IUPAC name
14,15,25,34,35,36-Hexahydroxy[11,21:24,31-terphenyl]-12,22,32-tricarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C21H14O12/c22-12-2-6(7-3-13(23)14(24)4-9(7)20(30)31)8(19(28)29)1-10(12)16-11(21(32)33)5-15(25)17(26)18(16)27/h1-5,22-27H,(H,28,29)(H,30,31)(H,32,33)
    Key: GAGOUOWDSKMVKE-UHFFFAOYSA-N
  • OC(=O)c1cc(O)c(O)c(O)c1-c2cc(C(=O)O)c(cc2O)-c(cc3O)c(C(=O)O)cc3O
Properties
C21H14O12
Molar mass 458.32 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

Flavogallonic acid is a hydrolysable tannin that can be found in valonea oak (Quercus macrolepis) [1] in chestnut wood [2] or in Terminalia myriocarpa . [3]

See also

Related Research Articles

Punicalagin Chemical compound

Punicalagin is an ellagitannin, a type of phenolic compound. It is found in forms alpha and beta in pomegranates, in Terminalia catappa and Terminalia myriocarpa, and in Combretum molle, the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae.

Phenolic content in wine

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.

Chebulagic acid Chemical compound

Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine.

Ethyl gallate Chemical compound

Ethyl gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant.

Chebulinic acid Chemical compound

Chebulinic acid is an ellagitannin found in the seeds of Euphoria longana, in the fruits of Terminalia chebula or in the leaves of T. macroptera.

Castalagin Chemical compound

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides.

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.

Grandinin Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

Gallagic acid Chemical compound

Gallagic acid is a polyphenolic chemical compound that can be found in the ellagitannins, a type of tannin, found in Punica granatum (pomegranate). It is a building block of the corresponding tannin punicalagin, punicalin, punicacortein C and 2-O-galloyl-punicalin.

Casuarictin Chemical compound

Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.

Terflavin B Chemical compound

Terflavin B is an ellagitannin, a type of hydrolysable tannin. It can be found in Myrobalanus chebula, the black chebulic, and in Terminalia catappa, the Indian almond.

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.

Flavogallonic acid dilactone Chemical compound

Flavogallonic acid dilactone is a hydrolysable tannin that can be found in Rhynchosia volubilis seeds, in Shorea laeviforia, in Anogeissus leiocarpus and Terminalia avicennoides.

<i>Terminalia myriocarpa</i> Species of tree

Terminalia myriocarpa, the East Indian almond, is a tree species in the genus Terminalia found in Southeast Asia.

Casuarinin Chemical compound

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

Luteic acid Chemical compound

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.

Alnusiin Chemical compound

Alnusiin is an ellagitannin found in Alnus sieboldiana.

Bicornin Chemical compound

Bicornin is an ellagitannin found in the Myrtales Trapa bicornis and Syzygium aromaticum (clove).

<i>Terminalia macroptera</i> Species of flowering plant

Terminalia macroptera is a species of flowering plant in the Combretaceae known by the Hausa common name kwandari. It is native to Africa, where it can be found in Benin, Burkina Faso, Ghana, Senegal, Sudan, Uganda, and Nigeria.

Methyl gallate Chemical compound

Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid.

References

  1. Molecular investigation of valonea tannin. Hasan Özgunay and Özcan Sari, The Journal of the American Leather Chemists Association, 2007, vol. 102, no5, pp. 154-157, INIST : 18744048, text
  2. Considerations on the macromolecular structure of chestnut ellagitannins by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry. Pasch H and Pizzi A, Journal of applied polymer science, 2002, vol. 85, no2, pp. 429-437, INIST : 14185517
  3. Pharmacologically Active Ellagitannins from Terminalia myriocarpa. Mohamed S.A. Marzouk, Sayed A.A. El-Toumy, Fatma A. Moharram, Nagwa M.M. Shalaby and Amany A.E. Ahmed, Planta Med, 2002, 68(6), pages 523-527, doi : 10.1055/s-2002-32549