A phenol with diverse biological activities
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Procyanidin B2

Item No. 19865

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,2'R,3R,3'R,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
29106-49-8
Synonyms
  • (−)-Epicatechin-(4β→8)-(−)-epicatechin
  • Proanthocyanidin B2
  • Procyanidol B2
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
281 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-/m1/s1
InChi Key
XFZJEEAOWLFHDH-NFJBMHMQSA-N
Origin
Plant/Grape seeds
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Procyanidin B2 is a phenol and a dimer of (–)-epicatechin (Item No. 11807) that has been found in apple pomace and has diverse biological activities.1,2,3,4 It inhibits MCF-7 breast cancer cell proliferation (IC50 = 19.2 µM).1 Procyanidin B2 scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and superoxide anion radicals in cell-free assays.2 It inhibits LDL oxidation in vitro by 79.5 and 98% when used at concentrations of 5 and 10 µM, respectively.3 Procyanidin B2 (100 mg/kg) prevents carbon tetrachloride-induced increases in serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities and hepatic injury in mice.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Avelar, M.M., and Gouvêa, C.M.C.P. Procyanidin B2 cytotoxicity to MCF-7 human breast adenocarcinoma cells. Indian J. Pharm. Sci. 74(4), 351-355 (2012).

    2. Lu, Y., and Foo, L.Y. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem. 68(1), 81-85 (2000).

    3. Teissedre, P.L., Frankel, E.N., Waterhouse, A.L., et al. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 70(1), 55-61 (1996).

    4. Yang, B.-Y., Zhang, X.-Y., Guan, S.-W., et al. Protective effect of procyanidin B2 against CCl4-induced acute liver injury in mice. Molecules 20(7), 12250-12265 (2015).