Valoneic acid

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Valoneic acid
Valoneic acid.svg
Names
Other names
Valoneaic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: YIWUPYVTWJLBDH-UHFFFAOYSA-N Yes check.svgY
  • 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
  • c1c(c(cc(c1O)O)C(=O)O)c2cc(c(cc2C(=O)O)Oc3c(cc(c(c3O)O)O)C(=O)O)O
Properties
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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 Valoneic vs sanguisorbic.png
Comparison of structures of valoneic and sanguisorbic acids

It can be chemically synthesized. [1]

See also

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A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

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Casuarictin Chemical compound

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Roburin A Chemical compound

Roburin A is a tannin found in oak wood or oak cork.

3,4,5-Tri-<i>O</i>-galloylquinic acid Chemical compound

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Terflavin B Chemical compound

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Valoneic acid dilactone Chemical compound

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Flavogallonic acid Chemical compound

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Flavogallonic acid dilactone Chemical compound

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Mallotusinic acid Chemical compound

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Dehydrohexahydroxydiphenic acid Chemical compound

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Mallojaponin Chemical compound

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus. This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

References

  1. 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