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Bicornin

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Bicornin
Chemical structure of bicornin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C48H32O30/c49-17-1-11(2-18(50)29(17)58)42(65)76-40-38-26(72-48(78-44(67)13-5-21(53)31(60)22(54)6-13)41(40)77-43(66)12-3-19(51)30(59)20(52)4-12)10-71-45(68)16-9-23(55)32(61)35(64)36(16)73-37-25(57)8-14-27(34(37)63)28-15(47(70)74-38)7-24(56)33(62)39(28)75-46(14)69/h1-9,26,38,40-41,48-64H,10H2/t26-,38-,40-,41-,48+/m1/s1Key: DOTJYWQAPHIAIF-TWNAEOARSA-N
  • InChI=1/C48H32O30/c49-17-1-11(2-18(50)29(17)58)42(65)76-40-38-26(72-48(78-44(67)13-5-21(53)31(60)22(54)6-13)41(40)77-43(66)12-3-19(51)30(59)20(52)4-12)10-71-45(68)16-9-23(55)32(61)35(64)36(16)73-37-25(57)8-14-27(34(37)63)28-15(47(70)74-38)7-24(56)33(62)39(28)75-46(14)69/h1-9,26,38,40-41,48-64H,10H2/t26-,38-,40-,41-,48+/m1/s1Key: DOTJYWQAPHIAIF-TWNAEOARBX
SMILES
  • c1c(cc(c(c1O)O)O)C(=O)O23(COC(=O)c4cc(c(c(c4Oc5c(cc6c(c5O)c7c(cc(c(c7oc6=O)O)O)C(=O)O3)O)O)O)O)O(2OC(=O)c8cc(c(c(c8)O)O)O)OC(=O)c9cc(c(c(c9)O)O)O
Properties
Chemical formula C48H32O30
Molar mass 1088.754 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bicornin is an ellagitannin found in plants of the order Myrtales, including Trapa bicornis (water caltrop) and Syzygium aromaticum (clove).

The molecule contains a luteic acid group.

References

  1. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K and Okuda T (1989). "Bicornin, a new hydrolyzable tannin from Trapa bicornis, and revised structure of alnusiin". Heterocycles. 29 (5): 861–864. doi:10.3987/COM-89-4951.{{cite journal}}: CS1 maint: multiple names: authors list (link) INIST 6780591
  2. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T (1989). "Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group". Chemical and Pharmaceutical Bulletin. 37 (10): 2655–2660. doi:10.3987/COM-11-12392.{{cite journal}}: CS1 maint: multiple names: authors list (link) INIST 19467830
  3. Yoshida, Takashi; Yazaki, Kazufumi; Memon, Muhammad Usman; Maruyama, Izumi; Kurokawa, Kenji; Shingu, Tetsuro; Okuda, Takuo (1989). "Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group". Chemical and Pharmaceutical Bulletin. 37 (10): 2655–2660. doi:10.1248/cpb.37.2655.
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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