Procyanidin B1

Chemical compound From Wikipedia, the free encyclopedia

Procyanidin B1[1] is a procyanidin dimer.

Quick facts Names, Identifiers ...
Procyanidin B1
Chemical structure of procyanidin B2
Chemical structure of procyanidin B2
Names
IUPAC name
[(2R,3R,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,2′R,3R,3′S,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H-[4,8′-bi-1-benzopyran]-3,3′,5,5′,7,7′-hexol
Other names
Procyanidin B1
cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1
    Key: XFZJEEAOWLFHDH-UKWJTHFESA-N
  • O[C@H]1Cc2c(O)cc(O)c([C@@H]3[C@@H](O)[C@H](Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
Properties
C30H26O12
Molar mass 578.52 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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It is a molecule with a 4→8 bond (epicatechin-(4β→8)-catechin).[2] Proanthocyanidin-B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf)[3] or in peach.[4]

Procyanidin B1 can be converted into procyanidin A1 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.[5]

See also

References

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