Valoneic acid

Valoneic acid
Names
	Other names Valoneaic acid
Identifiers
CAS Number	517-54-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	26233367 ;
PubChem CID	12444662;
CompTox Dashboard (EPA)	DTXSID60498505 ;
	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) Key: YIWUPYVTWJLBDH-UHFFFAOYSA-N ; 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).
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	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 synthesized.[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

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