Sanguisorbic acid

Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid.

comparison of structures of valoneic and sanguisorbic acids
Sanguisorbic acid
Chemical structure of sanguisorbic acid
Names
Preferred IUPAC name
3-(5-Carboxy-2,3-dihydroxyphenoxy)-4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C21H14O15/c22-6-1-4(19(30)31)2-8(12(6)24)36-18-11(21(34)35)10(15(27)16(28)17(18)29)9-5(20(32)33)3-7(23)13(25)14(9)26/h1-3,22-29H,(H,30,31)(H,32,33)(H,34,35)
    Key: IGSQOFHPQLBLHF-UHFFFAOYSA-N
  • InChI=1/C21H14O15/c22-6-1-4(19(30)31)2-8(12(6)24)36-18-11(21(34)35)10(15(27)16(28)17(18)29)9-5(20(32)33)3-7(23)13(25)14(9)26/h1-3,22-29H,(H,30,31)(H,32,33)(H,34,35)
    Key: IGSQOFHPQLBLHF-UHFFFAOYAB
  • Oc2c(c(c(Oc1cc(cc(O)c1O)C(=O)O)c(O)c2O)C(=O)O)c3c(cc(O)c(O)c3O)C(=O)O
Properties
C21H14O15
Molar mass 506.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is found in 2,3-O-hexahydroxydiphenoyl-4,6-O-sanguisorboyl-(α/β)-glucose, an ellagitannin found in Rubus sanctus.[1] It is also found in lambertianin A, B, C and D, all ellagitannins found in Rubus lambertianus.[2]

See also

References
  1. Hussein, Sahar A.M; Ayoub, Nahla A; Nawwar, Mahmoud A.M (2003). "Caffeoyl sugar esters and an ellagitannin from Rubus sanctus". Phytochemistry. 63 (8): 905–11. doi:10.1016/S0031-9422(03)00331-5. PMID 12895538.
  2. Tanaka, T; Tachibana, H; Nonaka, G; Nishioka, I; Hsu, FL; Kohda, H; Tanaka, O (1993). "Tannins and related compounds. CXXII. New dimeric, trimeric and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianus Seringe". Chemical & Pharmaceutical Bulletin. 41 (7): 1214–20. doi:10.1248/cpb.41.1214. PMID 8374992.
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