sanguisorbic acid

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| Name = Sanguisorbic acid

| ImageFile = Sanguisorbic acid.svg

| ImageName = Chemical structure of sanguisorbic acid

| PIN = 3-(5-Carboxy-2,3-dihydroxyphenoxy)-4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylic acid

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|Section1={{Chembox Identifiers

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| DTXSID = DTXSID801030309

| PubChem = 71308268

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| SMILES = 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

| ChemSpiderID = 28190826

| 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)

| InChIKey = IGSQOFHPQLBLHF-UHFFFAOYAB

| StdInChI = 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)

| StdInChIKey = IGSQOFHPQLBLHF-UHFFFAOYSA-N

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|Section2={{Chembox Properties

| Formula = C21H14O15

| MolarMass = 506.33 g/mol

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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.

File:Valoneic vs sanguisorbic.png

It is found in 2,3-O-hexahydroxydiphenoyl-4,6-O-sanguisorboyl-(α/β)-glucose, an ellagitannin found in Rubus sanctus.{{Cite journal|doi=10.1016/S0031-9422(03)00331-5|title=Caffeoyl sugar esters and an ellagitannin from Rubus sanctus|year=2003|last1=Hussein|first1=Sahar A.M|last2=Ayoub|first2=Nahla A|last3=Nawwar|first3=Mahmoud A.M|journal=Phytochemistry|volume=63|issue=8|pages=905–11|pmid=12895538|bibcode=2003PChem..63..905H }} It is also found in lambertianin A, B, C and D, all ellagitannins found in Rubus lambertianus.{{Cite journal|pmid=8374992|year=1993|last1=Tanaka|first1=T|last2=Tachibana|first2=H|last3=Nonaka|first3=G|last4=Nishioka|first4=I|last5=Hsu|first5=FL|last6=Kohda|first6=H|last7=Tanaka|first7=O|title=Tannins and related compounds. CXXII. New dimeric, trimeric and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianus Seringe|volume=41|issue=7|pages=1214–20|journal=Chemical & Pharmaceutical Bulletin|doi=10.1248/cpb.41.1214|doi-access=free}}

See also

References

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