Vitisin C

Vitisin C
Chemical structure of vitisin C
Chemical structure of vitisin C
Names
Preferred IUPAC name
(22S,23S,32R,33S,4E,62S,63S)-22,32,62-Tris(4-hydroxyphenyl)-22,23,32,33,62,63-hexahydro-2(3,4),3(3,5),6(4,3)-tris([1]benzofurana)-1,7(1)-dibenzenaheptaphan-4-ene-13,15,26,66,73,75-hexol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55+,56-/m0/s1 checkY
    Key: WZKKRZSJTLGPHH-WHSOPTDBSA-N checkY
  • InChI=1/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55+,56-/m0/s1
    Key: WZKKRZSJTLGPHH-WHSOPTDBBK
  • OC(C=C1)=CC=C1[C@@H](O2)[C@@H](C3=CC(O)=CC(O)=C3)C4=C2C=C(O)C=C4/C=C/C5=CC([C@H](C6=C([C@H](C7=CC(O)=CC(O)=C7)[C@@H](C8=CC=C(O)C=C8)O9)C9=CC(O)=C6)[C@H](C%10=CC=C(O)C=C%10)O%11)=C%11C=C5
  • Oc1ccc(cc1)[C@H]4Oc2cc(O)cc(c2[C@@H]4c3cc(O)cc(O)c3)\C=C\c%10ccc%11O[C@@H](c5ccc(O)cc5)[C@@H](c7cc(O)cc8O[C@H](c6ccc(O)cc6)[C@H](c78)c9cc(O)cc(O)c9)c%11c%10
Properties
C56H42O12
Molar mass 906.940 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

Vitisin C is a hydroxystilbenoid. It is a resveratrol tetramer found in plants of the genus Vitis (grapevines).

References

  1. ↑ Ito, J (1996). "Absolute structures of new hydroxystilbenoids, vitisin C and viniferal, from Vitis vinifera 'Kyohou'". Tetrahedron. 52 (30): 9991–9998. doi:10.1016/0040-4020(96)00543-1.
  2. ↑ Seya, K; Furukawa, K; Taniguchi, S; Kodzuka, G; Oshima, Y; Niwa, M; Motomura, S (2003). "Endothelium-dependent vasodilatory effect of vitisin C, a novel plant oligostilbene from Vitis plants (Vitaceae), in rabbit aorta". Clinical Science. 105 (1): 73–9. doi:10.1042/CS20020288. PMID 12605596. S2CID 41885739.