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Casuarictin

Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.[1]

Casuarictin
Names
Systematic IUPAC name
(10aR,11S,12aR,25aR,25bS)-2,3,4,5,6,7,17,18,19,20,21,22-Dodecahydroxy-9,15,24,27-tetraoxo-9,10a,11,12a,13,15,24,25a,25b,27-decahydrodibenzo[g,i]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b][1,5]dioxacycloundecin-11-yl 3,4,5-trihydroxybenzoate
Other names
Sanguiin H 11
Sanguiin H-11
1(β)-O-Galloylpedunculagin
Identifiers
  • 79786-00-8 Y
  • 96292-46-5 N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1076705 N
ChemSpider
  • 66302 N
  • 73644
  • DTXSID401000730
  • InChI=1S/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1 N
    Key: SWRFKGRMQVLMKA-JIZJWZDPSA-N N
  • InChI=1/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1
    Key: SWRFKGRMQVLMKA-JIZJWZDPBX
  • c1c(cc(c(c1O)O)O)C(=O)O[C@H]2[C@H]3[C@H]([C@H]4[C@H](O2)COC(=O)c5cc(c(c(c5-c6c(cc(c(c6O)O)O)C(=O)O4)O)O)O)OC(=O)c7cc(c(c(c7-c8c(cc(c(c8O)O)O)C(=O)O3)O)O)O
Properties
C41H28O26
Molar mass 936.64 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

It is formed from two hexahydroxydiphenic acid units and one gallic acid unit linked to a glucose molecule.

The molecule is formed from tellimagrandin II, itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and further into castalagin via glucose pyranose ring opening.

Oligomers edit

Sanguiin H-6 is a dimer, Lambertianin C is trimer and lambertianin D is a tetramer of casuarictin.

References edit

  1. ^ Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Okuda T., Yoshida T., Ashida M. and Yazaki K., Journal of the Chemical Society, 1983, number 8, pages 1765-1772, INIST 9467908

casuarictin, ellagitannin, type, hydrolysable, tannin, found, casuarina, stachyurus, species, namessystematic, iupac, name, 10ar, 12ar, 25ar, 25bs, dodecahydroxy, tetraoxo, decahydrodibenzo, dibenzo, dioxecino, pyrano, dioxacycloundecin, trihydroxybenzoateothe. Casuarictin is an ellagitannin a type of hydrolysable tannin It can be found in Casuarina and Stachyurus species 1 Casuarictin NamesSystematic IUPAC name 10aR 11S 12aR 25aR 25bS 2 3 4 5 6 7 17 18 19 20 21 22 Dodecahydroxy 9 15 24 27 tetraoxo 9 10a 11 12a 13 15 24 25a 25b 27 decahydrodibenzo g i dibenzo 6 7 8 9 1 4 dioxecino 2 3 4 5 pyrano 3 2 b 1 5 dioxacycloundecin 11 yl 3 4 5 trihydroxybenzoateOther names Sanguiin H 11Sanguiin H 111 b O GalloylpedunculaginIdentifiersCAS Number 79786 00 8 Y96292 46 5 N3D model JSmol Interactive imageChEMBL ChEMBL1076705 NChemSpider 66302 NPubChem CID 73644CompTox Dashboard EPA DTXSID401000730InChI InChI 1S C41H28O26 c42 13 1 8 2 14 43 24 13 48 36 57 67 41 35 34 65 39 60 11 5 17 46 27 51 31 55 22 11 23 12 40 61 66 35 6 18 47 28 52 32 23 56 33 19 63 41 7 62 37 58 9 3 15 44 25 49 29 53 20 9 21 10 38 59 64 33 4 16 45 26 50 30 21 54 h1 6 19 33 35 41 56H 7H2 t19 33 34 35 41 m1 s1 NKey SWRFKGRMQVLMKA JIZJWZDPSA N NInChI 1 C41H28O26 c42 13 1 8 2 14 43 24 13 48 36 57 67 41 35 34 65 39 60 11 5 17 46 27 51 31 55 22 11 23 12 40 61 66 35 6 18 47 28 52 32 23 56 33 19 63 41 7 62 37 58 9 3 15 44 25 49 29 53 20 9 21 10 38 59 64 33 4 16 45 26 50 30 21 54 h1 6 19 33 35 41 56H 7H2 t19 33 34 35 41 m1 s1Key SWRFKGRMQVLMKA JIZJWZDPBXSMILES c1c cc c c1O O O C O O C H 2 C H 3 C H C H 4 C H O2 COC O c5cc c c c5 c6c cc c c6O O O C O O4 O O O OC O c7cc c c c7 c8c cc c c8O O O C O O3 O O OPropertiesChemical formula C41H28O26Molar mass 936 64 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references It is formed from two hexahydroxydiphenic acid units and one gallic acid unit linked to a glucose molecule The molecule is formed from tellimagrandin II itself formed from pentagalloyl glucose via oxidation Casuarictin is transformed into pedunculagin via loss of a gallate group and further into castalagin via glucose pyranose ring opening Oligomers editSanguiin H 6 is a dimer Lambertianin C is trimer and lambertianin D is a tetramer of casuarictin References edit Tannins of Casuarina and Stachyurus species I Structures of pendunculagin casuarictin strictinin casuarinin casuariin and stachyurin Okuda T Yoshida T Ashida M and Yazaki K Journal of the Chemical Society 1983 number 8 pages 1765 1772 INIST 9467908 Retrieved from https en wikipedia org w index php title Casuarictin amp oldid 1152425949, wikipedia, wiki, book, books, library,

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