Valoneic acid

Valoneic acid
Names

Other names Valoneaic acid
Identifiers
CAS Number	517-54-4^N
3D model (Jmol)	Interactive image
ChemSpider	26233367^Y
PubChem	12444662
InChI InChI=1S/C21H14O13/c22-11-1-6(8(19(28)29)3-12(11)23)7-2-13(24)15(5-9(7)20(30)31)34-18-10(21(32)33)4-14(25)16(26)17(18)27/h1-5,22-27H,(H,28,29)(H,30,31)(H,32,33)^Y Key: YIWUPYVTWJLBDH-UHFFFAOYSA-N^Y InChI=1/C21H14O13/c22-11-1-6(8(19(28)29)3-12(11)23)7-2-13(24)15(5-9(7)20(30)31)34-18-10(21(32)33)4-14(25)16(26)17(18)27/h1-5,22-27H,(H,28,29)(H,30,31)(H,32,33) Key: YIWUPYVTWJLBDH-UHFFFAOYAX
SMILES c1c(c(cc(c1O)O)C(=O)O)c2cc(c(cc2C(=O)O)Oc3c(cc(c(c3O)O)O)C(=O)O)O
Properties
Chemical formula	C₂₁H₁₄O₁₃; C₂₁H₁₄O₁₅
Molar mass	474.32 g/mol, 506.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Valoneic acid is a hydrolysable tannin. It is a component of some hydrolysable tannins such as mallojaponin.

The difference with its isomer sanguisorbic acid is that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the HHDP group.

Comparison of structures of valoneic and sanguisorbic acids

It can be chemically synthetised.^[1]

References

↑ Enantioselective synthesis of valoneic acid derivative. Hitoshi Abe, Yusuke Sahara, Yuki Matsuzaki, Yasuo Takeuchi and Takashi Harayama, Tetrahedron Letters, Volume 49, Issue 4, 21 January 2008, pp. 605-609, doi:10.1016/j.tetlet.2007.11.154

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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