Gallagic acid

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Gallagic acid
Gallagic acid.svg
Names
Preferred IUPAC name
2,2′-(1,2,6,7-Tetrahydroxy-4,9-dioxo-4,9-dihydro-[1]benzopyrano[5,4,3-cde][1]benzopyran-3,8-diyl)bis(3,4,5-trihydroxybenzoic acid)
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C28H14O18/c29-5-1-3(25(39)40)7(17(33)15(5)31)9-13-11-12-14(28(44)46-23(11)21(37)19(9)35)10(20(36)22(38)24(12)45-27(13)43)8-4(26(41)42)2-6(30)16(32)18(8)34/h1-2,29-38H,(H,39,40)(H,41,42)
    Key: ZASJRRFAYSNSHU-UHFFFAOYSA-N
  • Oc4c6c1c(c5c(=O)o6)c(oc(=O)c1c(c4O)-c(c(O)c2O)c(C(O)=O)cc2O)c(O)c(O)c5-c3c(C(O)=O)cc(O)c(O)c3O
Properties
C28H14O18
Molar mass 638.39 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

Gallagic acid is a polyphenolic chemical compound that can be found in the ellagitannins, a type of tannin, found in Punica granatum (pomegranate). [1] It is a building block of the corresponding tannin punicalagin, punicalin, punicacortein C and 2-O-galloyl-punicalin.

See also

Related Research Articles

Pomegranate Fruit-bearing deciduous shrub

The pomegranate is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between 5 and 10 m tall.

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.

Punicic acid Chemical compound

Punicic acid is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13. It is named for the pomegranate,, and is obtained from pomegranate seed oil. It has also been found in the seed oils of snake gourd.

1-<i>alpha</i>-<i>O</i>-Galloylpunicalagin Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate and in Combretum glutinosum.

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.

Corilagin Chemical compound

Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from Caesalpinia coriaria, hence the name of the molecule. It can also be found in Alchornea glandulosa and in the leaves of Punica granatum (pomegranate).

1,2,3,4,6-Pentagalloyl glucose Chemical compound

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

Punigluconin Chemical compound

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 A Chemical compound

Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Osbeckia chinensis.

Punicalin Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

Punicacortein C Chemical compound

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 Chemical compound

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.

Punicacortein B Chemical compound

Punicacortein B is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate).

Punicafolin Chemical compound

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate) and in Phyllanthus emblica.

Granatin A Chemical compound

Granatin A is an ellagitannin found in the pericarp of Punica granatum (pomegranate). It is a weak carbonic anhydrase inhibitor.

Granatin B Chemical compound

Granatin B is an ellagitannin found in the fruit of Punica granatum (pomegranate). It is a molecule having an enantiomeric dehydrohexahydroxydiphenoyl group.

Pomegranate ellagitannin Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates.

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.

Pedunculagin Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

Brevifolin Chemical compound

Brevifolin is a bioactive compound found in pomegranate. The pharmacological profile of brevifolin is reported similar to ellagic acid, particularly with regards to absorption, distribution, and elimination rates.

References

  1. Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L. Reddy Muntha K., Gupta Sashi K., Jacob Melissa R., Khan Shabana I. and Ferreira Daneel, Planta medica, 2007, vol. 73, no5, pp. 461-467, INIST : 18773247