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Casuarictin

From Wikipedia, the free encyclopedia
Casuarictin
Chemical structure of casuarictin
Chemical structure of 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
3D model (JSmol)
ChEMBL
ChemSpider
  • 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 mass936.64 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Casuarictin is anellagitannin, a type of hydrolysable tannin. It can be found inCasuarina andStachyurus species.[1]

It is formed from twohexahydroxydiphenic acid units and onegallic acid unit linked to aglucose molecule.

The molecule is formed fromtellimagrandin II, itself formed frompentagalloyl glucose via oxidation. Casuarictin is transformed intopedunculagin via loss of a gallate group, and further intocastalagin via glucose pyranose ring opening.

Oligomers

[edit]

Sanguiin H-6 is a dimer,Lambertianin C is trimer andlambertianin 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
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules withchebulic acid
molecules withElaeocarpusinic acid
Oligomers
Other
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