Dehydrohexahydroxydiphenic acid

Dehydrohexahydroxydiphenic acid
Names

IUPAC name 5,6,9,13,13-pentahydroxy-10-oxo-8-oxatricyclotrideca-2,4,6,11-tetraene-3,12-dicarboxylic acid
Other names Dehydrohexahydroxydiphenoyl DHHDP
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	139031016
CompTox Dashboard (EPA)	DTXSID601045778
InChI InChI=1S/C14H10O11/c15-5-1-3(11(18)19)7-8-4(12(20)21)2-6(16)14(24,13(8,22)23)25-10(7)9(5)17/h1-2,8,15,17,22-24H,(H,18,19)(H,20,21)Key: ZMIDWLVYIBGXNC-UHFFFAOYSA-N
SMILES C1=C(C2C3=C(C(=C(C=C3C(=O)O)O)O)OC(C1=O)(C2(O)O)O)C(=O)O
Properties
Chemical formula	C₁₄H₁₀O₁₁
Molar mass	354.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Dehydrohexahydroxydiphenic acid is a group found in dehydroellagitannins. It is formed from hexahydroxydiphenic acid (HHDP) through oxidation of the plant hydrolysable tannins. 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.

References

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

Moieties

Lactones

Monomers

C-glycosidic ellagitannins

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic 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, B, C and D; Sanguiin H-6

Other

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