Carasinol B

Carasinol B
Names
Preferred IUPAC name
(2S,2′R,3S,3′R)-3′-(3,5-Dihydroxyphenyl)-4-[(2R,3S,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]-2,2′-bis(hydroxyphenyl)-2,2′,3,3′-tetrahydro[3,4′-bi-1-benzoxole]-6,6′-diol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C56H44O13/c57-33-9-1-27(2-10-33)53-47(31-17-37(61)21-38(62)18-31)49-43(23-41(65)25-45(49)67-53)52-50-44(24-42(66)26-46(50)68-55(52)29-5-13-35(59)14-6-29)51-48(32-19-39(63)22-40(64)20-32)54(28-3-11-34(58)12-4-28)69-56(51)30-7-15-36(60)16-8-30/h1-26,47-48,51-66H/t47-,48+,51-,52+,53+,54-,55-,56+/m1/s1 X markN
    Key: RAUCCLKIJHMTND-HFRYPGABSA-N X markN
  • InChI=1/C56H44O13/c57-33-9-1-27(2-10-33)53-47(31-17-37(61)21-38(62)18-31)49-43(23-41(65)25-45(49)67-53)52-50-44(24-42(66)26-46(50)68-55(52)29-5-13-35(59)14-6-29)51-48(32-19-39(63)22-40(64)20-32)54(28-3-11-34(58)12-4-28)69-56(51)30-7-15-36(60)16-8-30/h1-26,47-48,51-66H/t47-,48+,51-,52+,53+,54-,55-,56+/m1/s1
    Key: RAUCCLKIJHMTND-HFRYPGABBW
  • Oc1ccc(cc1)[C@@H]4Oc2cc(O)cc(c2[C@H]4c3cc(O)cc(O)c3)[C@H]6c7c(O[C@@H]6c5ccc(O)cc5)cc(O)cc7[C@@H]%10[C@H](c8cc(O)cc(O)c8)[C@H](O[C@H]%10c9ccc(O)cc9)c%11ccc(O)cc%11
Properties
C56H44O13
Molar mass 924.94 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Carasinol B is a stilbenoid tetramer found in Caragana sinica (Chinese : Jin Que-gen).

Acid-catalyzed epimerization of kobophenol A to carasinol B can be performed in vitro.

References

  1. ↑ Shu Na; Zhou Hong; Hu Changqi (2006). "Simultaneous determination of the contents of three stilbene oligomers in Caragana sinica collected in different seasons using an improved HPLC method". Biological & Pharmaceutical Bulletin. 29 (4): 608–612. doi:10.1248/bpb.29.608. PMID 16595888.
  2. ↑ Kejun Cheng; Gaolin Liang; Changqi Hu (2008). "Acid-catalyzed Epimerization of Kobophenol A to Carasinol B". Molecules. 13 (4): 938–942. doi:10.3390/molecules13040938. PMC 6245474. PMID 18463595.