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Valoneic acid

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Valoneic acid
Chemical structure of valoneic acid
Names
Other names Valoneaic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

See also

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

External links

Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other


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