A polyphenol flavonoid dimer of (+)-catechin and (−)-epicatechin
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Procyanidin B1

Item No. 22411

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,2'R,3R,3'S,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-[4,8'-bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol
CAS Number
20315-25-7
Synonyms
  • (−)-Epicatechin-(4β-8)-(+)-catechin
  • Proanthocyanidin B1
  • Procyanidol B1
Molecular Formula
C30H26O12
Formula Weight
578.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
280 nm
SMILES
OC1=CC=C([C@H]2OC(C=C(O)C=C3O)=C3[C@H](C4=C(O)C=C(O)C5=C4O[C@H](C6=CC=C(O)C(O)=C6)[C@@H](O)C5)[C@H]2O)C=C1O
InChi Code
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
InChi Key
XFZJEEAOWLFHDH-UKWJTHFESA-N
Origin
Plant/Grape seeds
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Procyanidin B1 is a polyphenol flavonoid existing as a dimer of (+)-catechin (Item No. 70940) and (−)-epicatechin (Item No. 11807). It inhibits hepatitis C virus RNA replication (EC50 = 72 µM), while (+)-catechin and (−)-epicatechin do not, up to concentrations of 200 µM.1 Procyanidin B1 (10 µg/ml) prevents phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells.2 It decreases TNF-α, phosphorylated p38 MAPK, and NF-κB levels following LPS administration.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, S., Kodama, E.N., Inoue, Y., et al. Procyanidin B1 purified from Cinnamomi cortex suppresses hepatitis C virus replication. Antivir. Chem. Chemother. 20(6), 239-248 (2010).

    2. Terra, X., Palozza, P., Fernandez-Larrea, J., et al. Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes. Free Radic. Res. 45(5), 611-619 (2011).

    3. Xing, J., Li, R., Li, N., et al. Anti-inflammatory effect of procyanidin B1 on LPS-treated THP1 cells via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling. Mol. Cell. Biochem. 407(1-2), 89-95 (2015).