Procyanidin B4

Procyanidin B4 is a B type proanthocyanidin.

Procyanidin B4
Names
IUPAC name
[(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Preferred IUPAC name
(2R,2′R,3S,3′R,4S)-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 B4
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • 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-/m1/s1
    Key: XFZJEEAOWLFHDH-VUGKQVTMSA-N
SMILES
  • 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
Chemical formula
 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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Infobox references

Procyanidin-B4 is a catechin-(4α→8)-epicatechin dimer. It is found in the litchi pericarp,[1] in grape seeds,[2] and, along with 4-cis-isomer of procyanidin B4, in beer.[3]

See also
  • Phenolic content in wine

References
  1. Immunomodulatory and anticancer activities of flavonoids extracted from litchi (Litchi chinensis Sonn.) pericarp. Mouming Zhao; Bao Yang; Jinshui Wang; Yang Liu; Limei Yu; Yueming Jiang, 2007
  2. Catechin and proanthocyanidin B4 from grape seeds prevent doxorubicin-induced toxicity in cardiomyocytes. Yu Du and Hongxiang Lou, 2008.
  3. Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, 1985 Archived 2011-07-06 at the Wayback Machine
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