Chemistry:Casuarictin

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Casuarictin
Chemical structure of casuarictin
Names
Systematic IUPAC name
(10aR,11S,12aR,25aR,25bS)-2,3,4,5,6,7,17,18,19,20,21,22-Dodecahydroxy-9,15,24,27-tetraoxo-9,10a,11,12a,13,15,24,25a,25b,27-decahydrodibenzo[g,i]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b][1,5]dioxacycloundecin-11-yl 3,4,5-trihydroxybenzoate
Other names
Sanguiin H 11
Sanguiin H-11
1(β)-O-Galloylpedunculagin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
Properties
C41H28O26
Molar mass 936.64 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

Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.[1]

It is formed from two hexahydroxydiphenic acid units and one gallic acid unit linked to a glucose molecule.

The molecule is formed from tellimagrandin II, itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and further into castalagin via glucose pyranose ring opening.

Oligomers

Sanguiin H-6 is a dimer, Lambertianin C is trimer and lambertianin D is a tetramer of casuarictin.

References

  1. Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Okuda T., Yoshida T., Ashida M. and Yazaki K., Journal of the Chemical Society, 1983, number 8, pages 1765-1772, INIST:9467908