Dehydrohexahydroxydiphenic acid

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Dehydrohexahydroxydiphenic acid
IUPAC name

5,6,9,13,13-pentahydroxy-10-oxo-8-oxatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraene-3,12-dicarboxylic acid

Other names

Dehydrohexahydroxydiphenoyl
DHHDP

Identifiers

 Jmol-3D images Image 1
Properties
Molecular formula C14H10O11
Molar mass 354.22 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dehydrohexahydroxydiphenic acid is a group found in dehydroellagitannins. It is formed from hexahydroxydiphenic acid (HHDP) through oxidation of the plant hydrolysable tannins.[1] It is found in ellagitannins such as euphorbin A, geraniin or mallotusinic acid.

In geraniin, it is forming an equilibrium mixture of six-membered hemi-ketal and five-membered hemi-ketal forms.[2]

References

  1. ↑ Correlation of oxidative transformations of hydrolyzable tannins and plant evolution. Takashi Yoshida and Tsutomu Hatano, Phytochemistry, November 2000, Volume 55, Issue 6, Pages 513–529, doi:10.1016/S0031-9422(00)00232-6
  2. ↑ Herbal Drugs in Traditional Japanese Medicine, Tsutomu Hatano, doi:10.5772/53126
Types of ellagitannins
Aglycones
Lactones
Monomers
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
  • Elaeocarpusin
  • Helioscopin B
  • Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other
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